Invest Like the Best with Patrick O'Shaughnessy

My guest today is Tim Ferriss. Tim is a writer, podcaster, and investor. He has written five best-selling books, has been an early-stage investor in Facebook, Uber, Shopify, & other household names, and is the host of one of the biggest podcasts in the world. He started The Tim Ferriss Show as an experiment in April 2014 and has deconstructed world-class performers ever since. Last year, his show crossed 1 billion downloads. Together, we deconstruct his podcast and approach to life. We talk about the art of interviewing, the business behind his podcast, and what motivates Tim to keep teaching through his writing and podcast. Please enjoy this great conversation with Tim Ferriss. Check Out Invest America 2024 Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:32) The Evolution of Podcasting with Tim Ferriss (00:09:56) Crafting Meaningful Conversations (00:13:26) What Makes Tim Feel The Most Alive (00:24:06) Who Tim Considers To Be His Mentors (00:29:06) The Ingredients Of A World Class Performance (00:31:06) The Business Side of Podcasting (00:43:15) Identifying Emerging Trends (00:50:12) Lessons From Building a Small, Efficient Team (00:52:32) The Power of Constraints in Personal and Professional Growth (00:53:10) Innovating Against the Grain (Anti-Video Experiment) (00:54:54) Navigating Fame, Money, and Power (01:02:00) The Impact of Sharing Difficult Stories (01:06:18) Meta-Learning: A Framework for Fast, Effective Learning (01:12:32) Reflecting on a Decade of Podcasting & What’s In Store (01:24:41) The Kindest Thing Anyone Has Ever Done For Tim

My guest today is Ken Langone. Ken is a legendary American businessman best known for his co-founding of Home Depot. He is also a former director of the New York Stock Exchange and a passionate philanthropist. He shares with us a lifetime's worth of wisdom, building Home Depot into a powerhouse and prioritizing his employees above all else. He says he still “bleeds orange” to this day. You’ll hear as he recounts his business endeavors, his strict belief in keeping your word, and his true pride in his country, which he knows to be the land of opportunity. We discuss his work with Ross Perot, the idea of an upside-down hierarchy, and the power of loyalty. For anyone who may find it easier to follow along, we have a transcript of the episode on joincolossus.com. Please enjoy this conversation with Ken Langone. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the go-to destination for bold investing. The investment research platform trusted by 95% of the top 20 global private equity firms just got even better. Building on their solid reputation for expert insights, Tegus has expanded to become the first true all-in-one research platform. The new Tegus makes diligence faster, easier, and more convenient than ever before. Your Tegus license gives you access to over 70,000 expert transcripts, more than 4,000 fully drivable financial models, and exclusive datasets like company management checks, industry KPIs, hard-to-find non-GAAP data, and more. Tegus is the fastest way to learn about a public or private company and the most cost-effective way to conduct investment research — now all under one roof. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:004:00) The Unforgettable Pitch to Ross Perot (00:08:37) Winning Over Perot with Honesty and Insight (00:16:08) The Art of Negotiation and Trust (00:19:31) Loyalty, Integrity, and the Power of Keeping Your Word (00:23:51) Home Depot's Culture of Service and Empowerment (00:29:16) Frank's Authentic Leadership and Its Impact (00:31:00) Transforming NYU Medical Center (00:33:45) Ken’s Investment Philosophy: Long Hold Only (00:39:56) The Power of Resilience in Business (00:45:37) The Kindest Thing Anyone Has Ever Done For Ken

My guest today is Robin Dunbar. Robin is a biological anthropologist, evolutionary psychologist, and specialist in primate behavior. He is the man behind Dunbar’s number, a theory about the number of stable relationships we can maintain at once. Robin unravels the thread of research that led him to Dunbar’s number and describes how this plays into every single person’s layers of human connection. It was fascinating to hear how his findings on social circles have implications for optimally structuring businesses and organizations, as well as the idea of homophily, all of which Robin thoughtfully explains. It was a treat to get to explore these topics with Robin Dunbar himself so please enjoy this great conversation. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for fundamental investors. Whether you’re trying to get up to speed on a new market or keep tabs on a portfolio company, Tegus is the end-to-end investment research platform you need. With Tegus, you can quickly understand a company's business model, drivers, benchmarks, and management quality. To monitor an entire market, download our pre-built financial models — or update your own with the latest data using Tegus’ new Excel Add-In. Tegus gives you all of this and more, all bundled into a single software license. Find out why 95% of the top 20 global private equity firms are Tegus customers. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:39) The Journey to Discovering Dunbar's Number (00:07:28) Exploring the Layers of Human Connection (00:12:27) The Significance of the 1.5 Layer in Social Circles (00:16:55) Surprising Insights from Social Network Studies (00:20:40) Applying Dunbar's Number to Organizational Structures (00:27:51) The Science of Social Bonding in Primates and Humans (00:33:23) Unlocking the Endorphin System Without Physical Touch (00:34:10) The Power of Laughter, Singing, and Storytelling in Group Bonding (00:36:00) The Limitations of Digital Interactions for Building Relationships (00:39:51) Reviving Social Clubs and Activities for Workplace Bonding (00:44:40) The Importance of Homophily in Friendships and Social Networks (00:50:40) Challenges and Solutions for Overcoming Loneliness and Building Trust (00:53:45) The Impact of Technology, Religion, and Mental Health on Social Connections (00:61:47) Reflecting on Time as a Fundamental Aspect of Social Dynamics

My guest today is Sean Feeney. Sean is the co-founder of Grovehouse Hospitality Group and the owner of Lilia and Misi, two of New York City’s most sought-after restaurants. He left his job in Trading to chase down a dream with Michelin star chef Missy Robbins. Sean leveraged his finance background to write his own rulebook for the restaurant industry, crafting several establishments that now boast several thousand people on the waitlist any given night. His story is as entertaining as it is inspiring. As we go step by step through his business endeavors, he points out all of the times he was told “it’s just always been done this way” and how that revealed to him where he could innovate. Sean’s restaurants are the perfect example of building a business into the fabric of a community, collaborating with other brands in authentic ways, and staying true to yourself along the way. Please enjoy this awesome conversation with Sean Feeney. Listen to Founders Podcast Join Positive Sum as a Research Analyst  For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:58) First Question - A Chance Encounter with a Michelin-Starred Chef (00:08:52) The Birth of a Culinary Partnership (00:12:49) Embracing the Genius Within (00:16:41) Innovative Approaches to the Restaurant Business (00:24:53) Creating Demand: The Art of Exclusivity (00:28:49) Learning from the Best: Insights from Kith's Success (00:34:21) Defining Exceptional Hospitality (00:44:20) The Power of Customer Relationships in Hospitality (00:52:31) Unlocking Team Potential (00:53:33) The Philosophy of the Perfect Turn (00:54:05) Balancing Art, Commerce, and Satisfaction (00:56:13) The Impact of Authentic Experiences and Brands (01:03:24) The Evolution of a Hospitality Brand (01:06:38) Community Engagement and the Power of Simplicity (01:24:40) Creative Responses and Business Lessons Learned (01:36:05) Lessons From Working In The Restaurant Industry (01:43:01) The Kindest Thing Anyone Has Ever Done For Sean

My guest today is Dave Fontenot, founder of HF0. Born out of Dave’s experiences in monasteries across the world, HF0 is a twelve-week residency for repeat founders to supercharge their next venture. For 12 weeks, 10 teams of engineers relocate to HF0’s house in San Francisco. During the residency, everything is taken care of so their sole focus is coding and building. It’s one of the most interesting incubators I have come across and we discuss the model and its monastic origins in detail. Please enjoy this conversation with Dave Fontenot. Become a Research Analyst at Positive Sum Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:05) First Question - Dave’s Journey to Meditation and Monastic Life (00:07:25) From Monastery to Coding: Finding Flow in Programming (00:08:32) Creating Spaces for Uninterrupted Creativity: The Birth of HF0 (00:20:24) A Day in the Life at HF0 (00:25:15) Why 12 Weeks? The Philosophy Behind the Duration (00:27:14) Selecting the Brilliant Minds for HF0 (00:31:43) The Thin Line Between Visionary and Crazy (00:34:39) Creating Space to Meditate (00:37:24) The Economic Model Behind HF0 (00:41:36) Building Successful Residencies (00:44:48) Expanding the Residency Model to Universities (00:52:52) Understanding Engineers and Hackers (01:02:01) The Kindest Thing Anyone’s Ever Done For Dave

My guest today is Anne-Marie Peterson. Anne-Marie is an equity portfolio manager at Capital Group, a storied investment firm managing 2.5 trillion dollars and getting ready to celebrate its centennial anniversary. Anne-Marie is a seasoned investor, approaching three decades in the industry, with nearly 20 of those years being with Capital. She has become an expert in retail and restaurants and shares her proven strategies in those sectors over her career. We discuss her people-first approach, simplicity as criteria for investment, and the idea that the best retailers are cults. Please enjoy this great discussion with Anne-Marie Peterson. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the go-to destination for bold investing. The investment research platform trusted by 95% of the top 20 global private equity firms just got even better. Building on their solid reputation for expert insights, Tegus has expanded to become the first true all-in-one research platform. The new Tegus makes diligence faster, easier, and more convenient than ever before. Your Tegus license gives you access to over 70,000 expert transcripts, more than 4,000 fully drivable financial models, and exclusive datasets like company management checks, industry KPIs, hard-to-find non-GAAP data, and more. Tegus is the fastest way to learn about a public or private company and the most cost-effective way to conduct investment research — now all under one roof. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:06) First Question - Understanding Capital Group's Investment Approach (00:05:43) The Importance of Teamwork and Culture in Investment Firms (00:07:38) The Role of Analysts in Investment Decisions (00:12:24) The Art of Running Effective Meetings with Company Management (00:18:12) Exploring the Dominance of Big Tech Companies (00:19:13) The Common Thread Amongst Great Retailing Companies (00:30:49) Comparing The Growth in The Tech Market to That of Healthcare (00:34:14) The Rise of Pharma and its Potential Opportunities (00:36:56) Power Dynamics in the Tech Industry (00:38:11) The Idea of Power in Investing (00:46:21) Unique Challenges and Opportunities in the Restaurant Industry (00:48:35) The Positive Signal of Enduring Companies (00:54:54) The Importance of Gratitude and Kindness in Professional Growth (00:58:40) The Kindest Thing Anyone Has Ever Done for Anne-Marie

My guest today is Aravind Srinivas. He is the founder and CEO of Perplexity, a startup that he describes as an “answer engine” built from scratch with AI. Aravind has set out for perplexity to become the most powerful answer engine backed by up-to-date sources. He helps me pick the technology apart, describing the behind the scenes of what it takes to build Perplexity to reach its potential and compete alongside the likes of Google and OpenAI. Our conversation goes deep into programming this type of infrastructure, the competition around latency, and constructing a business model around deep learning. There is so much on this horizon, so please enjoy my conversation with Aravind Srinivas. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for fundamental investors. How hard do you work to get the insights you need to make a great investment decision? How many hours do you spend digging through public records and expert transcripts, or manually updating complex models? Investors should compete on their ability to analyze investments, not how well they aggregate data. That’s why Tegus offers a unified, end-to-end research platform that combines robust qualitative content sets, up-to-date financial data, management and culture checks, and more — all in the same easy-to-use, streamlined user experience. 95% of the top 20 global private equity firms use Tegus. Shouldn’t you? Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:08) First Question - Redefining 'Great' in Search (00:07:16) The Mechanics of Perplexity (00:10:59) The Evolution of Perplexity From Wrapper to Robust Infrastructure (00:13:19) The Future of Large Language Models (LLMs) (00:22:39) Aravind's Strategy For Constructing The Business Model (00:28:16) The Process of Building an Index for a Search Engine (00:35:55) The Impact of Scaling and Data Quality on AI Models (00:40:00) Bottlenecks in AI Development (00:47:06) The Talent Landscape in AI (00:57:59) The Vision for the Future of Search (01:00:19) Importance of Execution in AI Startups

My guest today is Ali Hamed. Ali was first on Invest Like the Best six years ago. He was 26 at the time and four years into building his investing firm, CoVenture. Both then and now, Ali is an example of what’s possible when you think creatively. Six years later, CoVenture now manages two-and-a-half billion dollars, and Ali continues to find alpha in esoteric places. We talk about YouTube catalogs, creative opportunities in real estate, and how venture investing helps them get better at credit. We also talk about his lessons from building an investment firm and what it’s been like to work with Michael Ovitz. Please enjoy this great conversation with Ali Hamed. Listen to Ali host a Business Breakdowns on Spotter Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for fundamental investors. Whether you’re trying to get up to speed on a new market or keep tabs on a portfolio company, Tegus is the end-to-end investment research platform you need. With Tegus, you can quickly understand a company's business model, drivers, benchmarks, and management quality. To monitor an entire market, download our pre-built financial models — or update your own with the latest data using Tegus’ new Excel Add-In. Tegus gives you all of this and more, all bundled into a single software license. Find out why 95% of the top 20 global private equity firms are Tegus customers. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:03:11) First Question - The Journey of Building an Investment Firm (00:15:08) The Influence of Time and Scale on Asset Classes (00:22:39) The Power and Potential of YouTube's Asset Class (00:27:33) The Future of Real Estate and Housing Supply (00:30:15) The Challenges of Investing in Platform Economies (00:36:44) The Pitfalls of Capital Formation in Asset Management (00:45:17) The Evolution of Venture Portfolio (00:51:14) The Approach to AI and Other Emerging Technologies (00:54:42) The Mispricing in Private Credit (00:58:46) Building the People Side of the Business (01:04:21) The Challenges and Opportunities in Valuation (01:19:40) The Impact of Michael Ovitz on CoVenture (01:23:11) The Kindest Thing Anyone Has Ever Done For Him

My guest today is Cyan Banister. Cyan’s life story is remarkable. She was homeless at a young age, dropped out of high school, and five years ago she suffered an extremely rare stroke. Yet, in spite of everything, she is one of the most optimistic and curious people you can hope to meet. Cyan is also one of the great angel investors of this era, having invested early in SpaceX, Uber, Postmates, and Deepmind to name a few winners. She became the first female investing partner at Peter Thiel’s Founders Fund and now invests at Long Journey Ventures. Our conversation is as much about investing as it is about the essence of life and how connecting with that will help us in our professional pursuits. It is also full of awesome stories about people and companies like SpaceX and Bill Murray. Please enjoy this great conversation with Cyan Banister. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the only investment research platform built for the investor. With traditional research vendors, the diligence process is slow, fragmented, and expensive. That leaves investors competing on how well they can aggregate data — not on their unique ability to analyze insights and make great investment decisions. Tegus offers an end-to-end platform with all the data you need to get up to speed on a company or market: up-to-the-minute financials, customizable models, management and culture checks, and, of course, our vast and growing library of expert call transcripts. Tegus is changing the world of expert research. Learn more and get your free trial at tegus.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:03) First question - Spirituality as an Investable Category (00:06:51) Journey to Founders Fund (00:12:13) Overcoming Adversity and Embracing Optimism (00:14:28) The Power of Authenticity and Curiosity (00:25:28) The Skill of Feeling in Business (00:30:26) Investing in Uber (00:36:18) The Changing Dynamics of Early-Stage Investment (00:39:07) The Philosophy of 'Set it and Forget It' (00:42:24) The SpaceX Story: A Leap of Faith (00:48:02) Cyan’s Spiritual Awakening (00:61:34) Her Story of the Violin Kid (01:05:36) The Art of Trusting Your Gut in Business (01:07:47) The Spirit of Founders Fund and the Future of Venture Firms (01:15:16) What She Would Do With 1 Trillion Dollars (01:24:05) The Kindest Thing Anyone Has Ever Done For Cyan

Today, we're replaying my conversation with Danny Meyer. He is the founder and CEO of Union Square Hospitality Group, which comprises some of the most acclaimed restaurants in New York, like Gramercy Tavern and Union Square Café. Danny is also the founder and chairman of Shake Shack, which began in NYC but is now a publicly traded company with hundreds of locations worldwide. Our conversation focuses on how great hospitality leads to a great business, regardless of what sector it's in. We discuss why hospitality is the starting point for Danny’s business philosophy, why first impressions matter, Danny’s concept of ABCD - always be connecting dots, how to scale hospitality, and how to build a business with essentialism and soul. Please enjoy this conversation with Danny Meyer. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00) Welcome to Invest Like the Best (03:41) First question – Danny’s experience as a tour guide in Italy (08:17) Why hospitality is the center of business focus (08:19) Setting the Table: The Transforming Power of Hospitality in Business (11:50) Early lessons at creating an environment of hospitality (15:17) His strategy ABCD and learning from a trout fisherman relate and relate to hospitality (20:45) Scaling hospitality (24:56) What kind of people make a hospitality business work (29:34) How to be an effective leader (33:00) Handling mistakes well in the role of hospitality (36:28) Creating the spark in the early part of entrepreneurial ventures (40:32) When its time to start something new vs expand something you are already doing (45:52) The excellence reflex and an example of this in his career (50:25) Kindest thing anyone has done for him

Today, we're running a replay of my 2019 conversation with legendary investor Chuck Akre. Chuck founded Akre Capital Management in 1989, which now manages approximately $14B dollars. We discuss his investing style and his “three-legged stool” for evaluating companies. Please enjoy this great conversation. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:01:06] First Question – Advantage of being in Middleburg, Virginia [00:02:11] What a day looks like for Chuck [00:03:06] Why imagination is more important than knowledge [00:03:38] Difference between curiosity and imagination [00:04:38] The origins of the Nirvana Three-Legged Stool concept [00:10:14] First leg of the stool, extraordinary business and ROE’s with a focus on Bandag [00:14:36] How his evaluations of value have changed over the last 10-15 years [00:16:10] A look at recent businesses that he’s bought and why they are interesting [00:19:56] Why they keep things simple [00:21:35] Second leg of the stool, the people involved and characteristics of managers he has invested in [00:23:20] Role of capital allocation in the people he focuses on [00:29:34] Third leg of the stool, reinvestment [00:21:09] How does he think about diversifying across an investment area [00:33:32] Great businesses wrapped in a bad balance sheet [00:37:35] What would cause him to sell [00:38:52] What does he look for in people [00:43:27] How curiosity has impacted his interest in land conservation [00:43:51] Advice for investors, especially younger ones [00:46:14] Kindest thing anyone has done for him

My guest today is Alex Telford. Alex is the founder of Convoke, a software platform to help streamline drug development and commercialization. He also has been writing frequent blog posts on the biotech industry since 2019, keeping a pulse on the direction of innovation. He joined me today to talk about the history of the pharmaceutical industry and what’s becoming possible in medicine in the coming years. Alex helped break down the complexities of investing in new drug development, breakthroughs in gene therapy on the horizon, and the dance between timely progress and restrictive regulation. This industry has a lot to unpack, and he thoughtfully lays out the landscape. Please enjoy my conversation with Alex Telford. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:01) First question - Exploring public perceptions of Big Pharma (00:04:56) Providing an overview of the drug discovery process (00:07:22) Assessing the efficiency of the pharmaceutical industry (00:12:13) Anticipating the future direction of drug development (00:16:46) Categorizing different types of pharmaceutical drugs (00:21:19) Strategies to reduce the time from discovery to implementation (00:25:55) Gaining insights from cross-disciplinary research (00:31:13) The emerging role of AI in pharmaceuticals (00:34:32) Analyzing potential regulatory shifts in the industry (00:39:13) Discussing the importance of Randomized Controlled Trials (RCTs) (00:43:29) Examining the impact of blockbuster drugs (00:47:47) Deliberating on the complexities of drug pricing (00:54:09) Highlighting exciting developments and concerns in pharma (00:59:55) The kindest thing anyone has ever done for him

My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products. It’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why you need to focus on benefits rather than features, and how to pick the right monetization model. Please enjoy my conversation with Madhavan Ramanujam. Listen to Founders podcast. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes [00:00:00] Welcome to Invest Like the Best [00:02:48] First question - How he arrived at a radically different way of building products [00:05:07] An example of coming up with a price before the product [00:08:35] Distinctions between a willingness to pay and positive feedback [00:10:29] How to make sure you’re talking to the right potential customer in the first place [00:13:32] Productizing for different customer segments [00:16:16] Questions companies should be asking to get accurate feedback [00:21:18] What he’s learned about the motivations of potential buyers [00:22:43] What leaders, killers, and fillers are [00:24:37] Some of the biggest mistakes companies make while following his formula [00:25:35] A rule of thumb for what is a benefit versus a feature [00:27:35] Five distinct pricing models for charging a customer [00:30:46] Whether or not the value piece of all of this revolves around time and money [00:33:27] What he tells entrepreneurs about pricing their products that most surprises them [00:35:16] Defining the first four categories of failure [00:40:13] Reasons why so many innovations fail to monetize and pricing being a CEO topic [00:41:51] Good rules that leaders can use to have a general sense for effective pricing [00:47:38] Behavioral changes and observations as the absolute price move up and down [00:50:36] Is there a pricing genius we should take note of? [00:53:18] The single question every leader should ask themselves [00:53:46] The kindest thing anyone has ever done for him

This week, we are running a replay of my conversation with Daryl Morey from last year. Daryl is the President of basketball operations for the Philadelphia 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyball. I had a blast talking to him about negotiation tactics, systems thinking, hiring, and a ton more. Please enjoy this great conversation with Daryl Morey. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders Podcast. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes (00:00:00) Welcome to Invest Like the Best (00:03:15) The basic principles of sports and what makes for a great sport (00:09:54) How resource concentration influences outcomes in various sports (00:13:13) The degree of certainty in predicting sports outcomes based on existing data (00:16:32) Using the concept of KPIs to optimize for certain characteristics to win games (00:18:45) Training teams on specific systems and plays versus leveraging individual talent (00:21:07) Why superstar athletes are key to success in basketball (00:24:02) Dealing with constant expected value calculations to appease stakeholders (00:25:30) Building the organization’s back office to find talented athletes (00:28:32) How he and other GMs make organization-level decisions (00:34:12) Why he’s involved with basketball as opposed to other sports (00:36:17) How he uses his frameworks to figure out systems outside of mainstream sports (00:37:41) Problems with the rules and economic factors of professional soccer (00:41:53) Suggestions to mitigate huge point spreads that make viewers disinterested (00:42:54) Trends he’s observed in the worlds of music, movies, and books (00:45:33) His perspective on developing one’s own career path (00:48:22) How challenges in his youth benefited him in the long run (00:49:28) The person he would call for advice if he was stuck in a foreign prison (00:51:01) His emphasis on first principles and why he supports free speech (00:52:31) Takeaways from a Harvard negotiation class he took (00:57:07) The power of refining the terms and definitions of a deal post-negotiation (00:58:51) The four people in the world that intrigue him most (01:01:40) The kindest thing anyone has ever done for him

My guest today is Michael Ovitz. Michael is the legendary talent agent and co-founder of CAA, or Creative Artists Agency. Michael started CAA in 1975 and over the next twenty years, he built it into the world’s most formidable talent agency, changing Hollywood forever. The list of stars he’s worked with is endless, from Meryl Streep to Steven Spielberg and David Letterman. Since leaving CAA, he has become an investor and adviser to many prominent firms, most notably Andreessen Horowitz, and Michael’s work ethic is unmatched. Please enjoy this great discussion with Michael Ovitz. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Show Notes: (00:00:00) Show Introduction (00:03:25) First Question, Michael Crichton's Impact (00:04:14) The Art of Storytelling and Creativity (00:07:20) Michael Crighton’s Writer's Block (00:09:53) The Birth of Jurassic Park (00:12:42) The Importance of Pacing in Storytelling (00:17:43) Positional Power and Influence (00:20:04) Knowledge is Power (00:22:10) The Role of Agents in the Business World (00:36:18) The Importance of Momentum in Business (00:42:35) Branding and Image (00:45:44) The Art of Spotting Talent (00:46:20) The Role of Persistence (00:51:25) Investing in People (01:00:30) Building Mystique (01:06:30) The Importance of Relationships (01:10:39) The Role of Art in the Entertainment Industry (01:17:04) Telling the Truth to Clients (01:25:28) Winning the Coca-Cola account (01:42:18) The Kindest Thing Anyone Has Done for Michael

My guest today is Erik Serrano. Erik is the CEO of Stable Asset Management, which he started 14 years ago in his early 20s and has scaled to over $3 billion in AUM. Unusually, Stable’s strategy focuses on other investing firms. They look to back the Blackstone's of tomorrow and provide those founders with capital and support so their time is spent doing what they do best, which is typically investing. We discuss the commonalities among promising founders in this sector, how Stable serves as a full resource to their companies, and some harsh truths learned from building an investing business. Please enjoy my conversation with Erik Serrano. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:33) - (First question) Exploring the allure of investing in investment firms (00:08:20) - Discussing the scarcity of investors in investment firms (00:18:20) - Strategies for generating returns for investors (00:22:50) - Analyzing risk/return dynamics in portfolios (00:26:26) - Unveiling surprising insights from Project Legends (00:29:56) - Characterizing the ideal General Partner (GP) (00:37:23) - Identifying red flags in GPs' practices (00:44:10) - Viewing investment strategies as marketable products (00:52:52) - Delving into the emotional aspects of investing (01:01:57) - Tracing the lifecycle of an investment firm (01:13:04) - Offering guidance to aspiring young investors (01:18:24) - Reflecting on the notion that ‘nice people finish last’ (01:23:52) - The kindest thing anyone has ever done for him

This week we are replaying our episode with Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:21] - [First question] - What Don Valentine’s heart was like [00:06:30] - The most productive and unproductive parts of Don’s toughness [00:10:55] - Why it’s so important to understand someone’s core motivations [00:14:18] - Questions or topics he returns to when getting to know people [00:16:44] - The most formative experiences he had prior to becoming an investor that impacted his investing the most [00:20:37] - What venture looks like to him today relative to his prior career [00:23:51] - His style of approaching emerging technology markets like AI as an investor [00:26:37] - Whether or not he’d go into venture today if he was in his late 20s [00:28:30] - Commonalities between the very best at going to market effectively [00:31:11] - The key components of great product positioning [00:37:15] - How interacting with companies early on has changed over the ears [00:41:12] - Whether or not new entrants into venture should build firms with enterprise value [00:46:14] - Sussing out the killer gene in somebody [00:49:04] - How successful people can instill the lessons learned from hardship into their children [00:53:52] - Whether or not his view on competitive advantage has changed [00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like [01:00:40] - The most interesting question an LP has ever asked him [01:05:00] - Which dinner companions he’d pick to educate a newly successful founder [01:07:59] - The kindest thing anyone has ever done for him

My guest today is Justin Ishbia. Justin is the Founding Partner of Shore Capital. Shore is a private equity firm that invests in microcap businesses within industry niches. With $7 billion in capital deployed but an average transaction size of just $12 million, Justin has worked to build a system to drive success for hundreds of businesses through replicable operating procedures and championing young professionals. The firm has created a moat around volume with nearly 600 acquisitions over the last three years, some of the highest numbers in the world. We discuss identifying growth prospects, constructing a meaningful board, and the business mentality behind "main street," not wall street, as Justin puts it. Please enjoy my conversation with Justin Ishbia. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes: (00:03:10) - (first question) - “The system is the star” and how it applies to Shore Capital (00:07:10) - Shore Capital’s origin story (00:12:48) - What the perfect type of deal looks like for Justin (00:16:34) - The historical rates of return for their deals (00:18:12) - Shore Capital’s defensibility and strategic advantages (00:22:13) - Their board system and incentive structure (00:28:20) - Why they focus on the industrial subsector (00:31:21) - Overview of thesis evaluation and generation (00:37:24) - What they’re looking for during the diligence stage (00:40:45) - The bad reputation of levered rollups (00:43:57) - What he’s learned about negotiations (00:46:39) - The weak points of Shore Capital’s system (00:48:59) - The Innovation Stack; Thinking about stacking unfair advantages (00:52:11) - Selling a business and what buyers are looking for (00:55:08) - Heavy focus on operations and their portfolio performance group (00:58:00) - Why nobody above an associate level has ever left Shore Capital (00:60:46) - Lessons learned becoming the owner of a major sports franchise (01:03:56) - What’s surprising about how the league functions (01:05:05) - Key people and firms he’s learned the most from (01:07:17) - Where Shore Capital’s system could improve the most (01:11:06) - The kindest thing anyone has ever done for Justin

Today, my guest is 21-year-old Gavin Uberti, who dropped out of Harvard to build Etched, which is one of the most fascinating companies I’ve seen. The topic of our conversation is the ongoing revolution in artificial intelligence, and more specifically the chips and technology that powers these incredible models. To date, general-purpose AI chips like Nvidia GPUs have powered the revolution, but Gavin’s bet is that purpose-built chips, hard-coded for the underlying model architecture, will dramatically reduce the latency and cost of running models like GPT4. We’re about to embark on what Gavin calls the “largest infrastructure buildout since the industrial revolution”, and I won’t spoil what he thinks this will unlock for all of us. It is so uplifting to me that someone so young can be working on something so big. Please enjoy this great conversation with Gavin Uberti. Check out Etched.AI Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes: (00:03:41) - (first question) - Born too late to explore the world, too early to explore the stars (00:05:59) - Interpreting and defining superintelligence (00:07:20) - Excitement we can have for an AI driven future (00:09:25) - Overview and basic terminology of the transformers that power AI (00:15:53) - What Q* is and the rumors around it (00:20:41) - Robotics, machinery, and what’s interesting about them (00:23:18) - The problem of latency and computing power (00:8:55) - Needing to build physical infrastructure that doesn’t exist (00:32:18) - Inference and training AI models (00:36:00) - Major stages of chip design and the upper limits of speed (00:45:56) - Customers for billion dollar generative AI models (00:48:56) - A sci-fi-esque reality and the politicization of AI (00:50:38) - The Bitter Lesson and the implications of powerful AI models (00:56:27) - The most important companies in the AI space today (00:61:52) - Strategically building a defensible AI product (01:04:07) - Software development and why other AI companies fail (01:06:51) - Specialization and chip performance improvement (01:15:34) - Why the transformer remains the leading architecture (01:17:26) - A proliferation of models beyond the major players and data access (01:21:19) - The kindest thing anyone has ever done for Gavin

Today, we’re releasing a conversation between John Collison and Charlie Munger. We've had this interview with Charlie scheduled to air for a while, coinciding with Stripe Press's launch of the amazing reprint of Poor Charlie's Almanack, which is released today. We were all stunned last week when we heard the news of Charlie's passing, but having consulted with those close to him, everyone agreed that he'd want us to release this interview. I'm thankful to be able to learn from him just one more time in this interview. Please enjoy, and may Charlie Rest in Peace. Order your copy of Poor Charlie’s Almanack Worldly wisdom episodes in honor of Charlie Munger: Daryl Morey: Systems Thinking in Sports Boyd Varty: The Art of Tracking Sam Hinkie: Find Your People David Senra: Passion & Pain Priya Parker: The Art of Gathering Charlie Songhurst: Lessons from Investing in 483 Companies For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:52) - (First question) - The fixation on evaluating business quality (00:05:58) - Learning the big ideas across various disciplines (00:10:03) - The issue of adverse selection in legal services (00:11:42) - Societal solutions for the opioid crisis (00:17:34) - Reasons for not investing in Amazon (00:20:38) - Explaining Costco's model (00:29:08) - Discussing the increasing challenges in investing (00:32:08) - Ingredients for long-term success in business (00:33:18) - Debating cryptocurrency (00:37:37) - Offering guidance for navigating a potential recession (00:38:56) - Reflecting on the state of American society (00:45:20) - Sharing a passion for architecture (00:54:13) - “Win-win” business (00:57:53) - Countering arguments against capitalism (00:60:42) - The origins of Poor Charlie's Almanack (01:05:14) - Building a productive partnership (01:08:55) - Opining on the SEC (01:12:22) - Highlighting investment concerns (01:16:31) - Reasons for optimism about China (01:32:14) - The unique aspects of Berkshire Hathaway

My guests this week are Peter Fenton and Victor Lazarte. Peter and Victor are both General Partners at Benchmark. Of the six equal partners at the storied venture firm, Peter is the longest serving and Victor is the newest, having spent the past decade founding and building Wildlife Studios into one of the biggest independent mobile gaming companies in the world. Peter has been a board member at Wildlife for the past four years and has a remarkable track record of tech investing over his two decades at Benchmark. In our discussion, we talk about the core motivators behind great entrepreneurs, Benchmark's unique operating philosophy, and what it's like to transition from builder to investor. Please enjoy this conversation with Peter Fenton and Victor Lazarte. Listen to Founders Podcast: #326 Anna Wintour For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:04:10) - (First question) - Victor’s early expectations after being at the company for just three months (00:05:39) - What Victor misses from the operating life (00:06:59) - Peter’s opinion on what makes Benchmark a fascinating company (00:15:00) - Peter and Victor’s perspective on the significance of the phrase “life’s work” (00:24:19) - The influence of market tailwinds on success in investing (00:29:42) - How to keep founders’ generative drive at peak levels (00:32:39) - Balancing aggression, desire and generative drive when building and operating a business (00:34:22) - Victor’s approach to dealing with pleasure seeking as a successful operator (00:38:29) - Why Benchmark intentionally raises funds at half the suggested amount (00:43:13) - Lessons learned from navigating challenging scenarios in venture capital (00:46:27) - What excites Victor as he starts a new venture at Benchmark (00:48:19) - Why AI is more akin to the internet than crypto (00:52:41) - The significance of platform-based businesses in the contemporary landscape (00:57:45) - The impact tech giants exert on new entrants in the industry (00:61:00) - Victor’s opinion on what makes great games and great gaming businesses (01:13:44) - Where Peter and Victor feel they have areas to grow (01:19:48) - Perspectives on human progress (01:21:14) - The kindest thing that anyone has done for both Peter and Victor

Today's episode is a conversation with Lior Susan, the Founder of Eclipse Ventures, whose mission is to unlock solutions to age-old physical industry problems through the intersection of bits and atoms. Lior is Israeli, and served in Israel's special forces before founding Ecplise. The topic of conversation is one fellow investor's perspective of the terror attacks of October 7 and the path forward. I hope more than anything that collective action is in the direction of fewer people dying, and most importantly, zero innocent civilians dying in Israel and in Gaza and Palestine. This is not a political show, and it won't become one. This is a conversation with a person deeply and personally affected by the Hamas terror attacks of October 7, who I believe to be a very good person who wants to be a part of change in the right direction for everyone good in and around Israel and Gaza, regardless of their background, religion, or anything else about them. Please enjoy my conversation with Lior Susan. Listen to Founders Podcast: #326 Anna Wintour For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:57) - [First question] - Recounting Lior's career thus far (00:09:29) - Insights on the global situation post-October 7th (00:14:37) - Delving into Israel's historical backdrop (00:19:47) - Analyzing the wave of protests on college campuses (00:23:29) - Sharing thoughts on Palestine (00:28:49) - Planning for the use of his time ahead (00:31:41) - Evaluating the current state of leadership in Israel (00:36:27) - Concerns for the welfare of innocent people (00:40:47) - Assessing technology's role in future conflicts (00:44:08) - Crafting pathways to effective globalization (00:48:27) - Identifying traits that contribute to investment success (00:55:17) - Envisioning constructive steps post-conflict (00:57:10) - Reflecting on the lessons from strong leadership (01:01:04) - The kindest thing anyone has ever done for Lior

My guest today is Brad Jacobs. Brad’s resumé is remarkable. He has founded seven companies, all of which are billion-dollar or multibillion-dollar businesses. He has done 500 M&A transactions and raised $30 billion dollars of debt and equity capital. Currently, he is the Executive Chairman of XPO, a commercial trucking company that he started in 2011 and has grown into one of the largest logistics businesses in the world. He has also written a book that will be out in January, titled “How to Make a Few Billion Dollars”. Brad’s energy is infectious and our conversation unpacks his strategies for M&A, his propensity for speed, and methods for earning team buy-in. Please enjoy my conversation with Brad Jacobs. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:11) - (First question) - Identifying key factors in a market before investing (00:05:07) - Gleaning insights from early acquisition experiences (00:08:43) - Delving into the seller's mindset during a business sale (00:12:51) - Weighing pre-built against organic growth strategies in acquisitions (00:17:20) - Defining the elements of an ideal business (00:22:49) - Engaging constructively with Wall Street (00:24:36) - Discussing the substantial buyback of XPO shares (00:28:16) - Ambition as a recurring theme in entrepreneurial success (00:30:17) - Emphasizing the need to facilitate team agility (00:32:35) - Highlighting the joys of post-acquisition integration (00:36:09) - Drawing lessons from Ludwig Jesselson's principles (00:40:34) - Comparing the risks and rewards of early versus late adoption (00:44:09) - Reflecting on errors made in trend analysis (00:48:59) - Strategies for implementing new technologies in enterprises (00:51:59) - The significance of thought experiments in strategic decision-making (00:56:00) - Recalling transformative events from his early years (00: 57:22) - Outlining what makes a meeting 'electric' (01: 01:53) - Sharing experiences with exemplary leadership (01:05:02) - Strategies for maximizing team potential (01:07:37) - Deciding the right time to step away from a business (01:08:58) - Unveiling unexpected challenges in entrepreneurship (01:18:45) - Philosophies for leading a fulfilling life (01:21:04) - Finishing How To Make A Few Billion Dollars (01:22:53) - The kindest thing anyone has ever done for Brad

My guests this week are Elizabeth Zalman and Jerry Neumann. Jerry has been on this show two times before. He’s an early-stage Venture Capitalist, an adjunct professor of entrepreneurship, and an excellent writer. Liz is a two-time founder, most recently co-founding StrongDM, in which Jerry was a seed investor. Together, they have written a somewhat contentious book called "Founder vs Investor" that lays bare the relationship at the core of most new businesses. They take specific moments in a start-up’s life up to IPO and share their experiences on the friction that inevitably appears. In our conversation, we discuss the strong reaction to the book, the incentive problem at the root of the relationship, and explore best practices for other founders and VCs to follow. Please enjoy my conversation with Jerry Neumann and Liz Zalman. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes: (00:04:02) - (first question) - The controversy surrounding Founder vs Investor: The Honest Truth About Venture Capital from Startup to IPO (00:07:53) - Considering the idea of firing founders (00:10:44) - Navigating morally grey areas for founders and investors (00:11:57) - Understanding the role of the board and their power (00:15:05) - A PSA for founders (00:17:48) - Identifying where incentives are most broken (00:22:28) - Viewing founder friendliness as a temporary status (00:25:41) - Offering good advice during the fundraising process (00:32:41) - Ensuring delivery on promises as an investor (00:37:04) - Strategies for a long-term relationship between a founder and investor (00:41:44) - Structuring the ideal board meeting tactically (00:48:13) - Determining which investing terms matter most (00:51:18) - Managing the dynamic between a founder and an investor during company growth (00:56:44) - Establishing a sustainable, differentiated position (00:59:08) - Defining the distinction between a founder and an investor (01:00:18) - Reflecting on lessons from exiting a business (01:03:52) - Exploring the VC-to-VC relationship (01:08:01) - Plans following their book release (01:11:34) - The kindest thing anyone has ever done for Elizabeth

My guest today is Palmer Luckey. Palmer is the founder of Defense company Anduril Industries, which makes next-generation military technology for the US and its allies. Since bringing the company to life in 2017, Palmer and Anduril have disrupted the established order in the Defense industry. Prior to Anduril, Palmer founded Oculus VR, a virtual reality business that he sold to Facebook for $2 billion. Palmer is only in his early 30s, but he has already experienced more than most people will in a 40-year career. We talk about innovation, invention, differentiated thinking, and so much more. Please enjoy this great discussion with Palmer Luckey. Listen to Patrick's Business Breakdown with Anduril CEO. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully diluted shares outstanding? Access every publicly-reported data point and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard-to-calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building, and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes: (00:03:28) - The importance of synthetic long-chain hydrocarbon fuel (00:09:37) - Ranking America's potential for innovation (00:12:43) - Why there aren't more Thiel Fellowships (00:14:56) - The principles that motivate and drive him (00:18:21) - What it has been like working in the world of defense after the attack on Israel (00:20:34) - Surprising lessons learned when building a large company (00:24:02) - How to approach a new field initially (00:28:45) - Meeting other out-of-the-box thinkers (00:33:11) - Inventors working backward from existing systems versus forward from their ideals (00:34:51) - The most pressing issue in national security (00:41:01) - What matters most for America from a defense perspective (00:43:58) - How to determine which problems to prioritize (00:50:24) - Lessons learned from working with AI (00:57:21) - How Apple is shaping the future of VR (01:01:36) - Which videogame a prospective employee should excel at (01:04:06) - Why Oculus was so successful in marketing (01:11:13) - The kindest thing anyone has ever done for Palmer

Today’s guest is Aswath Damodaran, who is joining us for a second time on Invest Like the Best. Aswath is a Professor of Finance at NYU’s Stern School of Business and is often referred to as the Dean of Valuation for his clarity of thought on the subject. This conversation picks up where we left off 18 months ago and covers a wide range of topics from macro risks to Nvidia and the process of crafting a personal investment philosophy. Please enjoy this great discussion with Aswath Damodaran. Listen to Founders Podcast Episode #311 James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus Converge — the first virtual event centered on the world of investor research. When twin brothers Tom and Mike Elnick realized that the research process for investors was broken, they founded Tegus to fix it. Now the people behind the most trusted research platform are bringing institutional investors together to investigate the state — and the future — of fundamental research. On November 8th, join industry luminaries like IGSB Founder Reece Duca and Daniel Gross, AI Expert, Entrepreneur and Investor, to dig into the latest research trends and breakthrough technologies shaping the investment landscape. Register today at tegus.com/register. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:45) - (First question) - The general prevailing narrative in markets today (00:05:00) - The biggest business implications given the current market landscape (00:06:45) - Why it’s bad to have risky founders with cheap capital trying experiments (00:08:53) - The natural rate of interest and how it’s priced (00:09:55) - His updated view and thoughts on what’s currently driving inflation (00:11:05) - What it’s felt like valuing companies given rates being where they are (00:13:35) - Macro variables that most have his attention today (00:18:45) - Whether or not international equities will become a place of interest (00:21:53) - The unique absolute basis of NVIDIA’s growth (00:23:25) - His take on the new wave of AI in a broad sense (00:29:15) - Trying to value AI companies without tangible business models (00:32:45) - The parts of his own valuation process that are beyond automation (00:34:20) - Thoughts on a natural end state equilibrium for active management (00:35:55) - Commonalities between investors who beat the benchmark (00:38:35) - Episodes on his own path that lead him towards his investment philosophy (00:42:05) - How he goes about valuing non-traditional companies like sports franchises (00:46:45) - The world of entertainment and how he sees it as a business today (00:53:45) - The best business models he’s ever seen (00:55:40) - What valuing Instacart taught him about online grocery shopping (00:58:55) - The most interesting company he valued over the last year (01:03:25) - How bank failures changed his thinking on our financial systems and banks as businesses writ large (01:06:15) - The changing attitude towards ESG investing (01:11:11) - Why there are still so many pools of capital that pursue an active strategy (01:11:06) - Being sick and tired of the conversation always revolving around central banks (01:15:53) - What he’s most excited to look into over the coming year (01:17:53) - Major differences between a financial and an accounting balance sheet

My guests this week are the co-founders of Stripe, Patrick and John Collison. My conversation with John in 2020 is still one of our most popular. A key theme that emerged from that first discussion was John’s boundless curiosity for all things business and this conversation continues that thread. We talk about setting a strategy and culture that attracts ambition, why the returns to sweating the details are high, and how they view Stripe’s progress against their mission to increase the GDP of the internet. Please enjoy this great and wide-ranging discussion with John and Patrick Collison. Buy a ticket to Patrick and David Senra's live show this Thursday in NYC. Listen to Founders Podcast Founders Episode 311: James Cameron Subscribe to Colossus's New Show: Art of Investing For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:16) - (First question) - Stripe's curiosity-driven growth fuels enduring success and expansion (00:08:34) - Why companies should resonate with founders' ideas but also have strong enduring cultures (00:012:27) - Stripe aims to reduce friction and expand global commerce by solving practical barriers (00:25:59) - Simplifying processes for startups and large companies to drive growth efficiently (00:29:11) - Analyzing the enduring stories of ancient companies (00:35:44) - Success in Hollywood and academia depends on unmeasurable vision and knowledge (00:40:11) - Stripe's ubiquity, self-serve nature, and collective care drive its unique status (00:43:16) - Success in tech is grounded in user-centricity, care, and connecting with customers (00:48:17) - Parental influence on becoming entrepreneurs is complex (00:50:21) - Adult perspective on parents, admiration for their work, and ongoing philanthropy (00:52:30) - Stripe's challenges include complexity due to diverse payment methods and global programmable accessibility (00:57:27) - Aiming for long-term durability, Stripe prioritizes beauty and craftsmanship in its pursuit (01:02:50) - The most memorable conversation they had between them (01:05:30) - Why the launch of Atlas was a defining moment in Stripe’s history (01:06:35) - How their 25-year-old selves would react to what they are doing now (01:10:19) - The various ways in which they feel proud of each other (01:14:35) - The kindest thing anyone has ever done for them

My guest this week is Strauss Zelnick, the CEO of leading game publisher Take-Two Interactive. Maybe most well-known for its hugely successful Grand Theft Auto game, Take-Two is a sophisticated, top-tier developer, publisher, and marketer of interactive entertainment that owns Rockstar Games and 2K. Strauss’s passion for entertainment led him strong and fast into the industry as he worked his way from sales to CEO and transitioned from motion picture to gaming. Today we cover his approach to staying on the cutting edge of media development, unlocking talent and potential in those around you, and becoming the leader you were meant to be. His intensity and his standard for excellence come through clearly. Please enjoy my conversation with Strauss Zelnick. Subscribe to Colossus's New Show: Art of Investing Buy a ticket to Patrick and David Senra's live show. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus Converge — the first virtual event centered on the world of investor research. When twin brothers Tom and Mike Elnick realized that the research process for investors was broken, they founded Tegus to fix it. Now the people behind the most trusted research platform are bringing institutional investors together to investigate the state — and the future — of fundamental research. On November 8th, join industry luminaries like IGSB Founder Reece Duca and Daniel Gross, AI Expert, Entrepreneur and Investor, to dig into the latest research trends and breakthrough technologies shaping the investment landscape. Register today at tegus.com/register. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:39) - (First question) - Why the entertainment media sector is so interesting (00:05:08) - Key inflection points in the history of media (00:09:17) - The role of pure content in businesses today (00:10:32) - Requirements for being a successful media business operator (00:12:03) - Strategies for working effectively with creatives (00:16:13) - How to cultivate a conducive environment for creatives (00:25:54) - The allure of collaborating with Take-Two (00:30:09) - Strauss’ journey to becoming the chairman and CEO of Take-Two (00:37:42) - Strategies for reducing costs in business (00:41:16) - Embracing diversity in the video game industry (00:43:41) - Identifying high-quality intellectual property (IP) (00:46:04) - The inspiration behind Strauss’ book Becoming Ageless: The Four Secrets To Looking and Feeling Younger Than Ever (00:51:12) - Influential leaders for learning and growth (00:55:45) - The impact of technology and the rise of new platforms (00:57:00) - Common misconceptions about Take-Two (00:59:42) - Unique attributes of Take-Two projects (01:00:36) - Defining moments in the history of the business (01:04:19) - Anticipating the future direction of Take-Two (01:13:41) - Sources of motivation and inspiration (01:15:29) - The concept and value of a masterpiece (01:11:08) - Paramount values as a parent (01:11:38) - The kindest thing anyone has ever done for Strauss

My guests this week are Rick Buhrman and Paul Buser. Rick and Paul spent over a decade managing the public equity portfolio at Notre Dame’s Endowment before leaving in 2020 to set up a permanent capital vehicle called Sator Grove. As you’ll hear in this conversation, they know, have studied, or have invested with most of the world’s best capital allocators. A few years ago, they also set up a class at Notre Dame for 40 of the college’s brightest students, called Art of Investing. The class is devoted to exploring the joys of compounding and each week, they bring in a world class investor or operator to share in detail how they’ve built their lives, portfolios, and businesses around the principles of compounding. Starting next week, it will be available as a Colossus Podcast so that you too will be able to join their class and learn from the likes of Todd Combs, Andre Perold, Ho Nam and others. I’d encourage you to search Art of Investing in your podcast player and subscribe so you don’t miss the first episode. Now onto my discussion with Rick and Paul. Art of Investing: Trailer For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:30) - (First question) - Shifting from Notre Dame to Sator Grove (00:06:20) - An overview of Sator Grove (00:11:39) - Launching in April 2021, they manage $300M for diverse, flexible investments (00:15:47) - Investing in meaningful projects with trust, long-term focus, and high potential (00:25:30) - How Mitch Rales embodies insatiable curiosity and lifelong learning (00:39:33) - Embracing change, adapting, and experimenting for success (00:41:49) - How investors learn from failed companies (00:51:59) - Investment success hinges on talent's judgment, character, adaptability, and trust (00:56:53) - What they found concerning in firms and teams when assessing managers (01:02:16) - Analyzing asset allocation challenges (01:07:39) - Fostering disciplined habits for growth (01:13:06) - The importance of nurturing compounding (01:21:21) - Creating meaningful connections and providing lifelong lessons (01:26:58) - Wisdom from their mentors and its impact on their investing philosophy (01:43:49) - Defining the good life: Quality projects, quality people, and meaningful integration (01:45:29) - The defining moments of their investing careers so far (01:47:59) - The kindest thing anyone has ever done for Rick and Paul

My guests today are Jack Altman and Miles Grimshaw. Jack is the co-founder and CEO of Lattice, an HR software platform. Miles is a General Partner at Benchmark, an early investor and Board Director at Lattice, as well as a former guest on Invest Like the Best. Jack started Lattice in 2015 and has scaled it into a multi-billion-dollar business that already serves over 5,000 organizations. In our discussion, we look at all aspects of building and scaling a software product from both an investor and operator’s perspective, which made this particularly fun to do. Please enjoy my conversation with Jack Altman and Miles Grimshaw. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:55) - (First question) - How Jack & Miles met at Y Combinator in 2015 (00:04:22) - Lattice found a niche in mid-market HR software (00:07:55) - Discovering Lattice's true market need (00:11:14) - Fear of stalling drove the need for business growth beyond initial product (00:12:06) - Deciding on multi-product focus over up-market expansion (00:17:01) - Prioritizing quality of usage over frequency for customer health scores (00:20:06) - Balancing customer health scores and actual needs (00:24:31) - Prioritized community by spotlighting HR voices (00:28:20) - Building community helps companies sell a vision or lifestyle (00:31:05) - Cultivating broad awareness instead of hard-selling (00:35:33) - Overcoming the culture of 'perfection’ (00:37:22) - Flywheel effect makes suites efficient: lower go-to-market costs, more focus on product (00:41:06) - The challenges of juggling current needs and future demands (00:46:27) - Navigating disagreements and trust-building within a company (00:50:36) - Investors' roles extend beyond founders, focusing on their own goals and interests (00:51:52) - How transparency eases the founder-investor dance (00:55:16) - The changing employer-employee relationship (00:58:37) - Navigating growth from startup to public equity (01:05:43) - Lattice's ultimate aspiration (01:07:42) - Evaluating founders' authenticity (01:11:18) - What Jack & Miles are most embarrassed about, the most proud of, and the most excited for (01:14:30) - The kindest thing anyone has ever done for Jack and Miles

My guest today is Michael Simanovsky. Mike is the Managing Partner of Conversant Capital, a real estate investment firm he founded in early 2020. Conversant aims to be the most flexible capital provider in real estate, investing across public and private markets as well as equities and credit. The firm will also incubate platforms where they see an opportunity to take advantage of a compelling theme that lacks existing business models for investment. We cover the most undersupplied part of the market, why he’s building Conversant to be so flexible, and the surprising appeal of billboards. Please enjoy my conversation with Mike Simanovsky. Listen to Founders Podcast Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:32) (First question) - Real estate investing through the lens of the capital cycle (00:06:50) - The capital cycle in practice (00:12:07) - Using evaluation of supply to determine where you are in a capital cycle (00:13:16) - Why real estate drew Mike in (00:15:35) - The quality of investors in real estate (00:16:41) - What the US market needs most (00:20:26) - The range of returns in real estate (00:23:01) - Insights that stand out (00:26:45) - Starting a new company vs. building a portfolio of assets (00:28:46) - Key trade-offs and choices when building a firm (00:31:10) - Where things go wrong (00:33:59) - Best investment decision he ever made (00:38:06) - Philosophy on CapEx (00:39:52) - Misconceptions about real estate investing (00:41:31) - Cold storage real estate (00:43:13) - The most interesting corners of the real estate market (00:46:13) - AI and its impact on the future (00:48:30) - Common investor missteps (00:50:51) - Three guests Mike would invite to a dinner party (00:52:34) - The most impactful questions to ask a real estate investor (00:53:17) - A defining moment of his career (00:53:17) - The premise of the platform approach (00:56:20) - Possible opportunities and an understanding of the current landscape (01:03:38) - Lessons Mike learned from basketball coach John Wooden’s philosophies (01:04:30) - The kindest thing anyone has ever done for him

My guest today is David Senra, the creator and host of Founders Podcast. With an incredible appetite for biographies, David has delved into the lives of over three hundred entrepreneurs, extracting invaluable wisdom that he shares with his audience each week. Throughout the conversation, we discuss David’s love of podcasts, and what can be gained from studying the lives of not just entrepreneurs, but of athletes and film directors alike. I hope you enjoy this conversation with David Senra. Listen to Founders Podcast Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. Our first interview with David, Episode 292: Passion & Pain For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:43) - (First question) - David's journey so far (00:05:13) - Why there are no negative surprises linked to his work (00:07:13) - Being bullish on podcasts (00:13:27) - The importance of storytelling to the entrepreneurial journey (00:17:43) - The impulse of entrepreneurs who are world-builders (00:23:03) - The universal trait of successful entrepreneurs (00:27:43) - What David has learned from filmmakers (00:31:23) - The dark side of the Type-A personality (00:35:13) - What he has learned from athletes (00:42:27) - The effects of early childhood on success (00:43:48) - Insights gained from conquerors (00:49:33) - Ranking the importance he places on power, wealth, and fame (00:56:13) - The possibility of episodes on spiritual figures (01:02:17) - How Henry Ford created something bigger than himself (01:05:43) - His thoughts on ‘high agency’ people (01:11:57) - Why David is not afraid to talk about anything publicly (01:16:27) - His favorite line from Game of Thrones

My guest today is Will England, the CEO and Co-CIO of Walleye Capital. Walleye is a multi-strategy hedge fund headquartered in Minnesota that manages around $5 billion. Our conversation is a primer on multi-strategy hedge funds, which have become a force in markets through the success of firms like Millenium, Citadel, Point72, and Balyasny. We discuss the operational complexity behind the model, which managers best fit this type of investment style, and what happens in stress events like the Gamestop short squeeze in early 2021. We also talk about performance culture, the All Blacks, and Will’s experience as a US National Team rower. Please enjoy my conversation with Will England. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:22) - (First question) - His fascination with Robber Barons (00:04:49) - He explains the style of investing he has built at Walleye Capital (00:08:51) - The importance of scale and what it means for firms like this (00:13:01) - A breakdown of the component parts of a 15% return structure (00:16:56) - His advice to new portfolio managers trying to succeed with long/short investments (00:21:23) - His reaction to an efficient market hypothesis (00:27:33) - He tells us what happens above the individual manager level (00:29:42) - The universe of talented people behind the business (00:35:26) - The backstory of Walleye Capital and why he chose Minnesota (00:42:37) - He discusses the felt experience of being at Walleye versus other firms (00:47:25) - Whether he identifies more as an entrepreneur systems builder or as an investor (00:50:04) - What he says about the half life of successful quantitative strategies (00:54:03) - A breakdown of style allocations and the percentage of managers within each (00:56:30) - How he determines how much leverage to use and how to be great at applying it (00:59:59) - How the firm handles tough investment periods (01:02:34) - How he knew Citadel wasn’t taking down gross during the GameStop short (01:03:51) - What he looks for when hiring a portfolio manager (01:06:37) - His philosophy on performance and how he blends that into his firms culture (01:09:21) - Inspiration he’s taken from the All Blacks team (01:11:25) - Addition aspects of the firm he believes are important (01:13:46) - Historical finance pioneers that inspire him (01:16:07) - The kindest thing anyone has ever done for him

Almost exactly a year ago, Colossus entered into a partnership with David Senra and the Founders podcast to join the Colossus network. The show has since exploded with more devoted fans than any podcast that I've encountered. With that in mind, we are excited to share an example episode from his show here today on the director, James Cameron. It's my favorite recent episode of David's. Please enjoy this episode, and if you haven't already, subscribe to Founders. This is what he learned from reading The Futurist: The Life and Films of James Cameron by Rebecca Keegan and The Return of James Cameron, Box Office King by Zach Baron. Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:04:00) - I watched Titanic at the Titanic. And he actually replied: Yeah, but I madeTitanic at the Titanic. (00:07:10) - I like difficult. I’m attracted by difficult. Difficult is a fucking magnet for me. I go straight to difficult. And I think it probably goes back to this idea that there are lots of smart, really gifted, really talented filmmakers out there that just can’t do the difficult stuff. So that gives me a tactical edge to do something nobody else has ever seen, because the really gifted people don’t fucking want to do it. (00:07:20) - At 68 years old, Cameron wakes up at 4:45 AM and often kick boxes in the morning. (00:07:45) - Self-doubt is not something Cameron has a lot of experience with. His confidence preceded his achievements. (00:09:00) - I basically gave myself a college education in visual effects and cinematography while I was driving a truck. (00:16:00) - Every idea is a work in progress. (00:17:30) - He's been on a planet of his own making ever since. (00:18:00) - The Return of James Cameron, Box Office King by Zach Baron (00:22:00) - His outlook is that we can take fate in our own hands. (00:34:00) - Cameron had only been at Corman's for a matter of days, but he was already taking charge. He seems constitutionally incapable of doing otherwise. (What a line!) (00:35:30) - Your mediocrity is my opportunity. (00:37:40) - Cameron finds writing torture. He does it anyway. (00:43:00) - Cameron is willing to let ideas marinate for decades. (00:55:30) - I'd just made T2 for Carolco and I admired how they rolled, being their own bosses, mavericks, entrepreneurs. (00:57:30) - Mute the world. Build your own world. (01:04:50) - Opportunity is a strange beast. It commonly appears after a loss. Buy a book: All the books featured on Founders Podcast.

My guest today is Lee Ainslie, the founder of Maverick Capital. Lee started his investing career at Tiger Management where he worked for Julian Robertson. In 1993, he left to start Maverick and has built the firm into one of the top-performing hedge funds of the last 30 years. Lee doesn’t speak in public often so this is a fascinating insight into what it takes to build an enduring investment business - both psychologically and operationally. Throughout the conversation, we flick between his lessons building Maverick, his perspective on the market, and what he’s learned about the craft of investing. I hope you enjoy this great conversation with Lee Ainslie. Listen to Founders Podcast Founders Episode 311: James Cameron Join Colossus live in NYC with Patrick O’Shaughnessy and David Senra on Oct. 19. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:00) - (First question) - Lee tells us about his relationship with Steve Mandel (00:04:29) - Why he thinks Steve gave him a hand into the role he excelled at (00:07:22) - The concept behind investment talent (00:13:08) - Steps he takes to hire the right individuals for his team (00:16:14) - Why he stepped out on his own to start Maverick Capital (00:20:48) - What he thinks makes for a great investment or stock purchase (00:25:16) - How Maverick maintains its edge over other comparable firms (00:28:31) - Features of a business that get his attention in a unique way (00:32:03) - What he learned from Sol Price (00:38:21) - The difficult aspects of portfolio construction (00:42:04) - How zero interest rates affected the long short style of investing (00:47:22) - Positioning his team for success against other competitors (00:50:32) - How private market activity can affect public market activity (00:54:27) - Software companies and their strengths and weaknesses in the investment market (00:59:33) - Things he tells his team to watch for (01:04:10) - What Lee's learned about money (01:07:02) - The most important conversation he’s had in Mavericks history (01:12:38) - Advice for senior executives trying to pass on responsibilities to others (01:17:54) - What the next ten years for Maverick Capital look like (01:20:42) - Things Lee and Warren Buffett disagree on (01:24:11) - The components of a great investment pitch (01:25:08) - The hardest question anyone could ask him (01:28:48) - What he thinks is important having started Maverick Ventures (01:31:32) - The kindest thing anyone has ever done for Lee

Today, we are running a special episode from our show Founder's Field Guide. In this conversation, Nick Kokonas shares his experience of bringing a business mindset to the restaurant industry. It is one of our favorites at Colossus and there is something for everyone in this timeless conversation. Nick is the co-founder of 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. He majored in philosophy before becoming a derivatives trader and is now one of the most well-known names in the hospitality industry. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (3:02) – (First question) – Why he thinks it’s so important to own something (4:35) – Make decisions that have outcomes (7:00) – His interest in the restaurant business (8:54) – Why restaurants are so tough (12:05) – How their business mindset changed their running of the restaurant (14:35) – Words they would avoid in the restaurant (16:19) – Asking the right questions in the restaurant business (20:40) – Importance in taking the right risks (22:02) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing (30:08) – Can dynamic pricing be extended to other businesses (31:20) – Origin of Tock (36:17) – Early days of Tock and identifying the right customers/challenges (41:33) – Importance of the first customer (44:22) – The typical restaurant business model (49:23) – Lessons from Tock and the importance of knowing what your selling (53:47) – Lessons from publishing (55:44) – Other aspects of business that people know but do nothing about (1:00:19) – Their response to Covid and lessons learned (1:07:43) – The real impact to the food delivery companies (1:09:24) – How businesses communicate their end processes to their customers (1:14:07) – Kindest thing anyone has done for him

My guest today is Des Traynor. Des is the co-founder and Chief Strategy Officer of Intercom - a customer service solution that helps businesses answer product questions, offer instant support, and automate sales. The business was founded in 2011 and its products operate within 25,000 businesses, including the likes of Amazon, Lyft and Atlassian. Our conversation is roughly split in half. First, we talk about AI and how it’s actually changing businesses like Intercom through products such as their OpenAI powered bot called Fin. We then talk about Des’s views as an investor, which includes an answer about software that I’ll remember for a long time. Please enjoy my conversation with Des Traynor. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 drivable global models hand-built by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:42) - (First question) - Des's high level thoughts on Open AI and new technology (00:07:07) - Advanced AI tech for existing businesses versus start-ups ventures (00:11:14) - Where Intercom falls on the spectrum of existing and new AI technology (00:13:16) - Training AI to be tailored to specific fields of work (00:18:25) - The natural end point is for Intercom incorporating AI (00:22:25) - Des's product philosophy behind this technology (00:24:03) - Choosing an AI provider that best suited his customer service industry needs (00:26:55) - The value comparison between using AI-led customer service versus human (00:29:18) - Why outsourcing automated data is not for everyone (00:31:15) - Des's advice for other companies beginning to integrate AI into their operations (00:36:33) - What he is excited for as an investor in this area (00:37:50) - The most common discussions he’s having about this technology (00:41:21) - The inherent risks of using AI models that are not 100% accurate (00:45:10) - Des's evolution as an investor (00:48:25) - How Intercom solved it’s AI execution problems (00:50:46) - Combating other companies that are trying to overtake the field (00:53:44) - Counter arguments for using AI technology (00:57:22) - His view on the best software out there (01:03:00) - The kindest thing anyone has ever done for him

My guest today is Samo Burja. Samo is the founder of consulting firm, Bismark Analysis, and has dedicated his life’s work to understanding why there has never been an immortal society. His research focuses on institutions, the founders behind them, how they rise and why they always fall in the end. As you’ll hear, Samo has an encyclopedic grasp of history and his work has led him to some fascinating theories about human progress, the nature of exceptional founders, and the future of different societies across the world. Please enjoy my conversation with Samo Burja. Listen to Founders Podcast Founders Episode 311: James Cameron For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:52) - (First question) - The core thesis behind the Great Founder Theory (00:06:40) - Great ideas inevitably being discovered at some point in history (00:08:45) - The historic implications of a global adoption of the Great Founder Theory (00:10:51) - The different possible directions of future trends (00:17:08) - Distinctions between great founders versus live players (00:22:15) - Common misconceptions about what qualifies one as a great founder (00:24:38) - Noteworthy great founders in the United States (00:28:34) - Recurring observable traits and common themes of great founders (00:31:29) - Using caution when projecting a mythic lens onto great founders (00:37:53) - Social technology as the upstream effects of prior material technology (00:43:32) - Whether or not institutions play a role in propagating the work of great founders (00:49:08) - The role of power and differences between owned and borrowed power (00:56:51) - Additional ideas that play an outsized role in shaping the world (01:01:09) - A differing worldview to his own that he finds interesting (01:04:53) - Whether or not capital allocators can benefit from the Great Founder Theory (01:07:37) - The kindest thing anyone has ever done for him

My guest today is Chris Paik, who is a General Partner at early-stage venture firm, Pace Capital. Before Pace, Chris spent eight years building and investing alongside last week’s guest, Josh Kushner, at his firm Thrive Capital. During that time, he sat on the board of Twitch. Our conversation explores Chris’ frameworks for investing, from atomic value swaps to business model product fit and the seven deadly sins. We also discuss different consumer trends like the rise of virtual YouTubers, Apple’s Vision Pro, and why everyone graduates off YouTube. Please enjoy my conversation with Chris Paik. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:00) - (First question) - The history of humanity as a data storage and transfer problem and how that relates to new kinds of computer interfaces (00:14:47) - Investing strategies; knowing when to invest in new technology (00:16:39) - Assessing the gray areas of a potential investment (00:22:13) - CodeMiko and VTubing (00:32:51) - An explanation of atomic value swap (00:39:55) - The 7 deadly sins and the degrees to which each sin is monetizable (00:45:05) - Evaluating the people behind new technologies (00:50:03) - The Reddit Revolt - the current changes happening at Reddit (00:53:09) - Business model alignment; the steps to take when determining a business’ value capture mechanism (01:03:52) - The investment decision that Chris is most proud of (01:08:14) - The consumer investing landscape today (01:11:19) - Chris’ methods for finding new content, technology and potential investments on the internet (01:14:06) - The fundamentals of value creation (01:15:06) - The dark side of tech, how can it be more than just friction reduction (01:17:22) - Chris’ opinion on why so many innovations come from the US (01:20:37) - Defining market places and how to start and grow a successful one (01:23:23) - Chris’ thoughts on opportunities with bad business models (01:26:19) - A breakdown of Chris’ analogy “Sculptors versus painters” (01:29:34) - The kindest thing that anyone has ever done for Chris

My guest today is Josh Kushner, founder and managing partner of venture firm, Thrive Capital. Josh started Thrive in 2010 and launched its first institutional fund in 2011. That first institutional fund was $40 million and, in it, Thrive led Warby Parker’s Series A, invested in Instagram, and incubated a business, which Josh co-founded, called Oscar. Thrive has gone from strength to strength since then and now manages $15 billion with a small team of 9 investors. Their portfolio is stage agnostic and their track record includes many of the best known businesses from the past decade, including Spotify, Unity, Stripe, and Twitch among many more. Josh rarely speaks in public about the firm and their philosophy so it was a blast to do this with him. Please enjoy my great conversation with Josh Kushner. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:14) - (First question) - Why do this podcast (00:06:14) - The development of taste and quality (00:10:20) - CS Lewis tweet; The Inner Ring (00:11:53) - Founders being heroes and motivating quietly from the background (00:16:14) - Overview the founding story of Oscar Health (00:21:30) - Is a big business different from a small one (00:23:18) - Learning to identify good problems and creating a business to solve it (00:25:43) - The birth story of Thrive Capital (00:30:14) - Lessons learned from creating the first three Thrive funds (00:33:35) - Industry wide competition today and models for building a firm in general (00:37:44) - Talent, recruiting and seeing potential in younger generations of people (00:45:40) - Investments he made during the early foundation of Thrive that had significant impact (00:49:12) - His analogy for investing in early versus late stage (00:54:22) - The current macro environment (00:57:52) - Giving AI companies computing power instead of money (00:58:57) - Why he sold small stakes of Thrive (01:03:10) - His philosophy on what makes a good product (01:05:20) - What he thinks about the models like Mobile and Cloud (01:08:10) - His absence from crypto and why he refrained during the boom in 2021 (01:10:33) - Thoughts about the opportunity set in FinTech today writ large (01:12:04) - Other potential opportunity sets beyond what’s already been discussed (01:13:39) - Lessons learned from his time spent with Marc Andreessen, Stan Druckenmiller, Henry Kravis, and David Geffen (01:21:59) - Balancing magnitudes of capital between investment funds (01:23:32) - Why founders choose Thrive (01:29:15) - Vision as a key ingredient for founders (01:32:19) - His view of the investment industry in the world today writ large (01:40:19) - Other investment firms he would invest in (01:42:48) - The kindest thing anyone has ever done for him

My guest today is Jeremy Giffon. I spend all my time trying to find people who have some “singularity” to them. People who seem like they can do an N of 1 something. Having spent many days with Jeremy recently, he strikes me as one of those people. He was the first employee and general partner at private equity firm, Tiny, which buys and holds internet and technology focused businesses. Prior to that, he was on the founding team of MediaCore, which was acquired by Workday. The focus of our discussion is about esoteric opportunities that exist in private markets. How misaligned incentives and co-ordination problems create special situations for people like Jeremy to invest in. The rest of the conversation is wide-ranging and covers everything from compensation advice to meeting your heroes. Please enjoy my discussion with Jeremy Giffon. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 60,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:15) - (First question) - What defines the nature of a perfect business in his mind (00:05:21) - Key characteristics he’d look for in a perfect investment (00:09:58) - Coordination problems that excite him (00:14:02) - Raising funds and ghostship companies (00:16:17) - Examples of a special situations transaction in private markets (00:18:55) - Building up a sourcing mechanism (00:22:18) - The biggest mistakes he’s seen in buying and selling companies (00:25:42) - Refining the underwriting process (00:28:57) - Thoughts about minimum rates of return and multiples on capital for the investments he makes (00:30:44) - Being lazy enough to wait for good deals on enduring businesses (00:33:32) - Why people do things they don’t like (00:35:47) - Whether or not he feels like he knows what he wants in life (00:40:48) - Invest Like The Best - Kevin Kelly; The reward for good work is more work (00:42:58) - Hiring CEOs (00:44:54) - Really good respective returns in low risk companies and why those opportunities continue to persist (00:47:05) - Tactics for negotiating with and sourcing CEOs (00:50:37) - Binaries - pre and post fall (00:55:58) - Being hard to kill (00:59:15) - His favorite interview question (01:06:07) - Having an audience is incredibly underpriced (01:10:13) - What else is significantly underpriced (01:12:14) - Things he feels are overpriced today writ large (01:15:54) - Criticisms of the cult of learning (01:20:21) - The one call that everyone needs to make (01:27:18) - Meeting your heroes and having mentors (01:30:48) - Notable differences between the business environments of Canada and the US (01:33:13) - Lessons learned from people he admires and models for seeing the world (01:35:35) - Views he holds that would make people scratch their heads (01:40:02) - The kindest thing anyone has ever done for him

My guest today is Dave Yuan. Dave is the Founder and Partner of Tidemark Capital, which he started in 2021 after 15 years as a General Partner at Technology Crossover Ventures. Dave has been investing in vertical market software as long as anyone I know and he currently sits on the board of two VMS businesses, Toast and Karbon. He is the perfect guest to deliver a primer on VMS, which is exactly what we do in this episode. Please enjoy my conversation with Dave Yuan. The Vertical SaaS Knowledge Project - Tidemark Capital Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:57) - (First question) - Vertical Market Software (VMS) offers unique business models and customer benefits (00:04:02) - Industry-specific software serving SMBs with tailored functionality (00:06:53) - Assess market based on TAM, competition, and growth dynamics (00:10:00) - Trust as a nuanced factor in evaluating market opportunities (00:11:59) - Leverage account-based marketing and local network effects for VMS solutions (00:14:22) - Vertical solutions offer tailored value and quick results for specific industries (00:16:21) - Disrupting legacy control points through integration and surrounding functionality (00:19:07) - Building demand is crucial for small merchants (00:21:31) - VMS entrepreneurs need operational experience and multi-product mindset (00:23:13) - Investors need to adapt to the specific growth stage and market dynamics (00:25:22) - Gross retention is driven by control points, individual-based retention, and distribution (00:29:43) - Multi-product vertical SaaS: Integrated solutions for efficiency and value (00:32:33) - Diverse offerings to serve merchants' needs in a multi-product approach (00:34:07) - FareHarbor's unique strategy led to success in the tour industry (00:38:43) - LA-based company revolutionized commercial casting with a free software tool (00:40:03) - Opportunities remain in VMS, with greenfield areas and specific markets (00:45:12) - Key valuation considerations for VMS businesses (00:47:27) - Time horizon is crucial for investing in VMS businesses (00:48:04) - Businesses worth studying in this category (00:51:12) - The kindest thing anyone has ever done for him

My guest today is Kevin Kelly. Kevin co-founded Wired magazine and has published a number of seminal books and essays on technology over the past three decades. I have devoured everything Kevin has put out into the world and many of his ideas shape the way I live today. Our conversation explores media, family, money, his concept of the Technium, AI, and more but the central theme of this episode is that we should be as generous and unique as possible. You will hear us refer to his latest book, Excellent Advice for Living, throughout and I highly recommend reading it if you haven’t already. Please enjoy this great conversation with Kevin Kelly. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visitingtegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:05) - (First question) - Excellent Advice for Living - a journey towards authenticity (00:05:05) - Uncovering the essence of oneself is a lifelong journey of self-reflection (00:06:47) - What he would have done differently at 30 had he internalized this concept earlier (00:08:51) - The highest form of self-expression is being authentically unique and redefining success (00:11:05) - Conforming to others' definition of success and societal biases hinders progress (00:13:07) - Surrender and collaboration are both essential in becoming your authentic self (00:14:38) - Prototype your life to embrace imperfections and make ideas tangible (00:17:34) - Mastering cultural photography in Asia and developing a keen ability to spot trends (00:19:59) - Energy signatures reveal depth, breadth, discovery, and momentum in events (00:22:02) - The reward for good work is more work (00:23:42) - Money is a tool for doing things, but beware its imprisoning burden (00:28:35) - Imagination can be cultivated and improved, often by challenging expectations (00:31:38) - Imaginative individuals include lateral thinkers who challenge norms (00:34:41) - Rites of passage and rituals provide stability and identity for children (00:38:15) - Mealtime without screens, family traditions, and cultivating a family identity (00:41:44) - An overview of “The three gates” (00:43:02) - Humans are naturally kind (00:47:23) - The Technium: an evolving ecosystem of interdependent tech and their tendencies (00:52:01) - Thoughts on AI (00:55:55) - Overestimating the existential threat of AI (00:57:38) - Idiosyncratic expression of creators (00:59:48) - Lessons learned about media (01:01:34) - Be the only, not the best. (01:05:09) - The kindest thing anyone has ever done for him

My guest this week is Justin Mares. Justin is the founder of TrueMed and has previously founded three different health food brands that collectively do $100M+ in annual revenue. Every time I speak with him, he makes me reflect on my own health and the state of our health more broadly. This conversation is no different. As Justin puts it, we're in a health crisis that could ultimately bankrupt our country. We talk about the inputs, incentives, and potential solutions related to that crisis, and then move into his experiences building and investing in consumer brands. We finish with a fascinating discussion on why it's more common to see repeat founders these days. Please enjoy my great conversation with Justin Mares. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:06) - (First question) - Framing the overall problem of the US health system (00:04:12) - What it would take for America’s health crisis to affect global competitiveness (00:11:05) - Important changes that have contributed to the decline of health in the US (00:14:53) - Other system settings and incentives have contributed to America’s health crisis (00:16:51) - Thoughts on Ozempic and attempts to engineer solutions for chronic disease (00:20:07) - Mental health decline, infertility, and other problems tied to the health crisis (00:24:33) - When he first discovered this problem and became passionate about it (00:26:56) - The difficulties of building a health-centric bone broth company (00:31:49) - Why no one has a built supply chain sourcing service to create scale economies (00:34:44) - Other companies he’s built and other things he’s doing to fight the problem (00:40:15) - Going to market to simplify the HSA consumer experience (00:43:04) - The world of water, environmental toxins and forever chemicals writ large (00:47:17) - The difficulty in avoiding forever chemicals in our everyday lives (00:51:51) - How he searches for and decides on new businesses to start or invest in (00:56:52) - The growing popularity and promise of psychedelic therapy (00:58:48) - Personality traits of people who feel most at home in Edge City (01:01:36) - Strategies on sourcing and connecting with ambitious and talented people (01:06:56) - Childhood nutrition and the impact of their diets and health on society (01:11:26) - Capital formation and creating new businesses in a systematic way (01:19:57) - The kindest thing anyone has ever done for him

My guest this week is Scott Goodwin. Scott is the co-founder and managing partner of Diameter Capital Partners, which he started as a credit hedge fund in 2017 and has expanded into a $13 billion investment firm that covers all credit markets. Scott spent the first 8 years of his career at Citi where he rose to head of High Yield Trading before moving to Anchorage Capital in 2010 where he led their global trading desk. Scott is one of my favorite examples of the joke I used to make about this show, when I said it should be called - "This is who you're up against." He's one of the sharpest investors I know and I'm sure you'll see why. Please enjoy my great discussion with Scott Goodwin. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 35+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:07) - (First question) - Comparing the investing themes of the ‘10s to the ‘20s (00:04:59) - The skillset differences between investing in equity versus credit (00:06:28) - Why Carvana’s stock plummeted and thoughts on the destruction of value (00:07:33) - General overview of credit cycles and what they are (00:15:42) - Opportunities come from knowing the names well enough (00:19:17) - Making substantial decisions in a matter of minutes as a credit investor (00:22:23) - How he thinks about the evolution of sourcing alpha in credit markets (00:27:37) - Why so many institutional capital pools have fewer credit managers (00:31:08) - His childhood and the unique aspects of it that set him apart (00:37:28) - Lessons learned early on about running an investment firm (00:43:34) - The role imagination plays in credit investing (00:46:35) - How weekly breakfasts lead to an investing partnership (00:50:51) - What Tracy Fenton has done for Diameter (00:53:05) - Things that should change about investing firms writ large (00:57:09) - Calling balls and strikes and how his team learns and works together (00:59:37) - Why he’s motivated more by failure than success (01:00:54) - Where he finds the most joy in his investing process (01:04:07) - Non-negotiable attributes he’d look for when investing in other GPs (01:05:22) - New variables that have his attention in the current market (01:08:27) - What feels like unfinished business to him (01:09:43) - His reaction to everything going on today in real estate (01:10:52) - The kindest thing anyone has ever done for him

Today, we are running a special episode from our show Business Breakdowns. In this conversation, Ben Clymer does an incredible job breaking down what makes Rolex so special. If you enjoy this episode, follow Business Breakdowns for more discussions like this. Founded in the UK in 1905 under the name Wilsdorf & Davis, Rolex has become the leading name in luxury watches. But, while the company’s products are iconic, the business itself is highly secretive. Owned by a Foundation and run as a non-profit entity, little is known about Rolex. To unlock the secrets, we are joined by Ben Clymer, founder of HODINKEE, and an expert on all things luxury watches. Ben has had rare access to Rolex and the people behind the manufacturer, making him the perfect person to dissect this business with us. Please enjoy this excellent Breakdown of Rolex. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. —-- Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss Show Notes [00:03:01] - [First question] - His favorite Rolex watch ever [00:04:24] - What makes the Rolex Daytona such a special watch [00:07:19] - The job-to-be-done for high-end watches beyond just telling them the time [00:12:18] - The strategy behind marketing luxury products: The Luxury Strategy [00:14:34] - An overview of the Rolex business [00:19:38] - The history of Rolex [00:38:45] - Their genius in marketing and distribution [00:41:55] - How they make decisions and what others can learn from them [00:47:14] - The financials of Rolex and other luxury watch brands [00:49:02} - Most important business lessons others can learn from Rolex [00:52:54] - Other luxury brands worth studying [00:57:26] - Negative lessons gleaned from Rolex

My guest today is Kieran Goodwin. Kieran spent over two decades at the frontier of credit investing. During the global financial crisis, he was a Partner and Head of Trading at King Street Capital, which grew from $4 billion to $20 billion while he was there. He then left to start his own credit hedge fund, Panning Capital Management. In our discussion, we cover the state of private credit today, which forms of alpha he’s most skeptical of, and the blend of EQ and IQ necessary for success and investing. Please enjoy my conversation with Kieran Goodwin. Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 55,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:00) - (First question) - His view of the state of private credit in capital markets (00:06:56) - The notion of ball washing and why it’s important to understand (00:09:04) - What the worst-case domino effects of ball washing could be (00:12:21) - Arriving at a place where JP Morgan could borrow so much at the fund level (00:14:20) - Lessons learned from the worst trade he made (00:16:53) - What could happen in the world of private credit in the next few years and how the bigger players tend to benefit (00:19:29) - Thoughts on the world of venture capital right now (00:21:13) - The time he was at the peak of his power as an investor (00:24:03) - From being new at something to incredibly successful seemingly overnight (00:26:42) - What kinds of alpha he believes exists and which ones he’s skeptical about (00:29:30) - Thoughts on income share agreements (00:31:24) - Why there aren’t more initiatives for new talent to trade their student loans for future earnings (00:33:13) - The power of EQ over IQ and why it’s important for investor success (00:35:49) - Whether or not now is a good time to get into the field of capital markets (00:37:54) - Key tenants to know when learning credit investing specifically (00:40:09) - Things people misunderstand about the power of volatility (00:42:39) - Ways he managed to stretch his own imagination effectively (00:48:06) - The natural inclination to be short volatility (00:49:24) - Incorporating long volatility into his portfolio and life (00:52:20) - Thoughts on synergy in relationships (00:55:48) - Other interesting lessons learned from sports (00:57:50) - The roles of the multiple coaches that sit in for an NBA team (00:59:42) - The kindest thing anyone has ever done for him

My guest today is Henry Schuck, the founder and CEO of ZoomInfo. I’ve gotten to know Henry over the past year by virtue of him being on the board of Tegus, where I’m a board observer. I meet a lot of people and Henry is one of my favorites. His energy is unmatched and he knows his business down to the tiniest details. He has tenacity and curiosity in spades. ZoomInfo is a go-to-market software and data solution for B2B sales. Henry founded the business as DiscoverOrg in 2007 and bootstrapped it for the first 7 years of its life. Today, it’s an $8.5 billion public company with a database of over 140 million business contacts. We delve into the science of great sales, Henry shares some awesome stories, and we talk about his business philosophy more broadly. Please enjoy my great conversation with Henry Schuck. ZoomInfo Business Breakdown Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors, and provider of Canalyst. Tired of calculating fully-diluted shares outstanding? Access every publicly-reported datapoint and industry-specific KPI through their database of over 4,000 driveable global models handbuilt by a team of sector-focused analysts, 25+ industry comp sheets, and Excel add-ins that let you use their industry-leading data in your own spreadsheets. Tegus’ models automatically update each quarter, including hard to calculate KPIs like stock-based compensation and organic growth rates, empowering investors to bypass the friction of sourcing, building and updating models. Make efficiency your competitive advantage and take back your time today. As a listener, you can trial Canalyst by Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:19) - (First question) - The story of Henry’s famous email about building a championship team (00:07:01) - Dealing with pressure in business (00:09:14) - Applying pressure from the top down as a CEO (00:10:28) - How ZoomInfo’s C-suite was constructed and how it operates (00:13:17) - A high-level picture of their product philosophy (00:19:29) - Rating the effectiveness of the average B2B go-to-market engine (00:21:25) - An anecdote about meeting with the head of commercial banking at one of world’s largest banks (00:23:06) - What separates the good from the great B2B go-to-market strategies (00:27:30) - Specific questions for screening potential salespeople; characteristics to look for (00:31:39) - The story of bootstrapping his startup (00:36:05) - His view on the process of pricing (00:40:54) - The importance of M&A in building the business (00:47:01) - The story of how ZoomInfo was acquired (00:50:06) - The ever-shifting goal posts of mergers and acquisitions (00:53:15) - Anecdotes of hustling in the early days (00:59:34) - Another story from the early days of selling (01:03:40) - Using information to influence a potential lead into a sale (01:04:57) - How companies can prepare for the advent of generative AI (01:12:10) - The stages of what it means to be a CEO (01:13:15) - Learning how to execute M&A (01:16:43) - What it means for a company to work in unison at scale (01:18:26) - His advice on M&A, company core values, and corporate communication (01:26:57) - Tips for going public with a company (01:28:33) - Lessons learned from leading a public company (01:34:47) - The kindest thing anyone has ever done for him

Today’s conversation was recorded during last week’s Sohn Conference. I sat down with Karen Karniol-Tambour, Co-CIO at Bridgewater Associates. I hosted Karen on this show two years ago and if you listened to that, you’ll remember she has a rare skill for distilling and analysing complex macro topics. Today’s environment is strikingly different to the summer of 2021 so this is a timely conversation on the big macro variables that are on investors’ minds today. Please enjoy my conversation with Karen Karniol-Tambour. Sohn 2023 | Kiril Sokoloff in conversation with Stanley Druckenmiller Sohn 2023 | Patrick Collison in conversation Sam Altman Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:05) - (First question) - Her take on AI and watching this new technology unfold (00:06:39) - Things she’s watching in the AI space that might lead to taking portfolio action (00:09:19) - Potentially using AI to inform or make investment decisions (00:10:17) - Why might it be the case that no one can use AI for investing in macro markets (00:11:14) - What she’d write about regarding the general state of capital markets today (00:13:46) - What pricing is telling us about market sentiment writ large (00:15:47) - Thinking about portfolio positioning in light of the unattractive state of risk assets (00:17:17) - Her perspectives on gold historically and today (00:20:09) - Big long-term slow-moving macro variables that aren’t quite visible yet (00:22:09) - The all-weather portfolio and building one in light of so much uncertainty (00:24:38) - The rise of China, its growing power, and potential conflicts with the US (00:28:01) - Monitoring for things like the banking crisis beneath the public narrative (00:31:13) - Non-obvious variables that currently have her attention (00:33:29) - “Overrated or underrated” rapid-fire questions (00:36:04) - What it’s been like being the CIO of Bridgewater so far

My guest this week is Fidji Simo, the CEO of Instacart. Fidji grew up in a small town in the South of France and was the first person in her family to graduate from high school. Since then, she has had a dazzling career with stops at France’s leading university, eBay, and Facebook. Fidji spent the better part of a decade at Facebook where she led the Facebook App before joining the online grocery platform, Instacart, in mid 2021. We talk about Fidji’s consumer product experiences, Instacart’s role within the grocery ecosystem, and delve into her personal philosophy on leadership. Please enjoy this wide-ranging discussion with Fidji Simo. Apply for the Investigative Research Analyst position at Positive Sum. Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:51) - (First question) - Comparing her experiences with Facebook and Instacart (00:06:22) - The dimensionality of creating great consumer products online (00:07:50) - How Instacart uses AI now and her advice to other companies who are ready to incorporate AI into their business (00:15:41) - What being a pragmatic technologist means to her (00:18:02) - Influences in younger years that led to her career path in technology (00:21:00) - The landscape Instacart seeks to build and how major key players within the industry are involved (00:27:09) - Data algorithms and their role in helping consumers (00:29:24) - Scale around the original core business (00:32:12) - The functional difference between Instacart shoppers and delivery drivers (00:34:59) - Issues with fully automated grocery store facilities (00:37:32) - Insight into working with brands and consumer brand loyalty (00:43:16) - Her vision for the future of Instacart (00:49:34) - Her principles for capital allocation (00:52:34) - Common misperceptions about Instacart from prospective investors (00:54:21) - Her philosophy of seeing the magic in team members (00:56:46) - Expanding knowledge while managing a complex business environment (01:01:01) - When she felt the most helpless in her career (01:03:46) - Insight into generative AI and how it could shape the online grocery experience (01:08:00) - The role of content and its importance for businesses like Instacart (01:12:35) - The kindest thing anyone has ever done for her

My guests this week are Jeremy Levine, Kent Bennett, and Brian Feinstein. They are partners at one of the oldest and most storied venture firms in the world, Bessemer Venture Partners. Our conversation is split into two parts. First, we explore Bessemer itself. It’s over 100 years old and has a unique operating model with lessons for every investment firm in the market. We then discuss Jeremy, Kent, and Brian’s investing styles and outlook. What they look for in businesses, their thoughts on various sectors like vertical market software, and we close with a discussion about AI and defensibility. Please enjoy this great conversation. Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Tired of running your own expert calls to get up to speed on a company? Tegus lets you ramp faster and find answers to critical questions more efficiently than any alternative method. The gold standard for research, the Tegus platform delivers unmatched access to timely, qualitative insights through the largest and most differentiated expert call transcript database. With over 55,000 transcripts spanning 22,000 public and private companies, investors can accelerate their fundamental research process by discovering highly-differentiated and reliable insights that can’t be found anywhere else in the market. As a listener, drive your next investment thesis forward with Tegus for free at tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:14) - (First question) - The unique history of Bessemer and how the firm stays current (00:08:55) - The role of heritage and cooperative partnership in Bessemer’s model (00:14:36) - How giving each partner autonomy and commissions can lead to better personal and company outcomes (00:17:18) - The extent of freedom a partner has in terms of the style of investments made (00:20:38) - Retro-analyzing the effectiveness of their investment roadmaps and core insights (00:25:10) - What conflict typically looks like in partners’ conversations and how they resolve it (00:27:06) - How they enable their junior staff using apprenticeship and open dialogue (00:31:31) - Their different taste in investment targets (00:35:11) - How they each evaluate companies based on their unique interests (00:42:32) - Their thoughts on valuations and how they have dealt with with run-ups in the tech market (00:45:46) - What they anticipate in the future of early-stage investing (00:49:43) - The significance of Centaur companies that have hit $100-million in revenue (00:52:38) - The success of Bessemer’s writing and online content (00:55:13) - Where the vertical market software industry is in its life cycle (00:59:12) - How the next wave of innovation may revolutionize software or even depart from it (01:02:33) - Advice they give to companies looking to prepare for future shifts in tech and AI (01:04:46) - What excites them and what scares them within the development of LLMs (01:08:18) - Defensibility of an LLM-based company, given the high level of competition (01:10:39) - How their firm deals with terminating partners if and when they aren’t a good fit (01:14:53) - The kindest thing anyone has ever done for each of them

My guest this week is Alexis Rivas. Alexis is the co-founder and CEO of Cover, which is pioneering a new way of building homes. It’s no surprise to anyone that aspects of our housing market is broken. The market is undersupplied and littered with regulatory issues. The homebuilding process has also not changed for the better part of a century. Alexis is attacking the problem and has taken a leaf out of the car industry’s learnings to create a similar production process for home building. In our discussion, we talk about his idea of lego pieces for homes, how they’re refining production with backyard homes first, and how this may change the way people buy and sell homes in future. Please enjoy my conversation with Alexis Rivas. Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. For a limited time, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:39) - (First question) - Supply and demand situation writ large for housing in the United States (00:06:34) - Lack of workforce growth to meet housing development needs (00:10:23) - Insight into “lego piece” style construction (00:11:41) - The comparison to automotive manufacturing (00:16:15) - Strategic description of a good “lego piece” from Cover (00:20:08) - Utility continuity comparison between panels versus tradition construction (00:21:05) - Potential criticism from skeptical contractors (00:22:53) - The marginal cost for a typical home buyer (00:25:59) - The role of software in the business (00:28:47) - Insight into support model and “The Last Mile” theory in construction and possible solutions to combat errors during assembly (00:30:46) - Support system integration for inevitable repairs (00:32:17) - The changing reality of initial ideas as projects are completed (00:34:27) - Building factories and streamlining production logistics (00:37:28) - Focusing on constraints and an example relatable to real life scenarios (00:38:37) - The value of moving slow to perfect processes early on versus an all in head first approach (00:40:09) - The scope of ambition over the next several decades (00:41:18) - The evolution of homes and how they could change based of consumer wants (00:43:37) - Vertical capabilities of cover panels (00:43:21) - Types of panels that could be introduced moving forward (00:45:14) - Timeline for Cover expansion into new states (00:46:06) - Advice for upcoming entrepreneurs when building similar business models (00:47:58) - The kindest thing that anyone has ever done for Alexis

My guest this week is Dr. Peter Attia. I’ve had Peter on the show twice before but it’s been over 5 years since his last appearance. In that period, his work has exploded and today he’s one of the clear leaders on the topic and practice of longevity and health span. He has a new book out called Outlive, which I heartily recommend. You’ll hear us refer to the last chapter of his book early in our conversation but we chose not to reveal the whole story live so you can read and enjoy it. We highlight the big picture in our conversation, including the transition from Medicine 2.0 to Medicine 3.0. I always leave these conversations with Peter full of ideas, and in this case, highly motivated to go outside and move my body in nature. I can think of no better actionable advice. Please enjoy my conversation with Peter Attia. Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. Stretch your research budget with Tegus Expert Calls. Tegus delivers expert calls at a fraction of the cost of legacy vendors, with white-glove custom sourcing for every project at the speed you need to keep your research moving. And we don’t stop there. With rigorous compliance processes baked into everything we do, you can rest assured we’ve vetted every expert to ensure your privacy and protection. Start your next project today with Tegus Expert Calls. As an Invest Like the Best listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes Peter on The Tim Ferriss Show Podcast (00:04:15) - (First question) - How Patrick influenced Peter’s decision to launch his podcast (00:05:45) - How Peter has changed in the process of writing this book (00:08:11) - Process of writing the last chapter of this book (00:11:12) - How he stopped dealing with imposter syndrome (00:15:58) - Slow vs. fast death and medicine 2.0 vs. medicine 3.0 (00:22:55) - Doing more early detection screening to avoid slow death (00:27:00) - Impacts of compounding risks (00:31:24) - How do we shift thinking to better lifestyle changes vs. pill popping (00:35:32) - The outsized impact of exercise on health (00:46:18) - Peter’s exercise portfolio (The Comfort Crisis book) (00:50:55) - Why habitual workouts create euphoria for exercise (00:54:45) - How Peter’s views on nutrition have evolved (00:59:30) - Measuring metabolic health (01:01:55) - Where Peter hopes the future of healthcare is heading (01:05:40) - Benefits of mindfulness to health (01:12:55) - Defining your purpose in life (01:16:46) - An index card summation of this book (01:19:45) - Lessons learned being a better interviewer (01:21:46) - Frontier of Peter’s curiosity

My guests today are Scott Davis and Rob Wertheimer. Scott and Rob head up Melius Research and are the authors of a great book called Lessons from the Titans. The book explains what the industrial giants of old can teach the new generation of high-growth businesses about how to survive and deliver shareholder value over multiple decades. Drawing on their experience as industrial analysts, they present case studies on businesses like Danaher, Roper, Honeywell, Boeing and GE to reveal both what does and doesn’t work when it comes to capital allocation and business strategy as a company enters a more mature phase in its lifecycle. Please enjoy my conversation with Scott and Rob. Read Lessons from the Titans Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:20) - (First question) - The intersection between the current tech sector drawdown and the historical track record of industrial titans (00:07:10) - The most common ways they see companies start to fail and the types of errors they commit (00:11:01) - The best historical examples of companies that have gone from non-operational excellence to operational excellence (00:15:04) - Teaching the value of a business system and installing one for longevity (00:24:06) - Questions they’d ask and points of evaluation to uncover the health of a business (00:31:19) - Thinking about sustainable value creation in a lower growth environment (00:37:04) - Lessons from operating leverage and the rental industry (00:39:11) - Ways industrial companies have handled growth CapEx well and badly (00:43:52) - The line between discovering the future in a lab versus major pivots in reality while trying to solve today’s problems (00:49:37) - How the best managers nurture a great shareholder base (00:55:35) - Lessons to learn about business model transitions (01:00:13) - Further important messages from their book that businesses would benefit from (01:04:30) - The kindest things anyone has ever done for them

Today’s episode is a little different. Rather than share a new conversation, I have put together a few of my favourites from the past six and a half years of doing this show. I often listen back to these for inspiration, energy, and their timeless ideas on life and investing. Each of these is a significantly shortened version of the original episode. The first conversation you’ll hear is with Sam Hinkie, the second discussion is with Boyd Varty, and the last conversation you’ll hear is with Charlie Songhurst. Sam, Boyd, and Charlie are all exceptional in their own way and I hope you enjoy these condensed versions of our conversations. Sam Hinkie - Find Your People Boyd Varty - The Art of Tracking Charlie Songhurst - Lessons from Investing in 483 Companies For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:04:40) - (Sam Hinkie) (00:05:55) - The most amazing thing he’s seen from someone he has worked with (00:09:51) - His interest in finding “digital breadcrumbs” on his pursuit of knowing a person (00:13:18) - The impactful story of meeting the assistant GM of the Houston Rockets (00:17:22) - Strategies he has developed to avoid transactional people (00:19:22) - How he shapes his career and optimizes from an investment perspective (00:24:06) - The strangest things he has come across in early-stage investing (00:29:47) - (Boyd Varty) (00:33:04) - His early experiences with tracking wildlife and how it applies to investing (00:44:46) - What can be learned about life goals and paths from the experience of tracking (00:47:59) - The influence of culture on decision-making and goal-setting (00:50:39) - His concept of “the ordering of chaos on behalf of others” (00:54:41) - The importance of moving towards the unknown to start approaching goals (00:57:15) - His most memorable tracking experience (01:12:40) - (Charlie Songhurst) (01:15:10) - His diverse career highlights (01:16:29) - His analysis of why startups succeed or fail (01:21:21) - What founders can learn to enable and maintain productivity in their company (01:25:21) - Nature versus nurture as it applies to adept founders, and the controversial “alien founder” concept (01:30:10) - The importance of good recruiting from an early stage (01:33:32) - How founders can make their companies attractive to prospective talent (01:35:53) - Why he is interested in investing in highly boring and highly complex ideas

Hello everyone. A few days ago, we discussed what we call forever episodes, which are the few episodes of our show that we think will be as popular a decade from now as they are today. When I re-listened to this episode with David Senra, I left wildly energized and wanting to share that feeling. So we are re-releasing it today for anyone who missed it the first time or hadn't yet discovered Invest Like the Best. Please share with your friends and loved ones as I think anyone will benefit from David's perspective and enthusiasm. Have a great weekend and we'll be back with more next week. David Senra has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. Please enjoy this great conversation with David Senra. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:01] - [First question] - When he first fell in love with reading [00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast [00:10:34] - The first time he connected with someone as a positive role model that he was reading about [00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies [00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives [00:22:45] - The dynamic and relationship between inspiration and perspiration [00:27:11] - Commonalities between the layers of leadership and support underneath founders [00:31:52] - Where else he’s seen ego rear its head in good and bad ways [00:38:34] - How often do great founders break the law or enter gray areas of it [00:41:22] - The role constant learning and listening plays in success [00:45:12] - Talking about how anything worth doing is worth doing to excess [00:52:18] - Describing the soul of founders and businesses [00:58:39] - What he’s learned about all of these founders as it relates to marketing [01:04:38] - A common story that process is often art [01:08:10] - Who his idols are in podcasting specifically [01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet [01:19:55] - The kindest thing anyone has ever done for him

My guest today is David Einhorn. David is the President of Greenlight Capital, a long-short hedge fund that he co-founded in 1996. He is a prominent value investor with a reputation for rigorous security analysis. In 2002, he revealed a short position in Allied Capital, which was ultimately proven correct and similarly in early 2008, he told the Sohn Conference he was short Lehman Brothers. Over his near three decades managing money at Greenlight, he has delivered impressive returns but it has not been without challenge. Our conversation covers both the highs and lows, his views on the current banking issues, and how he has evolved as an investor. Please enjoy my great conversation with David Einhorn. The Sohn Conference 2023 Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:50) - (First question) - Why he is glad he started his fund in 1996 rather than today (00:05:58) - His view of how companies’ personnel and goals have changed since the 90’s (00:07:01) - His counter-momentum approach to markets and how he views current trends (00:11:17) - The jelly-donut theory of monetary policy (00:14:46) - His outlook on inflation and the Fed from a fiscal perspective (00:16:48) - The evolution of Greenlight’s portfolio and philosophy through history (00:20:11) - Periods in his career that stand out as the most challenging (00:25:58) - How tech advances have influenced his core concept of figuring out worth (00:28:17) - His three-step process to picking investment targets (00:29:10) - The companies he has learned the most from studying (00:30:52) - His experience with investing in Apple (00:33:33) - How he considers the notion of quality in a business (00:35:05) - His views on shorting, concentration, and holding periods (00:38:37) - What he learned from a deep dive on airline businesses (00:40:31) - His perspective on sports franchises as an asset (00:42:12) - His new interest in poker and how he got so good at it (00:45:22) - Applying traditional valuation styles to the modern market (00:47:13) - Cultivating relationships with his limited partner investors and his team (00:54:26) - His perspectives on the insurance space (00:57:33) - The health of the economy and financial infrastructure as he understands it (01:01:51) - How he thinks about housing and the construction industry (01:03:54) - How AI and other high-tech are affecting his investment decisions (01:05:28) - Other topics on his mind, from national politics to social psychology (01:08:22) - The kindest thing anyone has ever done for him

My guest today is Avi Goldfarb. Avi is a Professor at the University of Toronto’s Rotman School of Management, the Rotman Chair in Artificial Intelligence and Healthcare, as well as the co-author of two bestselling books on AI and its economic impact. His most recent book, Power and Prediction, is probably the best piece of content I have read in explaining how AI may reshape business models, systems, and products. We recorded this before GPT-4’s release last week which, if anything, makes Avi’s ideas on AI’s impact all the more poignant. Please enjoy my conversation with Avi Goldfarb. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:15) - [First question] - His initial reaction to chat GPT when it first launched (00:07:08) - Prediction Machines; The impact price has on how much something is used by humans (00:11:07) - The shift from steam powered factories to electric ones and the transition between the two in regards to systems and application solutions; Power and Prediction (00:17:06) - Midpoints between a point solution and a systems solution and applications that are being built in the middle of them (00:19:10) - What application, system, and point solutions feel like today in the world of AI (00:27:03) - The transition from a world governed by rules to one by decisions (00:30:58) - How the power of prediction moves us from a binary to a decimal framework (00:34:48) - Ways power disruption will occur as we navigate the emerging AI frontier (00:44:33) - Other functions like personalization that entrepreneurs should think about putting into their products and features (00:47:18) - How we should be thinking about the generation of information and data (00:51:32) - A future where technology either desimates or empowers specific industries (00:54:16) - What he’s most excited and worried about given the emerging frontier of AI (00:55:41) - The kindest thing anyone has ever done for him

My guest this week is Auren Hoffman. Auren is the CEO of Safegraph, which curates data on physical locations. He also founded LiveRamp, a public data connectivity business. Auren knows more about data businesses than almost anyone I know and that is the topic of today’s discussion. We look at the business of data from every angle and finish with a fun masterclass on how to host a dinner party. Please enjoy my conversation with Auren Hoffman. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:16] - [First question] - His 2x2 matrix for categorizing different types of data businesses [00:04:59] - An example of what he calls a religion company in his matrix [00:07:03] - His notion of data currency [00:08:23] - His definition of a great business [00:09:46] - An example of a so-called application religion company in his proverbial matrix [00:11:24] - Co-op and non-profit business models within and outside of the data sphere [00:13:35] - The truth application quadrant of his matrix [00:16:18] - How data has exploded in prevalence for the business world as a whole [00:18:57] - How to think about the end market for data and its demand [00:21:09] - Characteristics of a good data set and how to identify it [00:23:14] - Other factors that impact the usability of a data set [00:24:30] - Optimizing data collection itself [00:26:30] - The slow growth that’s typical of early-stage data companies [00:27:27] - Market share considerations for data businesses [00:30:03] - Common struggles for data entrepreneurs [00:34:01] - The genesis of his business; SafeGraph [00:37:08] - The power of self-maintained and user-maintained databases [00:40:16] - Typical customers and use cases for SafeGraph’s data [00:41:08] - How SafeGraph and other companies protect against data theft [00:42:12] - Frequency of change as a proxy for the value of a given data set [00:45:32] - Categorizing inbound data based on the most important criteria [00:47:07] - The founder personalities he finds in the data industry [00:49:53] - Why he feels the data truth quadrant of his matrix is underdeveloped [00:50:30] - Bloomberg as an important data company to study [00:51:42] - The importance of transparency in business and in data distribution [00:53:07] - Failure modes that he sees most commonly in data-based startups [00:53:53] - Data businesses becoming application businesses and vice-versa [00:57:35] - The great dinner parties he’s known for [00:59:50] - How he makes the dinner parties appeal to introverts [01:03:11] - Dead people he would most like to have as dinner guests [01:04:09] - Questions he would ask the most influential religious figures [01:06:20] - The kindest thing anyone has ever done for him

My guest this week is Trae Stephens. Trae is a partner at Founders Fund and co-founder and Executive Chairman of Anduril. Trae’s philosophy can be boiled down to finding good quests, which has led him to investing in businesses that work closely with the government on societally important issues. Clearly, that extends to co-founding Anduril and I would highly recommend listening to my Business Breakdowns episode on Anduril if you haven’t already. In this conversation, we discuss the importance of lobbyists, why the high-tech defense firms of the past became stale, and how he hunts for disagreeableness in founders. Please enjoy my conversation with Trae Stephens. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders Podcast Founders Episode 136 - Estee Lauder Founders Episode 288 - Ralph Lauren ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:17] - [First question] - Why Trae thinks most high-margin businesses are bad for society [00:04:28] - What would he change to impact energy technology most if he were in charge [00:06:18] - His investing focus on dynamism and mission-driven tech companies [00:09:42] - Analyzing why relatively few people strive to make society-level advancements [00:11:35] - What he’s done as a parent to enable his kids to develop passions [00:12:41] - The most noteworthy adventures in his career [00:14:41] - Founding Anduril and what it taught him about the tech industry [00:18:40] - The cutting-edge of defense technologies today [00:21:29] - What Shyam Sankar of Palantir taught him about defense tech [00:23:34] - Why some of the biggest defense tech companies have stopped innovating [00:28:29] - What he and Anduril have learned about sales and scaling in the public sector [00:35:22] - His take on Peter Thiel’s notion that competition should be avoided [00:38:24] - The importance of being psychologically disagreeable when building a start-up [00:39:54] - The origin story that stands out the most from companies he has interviewed [00:41:12] - How he developed an investor mindset on his unorthodox path to the venture world [00:43:57] - What he has learned from playing supporting roles and aligning with great leaders [00:46:11] - Important but uncommon lessons about entrepreneurship [00:48:21] - Venture investing lessons he’s learned from Lauren Gross [00:50:00] - His first VR project and aspirations for the future of VR [00:54:50] - The role of religion and spirituality in his business philosophies [00:59:13] - Why he tries to capitalize on morality as opposed to sin [01:03:57] - The kindest thing anyone has ever done for him

My guest this week is Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:21] - [First question] - What Don Valentine’s heart was like [00:06:30] - The most productive and unproductive parts of Don’s toughness [00:09:01] - Being the opposite of insufferable and how it was different when he was younger [00:10:55] - Why it’s so important to understand someone’s core motivations [00:14:18] - Questions or topics he returns to when getting to know people [00:15:31] - How much time he believes it can take to really get to know someone [00:20:37] - What venture looks like to him today relative to his prior career [00:23:51] - His style of approaching emerging technology markets like AI as an investor [00:26:37] - Whether or not he’d go into venture today if he was in his late 20s [00:28:30] - Commonalities between the very best at going to market effectively [00:31:11] - The key components of great product positioning [00:32:10] - Helping companies circumnavigate mediocre positioning [00:33:25] - Generating demand and leads and doing it well [00:37:15] - How interacting with companies early on has changed over the ears [00:46:14] - Sussing out the killer gene in somebody [00:47:25] - What high school was like for him when he first came to the US [00:49:04] - How successful people can instill the lessons learned from hardship into their children [00:50:45] - The most common failure modes he’s seen for investors [00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like [00:59:06] - What he’s learned about picking the right LPs and partnering with them [01:00:40] - The most interesting question an LP has ever asked him [01:02:18] - Making sure that performance is on everyone’s minds all the time [01:04:04] - What the components of a fantastic investment memo are [01:05:00] - Which dinner companions he’d pick to educate a newly successful founder [01:05:29] - What first popped out at him as black magic when he started investing [01:07:59] - The kindest thing anyone has ever done for him

I’m excited to share this conversation with Tim Urban. Tim is, in my opinion, one of the best and most engaging writers of our era. He’s tackled many of the most interesting topics in the world from AI to procrastination. I interviewed him in 2017 in an episode we called “Grand Theft Life”, and it remains one of my favorite episodes ever. In the 6 years since that episode, he hasn’t published almost anything. That’s because he’s been writing the book we discuss in this episode. The book is called “What’s Our Problem”, in which Tim investigates the big issues facing society. The reason I love Tim’s writing so much is its density of ideas and ridiculously clear explanations: a rare combo that makes reading a joy. I hope you enjoy this great round two with Tim Urban, and go buy and enjoy his great new book. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders podcast. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:50] - [First question] - What it’s been like spending seven years thinking about a single topic: Tim's book, What’s Our Problem? [00:05:05] - How he’s come to articulate the big question he’s trying to answer in his book [00:07:58] - A dinner experience where a single question showed just how much of a problem there was to solve [00:09:47] - Group ideology and the different ladder rungs of human thinking [00:17:28] - The concept of a social golems and genies and their implications for society [00:23:02] - His favorite genies and golems throughout history and their impact [00:29:07] - Examples of canonical high functioning genies across history [00:34:20] - The key ingredients within liberal democracies that allow for and correct golems [00:40:44] - Media’s role in shaping ideas and society and what’s changed about it in today’s media landscape [00:46:46] - What else is going on that has him worried about modern institutions that are failing as social immune systems [01:01:15] - The gap between what we say publicly versus what we feel privately and the growing pile of unsaid things [01:07:18] - What’s to be done in order to help society repair itself [01:14:09] - Whether or not the direction we’re most afraid to run is where we should [01:17:37] - Thoughts on AI having written extensively on it and the new wave of emerging tools [01:22:13] - The role and impact of leadership in regards to golems and genies

My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, and Sheryl Sandberg. He’s had a front-row seat to the defining products and founders of our era and his lessons from those experiences do not disappoint. Please enjoy this great discussion with Dan Rose. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:27] - [First question] - The story behind Amazon’s Kindle and the lessons it taught him [00:09:19] - Amazon’s philosophy of working backwards and the most creative solutions he and his team had to come up inside of that framework [00:13:04] - What he did to convince publishers to get on board with his vision [00:16:02] - His overall experience of the relationship between innovation and constraints [00:18:43] - Thoughts about the fine line between genius and nutcase [00:22:02] - What the key points of his theory on partnerships would be [00:24:28] - When advising portfolio companies becomes relevant [00:26:09] - The dark arts of building companies that could be adopted by partnerships [00:28:40] - Why he thinks the best technology companies drive strategy through product [00:32:23] - Resolving micro management while also giving skilled talent their own space [00:36:07] - Where Javier Olivan fits into his ideal executive team [00:36:57] - What about growth requires its own expertise [00:37:35] - What makes Dave Schneider an ideal sales leader [00:39:08] - The most stressful period of time while working at Facebook [00:42:51] - General thoughts on great versus good business models in tech [00:45:36] - Topics where Jeff Bezos and Mark Zuckerberg would disagree the most [00:47:13] - Defining the platonic ideal of a great investor approaching corporate enterprises [00:50:25] - Overview of the investing environment we’re in today from coast to coast [00:55:07] - What made Sheryl Sandberg so successful; Lean In [01:00:35] - Why he started his career at Life Mastery selling personal growth seminars [01:05:47] - What will define the next generation of leaders [01:07:59] - A product he would build if he could that doesn’t exist yet [01:08:59] - The kindest thing anyone has ever done for him

My guest today is Jeff Green, the CEO and co-founder of advertising platform, The Trade Desk. The Trade Desk is the second advertising exchange Jeff has built, having sold his first venue to Microsoft in 2007. He started The Trade Desk in 2009 and has built it into a $30 billion public business. In our discussion, we talk about the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers not sellers, and how he shapes the culture of his firm. Please enjoy my conversation with Jeff Green. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Founders Episode #288 Ralph Lauren Invest Like the Best with David Senra: Passion & Pain ----- This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:09] - [First question] - What he’s learned about human behavior and how it’s impacted his business [00:05:45] - Big differences in generational and perennial behavior [00:06:56] - The strong link between vulnerability and creativity [00:07:42] - The necessary preconditions that allowed him to build Trade Desk the way he did [00:10:53] - What it would have felt like as an early stage employee at Trade Desk [00:12:43] - The hardest parts about maintaining his type of company culture [00:14:05] - How much of his company culture is interwoven systemically or whether it arises naturally based on talent choices [00:15:59] - Defining what talent means to him and the dimensions of it that matter [00:22:03] - What he’s learned about delivering messages effectively [00:23:49] - The founding story and history of Trade Desk [00:28:33] - How he thinks about the key stakeholder groups around Trade Desk’s platform [00:30:50] - Figuring out who Trade Desk’s key customers were and identifying them writ large [00:34:55] - The composition of the universe and market of those who buy advertising [00:36:11] - Practical product implications based on their choice of service [00:40:16] - Building inventory legibility and its dimensions and importance [00:47:55] - The time between the first line of code to a multi million dollar revenue stream [00:50:29] - Markers for technology companies he’d look for that could achieve a similar scale [00:53:35] - How not being able to simulate poverty or hunger translates into his parenting [00:57:10] - Describing the margin differences between Trade Desk and Google [00:59:00] - What stands out as the defining moment in his firm’s history [01:01:50] - The kindest thing anyone has ever done for him

My guest this week is Carl Kawaja. It’s the second time I’ve had Carl on the show and my first conversation with him is one I go back to often. Carl is a portfolio manager at Capital Group, where he’s quietly overseen a huge portfolio for decades. He is one of the top investors operating today as well as one of my favorite people. The investing world has changed quite a bit since Carl and I first spoke in mid-2021 so this was a great chance to use Carl’s curious mind and wide range of experiences to discuss the regime change taking place across capital markets. In true Kawaja fashion, we go all over the map and discuss Apple, the Amazonian rainforest, baseball, the oil & gas industry, Muhammad Ali, and more. Please enjoy my great discussion with Carl Kawaja. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it's quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:44] - [First question] - What the market feels like to him today [00:06:00] - The pros and cons of the cost of capital and experimentation [00:09:09] - Things we can learn from Oil & Gas stocks and resource commodities in general [00:14:38] - Pulling apart the key lessons from Berkshire’s purchases of IBM and Apple [00:20:37] - The practical implications of wanting to land more soft-wins in investing that aren’t apparent out of the gate [00:25:52] - How he approaches and considers products and product cycles writ large [00:31:10] - The Systems Bible [00:33:15] - Thoughts about making money from value based strategies [00:38:31] - His methodology to go about finding the next diamond in the rough [00:42:48] - A New Innings [00:45:13] - The Arc of Boxing; Lessons from Muhammad Ali fighting Cleveland Williams [00:48:54] - Someone he thinks is an exemplar in both business and the world [00:54:37] - Don’t Sleep There Are Snakes [00:59:41] - The role fossil fuels play in the energy transition and the current regime change [01:07:35] - What we can learn from uncontroversial transitions in the past

My guest this week is Daryl Morey, who is President of basketball operations for the Philadelphia 76ers. Daryl is a computer science graduate but has become one of the NBA’s most successful General Managers during his time with the Houston Rockets and the 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyball. Daryl is also the co-founder of the MIT Sloan Sports Analytics Conference, which has become the gold standard forum for leaders in sports analytics. I had a blast talking to him about negotiation tactics, systems thinking, hiring, and a ton more. Please enjoy this great conversation with Daryl Morey. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Invest Like the Best with David Senra: Passion & Pain For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:15] - [First question] - The basic principles of sports and what makes for a great sport [00:09:54] - How resource concentration influences outcomes in various sports [00:13:13] - The degree of certainty in predicting sports outcomes based on existing data [00:16:32] - Using the concept of KPIs to optimize for certain characteristics to win games [00:18:45] - Training teams on specific systems and plays versus leveraging individual talent [00:21:07] - Why superstar athletes are key to success in basketball [00:24:02] - Dealing with constant expected value calculations to appease stakeholders [00:25:30] - Building the organization’s back office to find talented athletes [00:28:32] - How he and other GMs make organization-level decisions [00:34:12] - Why he’s involved with basketball as opposed to other sports [00:36:17] - How he uses his frameworks to figure out systems outside of mainstream sports [00:37:41] - Problems with the rules and economic factors of professional soccer [00:42:54] - Trends he’s observed in the worlds of music, movies, and books [00:45:33] - His perspective on developing one’s own career path [00:48:22] - How challenges in his youth benefited him in the long run [00:49:28] - The person he would call for advice if he was stuck in a foreign prison [00:51:01] - His emphasis on first principles and why he supports free speech [00:52:31] - Takeaways from a Harvard negotiation class he took [00:57:07] - The power of refining the terms and definitions of a deal post-negotiation [00:58:51] - The four people in the world that intrigue him most [01:01:40] - The kindest thing anyone has ever done for him

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Please enjoy this conversation with Miles Grimshaw. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Invest Like the Best with David Senra: Passion & Pain For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:57] - [First question] - His notion of the investor as a biologist or a physicist [00:05:24] - Why he seeks out new companies with unique business models [00:07:53] - How his investments are based on present and future needs in the market [00:11:55] - Evaluating the genetics of a nascent or small company [00:13:38] - The half-life of information as it flows through a company or platform [00:17:26] - Unpacking how software companies can survive re-evaluation periods [00:21:03] - The power of environment creation and facilitation [00:25:10] - The importance of user conferences [00:25:45] - A company’s potential for a differentiated second act as a sign of good genes [00:30:21] - Product quality, timing, and reinvention in tech startups [00:33:10] - Why it’s crucial for companies to avoid copying their heroes [00:37:41] - Breaking down market perspective on pure API companies [00:41:29] - His views on software targeted to vertical versus horizontal markets [00:44:29] - Carefully leveraging relationships with core customers [00:48:06] - Operational lessons from his experience with the companies he’s invested in [00:50:26] - His maxim that software development is as much an art as a science [00:51:12] - His idea of a product magician in the software industry [00:52:19] - Effects of new products and categories at the forefront of the space [00:58:21] - How software founders should prepare for 2023 [01:01:41] - How both market structure and product shape the genetics of a business [01:04:32] - The challenge of pricing and packaging for SaaS companies [01:06:42] - Cardinal sins in software investing [01:07:42] - The kindest thing anyone has ever done for him

My guest today is John Fiorentino. John is a product inventor and entrepreneur who, in the space of a few years, has bootstrapped four products; Gravity Blanket, Moon Pod, Moon Pals, and Birthdate Candles which have collectively sold hundreds of millions of dollars of revenue. Our conversation is quite different than normal. Alongside his successful brands, John has had a range of life experiences – from starting as a Jazz musician to working for Justin Bieber - that give him an original worldview. I was especially interested in his points around product positioning, creating magic for consumers, not letting yourself become the product, and how to build enduring brands. Please enjoy this great conversation with John Fiorentino. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:25] - [First question] - The amazing story behind Gravity Blanket [00:08:51] - What he’s learned about positioning relative to product [00:13:17] - How fundamental truths drive creativity in commerce [00:16:17] - Real-world examples of magic as he defines it [00:19:50] - The investability of consumer businesses from his perspective [00:25:25] - His contrarian thoughts on venture-backed startups [00:28:00] - How unique personalities create compelling IP and monetize it [00:38:28] - The fine line between creative power and self-destruction for brand founders [00:45:13] - The importance of consumer business goals being larger than oneself [00:48:45] - The story of the Moon Pals weighted stuffed animals [00:53:15] - How investors undervalue IP and mythology [00:57:20] - Leveraging uniqueness as a founder to boost your brand power [01:00:53] - His eye-opening experience working on Justin Bieber’s team [01:05:20] - How he identifies potential magic-makers and enables them [01:09:16] - An odd commonality between high-level successful people [01:12:14] - Whether or not one could map out their own archetype framework [01:15:23] - The dangers of focusing on one’s own persona and image as the product [01:18:19] - The kindest thing anyone has ever done for him

My guest today is Amjad Masad. Amjad is the founder and CEO of Replit, whose mission is to bring the next billion software creators online. Replit has built a browser-based coding environment that makes coding more fun, collaborative, and approachable. We discuss how that is possible and why the way most of us interact with computers today is suboptimal. We then go into the effects of AI on software creation and its broader impacts on technology. Please enjoy my conversation with Amjad Masad. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes[00:02:18] - [First question] - The Steve Jobs black-pill [00:06:02] - Speculation on the near future of programming [00:09:38] - Potential convergence of simple software and coding tools [00:11:23] - What an IDE is and how it works [00:12:44] - The definition of REPL and the role of Replit in the space [00:14:21] - Decreasing friction in a programming environment using primitives [00:19:47] - Real-world effects of Replit’s low-friction design [00:23:27] - His perspective on new coding and AI technologies [00:30:29] - Promises and limitations of the user-friendly programming movement [00:33:16] - The dynamic nature of IDE technology and its challenges [00:39:53] - How he’s priming his team to react to new technologies like the upcoming GPT-4 [00:43:58] - Recommended skills and training for the AI world of the future [00:47:21] - The impact of IDE and AI tech innovations on existing tech giants [00:51:56] - His mixed but optimistic views on the trajectory of AI [00:54:40] - Recommendations for the curious listener without a programming background [00:56:50] - The role of smartphones in the IDE movement [00:58:28] - The kindest thing anyone has ever done for him

My guest this week is Rebecca Lynn. Rebecca co-founded early-stage investor Canvas Ventures in 2013 and is regularly featured as one of the best VCs in the market. She has deep positioning and go-to-market experience, which she honed during her time at Procter & Gamble, and that's the focus of our discussion. We cover the details of great marketing, why you should say no to customers, and how she has built Canvas. Please enjoy my discussion with Rebecca Lynn. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:37] - [First question] - What she’d do a great job teaching if she could teach a singular 401 level course [00:05:20] - Defining what the umbrella concept is [00:06:10] - What about her career at P&G applies most to the kinds of companies she spends her time with now [00:12:06] - What types of questions she asks to help someone building a product understand their marketing angle [00:15:34] - The top three things people do wrong when running a survey in tactics or strategy [00:19:33] - Categories of questions where surveys are always helpful and effective [00:21:06] - What the Go-To-Market Council is and what it does [00:28:21] - The ways that most funnels are commonly broken [00:31:17] - Defining great positioning and what it accomplishes [00:33:36] - How her knowledge and ideas most impacted the way she built Canvas [00:35:04] - Lessons learned about the world of digital health and the quantified self [00:39:15] - The base level attributes that most indicate investment potential when she’s investing in a company [00:42:32] - The shifts in the world that most have her attention today [00:46:10] - What has her worried systemically about venture investing [00:49:37] - The kindest thing anyone has ever done for her

My guest this week is Michael Mauboussin. Many of you will know Michael and his work well. He’s Head of Consilient Research at Counterpoint Global, one of the sharpest investment minds I know, and a frequent guest on this show. In this discussion, we go deep into his recent work on market share, returns on capital, and capital allocation - all of which are coming under increasing scrutiny for different reasons. Please enjoy this great conversation with my friend Michael Mauboussin. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Invest Like the Best with David Senra: Passion & Pain For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:46] - [First question] - Overview of Michael’s recent research on market share [00:05:48] - Market share dynamics in modern history [00:08:43] - How market share data is useful for investors [00:12:30] - Investing in early breakout companies from low-concentration markets [00:14:34] - Surprises from his recent research project [00:15:29] - Using the value stick for stakeholder satisfaction [00:19:12] - Examples of value creation using the value stick [00:23:33] - Market power in relation to markups and willingness to pay [00:32:00] - Identifying a company’s real ROIC numbers [00:44:00] - How important absolute ROIC is when picking investments [00:47:07] - Research on capital generation and allocation trends [00:54:25] - Characteristics of great capital allocation strategies [00:59:26] - Surprises in the market since his deep-dive research [01:02:54] - Artificial intelligence and other sources of disruptive innovation

My guest this week is Jeremiah Lowin. Jeremiah has been on the podcast a number of times over the years. He’s one of my oldest friends who has been a sounding board for me throughout my career. Today he is the founder and CEO of Prefect, which helps companies automate and orchestrate their dataflows. In full disclosure, Positive Sum is an investor in Prefect. We didn’t plan this conversation, but when OpenAI released ChatGPT, I called Jeremiah for a primer on what’s happening under the hood and how best to contextualize this product amidst the growing AI movement. We have these conversations often, but this time I decided to record it so we can all learn from someone I consider to be a leading mind in the fields of data science and machine learning. We start off in the weeds and zoom out as the discussion unfolds. Please enjoy this conversation with my friend, Jeremiah Lowin. Listen to Founders podcast Founders Episode #136 A Success Story: Estee Lauder Invest Like the Best with David Senra: Passion & Pain For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:38] - [First question] - What a pre-trained transformer is [00:06:12] - What latent representation means in the context of AI models [00:09:57] - Models using math to interpret input data and generate images accurately [00:11:43] - Whether or not understanding AI complexity in light of the results they arrive at will become a black box scenario [00:14:13] - A high level history of the companies involved in generative AI [00:17:51] - The precursory technology that makes generative AI art possible [00:21:01] - What people are doing to improve AI models in between versions [00:26:39] - Things that are literally happening during AI training [00:33:38] - Whether or not AI models might one day function as a utility like electricity [00:36:01] - Coding using GitHub Copilot and what it’s felt like to use it [00:40:30] - How he’d approach starting an AI company from scratch [00:44:40] - Developing this technology beyond general and into specific use cases [00:49:44] - The secret sauce for defensibility in the AI model space [00:53:02] - What he’s watching more closely as the story unfolds [00:56:32] - Whether or not he thinks that these toolkits will eventually learn how to use other systems like Unreal Engine on our behalf

My guest today is Bill Lenehan. Bill is the CEO of Four Corners Property Trust, a listed REIT and one of the leading owners of restaurant real estate in the US. Their portfolio is made up of 982 properties across 47 states. Real estate is something most of us own, whether as an investment or a home, and Bill’s insight into the asset class at this particular moment in time is fascinating to hear. Please enjoy my conversation with Bill Lenehan. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:19] - [First question] - Recent increases in mortgage rates and a frozen housing market [00:08:55] - Projected real estate trends over the next decade [00:13:38] - How a company’s ROI can be more consistent with backing from a real estate firm [00:16:41] - Risk-return rate and risk exposure in real estate compared to other asset classes [00:20:09] - The skills, traits, and circumstances that make a top-level real estate investor [00:22:38] - Stand-out learnings from his time at Farallon Capital Management [00:33:20] - The value of shopping malls and offices in a post-COVID, e-commerce US [00:39:27] - Pros and cons of different types of real estate investments, including REITs [00:43:22] - The impact of climate change on the real estate market [00:45:39] - The role of modern technology in investing and in real estate infrastructure [00:51:10] - Hard costs of building and renovating for the future [00:54:20] - How hard costs and supply levels impact rates of return and housing costs [00:57:17] - How the retail industry is adapting to consumer trends [01:01:23] - Why retailers need to adapt to a changing economy and how they’ll do it [01:04:03] - The relative magnitude of change in today’s real estate market [01:06:51] - The role health and wellness plays in real estate and finance [01:09:28] - What it feels like to be investing in 2022 [01:12:23] - The kindest thing anyone has ever done for him

Today I’m joined by two Hollywood greats, Ron Howard and Brian Grazer. They have produced, directed, written, and acted in a number of the most popular films and tv shows ever made, including Apollo 13, A Beautiful Mind, 24, and Frost/Nixon. Their partnership is one of the longest running in Hollywood, and the business they founded in 1985, Imagine Entertainment, has won 49 EMMY awards, 11 Golden Globes, and 10 Academy Awards. There are few better storytellers in the world and it was a thrill to talk about curiosity, trust, and business building with them both. Please enjoy this great conversation with Ron Howard and Brian Grazer. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:44] - [First question] - The value of trust and how Ron built it up over time with Brian [00:08:34] - The spark that allowed Brian to trust and work with Ron [00:14:45] - Ray Stark calling Brian and threatening him over their mermaid movie [00:16:37] - Keeping their creative spark alive as their business scaled and matured [00:20:20] - Principals like the universality concept that they return to most commonly [00:23:24] - Seemingly bottomless wells of inspiration that they both pull from [00:26:18] - Curiosity precedes innovation and the curiosity conversations Brian has [00:30:15] - The pitch format Brian uses to try and secure a guest for a curiosity talk [00:32:16] - The role of engaging with conversations or ideas Brian disagrees with [00:33:56] - How curiosity shapes the nitty gritty of Ron’s directing and producing [00:37:41] - The biggest mistakes they’ve come across that people make telling stories [00:40:27] - Pinpointing the defining moments of their careers outside of the obvious wins [00:44:27] - Thoughts about how the industry has changed across their careers [00:47:19] - How they’ve gotten better at taking a project from nothing to the finish line [00:49:53] - The kindest things anyone has ever done for them

Today’s episode is a special one, in a format that may turn into a series. It is a conversation between Ravi Gupta and Shane Battier. Ravi is a partner at Sequoia, one of our most popular past guests, and a good friend. Shane is Ravi’s friend, and one of the most successful basketball players ever, having won championships and awards at the high school, college, and NBA levels. I spent 10 years as a purely quantitative investor, so naturally I was obsessed with data in sports. When I was meeting with prospective investors, Michael Lewis’s book Moneyball—which chronicled the data analytics revolution in baseball—was my go-to analogy to explain what I did… “Moneyball, but for investing.” I used that line for years. I’ve learned firsthand that it’s wise to follow your curiosity, no matter how strange or different it may be. The podcast is my curiosity tour, and years ago it led me to Sam Hinkie—who is himself on the Mt. Rushmore of analytics in sports. Sam introduced me to Ravi. Then Ravi sent me Michael Lewis’ article written about Shane called “The No Stats All-Star.” I highly recommend you read it. All this serendipity around friends, data, investing, and sports gave me an idea: why not ask Ravi to interview Shane? Ravi likes the idea of playing for the front of the jersey, not the back. It is hard to imagine someone that lived that more than Shane. Shane shares his story, lessons learned from various coaches, and using data as an advantage. He also explains the four kinds of teams he’s encountered, which I found simple, and memorable. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:53] - [First question] - What people measure in basketball, what matters when it comes to winning, and why he was called a replaceable cog in the No-Stats All-Star [00:08:38] - Some of the plays that impact the overall points during a basketball game [00:14:33] - The power of curiosity and obsessing over details [00:16:16] - Embracing his role and how being a role player applies to life outside of the court [00:20:47] - Where his obsession for winning and being a good team mate comes from [00:23:23] - Some of the things great leaders and coaches did to inspire him [00:28:51] - An overview of the four types of teams and fundamental aspects of them [00:34:50] - What a person can do to elevate their team and make it a winning one [00:37:43] - Antifragility and the letter Shane wrote for Ravi when Amazon bought Whole Foods [00:44:56] - How to get everyone rallied around a long-term shared mission effectively [00:46:48] - Finding a No-Stats All-Star in a company and what to look for in one [00:52:34] - The kindest thing anyone has ever done for him

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. ----- This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:36] - [First question] - Overview of what a compound startup is [00:06:32] - What he’s learned about picking customers effectively [00:08:48] - Key chapters when it comes to building a compound startup [00:13:48] - What great looks like at the base level infrastructure of employee data [00:20:15] - His overall philosophy on product development writ large [00:25:09] - His role as a capital allocator and distributing resources to his teams [00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software [00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure [00:34:43] - Speed and the kinds of people that can sustain it for long periods of time [00:36:30] - What motivates him on a personal level and harnessing motivation in general [00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public [00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication [00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person [00:50:36] - The best example of a moment that required the most grit and perseverance while building his company [00:52:28] - How to successfully get former founders to come work for him [00:54:47] - What good private equity investors do [00:58:31] - The kindest thing anyone has ever done for him

My guest today is Bob Elliott, the CEO and CIO of Unlimited, which creates low-cost index ETFs for alternative investment strategies. Prior to co-founding Unlimited, Bob was a senior investment executive at Bridgewater Associates where he served on their investment committee and led Ray Dalio’s personal research team for a decade. His breadth and depth of experience makes him a great person to assess the current macro landscape. We discuss the relationship between rates, inflation, and asset classes, Bob's approach to identifying data with the most signal, and finish with his view on quantitative strategies in private markets. Please enjoy this great discussion with Bob Elliott. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - The Economic Organization of a POW Camp and key lessons one can learn from the paper [00:07:22] - The way that supply and demand clears a price and how that plays into his thinking about investing across asset classes [00:09:58] - Whether or not he has a generalized investing worldview or framework [00:11:46] - Deciding on what data is signal and matters most when analyzing markets [00:15:46] - A crash course on easy money and tight money regimes and the implications of both in a macro environment [00:20:28] - The rise and role of inflation and what should be done about it [00:24:00] - What the next couple of years will look like if we draw lessons from history [00:30:12] - Why gold could ever belong in someone's portfolio when it doesn’t produce or yield anything back to the investor [00:35:08] - Supply and demand constraints and the state of the housing market today [00:40:42] - What might happen in future labor markets given our current macro environment [00:46:27] - Currencies, energy, geopolitics, and what he’s most focused on globally [00:52:19] - What movements in the charts are worrying him the most [00:56:04] - The original “All Weather” portfolio and what one would look like if he built it today [01:02:05] - How his career has taught him to find talented individuals who might deliver alpha [01:07:19] - Lessons learned from early-stage and venture investing and thoughts on that world now [01:12:41] - Why there hasn’t been an iconic early-stage technology investing firm driven by systematic strategies [01:16:10] - The kindest thing anyone has ever done for him

My guest today is Kirsten Green, founder and managing partner at Forerunner Ventures. Kirsten launched Forerunner in 2012 and has built it into a leading consumer-focused venture firm with early investments in consumer brands like Dollar Shave Club, Bonobos, Faire, and Warby Parker. Our conversation is an exploration of consumer behavior and how to invest behind change in our society. We also discuss frameworks for identifying brands early, how to build deal flow, and the shift in power between buyers and sellers. Please enjoy my conversation with Kirsten Green. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:35] - [First question] - The insights gleaned from studying consumers in the modern era [00:07:02] - Whether or not the shift in consumer behavior is similar to a platform shift like mobile [00:09:58] - Which of her hypothesis going into the research was proven most wrong [00:11:31] - The leading persona archetype that drives consumer spending [00:13:58] - Thoughts about her investing focus after doing all of this research [00:16:23] - How much the digital world is good and bad for community [00:18:50] - Positive and negative impacts digital access has on children [00:21:17] - The investing criteria that she and her firm have developed for founders and business models they find desirable [00:32:00] - The beachhead problem for entry points, encouraging good focus and entry point selection, and who’s done it well [00:35:33] - The history of the consumer of how they buy and sell and where the shifts in power have been [00:39:47] - Other interesting trends she’s seeing in the seller empowerment era [00:43:35] - How different her investing models are for linear product businesses [00:46:45] - Frameworks she’s developed for evaluating a brand early on [00:49:57] - The most defining moment in Forerunner’s history and the hardest lesson she’s had to learn [00:53:13] - Ways she’s fostered and mentored young investors at Forerunner [00:54:04] - What the most underappreciated thing is today about the consumer [00:54:50] - User and customer development strategies that work well for early stage products [00:56:26] - Three businesses young investors should study to educate themselves on great consumer businesses; Shoe Dog [00:59:49] - Where they find the companies Forerunner tends to invest in, and how to build and effective deal flow pipeline [01:05:07] - The kindest thing anyone has ever done for her

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:52] - [First question] - What it was like at a high level building Uber Eats [00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it [00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats [00:15:17] - Things that Uber Eats got most right that he’s proud of [00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats [00:20:36] - What made India such a competitive environment [00:26:13] - What improved the most in his playbook for launching in a new city [00:27:14] - Defining what best means in this competitive sector [00:29:01] - Dealing with suppliers in different categories and finding an ideal balance [00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace [00:36:12] - Defining what founder market fit is and being “fingertippy” [00:37:29] - His views on the relationships between leaders of businesses and their cultures [00:40:26] - Why Uber believed in him more than he did [00:41:40] - What he learned about marketing to suppliers specifically [00:45:18] - Differing views he has on the concept of failure [00:47:31] - Thoughts about ideas versus execution and the relative importance of the two [00:49:10] - Effectively measuring opportunity cost and using it in decision making [00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark [01:00:15] - The kindest thing anyone has ever done for him

My guest today is Paul Orfalea. Paul founded Kinkos, the popular copy chain, in 1970. He started with a single photocopy shop in California and grew the business into a $2 billion multinational operation over the course of his 30 years in charge. Paul is a non-traditional leader in the best sense and we discuss his philosophy of business building, from why your subordinates should frustrate you, why you shouldn’t love your business and tips he learned on hiring well. Please enjoy this conversation with Paul Orfalea. Founders podcast on Paul Orfalea. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:58] - [First question] - What it was like to be a very bad student in highschool [00:04:22] - When he first realized he was unemployable [00:05:02] - The origin story of the very first Kinko’s [00:07:53] - Finding what has worked well in each Kinko’s and coaching managers [00:11:45] - The difference of working on and not in the business [00:13:57] - Why a good salesperson will sell you broke [00:15:36] - Why he teaches, what he teaches, and his teaching style [00:18:31] - Explaining the Federal Reserve in two minutes [00:21:58] - The role of anger in his career and something he’s worked on over time [00:22:31] - Where Kinko’s falls on the spectrum of bad to great businesses [00:26:18] - Lessons learned about using the word employee [00:27:21] - The most clever marketing strategy he ever deployed or designed [00:27:45] - Learning to spread the glory instead of the money [00:28:30] - The state of entrepreneurship today compared to when he started [00:30:42] - What motivated him across his career [00:31:35] - Why being in it for the money seems odd in today’s lens [00:32:34] - Who he most admired or most admires today [00:32:51] - Let My People Go Surfing: The Education of a Reluctant Businessman [00:33:08] - Preserving the alignment of integrity and action [00:34:57] - How good he is naturally with numbers and math being dyslexic [00:38:05] - His parents’ impression of him while he was building Kinko’s [00:39:56] - The most interesting person he’s ever worked with at Kinko’s [00:40:48] - What he would have done differently if he started from scratch [00:41:24] - Something that is most underappreciated about the United States [00:43:00] - The kindest thing anyone has ever done for him [00:43:57] - A big lesson he’s earned in a deeper way that he wishes he could share with others

My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products, it’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why you need to focus on benefits rather than features, and how to pick the right monetization model. Please enjoy my conversation with Madhavan Ramanujam. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:48] - [First question] - How he arrived at a radically different way of building products [00:05:07] - An example of coming up with a price before the product [00:08:35] - Distinctions between a willingness to pay and positive feedback [00:10:29] - How to make sure you’re talking to the right potential customer in the first place [00:13:32] - Productizing for different customer segments [00:16:16] - Questions companies should be asking to get accurate feedback [00:21:18] - What he’s learned about the motivations of potential buyers [00:22:43] - What leaders, killers, and fillers are [00:24:37] - Some of the biggest mistakes companies make while following his formula [00:25:35] - A rule of thumb for what is a benefit versus a feature [00:27:35] - Five distinct pricing models for charging a customer [00:30:46] - Whether or not the value piece of all of this revolves around time and money [00:33:27] - What he tells entrepreneurs about pricing their products that most surprises them [00:35:16] - Defining the first four categories of failure [00:40:13] - Reasons why so many innovations fail to monetize and pricing being a CEO topic [00:41:51] - Good rules that leaders can use to have a general sense for effective pricing [00:47:38] - Behavioral changes and observations as the absolute price move up and down [00:50:36] - Is there a pricing genius we should take note of? [00:53:18] - The single question every leader should ask themselves [00:53:46] - The kindest thing anyone has ever done for him

My guest today is Scott Wilson. Scott is the CIO of Washington University’s endowment, which manages over $13 billion. In this conversation we discuss WashU’s non-traditional endowment model and cover a variety of asset classes and geographies. We talk about the qualities Scott looks for in managers, lessons from investing in Asia and emerging markets, and red flags in the venture space. Please enjoy this conversation with Scott Wilson. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:38] - [First question] - What he learned about markets from quant fixed income trading [00:04:42] - How his experience shaped his degree of skepticism of the world [00:05:15] - The story that brought him to Grinnell College [00:06:45] - What his education was like back in 2010 and what seemed sensible and insane when he arrived [00:09:37] - His philosophy around trying to have more direct ownership [00:12:03] - Lessons learned about choosing good partners and doing it effectively over time [00:13:51] - Things that are most enjoyable about getting to know new managers [00:16:17] - Why they spend so much time in frontier and emerging markets [00:18:21] - Lessons learned from investing in China and thoughts on it today [00:23:16] - The worst things he sees from venture investors [00:24:39] - Whether or not venture investors should care more [00:27:55] - What percentage of investors in private equity are investors versus just involved to try and engineer returns [00:28:59] - His impressions on hedge funds and the evolution of the hedge fund model [00:31:18] - The role that credit can play in a portfolio like the one he manages now [00:36:34] - Everything he’s learned about asset managers acting as asset gatherers [00:39:35] - Ways he fights convergence and tracking error overseeing so much capital [00:41:49] - What it’s like to go through the bad side of tracking error [00:45:43] - What he sees as a normal level of tracking error for endowments and foundations [00:46:59] - Why such big pools of institutional capital tend to look so similar [00:48:10] - Whether or not real estate sits somewhere between stocks and bonds [00:51:10] - Colliding managers in a fun and spirited way at meetings [00:52:16] - An investing trip from his career that he finds most memorable [00:52:50] - The kindest thing anyone has ever done for him

My guests today are Julio Vasconcellos and Mate Pencz, who are partners at Canary and Atlantico, leading early-stage investment firms in Latin America. They’re also both successful entrepreneurs. Mate is the co-founder and CEO of Brazilian real estate unicorn, Loft. Julio was Facebook’s first country lead for Brazil, an entrepreneur in residence at Benchmark, and the former founder of Peixe Urbano which sold to Baidu. This conversation was a great opportunity to dive into the state of investing and business in Latin America today, what it looks like on the ground, and cover the most interesting findings from Atlantico's annual report on Digital Transformation in the region. Please enjoy my conversation with Julio and Mate. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:39] - [First question] - A broad perspective on what is interesting in Latin American investing today - Latin America Digital Report 2022 [00:05:15] - What makes up the existing 1.5% tech penetration index in Lat Am [00:06:11] - Florian Hagenbuch, Mate Pencz - Everything Will be Bought Online (Loft); David Velez - Building the Branchless Network (Nubank); How important it is to parse by country when it comes to building businesses in LatAm [00:08:31] - Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere [00:12:28] - Why the adoption of PIX was so successful and how it maps onto the banking system [00:14:27] - What PIX’s widespread adoption will enable for the coming wave of entrepreneurs [00:22:30] - Shifting to remote work and how it’ll affect LatAm workers and talent [00:30:06] - What it feels like for an entrepreneur today compared to when Loft launched [00:32:36] - Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants [00:40:12] - Sources of available funding for venture and private equity [00:42:54] - What valuations look like and whether or not there’s an entry multiple discount [00:45:12] - Seeking evidence that crypto is used in more valuable ways in emerging markets [00:48:00] - Areas where LatAm is operating in a future state more so than elsewhere [00:50:28] - What the right amount of global firm participation in capital partnerships looks like [00:52:38] - Big standout lessons from their operating days [00:55:53] - What is most exciting and concerning about their investing style and investing writ large in LatAm [00:58:51] - The kindest thing anyone has ever done for Julio

My guest today is Trina Spear, a former investor at Blackstone and the co-founder and CEO of FIGS. FIGS is a multi-billion-dollar public company that built a category-leading brand selling scrubs to healthcare professionals. It was a problem hiding in plain sight and FIGS solved it through vertical integration and customer obsession. Trina shares so many interesting, simple lessons that are often ignored in business. Please enjoy my great conversation with Trina Spear. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:28] - [First question] - The original insight that lead to founding FIGS [00:04:28] - Why obvious opportunities can go so long before being seized [00:06:23] - Key dimensions needed to improve the product and the early days [00:09:02] - Basic overview of a clothing retailer’s financial profile [00:10:49] - Financing the business and the early stage cash flow cycle [00:13:04] - Strategies to manage workflow and making sacrifices [00:14:43] - Advice for people trying to build their brands in a hands-on way [00:17:14] - The biggest calculated risk she took in the first five years [00:19:00] - Building a foundation that allowed for such explosive growth [00:21:44] - The story that allowed FIGS to connect with their customers [00:24:43] - Painting a picture of the size and scope of healthcare apparel [00:26:22] - Things lazy companies do and thoughts on product variety [00:28:54] - Defining SKU productivity and what to do with low productivity products [00:30:21] - Chip Wilson Book; Lessons learned from reading Chip’s story [00:31:58] - Balancing a healthy relationship with your CFO [00:33:59] - Where she sees the most runway to tackle and continue to execute [00:35:46] - A women-lead industry and her time spent with Meg Whitman [00:38:13] - The most essential jobs she feels she has and shouldn’t do as the CEO [00:40:03] - Thoughts about relationships with investors and messaging [00:42:14] - What she’d be most focus on in founders if she was just an investor [00:43:57] - The most stressful thing that has ever come across her desk [00:44:41] - What types of things bring her the most joy in building FIGS [00:45:27] - Philosophy of hiring given their small team and when it’s okay to hire [00:46:56] - Whether or not there’s a role for non A players in businesses [00:47:48] - The kindest thing anyone has ever done for her

Today, we are sharing an episode of Web3 Breakdowns with you. My Invest Like the Best conversation with Gabe Leydon last year was one of my favorites and became one of our most popular. Since that conversation, Gabe has become one of the most interesting builders in web3 that I know so I was excited to have him back to share his views of the space and how it might grow. If you enjoy this episode, subscribe to Web3 Breakdowns on your preferred podcast player. My guest today is Gabe Leydon, who’s episode last year was one of our most popular ever. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I know. He was the co-founder of Machine Zone, which pioneered free-to-play hits like Mobile Strike and Game of War. Over the past year, he has been in stealth mode building a web2 meets web3 video game company called Limit Break, which is founded on a brand new business model that he calls free-to-own. We dive into his vision for the future of gaming, how it could onboard a billion users onto the Ethereum network, and why the LTVs of crypto gamers are so far higher than their web2 counterparts. Please enjoy this conversation with Gabe Leydon. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Coinbase Prime. Coinbase Prime combines advanced trading, battle-tested custody, financing, and prime services in a single solution. Clients have used our comprehensive investing platform to execute some of the largest trades in the industry because they are the only publicly-traded company with experience trading and custodying crypto assets at scale. Get started with Coinbase Prime today at coinbase.com/prime. ----- Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @Web3Breakdowns | @ericgoldenx | @patrick_oshag Show Notes [00:02:19] - [First question] - What free-to-own gaming means and why it’s exciting [00:11:40] - Pre-existing behavior that sets up free-to-own for success [00:12:32] - The progression from PFP NFTs to clubs and the road ahead [00:14:16] - Overview of the business and monetization model for free-to-own games [00:17:51] - The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation [00:22:14] - Balancing supply and demand in a free-to-own market [00:24:35] - Creativity and extensions of the DigiDaigaku NFTs [00:26:13] - Tiering, breeding and the role the Genesis series will play in the Digi universe [00:27:32] - The level of brand marketing NFTs will unlock for businesses [00:29:57] - How free-to-own will be the primary monetization method for brands [00:31:21] - A future with a global marketing shift towards digital property and economies [00:33:06] - Why most of the winning PFP projects are of unique characters [00:35:50] - His Twitter strategy and how he’s created such a fervor around him [00:42:40] - What will define the legendary marketers over the coming decade [00:43:06] - Interoperability needed to make real-world NFT uses appealing to consumers [00:44:44] - Whether or not we’ll see more token-gated business in the future [00:45:40] - Stable Diffusion and his impression of the new AI art generating bots [00:48:56] - What great distribution looks like in a digitally native world [00:50:03] - The emphasis of innovation taking place in the metaverse being a bad thing [00:53:24] - Things he most admires in adjacent games and creators in his world [00:54:25] - Unique game mechanics that Web3 technology unlocks [00:56:16] - NFTs will be the gateway for people to acquire crypto

My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss the different dimensions of entrepreneurship and Shopify’s role in promoting it, as well as exploring the company’s transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:26] - [First question] - His interpretation and definition of a person’s life's work [00:05:50] - The story of the riverstone and the average polished executive [00:08:36] - The thing he can’t help but do; and focusing on our compulsions [00:13:12] - How he would boil things down to the most simple entrepreneurial formula; Distilled [00:16:38] - What is harder and easier about new business formation today [00:21:03] - The countervailing forces for small-to-medium business entrepreneurship [00:24:31] - What he’s learned about operationalizing ideas and mentor lessons [00:29:08] - A piece of fortune cookie advice that he finds terrible [00:30:49] - How Brands Grow; his philosophy on marketing & distribution [00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses [00:38:43] - What it was like getting their first app developer for the Shopify app store [00:41:17] - The state of ecommerce today writ large and what trends are interesting [00:45:46] - Lessons learned about the digital places that people are buying [00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic [00:52:25] - Tips for communicating effectively with Wall Street [00:54:14] - An investor that stands out in memory that really impressed him [00:55:10] - Important aspects of his world that are worth mentioning [00:57:04] - Lessons learned about motivating people through DJing [00:59:12] - Whether or not reading the crowd can apply to business [01:03:49] - The kindest thing anyone has ever done for him

My guest today is Mitch Lasky. Mitch is a partner at Benchmark and one of the leading figures in the video game industry. Over the last 30 years, he has built, led, and invested in a number of the best gaming companies in the world, including Activision, EA, Riot, Snapchat, and Discord. I couldn’t think of a better person to break down the anatomy of great gaming businesses and Mitch does not disappoint. His insights are remarkable. Please enjoy this excellent conversation with Mitch Lasky. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:31] - [First question] - Why there aren’t more famous gaming investors [00:05:08] - The most important features of the modern gaming business model [00:07:11] - Developing his aesthetic taste and investing decision skill [00:08:03] - What makes a game fun [00:09:26] - How delivering a pleasurable active user experience differs from passive content and media [00:11:09] - The developers of Doom being the first real modern video game company [00:13:09] - Half-Life’s important role in the development of the gaming industry [00:17:54] - How some of the big game aggregators get started in the first place [00:19:58] - What Riot can teach non-gaming businesses about business writ large [00:21:10] - Ways that the change from physical games to downloads changed monetization [00:31:47] - The impact of Apple’s privacy changes on gaming revenue [00:34:11] - How the access to professional game engines and a lower friction environment will change the industry [00:37:04] - Whether or not there is a step beyond mobile [00:39:42] - Ways platforms like Twitch and Discord have influenced gaming [00:42:26] - What he’s learned about games that allow them to seemingly exist forever [00:45:17] - Signs of a healthy gaming community [00:46:21] - The role of celebrities and influencers and generating retained audiences [00:47:45] - Whether or not crypto will unlock new opportunities for in-game monetization [00:52:50] - Key categories of motivators that could replace a ponzi-style in-game inflation [00:54:36] - Contrasting League of Legends versus a Ready Player One style world [00:58:22] - Emerging technologies and trends that may revolutionize the industry [01:02:41] - The most genius game pattern he’s ever played [01:04:44] - What attributes will define the great game investors in the coming decades [01:06:59] - How much his experience lends itself to investing in other sectors [01:11:07] - The kindest thing anyone has ever done for him

My guest today is David Senra. David has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. I found this to be one of the most energizing conversations I’ve had in a long time, and one I’ll return to often. David’s work and extraordinary energy aligns so well with our mission at Colossus that we’re excited to partner with him. You’ll soon be able to find his podcasts and transcripts at joincolossus.com where we hope you’ll learn as much from him as we have. If you like this conversation, be sure to subscribe to David’s podcast called Founders. Now onto our discussion. Please enjoy this great conversation with David Senra. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:01] - [First question] - When he first fell in love with reading [00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast [00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies [00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives [00:22:45] - The dynamic and relationship between inspiration and perspiration [00:27:11] - Commonalities between the layers of leadership and support underneath founders [00:31:52] - Where else he’s seen ego rear its head in good and bad ways [00:38:34] - How often do great founders break the law or enter gray areas of it [00:41:22] - The role constant learning and listening plays in success [00:45:12] - Talking about how anything worth doing is worth doing to excess [00:52:18] - Describing the soul of founders and businesses [00:58:39] - What he’s learned about all of these founders as it relates to marketing [01:08:10] - Who his idols are in podcasting specifically [01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet [01:19:55] - The kindest thing anyone has ever done for him

My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:34] - [First question] - What the enterprise software market looks and feels like to him [00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades [00:09:42] - Bringing an engineering mindset to enterprise software investing and culture [00:12:36] - A single change he made to a business that stands out most in memory [00:14:33] - Qualities that are most critical in defining a good enterprise software company [00:18:07] - How the profile of companies he’s bought has changed over the years [00:20:33] - Categories of software he tends to gravitate towards [00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples [00:27:17] - Lessons learned about customer churn over his twenty two year career [00:29:44] - Capital cycles and how much they truly impact the software world [00:31:53] - What elements of building Vista have most appealed to him over the years [00:38:06] - The war for talent and what his senior team would debate most [00:40:01] - Biggest mistakes Vista has made and what they taught him [00:41:09] - What has him most insecure or paranoid about the platform he’s built [00:43:10] - The advice he’d give on having good relationships with LPs [00:44:57] - The largest risk he or Vista has ever intentionally taken [00:46:15] - What he’s learned about having a winning negotiations and sales approach [00:49:27] - Who he’d give all of his capital to outside of Vista [00:53:08] - The work he does in the foster world [00:54:49] - The kindest thing anyone has ever done for him

My guest today is Katherine Boyle, a general partner at Andreessen Horowitz. Katherine started her career as a reporter for The Washington Post before moving into VC at General Catalyst. She now leads a practice at a16z called American Dynamism, investing in companies that are solving critical issues in areas like defense, housing, and education. For the full show notes, transcript, and links to mentioned content, check out the episode page here. The content here is for informational purposes only and should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security and is not directed at any investors or potential investors in any a16z fund. For more details, please see a16z.com/disclosures. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:42] - [First question] - The origin and overview of the term American Dynamism [00:05:01] - Why the shift to a move slow and make sure nothing breaks mentality [00:07:31] - What about the American system today feels broken and stale [00:09:48] - Becoming a journalist at The Washington Post [00:11:35] - Describing the power landscape of media as it exists today [00:12:28] - Major categories of American Dynamism that matter most [00:14:29] - What matters more or less to her as an investor in these categories [00:17:31] - Whether or not there’s anything fundamentally broken about our government [00:19:36] - The Systems Bible; What excites her about aerospace and defense and what creates opportunity and demand in these sectors [00:26:01] - An overview of how lobbying works and who does it and why [00:33:09] - The biggest problems that currently exist in the K-12 school system [00:37:34] - The role immigration will play in range of outcomes in these main categories [00:39:32] - Key takeaways about housing in light of American Dynamism [00:42:09] - Her interpretation of the chart that shows inflation in categories over time [00:47:56] - Whether or not expected returns and risk profiles are different in this area [00:49:55] - Overview of the anatomy of a great story [00:51:30] - The story she tells founders at this stage so establish a partnership [00:52:46] - The kindest thing that anyone has ever done for her

My guest today is Ravi Gupta. Ravi spent a decade in private equity at KKR before joining Instacart as their first CFO and COO. He navigated them through a critical moment in their history and returned to investing in 2019 as a partner at Sequoia. Our discussion gets to the heart of what it means to build and invest in great businesses, and we talk a lot about the personal side of the journey, which tends to get overlooked. Please enjoy this great conversation with Ravi Gupta. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:34] - [First question] - Why it’s important to keep the main thing the main thing [00:04:59] - His first exposure to this idea; How Will You Measure Your Life [00:07:50] - Thoughts on the conflict of the main thing for a business and a person [00:11:45] - The most painful episode of enacting this philosophy at Instacart [00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus [00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode [00:24:48] - Whether or not the feedback loop for things that work are very short [00:26:04] - The nature of joy and competitiveness in company culture [00:29:01] - How he assesses the depth that motivation runs through people and companies [00:32:43] - Analysis of his own motivations in life [00:35:34] - Differences and shortcomings of virtuous and vicious motivators [00:37:15] - How to accurately figure out someones motivators in a short period of time [00:40:22] - Being Demanding and Supportive; Why these words pair so well together [00:45:55] - What he’s looking for in companies given all of the ideas discussed so far [00:51:11] - How his ideology manifests inside of Sequoia [00:58:44] - What it’s like to mentor an apprentice and how to do it well [01:02:40] - Adjusting behaviors to meet current markets where they’re at [01:06:13] - Defining what a great product is [01:07:56] - What he did to turn around Instacart by narrowing their focus [01:12:28] - The things that most drove the switchover at Instacart [01:14:53] - The kindest thing anyone has ever done for him

My guest today is Will Thorndike. I first spoke to Will in 2017 about his excellent book The Outsiders and his career in private equity. I titled that conversation: How Skilled Capital Allocators Compound Capital. In many ways this conversation continues where that one left off. Through the lens of his new project, a podcast called 50X, we explore the power of multi-decade holding periods and the shared characteristics of businesses that are able to compound returns at high rates for abnormally long periods of time. Please enjoy this discussion with my friend, Will Thorndike, and if you haven’t subscribed to 50X, I highly recommend doing so. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - How working on The Outsiders project shaped his thinking [00:06:29] - His interest in long-term holding periods and dealing with multi-decade time horizons [00:09:42] - Shared characteristics among compounding machines [00:11:23] - Defining capital efficiency and the return on tangible capital metric [00:13:02] - An example of an attractive business that requires a lot maintenance CapEx [00:14:22] - Thoughts on the measurement of intangibles and whether or not he’d avoid great businesses that are intangible heavy [00:15:25] - Tangible ways capital efficiency rolls into compounding capacity [00:20:32] - Lessons learned about good game selection for companies [00:25:09] - An example of a decentralized structure and why it works so well [00:30:00] - What the best serial acquirers do for long-term holders [00:31:46] - Advantages of using debt for financing and acquisitions [00:33:39] - How different the future might be for young CEOs with capital allocator mindsets [00:39:09] - 3 companies that Housatonic Partners has owned for more than 25 years [00:40:29] - What made Karen Moriarty so good for so long [00:42:36] - The crossover between public and private investing and the virtues of each sector [00:47:10] - What is at the top of his wish list of the companies he wants to explore [00:50:25] - The development of investor conviction over time and what he’s learned about it [00:52:19] - Lessons learned about producing great media [00:53:43] - What he can teach us about deep research on companies with analysts [00:55:10] - Adjusting his thinking and investing in a high variance world

My guest today is Alok Vasudev. Alok is an early-stage investor who has been in the crypto space for a very long time. Before co-founding Standard Crypto, he was an investor at Benchmark and S28 Capital. Given Alok's experience and the prevailing mood right now in crypto, this is a particularly interesting discussion on the ecosystem writ large. We discuss whether the bubble can be thought of as productive speculation, his views on skeptics in the space, and look at some big, potentially, underestimated ideas. Please enjoy my conversation with Alok Vasudev. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:31] - [First question] - His history in venture and thoughts on the crypto ecosystem [00:06:06] - What it means to be great at searching for white space as a venture capitalist [00:08:00] - Things his original venture peers would say he was best and worst at [00:09:24] - How he would address crypto skeptics broadly given today’s market [00:13:35] - Whether or not it’s appropriate to look at each crypto token as a stock [00:15:32] - The pool of demand for Dai and the end use-case itself for the stablecoin [00:17:01] - What matters to him the most in the world of stablecoins [00:19:59] - Defining sound and unsound collateral [00:21:02] - Why the US doesn’t digitize the dollar and how being a government entity would impede some of their capabilities [00:23:21] - What a community operated computer unlocks compared to a standalone one [00:27:09] - What persistence and resilience from community computers open up [00:29:30] - Something going on that people aren’t talking about yet in regards to blockchains [00:33:54] - The notion of productive speculation and what it means [00:36:03] - One of the best historical examples of productive speculation [00:42:29] - How things outside of the blockchain become integrated and connected to it [00:45:43] - Ways crypto will impact the gaming world over the coming years [00:49:10] - Handicapping a potential future where NFTs work and blockchains don’t benefit [00:51:42] - Thoughts on the world of art, IP, NFTs, and its changing landscape [00:54:43] - Whether or not there are companies being built that can streamline and facilitate this form of connection between artists and their fanbases [00:58:13] - Other controversial opinions he holds in the crypto community [01:03:13] - What he’s most bullish and bearish on right now [01:07:29] - The kindest thing anyone has ever done for him

My guest today is Matthew Ball. Matt is an investor, the former head of strategy at Amazon studios, and one of the brightest minds in the media industry. Through his essays and now his book, which launches today, Matt has established himself as the foremost authority on the Metaverse, which has stormed into the public eye since I first had him on the show two years ago. The Metaverse is the focus of our discussion and I hope you enjoy this encyclopedic tour through all of its details as much as I did. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:37] - [First question] - Which most represents the Metaverse: Minecraft, Ready Player One, Fortnite, or Facebook’s Horizon [00:05:58] - Facebook trying to own the concept of the Metaverse by changing their name [00:09:22] - Defining what the Metaverse is and a good working definition of it [00:11:33] - The state of the engines behind 3D output and the history of them [00:16:32] - The role IP played in bootstrapping the first Metaverses [00:18:32] - Where the ability to create digital environments will lead, and what Unreal 7 could look like compared to Unreal 5 today [00:21:03] - Natural limits of the Metaverse compared to real-world experiences [00:24:16] - Other sensory inputs that will need to be improved for digital immersion [00:26:59] - Why the initial excitement of trying something like Oculus wears off over time, both for casual gamers and those excited about this new frontier [00:31:40] - Changes in technology and new projects that have him most excited that will empower the digital infrastructure for Metaverses [00:37:14] - What interoperability means and why it has its own chapter in his book [00:31:52] - How Roblox connects with Fortnite and how far down we need to go to build a bridge between digital worlds [00:46:13] - What will drive commerce in the Metaverse and the possibility for a singular currency standard [00:51:35] - Considering the demand for the Metaverse and whether or not it will be a constraint on adoption and success [00:57:37] - What the modern equivalent of a lemonade stand will be in the Metaverse [00:59:58] - The lower adoption rates for more participatory media consumption[01:03:19] - Potential pitfalls and the dark side of the metaverse [01:06:14] - Who the categorical winners of the Metaverse might be [01:14:15] - The top things he would suggest exploring to best understand the Metaverse

Today we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of 50X – a new series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus. Will’s book, The Outsiders, is one of the best business and investing books you will find. Now you will hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold. First up is TransDigm, an aerospace components manufacturer that has returned over 1,750X since its inception nearly three decades earlier. In this episode, Will is joined by Nick Howley, TransDigm’s long-time CEO and Chairman. Make sure to subscribe to 50X in your preferred podcast player. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. The team at Tegus has built a full company intelligence platform aimed at streamlining the investment research process. In preparation for the 50X series, we actively used Tegus to gain qualitative insights beyond traditional reported data. To learn more and enjoy a free trial, visit tegus.co/50x. ----- 50X is a podcast that dissects the anatomy of extraordinary long-term investments. The show is hosted by Will Thorndike and the team at Compounding Labs, and brought to you in partnership with Colossus. In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources. Learn more and dive into our research at 50xpodcast.com Follow us on Twitter: @50Xpodcast and @joincolossus Show Notes [00:00:00] – 50X Introduction [00:02:00] – Sponsorship: Tegus [00:07:04] – Episode Introduction [00:09:05] – Nick’s Background pre-TransDigm [00:11:56] – Original Acquisition from Imo Industries in 1993 [00:15:33] – Thesis and Performance under Kelso & Co.’s Ownership [00:18:42] – Genesis of Three Key Value Drivers: Price, Productivity, and New Business [00:21:07] – Building the Management Team [00:24:05] – Early Lessons on Value Drivers [00:27:53] – Capital Allocation under Kelso & Co. [00:28:51] – Sale to Odyssey Investment Partners in 1998 [00:30:26] – Strategy under Odyssey’s Ownership [00:31:51] – Early Acquisitions and Integration Playbook [00:37:26] – Early External Crises [00:41:13] – Snapshot at Conclusion of Odyssey’s Ownership in 2003 [00:43:19] – Building a Decentralized Culture [00:46:23] – Differentiated Approach to Compensation [00:52:12] – Sale to Warburg Pincus in 2003 [00:55:51] – Shift to Inorganic Growth under Warburg’s Ownership [00:58:08] – Evolution of M&A Process [01:05:37] – Post-Acquisition Expectations and Post-Mortem Process [01:09:48] – Divesting Acquired Assets to Maintain Focus [01:11:29] – Embedding Value-Generative Culture via Hiring and Training [01:13:54] – Quarterly Product Line Reviews [01:20:43] – Recap of Private Investment Returns and Snapshot pre-IPO

My guest today is Alice Bentinck, co-founder of Entrepreneur First. Entrepreneur First, or EF, invests pre-company by systematizing the way that talented individuals find co-founders, develop ideas, and scale into companies. They’re an incubator of teams and ideas on a mission to create impactful companies that, without their help, wouldn’t exist. I first spoke with Alice’s co-founder, Matt Clifford, over two years ago and have been fascinated with EF’s model of investing ever since. Please enjoy my conversation with Alice Bentinck. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:33] - [First question] - Overview of what Entrepreneur First is today [00:05:57] - How she identifies the people to bring into each cohort and convince them to quit their job to join EF for eight weeks [00:10:10] - Categories of the main types of people who join the EF program [00:12:32] - What she’s learned about negative screening at the first stage of recruits [00:14:07] - Positive signals she looks for in early admissions [00:17:46] - What the program itself feels like as a participant [00:21:29] - Reasons partners tend to fail and whether or not EF advises equity splits between founders [00:24:49] - How important the idea is that the team will be working on [00:28:04] - Exercises she enjoys doing with the new cohorts around social norms [00:30:38] - How the experience looks physically in each city [00:32:57] - Categories of data collected as the cohorts unfold and making investment decisions [00:36:46] - Ways the companies mature after EF and what kinds of investors fund the next stage of their startups [00:40:55] - Why aren’t there ten EF style initiatives or organizations [00:44:26] - Motivations for the change in their holding company structure [00:46:48] - The love of product and ideas she’s playing with right now [00:51:49] - Cities she has her eye on that EF is not a participant in today and criteria that makes a city desirable for EF [00:54:03] - A piece of software that EF could benefit from that doesn’t exist yet [00:55:30] - The keys to her harmonious relationship with her co-founder Matt [00:59:01] - National and international impediments that directly impact company building [01:01:36] - The kindest thing anyone has ever done for her

My guest today is Jess Lee. Jess is a partner at Sequoia Capital as well as their Chief Product Officer. Before becoming an investor, Jess co-founded fashion app, Polyvore, and was an early product manager for Google Maps. Most recently, she founded All Raise, a non-profit that is changing the gender balance in tech. Our discussion ranges from Burning Man to Marvel to Sequoia’s mobile app and I hope that Jess’s passion for delighting users rubs off on you. Please enjoy my conversation with Jess Lee. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:35] - [First question] - Why more investment firms don’t have a product mindset [00:05:22] - How to approach building a productized version of capital [00:08:00] - Ways Ampersand measures success and judging their own performance [00:08:49] - Driving reasons that Sequoia wins deals beyond their brand name [00:10:28] - How her work as CPO at Sequoia has changed her investing approach [00:12:28] - Everything she’s learned about community and its relevance to business [00:17:48] - What the gold standards are for studying strongly built communities [00:19:42] - What it is about Comic-Con that works so well from a community standard [00:21:18] - The role that scarcity plays in communities writ large [00:23:10] - Product mindset and customer obsession [00:24:33] - Knowing when it’s okay to begin expanding [00:28:12] - Rates of change in her investment progress and dollars going to female founders [00:29:36] - Systemic bias and what’s driving a lack of funds towards female founders [00:32:26] - How she applies community building lessons to All Raise [00:33:20] - The internal learning culture in Sequoia that others could adopt and benefit from [00:37:01] - Which Marvel superheroes her Sequoia partners would be [00:39:05] - Seeds of motivation for Arc and what it is [00:44:31] - The best ways she’s seen companies manage and support human capital [00:45:36] - Biggest mistakes made when managing human capital [00:46:42] - What working on Google Maps taught her about product development [00:48:42] - Someone she admires and has learned the most from in All Raise [00:50:02] - Measuring success at Sequoia over the next ten years [00:52:20] - The kindest thing anyone has ever done for her [00:53:42] - What it was that made the people who believed in her take a chance on her [00:55:03] - Things in pop culture today that most has her attention

My guest today is Ken Stanley. Ken is a Professor in Computer Science and a pioneer in the field of neuroevolution. He is also the co-author of a book called, Why Greatness Cannot Be Planned, which details a provocative idea that setting big, audacious goals can reduce the odds of achieving something great. We discuss that revelation in detail and how to apply it in our day-to-day lives. Please enjoy this great discussion with Ken Stanley. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:36] - [First question] - The best way to change the world is to stop trying to change it [00:06:26] - The kinds of goals his work addresses and the ones it doesn’t [00:08:46] - Almost no prerequisite to any major invention was invented with that major invention in mind [00:14:04] - Picbreeder [00:17:21] - How looking for specific results often makes arriving at them a longer process [00:24:00] - The importance of the individual in a web of invention and disruption [00:28:30] - How generations progressed in Picbreeder when consensus mechanisms were inserted into the process [00:31:24] - Examples of stepping stones that were invented that became something even greater [00:36:02] - What his research means for how we should conduct ourselves writ large [00:44:17] - Thoughts on necessity being the mother of all invention [00:50:08] - The ways that society is arranged is psychologically toxic [00:55:14] - The role that constraints play in creative output and outcomes in general; Brett Victor - Inventing on Principle [01:01:10] - What the constraints are that he sets for himself in AI development [01:04:44] - To know what’s new you need to know what’s not new [01:06:47] - The kindest thing anyone has ever done for him [01:08:28] - How he would allocate resources to create more innovation in the world

My guest today is Lydia Jett, Managing Partner of SoftBank Investment Advisers. Lydia leads the team’s consumer, internet, and e-commerce investments and has worked with many of the most significant consumer platforms in the world, including as a board member of Coupang and Flipkart. We cover all aspects of e-commerce and explore Lydia’s evolution as an investor alongside Masa Son at SoftBank. Please enjoy my conversation with Lydia Jett. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:34] - [First question] - What curiosity thread she’s been pulling on thus far in her career [00:05:17] - The biggest felt differences doing things one way for a decade and changing now [00:07:08] - Learning about tailwinds and what the predominant ones are that exist today [00:10:44] - Competitive frontiers that exist today in e-commerce [00:12:14] - What drives companies that grow faster than their competitors [00:13:15] - What areas the world’s most innovative e-commerce companies are focused on [00:16:38] - Unique characteristics that they select for in ecommerce CEOs and founders [00:19:03] - Upside down approaches to e-commerce that aren’t common in America yet [00:23:05] - Lessons learned about business models that don’t work in e-commerce [00:27:47] - What western investors should know about Coupang [00:30:12] - Everything she’s learned about vertical integration [00:33:01] - Everything she’s learned and cares about in regards to margins [00:37:17] - The most extreme version of efficiency gain she’s seen deployed [00:41:27] - The role the size of assets plays at SoftBank [00:47:42] - Focusing on efficiency and smart allocation first before trying to scale [00:50:33] - Companies as products that investors buy and defining what great looks like [00:53:16] - The danger of premature optimization around a set of KPIs [00:55:46] - How important the specific founder is for their given e-commerce company [00:58:18] - Why e-commerce companies tend to start from a worse place than offline ones [00:59:45] - Ways that she’s changed from working alongside Masayoshi Son for a year [01:03:31] - Who comes most to mind as a great investor [01:05:23] - The kindest thing that anyone has ever done for her

My guests today are Josh Wolfe and Chris Power. Josh will be a familiar voice to many of you and is the co-founder and General Partner of Lux Capital. Chris is the founder and CEO of advanced manufacturing start-up, Hadrian. Most of our discussion centers on the need to modernize the factories that supply our space and defense industries. But given the current market environment, we also talk about capital conditions and the responsibility to build products that really matter. Please enjoy this conversation with Josh Wolfe and Chris Power. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:40] - [First question] - An overview of the precision manufacturing industry writ large [00:08:28] - Why the manufacturing sector has so many great investment opportunities [00:12:58] - Anduril Breakdown; What Hadrian in its final form will unlock for manufacturing [00:16:08] - What the demand side looks like for manufacturers in its current state today [00:18:29] - How the nature of demand will shift for this style of manufacturing in the future [00:22:51] - Important rare earth materials, supply chain constraints, and the revival of commodities [00:27:55] - The key set of jobs being done by mom and pop shops that could be innovated on and done within a Hadrian factory [00:30:35] - What is going on inside of a Hadrian factory and how they will evolve over time [00:32:10] - Prosecuting diligence on someone's ability to execute on their behalf [00:37:14] - The PhD arrogance trap and how a Hadrian machine will be better in five years from now [00:48:08] - Breadth of ability versus focus and selling parts to buyers early on [00:50:42] - Lessons learned and advice for understanding the focus problem [00:56:39] - Fat startup vs. lean startups and making the hardest irreversible decision during Hadrian’s early days [00:58:31] - Enduring more schlep work than less being a good signal [00:59:06] - Chris’ thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes [01:03:36] - Josh’s thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes [01:07:22] - The kindest thing anyone has ever done for Chris

My guest today is Martin Casado. Martin is a general partner at Andreessen Horowitz where he focuses on digital infrastructure. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion in 2012. Martin has studied, built, and invested in digital infrastructure his whole career and is the perfect person to discuss the most interesting aspects of the industry. Please enjoy this great conversation with Martin Casado. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus. ----- Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:43] - [First question] - The state of the digital infrastructure industry today [00:04:02] - The major stages and eras of cloud technology [00:06:30] - Overview of Dropbox’s story and the two major trends at the time of its emergence [00:10:12] - Lost margin and lost market cap from big users of the public cloud [00:12:14] - Whether or not there is a headwind coming for public cloud providers [00:17:33] - How entrepreneurs might go after the biggest public cloud providers [00:19:37] - His view on API first companies and granular monetizable units in growing markets [00:23:20] - Developer facing tools and what works well when going to market [00:27:12] - The difference between a front-end and back-end developer and what is changing in their responsibilities [00:28:45] - What he looks for as an investor when he’s processing a new API first company [00:30:31] - Common redflags and disqualifying observations for an API first company [00:36:35] - Frank Slootman Episode; Snowflake’s offering for their users, their explosive growth, and primitives in their sector [00:39:06] - The history of digital security and potential opportunities as an investor [00:40:19] - How digital infrastructure intersects with the real world and hardware world [00:43:33] - How to screen out people for their potential to deliver transformative technology [00:47:45] - Things he’s most intrigued about by cryptocurrencies as an infrastructure person [00:52:49] - The kindest thing anyone has ever done for him

My guest today is Aswath Damodaran, a Professor of Finance at NYU’s Stern School of Business. Aswath is one of the clearest teachers of investing and finance in our industry and through his blog, books, and YouTube has open-sourced his wisdom for decades. This conversation is a masterclass of key investing concepts. We discuss inflation, narratives, disruption, the evolution of alpha and edge, and his thoughts on ESG. Please enjoy this great conversation with Aswath Damodaran. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:43] - [First question] - How he thinks about inflation as a now dominant force [00:04:33] - Why inflation is so important across the spectrum [00:09:02] - Big lessons from other periods of historically high inflation writ large [00:10:45] - Reasons why equities as an asset class struggle in high inflation environments [00:15:21] - The relationship betweens goods versus services in times of high inflation [00:16:59] - Broader economic implications especially for income inequality [00:19:03] - The Fed taking inflation seriously now when they didn’t and thoughts on the policy response to today’s situation [00:21:05] - How smart companies are defensively adjusting to inflation [00:27:46] - The importance of a capital allocation skill-set for executive team members [00:29:32] - Further historic lessons and how he’s being defensive against inflation [00:33:09] - Lessons learned about Amazon valuing them every year since their inception [00:42:25] - Whenever he sees Thanos in the Avengers he thinks of Amazon [00:44:51] - Thoughts on Facebook, Apple and Microsoft [00:48:26] - The evolution of edge and the search for alpha [00:54:37] - Whether or not there’s utility in studying other investors [00:57:16] - Skill versus luck and the most common valuation mistakes he’s made [00:59:09] - Assuming long-term growth rates and changing company life cycles [01:02:02] - Momentum and Value investing in today’s market [01:07:24] - Differences between interest rates and discount rates in regards to inflation [01:12:00] - How today’s market affects early stage equity investment [01:14:36] - The growing popularity of ESG and his seemingly contrarian view on it [01:24:03] - Nature of disruption as a force and companies that are protected from it [01:28:24] - Assigning a disruption risk premium when valuing companies [01:32:52] - What he makes of Elon Musk buying Twitter [01:34:24] - Other major topics he has a divergent view on [01:38:37] - Narrative And Numbers; The kindest thing anyone has ever done for him [01:38:55] - Teaching with a goal of changing mindsets

Today, we are running a special episode of Business Breakdowns. With geopolitics playing an increasingly important role in society again, this episode with Anduril’s CEO offers an inside look at the state of the defense industry and how it is changing. If you enjoy this episode, subscribe to Business Breakdowns on your preferred podcast player, where you’ll find past episodes on Block, Goldman Sachs, AutoZone and many others. Today, we are breaking down Anduril. Anduril builds high tech defense systems for the US Department of Defense and its allies. Crucially, it does so with speed that emanates from Silicon Valley. Founded in 2017 by Palmer Luckey, who previously built and sold Oculus to Facebook, Anduril has achieved the rare feat of challenging the established order in the defense industry. To break down Anduril, I’m joined by the company’s CEO and co-founder, Brian Schimpf. We discuss the history of the defense industry, how Anduril’s business is counter positioned against the legacy cost-plus model, and what Brian has learned about selling to the DoD. Please enjoy this breakdown of Anduril. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. If you're ready to go deeper on any company and you appreciate the value of primary research, head to tegus.co/breakdowns for a free trial. ----- This episode is brought to you by Daloopa. Daloopa streamlines a major pain point for investors. By capturing all of a company's KPIs and adjusted financials into their database - Daloopa makes it easy to quickly update your models for what matters. Daloopa uses AI to find every KPI disclosed - from charts, to text, and even from footnotes of investor presentations. Daloopa updates these KPIs and data points in your existing Excel models in one click, regardless of your source or format. Test Daloopa for free at daloopa.com/Patrick. ----- Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss Show Notes [00:02:52] - [First question] - The history of defense technology and the technological and competitive landscape when he set out to build Anduril [00:08:22] - What the early experience was like when approaching the government and finding an early adopter [00:12:44] - Necessity being the mother of invention when it came to developing drones [00:16:37] - What it’s like to develop hardware and software products at the same time [00:24:44] - The state of military technology and military conflict today writ large [00:31:10] - Are we heading to a future where warfare is mostly machine against machine? [00:33:34] - Comparing the ghost drone system to predator drones [00:38:40] - Guiding principles as a firm and deciding on their product roadmap [00:43:25] - An overview of their product lineup and what they’ve built so far [00:51:56] - Most difficult decisions he’s had to make through Anduril’s history [00:53:51] - How he overcame Anduril’s lowest points and biggest challenges [00:58:38] - Thoughts on effectively compounding hardware innovation [01:02:23] - A moment he’s most proud of and regrets most in Anduril’s history [01:04:20] - Lessons learned from observing Palantir and SpaceX [01:08:37] - The kindest thing anyone has ever done for him

My guest today is Tobi Lütke, co-founder and CEO of Shopify. Having first spoken to Tobi at the beginning of the pandemic, just two months into it, this felt an opportune moment to revisit Shopify and the world through Tobi’s eyes. Among many things, we discuss Shopify’s evolution into the world of atoms-based building through Shopify’s fulfillment network, the value of infrastructure writ large, and the impact of market volatility on day-to-day business building. Please enjoy my conversation with Tobi Lütke. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:44] - [First question] - His interest in infrastructure as a whole and why it’s underrated [00:07:18] - Whether or not we’re currently building enough digital infrastructure [00:09:45] - Base level principles for decision making around building infrastructure [00:13:17] - How much room is left for innovation and whether or not we’ll just reinvent basic human instincts [00:15:22] - Ways new ideas are fed into a product funnel at Shopify and greenlit [00:19:34] - Solving eCommerce infrastructure and what he attributes to Shopify’s success [00:24:23] - Overview of the Shopify Network and how it’s evolved over time [00:31:04] - Lessons learned in an atom-driven world in regards to fulfillment and logistics [00:34:37] - Common ways bits thinkers are often wrong when solving atom problems [00:35:50] - Spreadsheets tend to win meetings and how the ROI on a fulfillment network impacts its ecosystem [00:40:26] - Navigating becoming an aggregator that sits on top of their merchants and whether or not there are plans to participate as a distributor [00:45:45] - Fair market value, what it’s been like managing through such a volatile market, and important takeaways [00:50:54] - Thoughts on capital allocation decisions as Shopify continues to grow [00:53:25] - Advice for company leaders effectively communicating with their teams about stock-based compensation [00:59:04] - How much COVID altered their trajectory and what he’s most interested in as he looks out to the future [01:03:45] - What he’s learned about blockchains and the crypto space given recent events [01:08:45] - A new idea he’s encountered recently that he’s fallen in love with

My guests today are Tyler Cowen and Daniel Gross. Tyler is an economics professor and creator of one of the most popular economics blogs on the internet. Daniel is the founder of start-up accelerator Pioneer, having previously been a director at Apple and a partner at Y Combinator. Both Daniel and Tyler are prolific talent spotters and that is the focus of our discussion and their new book, which is called Talent. Please enjoy this conversation with Tyler Cowen and Daniel Gross. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:38] - [First question] - Defining what talent is to them writ large [00:03:34] - The differences between means and ends in regards to talent [00:04:14] - What the Diet Coke idea is and why it’s relevant [00:06:32] - Types of energy that are valuable and the subtle differences between them [00:07:40] - Thoughts on using a moneyball-like approach to acquiring and evaluating talent [00:11:49] - The talent market and thinking about pricing talent specifically [00:13:14] - What is seemingly overpriced in today’s talent landscape [00:15:50] - Relationship between experience and/or age when it comes to talent [00:20:34] - Lessons about the utility of intelligence and where they’ve lead them wrong [00:23:35] - What’s beneath being an outsider and why it’s important [00:24:46] - Why what people do in their downtime is worth considering [00:31:41] - Things to try and get out of a reference call as an objective [00:32:40] - Disabilities and what lead them write that chapter specifically [00:35:01] - Whether or not talented people are happier [00:38:40] - Lack of contentment and it’s dynamic influence over individuals [00:41:01] - Where they think the other is most talented [00:43:33] - Thinking about the physical side of mental performance [00:45:49] - What was frustrating about writing the book [00:48:25] - How they evaluate talent most differently now after having finished the book [00:50:41] - What makes for a good bat signal and how to cast one well [00:53:27] - Personality inventories and what they would and wouldn’t recommend [00:54:15] - Geographical frictions and their role in high success rates [00:56:08] - Antonio Gracias; Existing supply constraints on talent development [01:00:01] - How they would redesign the current attractors of talent that we rely on today [01:01:18] - Assembly line development and how we can improve and scale talent filters [01:02:29] - The biggest open questions for talent today writ large [01:05:16] - The kindest thing anyone has ever done for Tyler

My guest today is Jeff Jordan, General Partner at Andreessen Horowitz. Jeff has one of the most interesting set of experiences of guests that I’ve had on the show. As an operator, he has been the General Manager of eBay.com, President of PayPal, and CEO of OpenTable. As an investor, he was one of the first General Partners at a16z and sits on the board of Airbnb, Instacart, Pinterest, and other notable firms. Given his vast experience, he is the firm’s go-to-expert on all things marketplaces, which is the common thread in our conversation. Please enjoy this great discussion with Jeff Jordan. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:48] - The notion of perfect competition in marketplaces [00:04:31] - How to build a marketplace while thinking about perfect competition [00:05:32] - Promoting price discovery at eBay [00:06:52] - Features of a marketplace he focuses on [00:08:38] - Best way to do lead generation [00:10:20] - Red flags for marketplace businesses [00:11:00] - Major business lessons learned while at Disney [00:12:10] - Learning to be an operator while at eBay; Leaving It All on the Field [00:14:45] - How he got hired at OpenTable [00:16:22] - Taking OpenTable public and being its first public company CEO [00:17:44] - What they did well in financing OpenTable [00:18:54] - Communications between company leaders and its investors [00:19:45] - Going from operator to investor [00:22:08] - Lessons from the early years of becoming an investor and pricing companies [00:24:12] - Power of network effects on a startup [00:26:56] - Healthy tensions inside of a network [00:29:23] - When the supply side is the more difficult part of the equation [00:33:30] - The importance of being a perpetual learner as a founder [00:35:36] - When he starts focusing on unit economics and margin profile in a new marketplace [00:37:45] - Increasing convenience for a buyer as a business strategy [00:42:14] - Categories that could use better marketplace solutions [00:44:36] - Layers of growth inside a business [00:50:26] - Lessons with the unique business model of Pinterest [00:52:03] - Unique aspects of the Andreessen Horowitz business model [00:55:54] - Finding and recruiting talented general partner investors [00:57:37] - The morning basketball game and community strengthening [01:01:36] - Defining great mentor relationships [01:04:54] - Kindest thing anyone has done for him [01:06:05] - Lessons from his parents

My guest today is Eric Glyman, co-founder and CEO of Ramp. Ramp is best known for its corporate cards but it has a range of software products to help finance teams save money and time. Since its founding in 2019, the business has grown rapidly and was last valued at $8 billion. Eric and I discuss Ramp’s initial marketing wedge, how the business has dealt with such fast growth, and why they hold stablecoins on their balance sheet. Please enjoy my conversation with Eric Glyman. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:41] - [First question] - What was most notably awry about the industry before Ramp [00:04:45] - Breakdown of Visa; The business model of the Black Card compared to the business card offering of Ramp [00:08:40] - Causes and what he attributes their early success to [00:11:30] - Description of Ramp’s software in the beginning and the evolution of co-building it [00:16:34] - How he’s gone about building the company and team fast enough to handle their explosive growth curve [00:19:47] - Approaching all aspects of recruiting and acquiring such great talent [00:21:39] - Thoughts on the biggest mistake he’s made while building Ramp [00:24:05] - Lessons learned about marketing that this journey has taught him [00:26:13] - Learning to manage a senior team and advice for managing rapid growth [00:28:58] - Unique aspects of Ramp’s approach to the financing side [00:32:56] - Why they are storing some of their balance sheet in stablecoins [00:34:47] - What the idealized end state of Ramp looks like [00:37:26] - How the data and information he sees indicates trends in the economy writ large [00:39:33] - Providing secondary liquidity to employees in a world where companies stay private for longer periods of time [00:43:03] - Aspects of company building that are still unnecessarily hard [00:44:55] - What has him most excited about Ramp in the next 12-18 months [00:46:42] - The kindest thing anyone has ever done for him

My guest today is Dmitry Balyasny. Dmitry is the Managing Partner and CIO of Balyasny Asset Management, otherwise known as BAM. BAM runs a multi-strategy, multi-PM model that aims to produce consistent absolute returns. Since its founding in 2001, it has produced only one negative year and become one of the largest firms of its kind. Please enjoy my conversation with Dmitry Balyasny. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:53] - [First question] - The origin story of his firm and the key stages of evolution [00:06:43] - Describing the difference between good and great in platform hedge funds [00:10:25] - How a multi-strategy, multi-investor group works and managing capital allocation [00:13:58] - What he’s trying to solve at the end of the day as their CIO [00:16:21] - How close they are to their idealized end-state [00:18:26] - Typical amounts of leverage associated with these types of models [00:20:22] - Lessons learned about incentivizing talented investors [00:22:39] - Ways he tends to attract risk takers and their levels of variance [00:28:15] - Other characteristics that are common amongst great PMs [00:30:42] - The nature and source of edge and how it’s changed most over time [00:33:19] - Some of the hardest portfolio and business decisions he’s had to make [00:37:59] - One of his most important business decisions on the firm side [00:40:09] - How they’ve thought about shorting as a firm in general and more recently [00:43:52] - How interest rates affect this style of investing [00:45:29] - His view on the opportunity set in private markets and what does and doesn’t excite him about it [00:49:42] - How reading Ayn Rand most shaped his thinking [00:50:36] - Things Ayn most got right and most got wrong in his mind [00:51:24] - What the war in Ukraine has felt like for him as a Ukrainian-American [00:52:08] - Ways the future still has him excited as he continues to build his firm [00:53:53] - Where his trading instincts draw him today and areas of interest [00:55:11] - His most memorable trade of all time [00:56:37] - In which order the major asset classes will be affected by digital innovation [00:58:13] - The kindest thing anyone has ever done for him

My guest today is Henry Ward, co-founder and CEO of Carta. Started in 2012, Carta helps companies and investors manage their cap tables, equity plans, and ownership. Last year, they launched CartaX, a platform for private companies and their employees to access secondary market liquidity. Our discussion is a detailed exploration of private market infrastructure and Henry’s views on building an enduring business. Please enjoy my conversation with Henry Ward. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:57] - [First question] - The first key mental moment of how Carta came to him [00:05:30] - Initial thoughts on how to position Carta as a business model [00:06:47] - Historical divergence between private and public market infrastructure [00:08:33] - What a price discovery process for primary shares could look like in the future [00:11:09] - The end state Carta is trying to effect in their perfect state [00:13:29] - Why it’s so hard for private company staff to manage their illiquid wealth [00:15:45] - Lessons and challenges in the new market creation business [00:17:57] - The nature and dynamics of supply and demand in this space [00:22:45] - How Carta is mapped onto the success of its customers [00:25:27] - Deciding on what is a good idea and what isn’t when it comes to focus [00:28:07] - Describing the One of N versus N of One market frameworks and principles of this philosophy that manifests in how he runs Carta [00:32:11] - How working at Carta would differ from a payroll-type company [00:35:37] - Characterizing his leadership and management styles [00:37:57] - The types of circumstances that bring out his tough side [00:39:33] - Making hard decisions in a bottom up management model [00:44:05] - How he spends his time while building Carta [00:45:02] - What a great product looks like to him [00:47:10] - The Systems Bible; Defining what a great team looks like [00:49:13] - What he’s learned about being great at Go-To-Market [00:51:26] - Effective ways to beat competitors and build relationship pipelines [00:53:49] - Things he likes the least about leading a company of this size [00:55:13] - What he fears most as he thinks about the future of Carta [00:55:45] - Advice for entrepreneurs when thinking about data in modern businesses [00:58:26] - The biggest missing pieces in capital market structure writ large [01:00:17] - What’s next for CartaX and what he’ll be pushing to make it work [01:02:10] - Lessons learned from serving venture investors [01:04:25] - Whether or not investment banks are their competitors [01:05:18] - Public market dislocation and how long it will last [01:06:58] - The kindest thing anyone has ever done for him

My guest today is Alexandr Wang, the CEO and founder of Scale AI. Alexandr founded Scale in 2016, having been inspired to accelerate the development of AI through his work at Quora and his studies at MIT. Specifically, Alexandr realized there was a lack of infrastructure solutions for producing high quality data, the lifeblood for AI models. Today, Scale provides data solutions to leading AI teams at Meta, Microsoft, OpenAI, Flexport, the US Air Force, and many others. This time last year, the business was valued at over $7 billion. Our conversation is a primer on AI. We discuss the building blocks beneath successful artificial intelligence, AI’s role in both the public and private sector, and why data is the new code. We also cover the similarities and differences between AI and software from an investing perspective and what inspiration Scale takes from AWS. Please enjoy my great discussion with Alexandr Wang. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:04] - [First question] - The role that AI and data play in geopolitics and foreign policy [00:07:21] - The end state of a digital arms race akin to nuclear weapons [00:08:53] - Current state of things writ large and how the public and private sectors differ [00:11:33] - The flow and importance of talent when scaling AI and whether it’s more important than software [00:14:29] - His thoughts on how to communicate categories of what AI can do well and what is still a ways out [00:20:18] - The process of creating an AI model and the stages of development [00:27:16] - Principles of building a great engine for gathering data [00:29:04] - The state of technology around annotating data writ large [00:31:31] - What Scale does as a business and their product lineup [00:35:08] - The Storage and Compute equivalents in the AI space [00:37:08] - How Scale fills the gap in producing better and cleaner data [00:39:52] - What Scale will look like in 10 years if their vision is fully realized [00:41:11] - Where AI is in the S curve of acceleration and where AI and software intersect [00:44:32] - Questions to ask about how to incorporate AI and data sets in your business [00:46:23] - What worries him about the proliferation of technology that makes AI more accessible to the masses [00:48:27] - The most interesting AI model he’s ever come across and collapsing the friction between human intent and programmable outcomes [00:51:51] - The kindest thing anyone has ever done for him

My guest today is Antonio Gracias, founder, CIO, and CEO of Valor Equity Partners. Antonio is perhaps best known for his role at Tesla, as the earliest institutional investor and Director from 2007 to 2021. But he has deep operating and investing experience, having first acquired and managed a number of manufacturing and technology companies during his 20s. And it was during those formative years that Antonio and his team developed the skills that led to Valor, which provides operational expertise to the high growth private companies they invest in. Our conversation is a deep exploration of the drivers behind Antonio and Valor’s success. We dive into his concept of pro-entropic investing, what he learned as a 25-year-old running a manufacturing business, and trust me when I say, you don't want to miss his answer to the kindest thing ever. Please enjoy this great conversation with Antonio Gracias. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:51] - [First question] - Defining what a pro-entropic company is [00:07:26] - Understanding external forces of chaos and why they’ll continue to increase [00:11:32] - What he’s learned about identifying and investing in pro-entropic companies [00:13:43] - Investing with entropy in mind can be a bet on unchanging aspects of human nature [00:15:08] - Defining durability in contrast with resiliency and entropy [00:18:53] - Coming from a traditional background and the origin of Valor [00:22:05] - The theory of constraints and why it’s so powerful; The Goal [00:26:32] - Transitioning into a private equity structure and Valor’s 2001-2005 era [00:42:02] - Decision making bias and combating bias effectively in practice [00:44:30] - Where security and control figures into his thinking [00:45:45] - Identity in relation to ego; the tools he uses to combat identity related decisions [00:49:04] - Lessons learned from the Japanese language versus Western languages [00:53:07] - Questions he returns to when he’s getting to know a company [00:56:16] - An episode of operational deployment that most stands out in memory [00:58:54] - Key concepts that most stick with him from working alongside Elon Musk [01:01:32] - Why there aren’t more Musk’s or Bezos’ in the world [01:04:20] - Ensuring Valor invests in the best companies going forward [01:06:06] - How to pass the torch of what Valor is to others when his time is done [01:08:25] - The kindest thing anyone has ever done for him

My guest today is David Rubenstein, co-founder of The Carlyle Group - one of the largest private equity firms in the world. David has worked in the White House, built a $300 billion investment institution, become a prominent philanthropist, published books, and even hosts his own TV show. It was a thrill to sit down with him and cover the whole spectrum of his experience as a father, investor, historian, and titan of American business. Please enjoy this great conversation with David Rubenstein. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:02] - [First question] - What his perspective on the world today is compared to the last forty years [00:05:35] - The long term implications of the Ukraine war on a global scale [00:07:54] - Concerns and thoughts on the US’s role in a radically different world [00:10:07] - How inflation and reduced globalization impacts business behavior in the US [00:14:11] - His method when interviewing people and how it’s changed over time [00:15:03] - How his interest in leadership as a topic began; How to Lead [00:17:55] - The time he was the most personally in awe of a leader [00:19:05] - The most basic ingredients for strong leadership [00:21:34] - Learning from Oprah and developing his own interviewing style [00:24:25] - His leadership style while running Carlyle and key variables that drove Carlyle’s success [00:28:41] - The ways that were most effective in terms of investment for Carlyle’s brand [00:29:50] - How should a new investor think about the relationship between government and business [00:32:17] - What he’s learned about leadership that he thinks is the most portable for other people [00:34:04] - His interest in masters of leadership and what he has learned from them [00:35:08] - How Carlyle retained their talent and building relationships with LP investors [00:37:20] - Lessons from working in media with what worked and what didn’t; How to Invest [00:38:55] - How he approached writing How to Invest [00:41:13] - The importance of intuition when evaluating backers and why geniuses aren’t always chosen [00:43:04] - Big aspects of American history and why he finds it so interesting; The American Story [00:44:17] - Key drivers of American outcomes and biggest areas for improvement [00:47:00] - Lessons he learned going from humble beginnings to amassing wealth and how he’s teaching his children about it [00:49:20] - The state of private equity and what are its best and highest functions today [00:51:03] - Experience and impressions on the emerging cryptosphere [00:52:25] - What makes for a good chairman and why he is always drawn to that role [00:53:42] - The most interesting system outside of the US that he’s observed [00:55:33] - What he has learned about being a giving pledge signer and philanthropy [00:57:02] - His interest in Monticello and the Magna Carta [00:59:13] - View on how speeches from leaders have changed over the years; Citizenship in a Republic [01:01:24] - What subject he would write his next book on [01:03:58] - Thoughts on the line between giving your life for your country versus your state [01:05:17] - The American Experiment [01:06:10] - Looking back on his career at a time where he felt the most alive [01:08:07] - The kindest thing anyone has ever done for him

My guest today is Gaurav Kapadia, founder of investment firm XN. Gaurav is a veteran of the investing arena. We cover his lessons while rising to partner at TPG Axon, co-founding Soroban Capital, and his decision to launch XN in 2020. We then discuss his approach to building XN around a culture of rigor and kindness, the importance of relationships in investing, and finding investments that are obvious in retrospect. Please enjoy my great conversation with Gaurav Kapadia. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:05] - [First question] - What lead to kindness and rigor becoming pillars in XN’s company culture [00:05:30] - The types of situations where it’s hardest to be kind or rigorous [00:07:58] - Asking one question that can stump a founder can be a display of rigor [00:08:58] - An example of looking at a situation and reducing the problem to a single variable [00:12:51] - How he trains investors and team members to consider outcomes that would be obvious in hindsight [00:14:28] - Developing the art of interacting with company management [00:17:54] - Dimensions that typically find their way into his presentations and what tends to create complexity [00:21:13] - Whether or not rigor has declined in public markets over the years [00:21:55] - Why fewer talented people are going into public markets [00:23:01] - What it felt like when he first started XN and being successful at a young age [00:28:58] - Being impressed with his peers and rooting for each other [00:30:33] - The nature of public versus private investing today writ large [00:32:32] - How he gets to know a company when he’s never heard of them before [00:35:20] - Reasons he won’t invest from a personal policy standpoint [00:36:01] - Common problems he encounters that companies are dealing with [00:37:32] - Defining the strike zone of companies to invest in where he can be best-in-class [00:39:10] - The insane valuations of public markets in recent years especially in tech [00:40:42] - Why there are so few great businesses and common attributes of the great ones [00:44:12] - Biggest problems in the investment industry writ large [00:45:48] - The most remarkable business he’s ever seen [00:49:22] - How he would teach investors to deploy XN’s operating partner model [00:51:32] - His perspective and thoughts on diversity in the investing industry [00:56:58] - A business or institution he would own outright personally [00:57:37] - What outside of investing most has his attention lately [00:59:50] - Key touchpoints of coming from Queens and going to Hunter [01:02:15] - What stands out looking back on his relationship with his parents and how hard they worked to build a better life for their family [01:04:10] - Two things that manifest in a system that is seemingly rigged towards the wealthy and the problem with generational wealth [01:05:29] - What has him most excited and optimistic about the future in the investing landscape today [01:08:16] - Investing mentors deserve gratitude for believing in their pupils [01:09:12] - The kindest thing anyone has ever done for him

My guest today is Marko Papic, partner and chief strategist at Clocktower Group, where he leads the firm’s research on macroeconomics and markets. Marko has spent his career at the intersection of finance and geopolitics, making him a perfect person to speak to about current events in Ukraine and their potential impact further afield. Along with Russia and Ukraine, we discuss the Fed, inflation, China, the green energy transition, and the US’s position in the global order. Please enjoy this discussion with Marko Papic. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:48] - [First question] - His thoughts on what’s happened so far between Russia and Ukraine [00:06:18] - The geopolitical motivations for Russia and what they can gain from the conflict [00:10:52] - How his impressions of warfare have evolved watching this play out [00:13:45] - What to consider about nuclear war and different types of nuclear weapons [00:16:31] - The economic warfare from the West against Russia and its implications [00:21:06] - Whether or not the world is de-globalizing and how interconnected we all are [00:24:45] - How we should view post-covid inflation, specifically in the US [00:30:34] - The ways the Fed’s role has evolved [00:33:25] - Impacts of liquidity on asset prices and why it’s such a key factor in markets [00:34:16] - China’s positioning and how the Ukraine conflict could alter their plans [00:40:58] - Thoughts on Taiwan and how global supply chains might change [00:44:47] - Why so few people believe that China has peaked; Young China [00:48:52] - His take on income equality in the US and why it’s the number one issue [00:53:03] - What the US could do to improve itself as a country most going forward [00:55:35] - Having a green energy transition view is crucial and the surrounding politics [00:59:22] - The preconditions for doing well in atoms-based innovation [01:01:13] - What he’s watching most carefully about the conflict in Ukraine [01:02:51] - The kindest thing anyone has ever done for him

My guest today is Garry Tan, founder and managing partner of early-stage venture firm, Initialized Capital. Before starting Initialized, Garry was a partner at Y Combinator, employee number 10 at Palantir, and co-founder of YC backed blog platform Posterous. Our discussion covers what’s missing in the investment world, how to best systematize venture investments, and what he learned from Paul Graham. Please enjoy my conversation with Garry Tan. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - Why he’s interested by software and the global brain [00:06:23] - How the shift from global to local manifests in his investing and company activities [00:11:42] - Ways to increase throughput that would benefit everybody in the investing world [00:17:13] - What software he would build if there were no limitations and what happens at the systems level of securing deals at Initialize [00:23:33] - Why there is no objective application process for early-stage capital and how much human judgment we can remove from approving funding [00:26:49] - Shared characteristics amongst new inventions he finds favorable [00:31:49] - Whether he’s able to evaluate an idea without a prototype [00:33:33] - Why travel planning software was the worst idea of 2012 and what he sees as the bad idea of today [00:36:06] - The most common reasons for failure in these types of businesses [00:39:07] - Is big enabling technology shifts what manifests in successful outcomes? [00:40:37] - The role of media and how it intersects with investing [00:44:29] - What he attributes to the success of his firm and thriving in chaos [00:48:11] - Would he press a button that would have made his childhood easy, and whether he’s met founders who haven’t come across adversity in their lives [00:50:00] - His thoughts on the world today via the lens of his portfolio [00:53:12] - The kindest thing anyone has ever done for him

My guest today is Eric Mandelblatt, founder and CIO of Soroban Capital, a $10 billion investment firm. While many of my conversations focus on technology and emerging industries, Eric has deep roots investing in the industrial economy, which made this conversation a fun change of pace. We discuss why energy and materials represent such a small share of the market today, how the global push towards decarbonization could have massive impacts on the industrial economy moving forward, and how Eric evaluates this dynamic opportunity set. Please enjoy this deep-dive discussion with Eric Mandelblatt. Editor’s note: This conversation was recorded on February 15, before last week's invasion of Ukraine. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:01] - [First question] - Soroban’s history and why Eric is qualified to discuss industrial and commodity sectors [00:04:37] - Overview of what their portfolio looks like today [00:05:49] - How much of the commodity exposed equity sectors are owned by hedge funds [00:08:03] - The key history points that makes industrials more interesting today [00:11:17] - Commodity cycles, what drives them, the role CAPEX plays and how this world works [00:17:38] - Thoughts on natural demand and the societal push towards decarbonization [00:22:32] - How deeply one needs to know commodities in order to hold them [00:23:57] - Big categories to explore as decarbonization becomes more accessible to consumers and the lack of nuclear investing [00:28:50] - The resurgence of industrial production in the US [00:32:21] - Rail networks writ large and if we can expect new ones in the future [00:36:17] - The market gap between rail and technology businesses [00:41:38] - Commodities and the ways they differ from railroads [00:43:47] - Comparing the differences between businesses within the commodity industry [00:46:52] - Walkthrough of Alcoa’s business and how things like a carbon tax might affect an individual business [00:52:55] - What is the portfolio manifestation of the fact it's impossible to forecast commodities historically [00:56:08] - His view of the world in its current state and big things that matter [01:00:25] - Thoughts on inflation as an investor in the commodity space [01:01:42] - Utopian to dystopian takes on what growth looks like for the world [01:04:28] - Juxtaposed positions in big tech against the industrial story [01:08:45] - The kindest thing someone has ever done for him

My guest today is Sebastian Kanovich, CEO of payments company dLocal. Sebastian founded dLocal in 2016 to bridge the infrastructure gap between payments in developed and emerging markets. Since then, the initially bootstrapped start-up has enabled global merchants like Uber, Spotify, and Google to service billions of emerging market users. And in doing so, dLocal has created $10bn of equity market value, having IPOd last year. Our discussion covers dLocal’s playbook for facilitating payments in emerging countries, what Sebastian has learned about great API building, and how he challenges himself to improve personally. Please enjoy my conversation with Sebastian Kanovich. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders. ----- Founder's Field Guide is a property of Colossus, LLC. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:13] - [First question] - His take on global payments, what is interesting about this system today, and dLocal’s role within it [00:04:06] - Approaching a country that could benefit from low-friction payments and the playbook for helping them improve their system [00:06:10] - Differences between being an API business versus a protocol one [00:07:13] - What companies handle these systems outside of emerging markets and why they haven’t entered the emerging market space [00:08:59] - A specific example of the steps involved in getting a country integrated into global payments for an app or service provider [00:11:22] - Whether or not they interact with consumers [00:12:09] - The trading and foreign exchange component of global transactions [00:13:16] - Country specific product teams and consolidating their process [00:14:52] - What he would look for in early-stage payment companies to invest in [00:16:23] - Defining excellent when it comes to working with regulators and regulatory environments [00:17:53] - Their role in digital globalization and trends that might arise in the future [00:19:52] - Ways that low-friction payments have helped accelerate regional innovation [00:21:31] - The unit economics and costs of a single payment [00:24:05] - What the source of cost is to process a payment or transaction [00:25:10] - Variables in currencies that make them desirable to work with [00:26:38] - Lessons learned from distribution and customer acquisition of their service [00:29:23] - Advice he would give to developers building API products [00:31:16] - An example of wanting to build a function into an API that was never built [00:32:40] - How they’ve been able to move and scale so fast [00:34:23] - Ways their business could most improve [00:35:14] - The operating system he uses to run the company [00:36:38] - Ways he’s most improved or gotten better as a CEO over the years [00:37:58] - Why deep humility is such an integral part of his character [00:38:30] - The biggest mistake they’ve ever made as a business and what they learned [00:39:20] - The kindest thing anyone has ever done for him

My guest today is Frank Slootman, Chairman and CEO of cloud platform Snowflake. Frank has become one of the most revered CEOs in business. Over the past twenty years, he has three times taken over emerging enterprise software businesses – first Data Domain, then ServiceNow, and most recently Snowflake - and led them across the chasm into large, billion-dollar businesses. Please enjoy this great discussion with Frank Slootman. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best in class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. Head to tegus.co/patrick for your free trial. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:33] - [First question] - How he evaluates the team of a company he’s working with [00:04:48] - The pace of decisions made around changing team members [00:06:10] - Understanding the potential quality of outside leaders being brought into the company [00:08:13] - How he characterizes great and constructive confrontation [00:09:53] - What he’s found to be most effective in convincing senior talent to join a team [00:11:36] - Ways he personally generates energy to sustain himself in this pace of business [00:14:17] - How he fosters and nurtures healthy communication pathways [00:15:36] - Narrowing the focus when evaluating a new product [00:17:58] - Is it possible for a focus to be too narrow? [00:19:31] - An example of a dazzling customer that he’s worked with [00:21:04] - Working backwards from a problem and building something that solves it [00:23:03] - Building trust between a company and its customers over time [00:25:37] - Overview of the base layer ingredients of trust [00:28:12] - Sequential versus parallel processing and how they affect building trust [00:30:22] - Lessons in successfully translating between engineers and business people [00:32:58] - Crossing the chasm and effective sales organizations [00:35:17] - Working compensation into getting more out of an organization [00:38:45] - How much a sales organization needs to work backwards to serve their product [00:41:40] - Great questions for board members to ask their executive team [00:46:07] - Where the analogy of ‘business as war’ falls down and defining the highlander concept [00:48:01] - What he feels he could still hone in his skillset [00:49:16] - The kindest thing anyone has ever done for him

My guest today is Tim Flannery, co-founder of venture fund administrator Passthrough. Passthrough is removing friction from the manual, time-consuming fundraising process by making investor onboarding as simple and automatic as possible. Their software helps investors fill out subscription documents in minutes rather than hours and allows GPs to easily track LP subscriptions during a fundraise. In our conversation, we discuss the power of identity as a feature to build products around, the double-edged sword of solving an unsexy problem, and how Passthrough has thought about pricing their software. Please enjoy my conversation with Tim Flannery. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs so you can focus on what matters most — building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders. ----- Founder's Field Guide is a property of Colossus, LLC. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:08] - [First question] - The push and pull nature of what Passthrough is trying to solve [00:04:17] - What the idealized end state 10 years from now looks like [00:07:33] - A history of friction in investing and what barriers still remain today [00:12:35] - The spark of insight that led to starting this new venture [00:17:45] - Lessons learned from Okta and why identity is so powerful [00:19:39] - Plans to expand this concept deeper into the tech stack [00:22:24] - Adjacent problems that they plan to tackle as they continue to scale [00:24:30] - What it feels like to use their product as an LP today [00:26:10] - Working with service providers without becoming one [00:28:06] - What great sales and distribution looks like to him at the infrastructure level [00:31:50] - Defining what “bring your collaborators” means [00:33:19] - His secret to recruiting talent to help solve an unsexy problem [00:37:46] - His love for the intersection between process, pipelines, and efficiency [00:40:12] - Having a process for designing processes [00:42:11] - How they arrived at their pricing and thoughtful pricing in software [00:45:08] - Lessons from building Passthrough that other builders could benefit from [00:47:16] - The kindest thing anyone has ever done for him

My guest today is IAC’s CEO, Joey Levin. IAC is a unique business in that it’s a holding company which builds world-class digital businesses. Since Barry Diller created IAC over two decades ago, it has produced 11 public companies, including Match Group, Expedia, and Live Nation. Today, the business is comprised of category-leaders like Angi, Dotdash Meredith, and Care.com. Joey joined IAC in 2003 and became CEO in 2015. We talk about why he tries to avoid centralization between businesses, what he's learned from Barry Diller, how he approaches capital allocation, and so much more. This conversation serves as an excellent reminder that there’s no formula to company building. Everything is idiosyncratic and requires its own best decisions. Please enjoy this great discussion with Joey Levin. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:05] - [First question] - The unique nature of IAC; the business of building businesses [00:05:27] - The first business spun out of IAC and its bottom-up philosophy [00:06:41] - The differences of IAC and how they manifest [00:09:39] - Agility and history of respecting the core functions of the internet [00:12:36] - Simplified, faster, and larger choice digital experiences [00:15:57] - His thoughts on the shared characteristics amongst their winners [00:18:26] - Lessons from building competitive products in online dating simultaneously [00:21:37] - Navigating customer acquisition cost and embracing change [00:24:04] - What makes someone great at customer acquisition [00:26:26] - Fostering a unique approach compared to typical customer funnels [00:27:48] - What most explains his move from a pip-squeak to CEO [00:29:44] - The process he uses to get to know the critical aspects of a new business [00:31:59] - Indications that a leader may no longer be suited to run a business [00:33:13] - Characteristics of vertical markets that he finds attractive to get involved in [00:34:08] - The early stages of incubating a new business and an overview of their process [00:38:10] - Enabling new consumer experiences and infrastructure fading away [00:40:17] - Distilling big ideas down to streamlined approachable consumer products [00:42:22] - High-level internal conversations around capital allocation [00:45:06] - Quantitative versus qualitative analysis in their decision-making process [00:46:50] - What idea felt the most right but turned out to be a disaster [00:51:26] - Brand rollup versus brand consolidation and when either strategy is appropriate [00:54:03] - Having a good sense of identifying, defining, and positioning categories [00:56:23] - Which aspects of his perspectives have shifted since becoming CEO [00:57:59] - Thoughts on the toolkit available for sourcing and the cost of capital [01:01:08] - What personally brings him the most joy in what he does [01:02:37] - Working with Barry Diller and what it taught him [01:06:39] - The kindest thing anyone has ever done for him

My guest today is Peter Chernin, who’s had a Hall of Fame career in the entertainment business. Peter ran News Corp and Fox for fifteen years between 1996 and 2009 before co-founding The Chernin Group, which has become one of the leading investment firms in the consumer space. Along the way, he has also produced a number of blockbuster films, including Titanic, Avatar, The Greatest Showman, and The Planet of the Apes Trilogy. Please enjoy this wonderful discussion with Peter Chernin. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ----- This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies. And it was the only product that ever made me willing to log food. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:06] - [First question] - Business and investing lessons from producing Titanic and Avatar [00:06:44] - Defining great content and why James Cameron’s franchises have done so well [00:10:26] - Contributing factors to box-office domination of pre-existing franchises [00:12:56] - Tailwinds in his earlier career and identifying them in time to get behind change [00:16:07] - Identifying Showcase was a subscription business early on, unlike broadcast businesses [00:19:40] - Signals of passion and how powerful niche audiences can be [00:23:24] - What a phony aggregator is and the slow dissolution of the middle market [00:27:01] - The era of unbundling and direct relationships with superfans [00:30:27] - Lessons learned from building Hulu [00:34:29] - Working with Rupert Murdoch and qualities that separate him from the crowd [00:37:07] - Defining what bravery means in a businesses sense [00:39:22] - A movie he’s made in the past decade that he’s most proud of [00:43:27] - The keys to being an effective partner to creative individuals [00:49:53] - What exists today that may change the future landscape of media writ large [00:52:19] - The kindest thing anyone has ever done for him

My guest today is entrepreneur and investor, John Pfeffer. John was a partner at private equity firm KKR in the 2000s, Chairman of leading French IT company Groupe Allium in the 90s, and now invests his own money through his private family office, Pfeffer Capital. John is one of the smartest investors I know, and our conversation spans all of John’s experience and investment ideas. We discuss the difference between value creation and wealth creation, why John has made such a big bet on one asset, and why adaptation is more important than ever. I hope you enjoy this conversation as much as I did. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:08] - [First question] - John’s background and the experiences that shaped his worldview and sparked his curiosity [00:07:34] - Aspiring to grow with a lack of inertia [00:10:31] - Why he invests primarily in technology and technology dependant businesses [00:15:22] - What it’s felt like being a tech investor from 2011 leading up to today [00:19:26] - How he defines good and bad business [00:21:24] - Why good businesses don’t often have technology disruption risks [00:22:26] - An (Institutional) Investor’s Take on Cryptoassets; key points from his paper [00:35:28] - What else is interesting in the crypto space and potentially strong business models that exist outside of Bitcoin [00:48:46] - How capital has changed over time and what makes capital efficiency or formation superior [00:51:51] - Value creation and why a shift in value can affect your returns [01:01:12] - Whether or not crypto and the founding protocols will fade out of the public eye [01:11:52] - A consensus on store of value in crypto and how it could change [01:18:03] - Why he is so heavily allocated to Bitcoin compared to other tokens [01:25:19] - General take on the nature of buying and selling capital and European markets [01:35:28] - The interconnectedness of the globe and the future of globalism [01:39:46] - Why he doesn’t ask people where they’re from and how he prefers to get to know people that can sometimes be unorthodox [01:41:59] - Market index investing and why it may not be the best strategy going forward [01:47:36] - The kindest thing anyone has ever done for him

My guest today is the renowned tech author, consultant, and venture partner at Wildcat Ventures, Geoffrey Moore. Geoffrey has spent his career focused on the dynamics surrounding disruptive innovations and his book, Crossing the Chasm, has become a canonical work for young businesses trying to unlock mainstream markets. This discussion is a masterclass on business strategy. We start with Geoffrey’s more recent work on category-defining businesses, break down his life cycle of adoption framework, and close with the ways messaging should change as a company evolves. Please enjoy this great discussion with Geoffrey Moore. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:08] - [First question] - What he means by a gorilla business [00:07:10] - An example of how companies self-organize into gorillas, chimps, and monkeys [00:09:41] - Why architecture is so important and how it applies to company building [00:13:11] - How and when businesses should think about open and closed systems [00:14:50] - Ways in which enabling tech companies are superior to application ones [00:16:39] - Thoughts on approaching and hiring a singular use case company [00:18:23] - Markets underestimate competitive advantage periods for technological gorillas [00:20:38] - The inertia and duration of being the creator of a space’s architecture [00:23:28] - Advice for early-stage companies when creating or dominating categories [00:25:16] - What he’s learned about identifying trapped value [00:26:49] - Questions that can identify trapped value, factoring for time, and horizontal uses [00:41:49] - Problems with risk exposure in B2B and applying this model for value creation [00:33:37] - His initial discovery of the life cycles of adoption and its five categories [00:39:29] - Perspective on venture capital funding and going from idea to the chasm [00:44:10] - What good pragmatists in pain look like [00:47:29] - Successful vertical uses-case sales motions [00:50:03] - Guarding from becoming over-specialized in a singular focused effort [00:50:52] - The Diffusion of Innovations; Ways messages work their way through a company to keep up with category evolution [00:55:00] - How extensible these ideas are to non-technology businesses [00:56:04] - The race between innovation and distribution [00:56:44] - What about the world today has changed or influenced his thinking [00:59:17] - Ways big companies can stay competitive in emerging categories [01:02:23] - The company he’s most enjoyed studying over his career [01:05:25] - Shared characteristics of exceptional leaders he’s met and talked to [01:07:48] - The Gorilla Game, Crossing the Chasm [01:08:14] - The kindest thing that anyone has ever done for him

My guest today is past guest Gavin Baker, managing partner and CIO of Atreides Management. Gavin’s focus is on consumer and tech growth investing, which makes him the perfect person to discuss the bloodbath we’ve seen in many growth equities over the past few months. We also cover inflation, semiconductors, and the disconnect between private and public markets. Please enjoy this conversation with the always great Gavin Baker. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:30] - [First question] - What it’s been like investing over the pandemic [00:06:14] - The way he thinks about multiples, how they’ve done, and where they’re going [00:09:14] - Themes that most have his attention in our current economic landscape [00:19:25] - The ways in which wage inflation negatively impacts the market [00:25:39] - How semiconductors have evolved and what matters in that subsector [00:32:47] - Software volatility and the roller coaster it's been on lately [00:35:52] - A future state where infrastructure overtakes apps [00:41:03] - Key differences between internet and software and how they behave [00:43:44] - The coming trend of the metaverse and his reaction to public adoption [00:49:26] - Investor and business opportunities in adopting tech trends [00:53:54] - An unfolding mismatch between private and public market multiples [00:57:17] - How the competitive landscape of venture capital might evolve [01:05:54] - Differences in recruiting and training talent in private and public markets [01:10:20] - Sci-Fi novels that he’s read recently; Dune, A Wizard of Earthsea, Culture, Hyperion

Today, my guests are Sam Englebardt and Richard Kim, general partners at venture fund, Galaxy Interactive. Having come from the media and finance sectors, respectively, Sam and Richard joined forces in 2018 to invest in their shared thesis that immersive digital experiences would become the dominant way people engage with each other in the future. Our conversation centers around the evolution of art, finance, and gaming as they proliferate in Web3. Please enjoy my conversation with Sam and Richard. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've ever used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. If you want early access to become a Member of their private Beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:50] - [First question] - Their thoughts on the digital art market [00:11:33] - What motivates traditional art collectors and what has been carried over into digital art [00:17:27] - Is there an attractive beta opportunity in the digital art space? [00:24:32] - Why investors should do more work understanding NFTs and ways to consider incorporating them into your portfolio [00:27:55] - The history of Galaxy and their thesis writ large [00:33:09] - Exciting and terrifying aspects of the financialization of everything [00:37:27] - Places where inserting markets could be beneficial with Web3 [00:45:27] - Their perspectives on gaming as a subcategory of Web3 [00:51:38] - Tokenomics and the importance of building great game communities [00:59:18] - What we can learn from successful gaming companies and in-game monetization [01:04:19] - How Diablo 3’s auction house detracted from the core player experience [01:06:36] - Where they disagree with the Web3 investing community [01:10:37] - The kindest things anyone has ever done for them

My guest today is Ricky Sandler, founder of Eminence Capital. Ricky is a hedge fund veteran managing over $8bn of assets across Eminence's strategies. We cover Ricky's evolution as an active investor, why he thinks this is a stock-picker's environment, and what keeps him competitive after a long and successful career. Please enjoy my conversation with Ricky Sandler. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- This episode is brought to you by: Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. ----- This episode is brought to you by Levels. As one of their early access members, Levels was one of the most interesting products I've used. Levels is attempting to make continuous glucose monitoring mainstream by using real-time biosensors to see how food affects your health. Using Levels made me realize how little we understand about what's happening in our bodies - and it was the only product that has ever made me willing to log food. If you want early access to become a member of their private beta, (the waitlist is currently at 150K+ people), use this link – levels.link/PATRICK ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:42] - [First question] Whether or not great investment firms should be led by a single investor [00:03:25] - Episodes where singular investment power has proven effective and powerful [00:05:06] - Where he finds joy in the investing process on a regular basis [00:06:19] - Ways he’s learned to become better at guiding and helping teams he works with [00:08:14] - The most common types of fool's gold he comes across [00:11:00] - Evolution of the pricing mechanisms in ever-evolving markets [00:16:14] - Common features of a good mispricing opportunity [00:18:42] - How he interacts with other hedge funds and long-only investors [00:21:14] - An investor he often disagrees with but loves talking to [00:22:13] - The investment he’s most proud of historically [00:25:11] - What the healthy draw that keeps him coming back to investing is [00:28:31] - His opinion on crossover funds and their growing popularity [00:32:09] - What the world in 2022 looks like to him and what both excites and worries him [00:38:19] - Key contributors that influence liquidity and how it flows into equity prices [00:41:26] - A macro view of the healthcare sector and why it’s so interesting today [00:42:59] - Lessons from the Titans [00:43:52] - Advice he’d give to younger investors for stepping into the space [00:46:45] - The kindest thing anyone has ever done for him

My guest today is Orlando Bravo, co-founder and Managing Partner of leading private equity firm, Thoma Bravo. Thoma Bravo manages over $90bn of assets and is best known for investing in software and technology businesses. It was Orlando who led the firm’s early entry into software buyouts some twenty years ago, and he has overseen more than 350 software acquisitions since. There are few, if any, people better placed to discuss private equity and software investing. Please enjoy this excellent discussion with Orlando Bravo. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:36] - [First question] - His belief about an opportunity/capital mismatch in private equity [00:04:26] - Adjusting his own approach to take advantage of seemingly niche opportunities [00:06:13] - Differences between software businesses they invest in versus traditional ones [00:08:25] - Outline of how he runs their four-hour portfolio meetings [00:09:53] - Overview of the very first deal he ever made in the software sector [00:14:01] - The dissonance between the average SaaS company and the ones they try to manage [00:18:22] - Major contributors that allow for their higher margins [00:20:16] - Common mistakes of companies that mis-invest capital for growth only [00:22:28] - Defining what market leader means writ large [00:23:45] - Why the subsector of cyber security is such a good opportunity set [00:26:25] - The evolving nature of the private equity world in general [00:28:41] - Where returns will come from going forward [00:31:47] - How good the opportunity for returns in this style of investing today is [00:35:32] - Lessons learned on knowing when to exit or sell a position [00:37:59] - How short their holding periods can be and how much influence they can have in such a short time [00:40:04] - Surprising things about deal-making that he’s learned over his career [00:41:20] - Difficulties and points of frictions in deals that still exist for him today [00:43:11] - What part of the deal-making process he loves the most [00:44:30] - If your job title has a C in it you’re not allowed to complain about it [00:46:27] - Deeply held beliefs about operating excellence [00:47:33] - What the word service means to him given everything we’ve talked about [00:50:27] - How we do a better job of inviting talent into this space [00:52:51] - How decentralization will define the 2020s and beyond [00:55:48] - What is most interesting about Web3 that might affect cyber security [00:57:42] - Where there is a lack in innovation in private equity today [01:00:45] - Advice for young talent for building their careers [01:03:16] - The kindest thing that anyone has ever done for him

My guest today is Nick Saltarelli, co-founder of the functional chocolate bar business, Mid-Day Squares. Nick started the company with his wife and brother-in-law a few years ago to build on a simple idea: if the big chocolate bar brands were to start today, what would they look like? In our conversation, we discuss the importance of Mid-Day Squares’ $100 million revenue target, what’s wrong with the CPG industry today, and how to keep a long-term mindset while making the most of every day. Please enjoy this unique conversation with Nick Saltarelli. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Pilot. Pilot handles your startup’s finance, accounting, and tax prep needs, so you can focus on what matters most—building your business. Join over 1,000 startups that rely on Pilot to help them scale. Founder’s Field Guide listeners get 20% off their first six months. Get in touch with Pilot at https://pilot.com/founders. ----- Founder's Field Guide is a property of Colossus, LLC. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:01] - [First question] - What Mid-Day Squares is and how he started the business [00:04:48] - Why they’re so publicly open about their company’s goals [00:09:05] - Major lessons he learned from his father’s early passing and being around very successful entrepreneurs at a young age [00:16:51] - What long term thinking unlocks for him in short term progress [00:21:05] - Becoming unexpectedly close and learning from Rory Olson [00:25:44] - What Rory taught him about deal-making [00:28:35] - Lessons from Rory about raising capital [00:33:25] - Opportunities in a seemingly oversaturated market like chocolate [00:42:46] - An example of doing something contrarian that worked out [00:47:11] - Their unique approach to marketing Mid-Day Squares [00:57:33] - Lessons learned about building a manufacturing operation after years in China [01:02:35] - What we can expect from Mid-Day Squares in the near future [01:06:59] - The kindest thing anyone has ever done for him [01:08:05] - Mid-Day Squares Uncensored Podcast

My guest today is Jenny Johnson, President and CEO of one of the world’s largest asset managers, Franklin Templeton. Jenny joined the business in 1988 and has worked in the organization ever since. In early 2020 she became CEO of Franklin, which now manages some $1.5 trillion. I should, of course, note that I met Jenny as our two firms explored a partnership, which we cemented 3 months ago when we announced that Franklin Templeton would be acquiring O'Shaughnessy Asset Management. During our conversation, we discuss Jenny’s thoughts on leadership, how she manages the needle-moving problem that afflicts many large companies, and the ways in which she sees private markets becoming more accessible to retail investors in the future. Please enjoy this great conversation with Jenny Johnson. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:19] - [First question] - The four P’s of leadership and what she thinks are the most important roles of a CEO [00:06:00] - The difficulty of finding and recruiting great people and keeping them invested [00:07:18] - Things she looks for in her senior leadership team [00:07:59] - Knowing when to be more or less involved as a leader [00:09:30] - Her takeaways from working in a family-owned business [00:11:20] - Advice she’d give to families who are building businesses together [00:12:06] - Thoughts on the role technology will play in the asset management industry [00:16:13] - Costs and frictions that blockchains could alleviate [00:18:17] - General views on disruption and considering ones position when thinking about the future [00:20:09] - Knowing when to start a project internally or acquire an existing project [00:23:10] - The hardest things about effective M&A decisions [00:23:42] - Overseeing a hybrid model of singular focus between multiple investment groups [00:28:26] - The pros and cons of active management against passive adoption [00:31:15] - Costs and fees in the industry and how they might change in the future [00:33:04] - Talking to clients when they don’t have one specific view on strategy [00:36:10] - Formative experiences in her career that has shaped her worldview [00:38:34] - Managing emotions through seemingly chaotic situations [00:39:13] - The impacts on psychology when being a top performer and an average one [00:41:15] - Managing and adapting strategy when faced with highs and lows [00:42:55] - Acquiring alternative managers and defining what alternative assets are [00:46:26] - Relevant trends on how capital is pooled and their client base over time [00:47:52] - What is under-discussed in the world of asset management today writ large [00:49:01] - Other leaders she’s met or knows that have had her in awe [00:50:30] - What about Cathie Wood has made her story and approach so successful [00:51:38] - How she runs a great board meeting and ways to improve meetings themselves [00:53:34] - Lessons learned about time management as the leader of a public company [00:54:52] - What purpose means to her [00:56:18] - Ways we can incentivize young and new people to start investing [00:59:10] - Her favorite things that her dad has taught her and how she’d describe him [01:00:57] - What has her most excited about the future [01:01:34] - The kindest thing that anyone has ever done for her

My guest today is Doug Colkitt. Doug has spent his career searching for and trading inefficient markets, first at Citadel’s high-frequency trading group, then for himself, and then as an operator building CrocSwap - a decentralized exchange or DEX designed to bring modern functionality to crypto markets, which is closer to what large traders have come to expect from a modern electronic market like the NASDAQ. My interest in market infrastructure has continued to grow since my great conversation with FTX founder Sam Bankman-Fried. So my conversation with Doug covers the evolution of market and trading infrastructure. We unpack the trading stack as it exists today, dive into DeFi’s innovations, and explore the new category of single contract DEXs that Doug is creating. After learning so much from Doug about how markets function and how crypto markets should function, I became an investor in his new business via my venture capital firm Positive Sum. Please enjoy this great conversation with Doug Colkitt. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:31] - [First question] - Doug’s career and history working with markets [00:08:55] - Defining what a trading stack is [00:13:41] - How HFT firms are such reliable money-making models [00:16:27] - What’s at the cutting edge of traditional markets that provides an edge [00:18:45] - The mechanical parts of infrastructure involved in building an exchange [00:21:00] - Classes of data that matter for operating an exchange [00:22:11] - Capacity and what good returns are as an HFT firm [00:28:45] - Overview of the mechanics of an AMM [00:31:53] - Earning a yield as a liquidity provider [00:33:59] - Other ways to think about AMMs and liquidity providers [00:36:42] - Key players in the AMM space and the evolution of them [00:41:20] - How asset holders can approach DEX tools and be liquidity providers [00:42:55] - The function of an exchange’s native token [00:45:25] - Token distribution and how to earn them without buying them [00:48:31] - How you receive payment for providing liquidity [00:51:31] - What CrocSwap will do and what a single contract DEX unlocks [00:57:36] - How CrocSwap is able to do this when other exchanges can’t [00:59:27] - What single contracts will improve for users [01:00:43] - The impact CrocSwap will have for all participants writ large [01:02:28] - Whether or not CrocSwap will cultivate an ecosystem [01:03:30] - What’s next for CrocSwap in the near future [01:04:58] - The promise of DeFi and the future of blockchain technology [01:07:04] - Whether or not DeFi is a threat to centralized exchanges [01:09:52] - Defining what MEV is and why it’s important for DeFi [01:13:04] - Missing pieces in the DeFi world and how we can address them [01:15:24] - The kindest thing anyone has ever done for him

My guests today are Philip Rosedale and Bill Gurley. Philip created Second Life in the early 2000s and helped build it into the largest virtual 3D world ever created at the time. Frequent listeners will recognize Bill, who was an investor in Second Life via Benchmark Capital. During the conversation, we cover the fascinating story of Second Life and the billion-dollar economy that persists through to this day. Bill and Phillip share their key learnings from the experience, including the importance of usability, their views of the current metaverse opportunity, and what excites them most about the current focus on virtual realities. If you’re curious about what the metaverse might become, these two experts have seen much of this already and are kind to share their lessons with us. Please enjoy my conversation with Phillip and Bill. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:22] - [First question] - The origin story of Second Life and why they created it [00:05:38] - How many people were playing Second Life at its peak, the in-game economy and its growth trajectory [00:06:49] - The interface between the in-game currency and its function for players [00:10:53] - An example of early entrepreneurship and user-created IP in Second Life [00:12:13] - Was technology a rate limiter to success in such an early version of the metaverse? [00:14:35] - What was most exciting about creating it and it’s early-stage potential [00:18:23] - Why Unity isn’t more adopted by creators and players like Minecraft [00:24:42] - Defining what the metaverse means to each of them today [00:28:50] - What Discord has taught them about aggregating people digitally [00:33:02] - Simultaneously crossing the digital chasm and the uncanny valley [00:38:16] - Key differences between games and platforms and the role of purpose [00:42:04] - Why cryptocurrencies and blockchains haven’t produced experiences akin to the virtual Travis Scott concert [00:47:13] - Why removing friction and centralizing financial structures can help growth and thoughts on play to earn gaming and user spending [00:53:27] - Digital asset ownership and digital trustless exchanges in the metaverse [00:57:30] - Pros and cons of today’s speculative digital asset valuations [01:01:05] - Interesting pockets of opportunity that could benefit the metaverse ecosystem [01:04:28] - How they’d build and construct an ETF with metaverse exposure [01:07:18] - Thoughts on AR and VR and which holds more promise for public adoption [01:08:02] - Surprising findings about the role audio plays in digital worlds [01:10:23] - What they’re watching most closely in this emergent sector [01:11:29] - Limitations of visual and sonic barriers when recreating real-world interactions [01:12:42] - The kindest things anyone has ever done for them

My guest today is Francis Davidson, founder and CEO of the hospitality brand Sonder. Francis launched Sonder in 2013 as an alternative to traditional hotels and rentals with a specific focus on technology and design. During our conversation, we discuss where Sonder fits into the hospitality ecosystem and why design is so key to their offering. We also touch on Francis’s unique views around customer-centric focus, the nuances of hiring a team, and how they approach decision-making. Please enjoy my conversation with Francis Davidson. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:38] - [First question] - Thoughts on the obligation of a business to deliver the best possible customer experience [00:03:43] - Making a decision that actively went against improving the customer experience [00:06:00] - What Sonder is and the key insight that led to building the business [00:08:43] - Ways they cut down costs by leveraging technology available today [00:10:44] - The economic model of the business and where it differs most from other hotels [00:12:15] - The journey of $100 coming in to Sonder and working through the company [00:13:20] - How the building or asset owner is integrated into the business model [00:14:18] - Network density and how he thinks about it when it comes to scaling Sonder [00:16:18] - His philosophy on design and why he thinks it matters in hospitality [00:18:05] - What you can overspend on and underspend on to keep a guest happy [00:21:05] - Making decisions on building in house or partnering to provide a new solution [00:22:29] - Do property owners dress up their own hotels or are there guidelines and retailers [00:23:51] - Lessons learned from working with overseas manufacturers [00:24:44] - The key levers that will drive the growth of Sonder [00:26:59] - What a typical occupancy rate is for them versus other hospitality options [00:28:23] - Category creation and design that influence and change how people behave [00:29:45] - Qualities of a new market and what drives success in attacking it [00:31:15] - His contrarian viewpoint on building a business and talent density [00:33:40] - The features of his job’s product and the interview process [00:36:21] - Does everyone at a company need to be an A player? [00:38:00] - His philosophy on team culture and developing synchronicity [00:41:01] - Ways to build strategic competitive advantage inside of Sonder [00:43:22] - What the most successful version of Sonder will look like ten years from now [00:45:16] - New features and tech improvements that are coming soon he’s excited about [00:46:48] - Trends in hospitality that have been accelerated and changed by COVID [00:48:36] - Growing changes in the glamping and nature-forward guest experiences [00:51:04] - The kindest thing that anyone has ever done for him

My guest today is Niraj Shah, the CEO and co-founder of Wayfair. Wayfair started life in 2002 as a collection of independent websites selling category-specific home furniture but became a one-stop-shop for the home category in 2011 when, at $500 million in sales, the team consolidated their 240 websites into Wayfair.com. Today, the business offers 22 million products from 16 thousand suppliers to more than 30 million customers. During our conversation, we discuss how the competitive frontiers in e-commerce have changed, what it was like to build out a proprietary logistics operation, and what makes the home goods market more attractive than other physical goods markets. Please enjoy this great conversation with Niraj Shah. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ----- At WatchBox, the world’s finest watches are at your fingertips with an ever-expanding collection of luxury timepieces, all certified authentic and collector quality. WatchBox’s global team of expert client advisors is ready to help you find the watch you’ve always wanted. Step into the collector’s circle at thewatchbox.com/patrick ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:50] - [First question] - The global supply chain and its issues today in 2021 [00:05:13] - Why he finds the ocean leg such a problematic area and how to resolve it [00:07:04] - Overview of the physical goods market around the world [00:10:50] - The role of magazines and devout subscribers in certain sectors [00:11:50] - Are physical goods trends in flux or fairly steady and less geared to change [00:13:06] - From 240 separate websites into what became Wayfair as we know it today [00:16:36] - The competitive frontier of eCommerce in its early days and why they won [00:18:29] - Expanded logistics control, developing their brand, and becoming Wayfair [00:21:40] - Aggressively building for the future as a public company with investors involved [00:27:23] - Key differences between Wayfair, IKEA, Restoration Hardware and others [00:34:22] - Other areas of interest and drivers of future investment opportunities for Wayfair [00:38:39] - What excellent marketing means to him and why Netflix does it so well [00:42:02] - The margin profile of Wayfair and all of its major components [00:47:13] - Lessons learned from major mistakes while building the business [00:49:54] - Company culture and deliberately investing time and money into it [00:51:50] - Evaluating the importance and success of their adapt and grow philosophy [00:53:18] - How he would measure his own improvement as a CEO over time [00:55:17] - Thoughts on the dimension of competition as they scaled [00:56:57] - The most stressful episode of growing the business and what he learned [01:00:16] - What the best outcome for Wayfair would look like in the future [01:01:38] - The kindest thing anyone has ever done for him

Today, I am excited to share our newest show, Web3 Breakdowns. Similar to our Business Breakdowns series, Web3 will have it's own dedicated feed so make sure to hit this subscribe link or find it on your preferred podcast player. The first episode of Web3 Breakdowns covers Bored Ape Yacht Club. You will hear from guest, Eric Golden, who will also be coming back to host his own Web3 Breakdowns moving forward. We are sharing this first episode to make sure no one misses this launch. ---- Welcome to our new show, Web3 Breakdowns. We want to be your on ramp into this new decentralized world, and through conversations with builders, creators, and investors, we will do our best to help you understand and navigate this emerging ecosystem. First up, we are breaking down the NFT project and cultural phenomenon, Bored Ape Yacht Club. To help break down Bored Apes, I am joined by Eric Golden, former Portfolio Manager at Fidelity and current Bored Ape owner. Eric and I start with an overview of the Bored Ape Yacht Club and his path to owning an NFT in the collection. We then use Bored Apes as a lens to understand how NFT projects are not just creating rare art but strong membership communities too. Beyond the cultural differences between NFT communities, it was fascinating to hear how projects are differentiating themselves with IP ownership, roadmaps, and DAOs. Please enjoy this breakdown of the Bored Ape Yacht Club. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @Web3Breakdowns | @patrick_oshag | @JoinColossus Show Notes [00:02:30] - [First question] - What the Bored Ape Yacht Club is [00:03:39] - Motivations for owning a Bored Ape compared to traditional art [00:07:46] - The scope of prices, hierarchy, turnover, and trading overview of these NFTs [00:09:51] - Distribution of rarity and why it matters [00:11:29] - How the project roadmap is managed by the member community [00:16:23] - Who are the members and the key stewards of steering the ship [00:18:08] - An example of a project where the owners don’t own the IP of their NFT [00:20:56] - Underlying fundamentals and utility behind owning a Bored Ape [00:26:36] - Thoughts on fungible tokens inside of non-fungible projects [00:29:06] - Ways to think about the value proposition of owning an Ape and an Ape token [00:30:36] - Different options for minting NFTs and their pros and cons [00:34:36] - Literal mechanics of the minting process [00:36:59] - Smart contract mediating of combining NFTs to generate rare ones [00:39:20] - Building a bottom up brand and other examples of this trend [00:41:50] - Are NFTs just gambling, or will they become investable assets like physical art [00:46:09] - Blockchain infrastructure of the NFT space and whether it’ll stay on Ethereum [00:48:48] - What makes the Bored Ape Yacht Club so innovative compared to other projects

My guest today is Will Marshall, the co-founder and CEO of Planet. Will founded Planet in 2010 with a small team of NASA scientists to build a constellation of satellites that would image the entire Earth every day. Since then, Planet has successfully built and deployed 450 satellites into space, which the company is using to create a time series of images for every place on Earth. Our conversation covers the untold space story. How space is going through an internet moment where cost reductions and performance enhancements have led to a seismic shift in what’s possible above our atmosphere, and how that can drastically improve life on Earth through unique datasets like the one Planet is piecing together. Once you listen to Will speak about Planet’s progress and mission, it’s hard to think of a more underappreciated company in business today. Please enjoy this great conversation with Will Marshall. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:57] - [First question] - His thoughts on the renaissance of the space industry [00:05:09] - The earliest days of Planet and why he started the business [00:09:22] - Unique data units captured by their satellites [00:13:35] - The real estate of space and interesting angles to consider [00:15:59] - How customers interface with Planet and their early use cases [00:20:57] - Thoughts on the sovereignty of space and the laws that exist currently [00:23:43] - Figuring out the dynamics and pricing of Planet’s business model [00:27:34] - Examples of stress and tensions when working in space [00:29:08] - The future of privacy and concerns we should have there collectively [00:30:29] - Five different types of satellites and their functions [00:31:39] - The most sci-fi potential futures that Planet may unlock someday [00:32:54] - Indexing the Earth and using data to train machine learning algorithms [00:34:02] - What he’s learned about Earth that is most surprising [00:37:12] - Contributing factors to a 70% decline in life on the planet in 40 years [00:38:35] - Ways that going public might impact Planet’s long term goals [00:40:23] - The hardware story of building various prototypes of satellites [00:42:18] - How much is built in house versus outsourced to fabricate their satellites [00:43:48] - Complimentary space trends that are compounding beyond imagery [00:45:32] - Whether or not they plan on making their data open-source [00:47:15] - Democratizing their data and allowing other companies to build on top of it [00:48:30] - The kindest thing anyone has ever done for him

My guest today is Roelof Botha, a partner at one of the world’s oldest and most successful venture firms, Sequoia Capital. A few days ago before I sat down with Roelof, he announced Sequoia’s boldest innovation since the firm was founded by Don Valentine in the early 1970s. Going forward, the firm will break from the traditional VC mould of fund cycles and instead restructure around a single, open-ended, permanent structure named The Sequoia Fund. In our conversation, we first discuss the details of this change from all different angles and then dive into Roelof’s career. We talk about what’s changed over the past twenty years, his days at PayPal, what legendary investors he’s worked with have had in common, and what he’s learned from being involved in businesses like Square, YouTube, and Unity. Please enjoy this great conversation with Roelof Botha. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:53] - [First question] - What led Sequoia to change their structure [00:05:53] - Parallels between their approach and the problem Square set out to solve [00:07:36] - The mechanics of the new fund and how it’ll affect their clients [00:13:11] - What the future looks like and how public securities could be a dominant force [00:15:02] - Benefits and value-unlocks that the new fund offers that weren’t available before [00:16:55] - Comparing their structure to the current crossover funds we see emerging [00:18:21] - What alignment looks like in this new structure for LPs [00:22:02] - Cost of capital, interest rates, and their impacts on rates of return [00:25:39] - Changes in the industry and founders that he’s noticed [00:28:56] - What matters to him when meeting with young companies for the first time [00:31:47] - The importance placed on value creation over value capture in the early days [00:33:09] - Things that would dissuade him from partnering with a company [00:34:18] - What the growth and leadership at Square has taught him over the years [00:35:44] - Things he’s most excited about for payments looking forward [00:37:34] - How often a company lowering friction with technology appeals to him [00:38:38] - Thoughts on Unity and its role in the growing trend of the metaverse [00:40:28] - Why the open and decentralized nature of the future is so beneficial [00:42:05] - Lessons learned about content and internet from working with YouTube [00:44:08] - The landscape of developers today and MongoDB's role in it [00:49:26] - Learning to identify and hunt for crucible moments [00:50:50] - Curiosity is the key ingredient of a great investor [00:52:05] - What makes for a fantastic investment memo [00:53:20] - The most memorable investment memo he’s ever read [00:54:07] - Honing his leadership as his role has changed at Sequoia these past years [00:55:51] - Thoughts on Sequoia’s brand and the scope of his ambition [00:58:05] - What he’s most curious about in the world today [00:58:46] - What technology wants most from people today [01:01:13] - The difference between an accountant and an actuary's mindset and when each one is appropriate to inhabit [01:02:38] - Differences between talent and genius [01:04:12] - Closing principals about business building he finds important to consider [01:06:17] - The kindest thing anyone has ever done for him

My guest today is Sarah Friar, the CEO of Nextdoor, which connects people in local neighborhoods together. Sarah’s CV sparkles with impressive achievements at interesting businesses, and we spend a lot of time in this conversation thinking through what excellence looks like as a CEO, CFO, equity analyst, and board member. The rest of our discussion is focused on Nextdoor and how the soon-to-be public business is fostering connections between people and businesses in their local areas. I do this podcast so I get to meet and learn from people like Sarah. I could have talked to her for hours. I hope you enjoy this great conversation with Sarah Friar as much as I did. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:03] - [First question] - What makes an excellent equity analyst [00:05:51] - Things Sarah does differently as an operator because she was an investor [00:08:29] - Key factors that make a great CFO [00:09:31] - The role of the CFO in regards to capital allocation as a company grows [00:11:50] - What convinced her to join Salesforce and Square [00:14:45] - The initial spark and appeal that led her to join Nextdoor [00:17:35] - Existing problems with ‘community’ and how they approach fixing them [00:21:36] - Interesting and compelling data points about in-person interactions [00:23:54] - Network density as a driving factor of product quality [00:26:43] - What gives Nextdoor a unique angle against some of its existing competitors [00:28:51] - Thoughts on platform leakage and user retention [00:30:57] - Successful strategies for deploying Nextdoor in a new country [00:35:32] - Having a feed and trying to avoid creating echo chambers [00:37:04] - Some of the biggest mistakes they’ve made while trying to grow [00:38:49] - Options for a business model and thoughts on advertising [00:43:25] - The importance of scale, advertising, and their relationship dynamic [00:45:55] - Ways she’s learned to effectively steer the businesses strategy [00:49:48] - Why she doesn’t like titles [00:51:07] - Key levers that will allow Nextdoor to succeed in the future [00:53:35] - How advertisers evaluate platforms like Nextdoor compared to Google or Facebook [00:57:19] - What a successful board member looks like and how she’s learned to be one [00:59:34] - Leading with transparency and empathy [01:02:00] - An overview of what Ladies Who Launch is and what they do [01:03:57] - Way to educate our children about finance and encourage financial literacy [01:07:51] - Making your platforms welcoming and guiding users away from conflict [01:10:30] - The kindest thing anyone has ever done for her

Today, we are running a special episode of Business Breakdowns on our Invest Like the Best feed. When we launched Breakdowns, we hoped to cover industries and businesses that we were “well known but poorly understood.” This deep-dive on UMG and the music industry is just that - you will walk away with a whole new appreciation for artists, labels, and what streaming technology has done for a historic industry. If you enjoy this episode, please be sure to subscribe on your preferred podcast player and check out our growing catalog of episodes. Today we’re breaking down Universal Music Group. As one of the largest music businesses in the world, UMG is home to many of the world’s greatest artists, including Taylor Swift, U2, and The Beatles catalog. A discussion on UMG requires a deep dive into the history of music itself, how it was historically monetized, the shift from physical to digital, and what streaming has meant for the various pieces of the ecosystem. Our guest, Arman Gokgol-Kline, a partner and investor at Ruane, Cunniff & Goldfarb, walks us through that evolution of the music industry before we dive in on UMG. In our discussion, we first break down the industry pre and post Napster, looking at the ways music was sold historically, and how that led to both record profits and a consumer revolution. We then assess streaming’s impact on the industry and how, contrary to what you might think, labels may be more important in a marketplace where it’s easier than ever for creators to record and release music. Finally, we finish with UMG’s place in the ecosystem. The primary drivers of the business, how they’re able to attract the world’s superstars, and how they think about deploying dollars to acquire new artists and timeless catalogs. Please enjoy this fantastic breakdown of Universal Music Group. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ----- Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss Show Notes [00:04:01] - [First question] - How technology disrupted the music business and it’s evolving history [00:12:44] - What the industry of music labels looks like from the 90s to today [00:21:19] - How it feels as a high-tier artist to engage with a label directly today [00:28:20] - The revenue and business model of an artist akin to Taylor Swift [00:30:44] - The differences between UMG's main sources of revenue; music publishing and recording [00:35:08] - General margins and trends for music publishing [00:36:22] - Ownership and mechanics of monetizing an artist’s Intellectual Property [00:40:57] - How streaming revenues are divided among stakeholders [00:46:23] - History of the bargaining power of labels and streaming platforms [00:51:25] - Capital allocation, ROI, and acquiring IP and catalogs [00:57:39] - Thoughts on the growth profile of the industry as an investor [01:02:23] - Potential risks to UMG in emerging technology and new creator trends [01:08:50] - Reasons why an artist would pick UMG over other major labels [01:12:42] - Diversity and how artists are sometimes treated by labels [01:14:02] - A growing increase in music consumption across the world

My guest today is Alex Rampell, General Partner at Andreessen Horowitz. Alex has a long history in fintech, having co-founded six companies in his career, including Affirm and TrialPay. During our conversation, we cover Alex’s framework for positive selection in investing, why the best investments are often operating systems or systems of record, and Alex’s views on the future of fintech. For those that have listened to our Business Breakdown on Visa with Alex - you know the intellectual horsepower he brings to every discussion. This conversation is no exception. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:32] - [First question] - Lean into positive selection and avoid adverse selection [00:07:48] - Thoughts on growing capital formation in private markets [00:14:01] - Why it’s useful for investors to think in terms of bonds and call options instead of equity [00:18:39] - Doing more with less and hunting for operating systems to invest in [00:28:08] - His views on infrastructure and the presentation layer conundrum [00:33:32] - The sequencing involved in building an operating system over time [00:40:11] - Rise of the creator class and the coming tailwind post-cloud technology; the rise of the solopreneur [00:43:32] - The pig joke and his thoughts on the FinTech space [00:47:47] - Big financial services functions that will be embedded in non-financial businesses [00:51:07] - Deciding which functions and financial services models are most attractive [00:57:01] - What a shift towards data and FinTech might unlock for the world writ large [01:02:40] - How to improve payment profits by reducing credit rates [01:04:12] - The threat that Buy-Now-Pay-Later companies pose to Visa and Mastercard [01:12:17] - How the struggle between distribution and innovation continues to change [01:15:04] - The kindest thing that anyone has ever done for him

My guest today is Sam Bankman-Fried, founder and CEO of leading cryptocurrency exchange, FTX. In a little over two years, FTX has registered 1.2 million users, grown to facilitate $10.9 billion of daily trading volume, and reached an $18 billion valuation. Prior to FTX, Sam worked at Jane Street Capital before founding a quant trading firm of his own, Alameda Research. At just 29, Sam has packed a lot into a short period of time, and as I’m sure you’ll hear, he has a special ability to harness uncertainty and think deeply across a range of topics. In our discussion, we cover the building blocks of a perfect market, the key areas of inefficiency in today’s exchanges, and Sam’s north stars of product design and effective altruism. We also talk about fairness in crypto markets, how FTX thinks about user acquisition, and derivatives as key enablers of properly functioning markets. Please enjoy my great conversation with Sam Bankman-Fried. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:57] - [First question] - What motivates him and what the true north of his vision is [00:07:12] - Evaluating the impact of well-functioning markets and philanthropic spending [00:11:55] - The key functions and building blocks of a perfect market [00:14:59] - Who pays $50 million to access fiat market order books [00:21:49] - What is valuable about having access to order book data [00:25:41] - Assessing and understanding the state of fairness in crypto markets today [00:31:51] - Can crypto only move as fast as the fiat system keeps up [00:32:43] - The advantages and disadvantages of stablecoins and USDT [00:34:46] - How much fiat inflow there is into crypto markets and exchanges today [00:37:36] - What it is about cryptocurrency exchanges that are so appealing to him [00:42:21] - Building in a dynamic world and deciding the sequence of problems to solve [00:45:12] - Whether or not the US is on the wrong side of crypto and countries competing for healthy regulatory environments in this emerging asset class [00:47:25] - Thoughts on centralization and what being decentralized unlocks [00:50:22] - Why derivatives are such a key function of properly functioning markets [00:52:38] - The competitive landscape between derivatives and exchanges [00:54:35] - Spending marketing dollars and paid acquisitions for FTX [00:57:30] - The growing trend of user-generated content becoming user-generated assets [01:02:24] - How many layer one blockchains we’ll need and the competition for dominance [01:05:18] - Thoughts on Bitcoin as the pioneer of the space and how relevant it still is [01:06:26] - Possibly reaching a state where everything happens on-chain [01:08:23] - What he means when he says he has more RAM than hard drive space [01:09:39] - Amassing wealth insanely fast and whether or not it affects him [01:10:26] - Important things to consider in this rapidly growing space [01:12:02] - A decision he made while respecting the power laws that govern us [01:13:10] - The kindest thing anyone has ever done for him

My guest today is Nick Neuman, CEO and co-founder of Casa. Casa helps bitcoin investors and owners keep their digital assets safe from loss or theft by providing managed self-custody services. In our discussion, we cover the history of asset custody from ancient temples to decentralized ledgers, look at the mechanics of how private keys work, and explore why people are better off holding the keys themselves. We then dive into the future of digital wallets as gateways into our virtual lives, what’s interesting about identity authentication more broadly, and whether these innovations may lead to unintended consequences. Please enjoy this great conversation with Nick Neuman. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:23] - [First question] - The history of asset custody [00:07:56] - What private keys are and their role in financial security [00:12:21] - Overview of storing a token in a wallet and accessing with a private key [00:15:28] - Thoughts on private keys through the lenses of convenience and safety [00:18:49] - Solving both self-custody of assets and peace of mind [00:21:39] - How the user experience will feel once self-custody is properly developed [00:24:11] - Why asset custody is so interesting and what a perfect scenario unlocks [00:27:05] - Is the DeFi ecosystem an early manifestation of a self-custody financial system [00:28:57] - Ways Casa is planning to become a convenient and diverse platform for users [00:32:16] - The role wallets will play in the future of a digital world [00:34:56] - Forms of authentication that are most appealing in creating a seamless user experience [00:37:39] - Overview of what hardware wallets are and how they work [00:40:17] - Different security options that Casa offers from the simplest to the most secure [00:44:51] - How many crypto holders there are and how many use self-custody [00:47:31] - The craziest security set up around Bitcoin he’s ever heard of [00:48:49] - What the most ideal outcome for Casa looks like in the coming decade [00:51:26] - Thoughts on the competitive landscape and potential growth challenges [00:53:07] - Important aspects of the crypto ecosystem other than security [00:55:49] - How empowered people feel when they successfully adopt self-custody [00:57:13] - Whether or not there are ways that the current centralized system is more secure [00:59:58] - Thoughts on offering a way for users to display they are protected by Casa [01:01:31] - The kindest thing anyone has ever done for him

My guest today is Devin Finzer, co-founder and CEO of OpenSea, the world’s largest NFT marketplace. In a journey that started like many other founders in the space, Devin went deep down the crypto rabbit hole in 2017 and became particularly fascinated with the potential behind digital assets. During our conversation, we touch on the origin story of OpenSea, how Devin differentiates between the spectrum of NFTs in the market, and what he sees as the opportunity in the future for the industry. We also talk about the various risks within a blockchain, from security dynamics to market speculation. I hope you enjoy this great conversation with Devin Finzer. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:56] - [First question] - When he first thought up the genesis of OpenSea [00:06:00] - What is listed on OpenSea, assets and volume, and the scope of the platform [00:07:26] - Thoughts on potentially becoming the current era “everything store” [00:09:22] - How they managed to become the main NFT trading platform [00:12:28] - What NFTs are, their various classes, and ways they’re stored on the blockchain [00:15:25] - How much transaction and auction volume happens on-chain [00:17:07] - Profile picture style NFTs and what’s exciting about them [00:19:24] - ArtBlocks and the mass interest in AI-generated art [00:21:22] - What he’s learned and seen about the emerging crypto gaming space [00:24:38] - The user experience of buying an NFT on OpenSea [00:26:45] - How the ownership transfer works between wallets [00:28:04] - Whether or not they have plans to partner with other companies [00:30:32] - How they think about what gets placed on OpenSea and why [00:32:09] - Thoughts on take rate and their 2.5% take rate of transactions [00:33:22] - Why their take rate is so low compared to other sale platforms online [00:34:47] - OpenSea’s relationship with the Ethereum blockchain and other integrations [00:36:50] - Perspective on wallets both as businesses and products [00:39:16] - Potential risks and the dark side of the unregulated NFT space [00:40:48] - The massive boom and bust cycles of crypto and the high prices of NFTs [00:41:59] - Interesting areas of Web3 that are in development today [00:44:19] - The project he’s enjoyed watching grow the most in the crypto world [00:46:42] - What OpenSea might look like in the future if the best-case proves true [00:48:59] - The kindest thing that anyone has ever done for him

My guest today is Jenny Lefcourt, an equal General Partner at seed-stage venture firm Freestyle Capital, where she manages $450 million in seed investments. Jenny has been engrained in the tech world since the early days of the internet. She dropped out of her Stanford MBA program to co-found online wedding registry startup WeddingChannel.com with classmate, Jessica Herrin, which was subsequently acquired by The Knot. During our conversation, we cover Jenny's investment frameworks, why she believes a deep understanding of the customer is key for founder success, and what makes great go-to-market strategies. We also touch on some of Jenny's favorite market themes around technology for the aging population, the future of work, and the growing low-code/no-code market. Please enjoy my conversation with Jenny Lefcourt. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:24] - [First question] - Her background and some formative experiences that lead her to where she is today [00:08:38] - Common patterns of desirable founders when it comes to customer focus [00:09:50] - Her investing framework for evaluating and deciding which companies to invest in [00:15:11] - The biggest jobs to be done in this space currently today [00:17:33] - Cultural differences in how the West views and treats their elderly [00:21:02] - Business model options for turn-key apartments offered by UpsideHoM [00:22:48] - Other categories and potential opportunities in tech geared towards the elderly [00:24:59] - What you need to do differently when building products for the elderly [00:27:32] - How she learns about a new prospect’s go-to-market approach and reverse engineering an action plan to execute it [00:32:03] - Founders, You Want to Sell Viagra [00:33:33] - Selling transformation and an overview of this idea with BetterUp [00:36:30] - Her thoughts on how the world and the future of work might change [00:43:24] - The emerging movement of low code/no code tools [00:46:58] - How she as an investor adjusts as the world becomes more digitally connected [00:49:02] - Ways her life has most dramatically changed over the past few years [00:51:33] - Lessons learned from her time at All Raise [00:53:40] - Outstanding and remaining barriers to inclusive and diverse teams [00:58:47] - The kindest thing anyone has ever done for her

My guest today is Dave Girouard, co-founder and CEO of Upstart, a lending platform that leverages AI to make loans more accessible and affordable. Dave started in Silicon Valley as a Product Manager at Apple and later spent eight years at Google, where he built their suite of cloud apps. In our discussion, we cover the lessons Dave has learned about building speed into a habit, the intricacies of training an AI model to predict the future, and what it was like to start a fintech business as an outsider. We also discuss the past, present, and future of lending, why Dave and his team have no plans to build a super app and the differences between public and private market investors from a founder’s perspective. One of the tropes you hear these days is that lending has become a customer acquisition tool for FinTechs, but as Dave explains, the market and opportunity set in lending itself should not be underestimated. Please enjoy this great conversation with Dave Girouard. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:54] - [First question] - Lessons learned about adopting speed as a habit [00:05:39] - Knowing which decisions require your attention and are worth it as a CEO [00:07:00] - What slows down decision-making execution and overcoming it [00:09:34] - Ways to persuade partners to move as fast as you do [00:10:44] - One of his most valuable lessons learned from his time at Google [00:12:20] - The key insight that first lead him to the idea of creating Upstart [00:15:10] - The early days of learning about the financial lending space [00:16:49] - Figuring out how to improve on an age-old rigid and regulated system [00:20:57] - Overview of building an AI learning model and applying it to loans [00:25:16] - Machine learning algorithms and interwoven programmer bias [00:28:34] - Revenue model and transactions that fund Upstart [00:31:43] - Who the typical customer is and their user experience [00:35:10] - The biggest hurdle encountered when building Upstart [00:36:55] - How he’s seen the FinTech space in his area change over time [00:38:39] - A pie chart on revenue for financial services today [00:40:24] - Why there are more profits in lending than payments [00:41:25] - Major loans types and how they might change in the future [00:44:12] - Disruptive aspects of the buy now pay later consumer movement [00:46:09] - How much Upstart could change the future of lending over a decade [00:49:43] - The most important decisions he’s made while building Upstart [00:51:59] - Things to know when building a business that sells to banks [00:52:49] - How it feels to interact with hired CEOs versus founder CEOs [00:55:05] - Thoughts on cryptocurrency and AI writ large [00:57:00] - Areas that have his attention and get him excited lately in FinTech [00:58:58] - State of the art AI growth and what lingers over the horizon [01:00:36] - What he’s learned about being a public market CEO versus a private one [01:02:38] - Differences between public market and private market investor philosophies [01:03:53] - Major battle scars from raising capital for Upstart [01:05:12] - The kindest thing anyone has ever done for him

My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this episode. Please enjoy my conversation with Jay Hoag. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor [00:06:29] - How much software businesses have changed since he started investing in them [00:08:28] - The key insight that led him to create TCV [00:11:36] - Generating returns by swinging less and raising your average [00:15:06] - Understanding and evaluating a value proposition in its early stages [00:22:08] - What slightly crazy founders look like and why it’s important for a company [00:25:47] - Whether or not we’re in the golden age of content already [00:28:27] - Why Peloton was rejected so many times before TCV invested in them [00:32:32] - Things founders often need from him and how he helps them succeed [00:36:15] - Lessons learned from investing in public markets versus private ones [00:41:35] - Advice for founders when it comes to conveying their ideas to investors [00:44:55] - The social dimension of interactive and network building content [00:46:18] - How important maintaining a focus in the early days is for a new company [00:48:07] - The most challenging aspect of executing his strategy today [00:50:48] - One of the most emotionally stressful episodes while launching TCV [00:53:44] - Supporting your founders during the good and tough times [00:55:16] - New potential headwinds and tailwinds in the tech space writ large [00:59:14] - Things people might be overlooking today that could be great opportunities later [01:02:58] - Whether or not internet companies are threatened by the crypto boom [01:04:32] - What most has him most excited about the world today [01:06:20] - Advice for company building in the investing world in general [01:09:48] - The kindest thing anyone has ever done for him

My guest today is Gina Bianchini, founder and CEO of Mighty Networks, which gives creators a platform to start, grow and own their social communities. In our conversation, we cover the differences between leadership and management, the lessons Gina learned building a similar business in the 2000s with Marc Andreessen, and the elements that make up a thriving community. We talk about community design, finding ways to connect like-minded people, why it’s so important to create movement, and what the future may hold for creators. Please enjoy this great conversation with Gina Bianchini. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambitious problem, then Versett is the firm to call. To check them out, visit versett.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:35] - [First question] - A period in Gina’s career of deep intensity that she learned from [00:04:28] - Solving ways to preserve her energy as a high performing entrepreneur [00:08:19] - How much of her day is spent doing things she wants to do [00:11:24] - What is unique to leadership that differs from management [00:14:49] - The insight that led to what eventually became Mighty Networks [00:27:19] - Enabling features of a community that Mighty Networks offers creators [00:31:51] - Key symptoms of a healthy online community [00:37:35] - Differences between their emerging communities and the power of belonging [00:41:38] - Turning movement and accomplishment into a software platform [00:47:32] - Tying passion into purpose and the structure of a movement [00:50:20] - The biggest potential risks and challenges that Mighty Networks faces [00:52:56] - The kindest thing anyone has ever done for Gina

My guest today is David Fialkow, co-founder of General Catalyst. If you are looking for a dose of fun, charismatic energy from a very unique investor then this is the conversation for you. David has a diverse background not only as an investor but also as a philanthropist and filmmaker. He won an Academy Award for his role as the producer of the 2018 documentary Icarus. During our conversation, David and I dive into what makes a great founder, the importance of storytelling, and the value of effectively convening people within your network. After listening to all of his great stories, I think you’ll see why David has so much fun and success helping founders. Please enjoy my great conversation with David Fialkow. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:03] - [First question] - How the process started that led to filming Icarus and becoming a VC [00:16:01] - Lessons learned about identifying creativity in potential founders [00:19:26] - What it looks like when a founder doesn’t clearly love their product [00:24:35] - Different aspects of building a successful investment firm [00:28:22] - Features of Ken Chenault that differentiates him from other CEOs [00:30:12] - Applicable lessons for the effective convening of people [00:35:20] - Whether or not he cares about the business model of new companies they back [00:40:57] - The story of Icarus [00:47:24] - What is David drawn to at the moment [00:51:13] - Key ingredients required to tell a powerful and convincing story [00:53:16] - The kindest thing anyone has ever done for him

My guest today is Justin Waldron, co-founder and President of Playco. Justin is a pioneer of the social gaming industry after he co-founded Zynga at age 19, and he has continued to build games ever since. In our conversation, we cover how Justin sees the future of gaming as social platforms evolve, how gaming may be the next tool for content creation, and how Playco has approached aligning incentives for game creators and players. As talk of the metaverse becomes more mainstream, it’s fascinating to hear directly from those around it. I hope you enjoy my conversation with Justin Waldron. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why brands like Living Proof, Solo Stove, and Nomad trust Klaviyo to grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:47] - [First question] - His thoughts on the metaverse and why it’s so interesting [00:06:07] - The ways hardware and software will shape the future of digital worlds [00:08:23] - Examples of how these digital experiences might look in the years to come [00:10:45] - His background, history, and his life before founding Playco [00:16:31] - Ways content creates human interactions and its role in user retention [00:18:43] - How successful social media platforms encourage user interaction [00:20:51] - Games becoming a way to create content and being a creation tool [00:23:06] - This history of user-generated content for pre-existing games [00:27:32] - Defining what instant gaming is and how it’s different from traditional gaming [00:30:24] - The technological problems and hurdles in creating games that load instantly [00:34:00] - Parallels between instant gaming and cloud-powered processing [00:36:43] - What types of games are most desirable for games shared via links [00:38:58] - The feel of this model working in real-time and the project that’s furthest along [00:41:37] - Lessons learned about working with and structuring partnerships with social media and content creation giants [00:45:06] - Ways in which social network platforms are evolving [00:48:04] - Playco’s business model and smart approaches to generating revenue [00:50:28] - The role NFTs might play in instant gaming and making crypto mainstream [00:53:03] - Crypto wallets and building one in house versus using a 3rd party wallet [00:54:17] - What the best case scenario will look like for Playco in a decade from now [01:00:44] - Other companies to go check out that leverage and empower individuals

Today is a special episode because it marks five years since I released the first episode of Invest Like the Best. Over those years, I’ve learned so much from so many investors and builders, but today’s guest may have taught me the most. Daniel Ek is the CEO and founder of Spotify, and I find him to be one of the most thoughtful business leaders in the world. Daniel is the perfect guest for this special occasion because he exemplifies the curiosity, humility, leadership, and dogged determination that I think characterizes the best investors and operators. In our conversation, we discuss the differences between the world of bits and atoms, how Daniel gets up to speed in challenging new fields, and why Europe might be a sleeping giant about to wake. We then bring the discussion back to Spotify, the evolving creator ecosystem, and Daniel’s frameworks for leading the business into its next chapter of growth. Over the past 5 years, we’ve produced more than 300 of these shows and reached nearly 30 million people. I am deeply thankful to the guests who’ve been willing to share their knowledge with us all and even more thankful to everyone who has taken the time to listen and learn alongside me. This has truly been the greatest pleasure of my career, and I don’t plan on ever stopping this journey. Now, Please enjoy my conversation with a great friend, Daniel Ek. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, and Ben Thompson. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:03:37) - [First question] - Building atoms versus bits and if we’re destined to return to atoms (00:08:04) - What makes early-stage atoms companies more challenging to build (00:10:20) - Whether or not we’re starting to see cross-pollinating of infrastructure companies into other sectors (00:13:00) - His process for learning about new fields when he knows nothing (00:16:12) - Big and interesting problems that we will need to solve (00:19:35) - The nature of healthcare’s technological adoption compared to other sectors (00:24:13) - Downstream unlocks of collecting and observing big pools of data (00:30:00) - What he has found effective about taking an idea from 0 to 1 (00:33:40) - Lessons learned about compounding change and staying patient (00:37:17) - History of European technology and its unique regional characteristics (00:42:40) - Cultural and continental traits that may make Europe a technological leader (00:45:42) - Characterizing the major lessons learned from his time at Spotify (00:50:31) - How artists are changing the ways they connect with their fans via Spotify (00:55:44) - What he would change about the legacy music industry given today’s tools (01:00:15) - The influence global exposure has on internet companies and creatives (01:03:02) - Interesting observations about the recent explosion of podcast popularity (01:07:36) - Working with, carrying, spreading, and maintaining Spotify’s sacred source (01:12:37) - Ways we can improve and sharpen our decision-making skills

My guest today is Gabby Dizon, co-founder of Yield Guild Games or YGG. In 2020, Gabby and his co-founders built YGG around the growing “play-to-earn” economy within blockchain-based games. Based in the Philippines, YGG effectively backs players - who might not otherwise be able to afford to play - in exchange for a share of their profits. Today, YGG is paying out over a $1m US dollars a week to players within its community - largely concentrated in their home country of the Philippines. The play-to-earn model has seen its most rapid growth in the popular NFT-based game “Axie Infinity”. Players earn tokens within the game which can be exchanged into local currencies or be used to purchase more digital assets. For a sense of how this market has expanded, Axie Infinity has already reported over $1.5b in sales over its history- and nearly $900mn over the last 30 days. The speed at which these games and the ecosystems around them are growing is remarkable. In our conversation, Gabby explains YGG’s decentralized structure, the unit economics of their business model, and how he deals with the volatility of crypto assets when trying to build a durable, long-term business. We also discuss the broader metaverse landscape, how it might evolve, what might derail it, and the technicalities of building a token-based, as opposed to equity-based, business. I hope you enjoy this wild conversation with Gabby Dizon. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:34] - [First question] - What Yield Guild Games is and what they do [00:04:30] - The growing popularity of play-to-earn games in the metaverse [00:06:07] - Major categories of digital assets that exist today [00:08:11] - How players can earn money playing Axie Infinity [00:10:47] - The business model of YGG and what they offer to players [00:12:42] - Potential earnings of playing Axie Infinity [00:15:03] - Possible risks to demand and what the Axie economy could be in a few years [00:17:54] - Evaluating games that are worth investing in [00:19:55] - The kinds of things that will be most valuable across games in the future [00:21:37] - Differences in value between cosmetic and utilitarian in-game purchases [00:23:04] - Key focuses of YGG over the near future [00:29:02] - Ways DAOs are better or worse than traditional equity tables [00:30:11] - The state of YGGs economics today [00:31:16] - The Guild’s player retention and growing their scholars [00:32:54] - Barriers to entry for building a competitive DAO like YGG [00:34:14] - What made Gabby so interested in crypto originally [00:36:38] - His personal journey to crypto games [00:37:53] - Jobs that may carry over from the real world into the metaverse [00:39:36] - Companies that will arise focusing solely on in-game item creation [00:41:18] - Base layers of infrastructure needed to create the best future for crypto gaming [00:44:32] - Shared qualities between games that have a high replayability rate [00:46:40] - Good and bad tokenomic ecosystem designs [00:48:17] - What the biggest risks are for the future success of crypto gaming [00:49:26] - What factors will ensure the future growth and adoption of crypto gaming [00:50:25] - How much fiat flows through Axie and the growing value of in-game assets [00:52:05] - Whether or not we’ll see purchasable utility items in the future [00:53:21] - What he’s most excited about for the future of the metaverse [00:54:52] - The kindest thing that anyone has ever done for him

My guest today is Scott Malpass. Scott was the CIO of Notre Dame's endowment for 32 years and has always been a pioneer at the forefront of the endowment investing world - leading Notre Dame's early investments into Sequoia as well as some of the premier fund managers in China decades ago. Scott built the endowment into a powerhouse, scaling it from $400 million to over $12 billion of assets under management across 175 managers. In our conversation, we talk about the qualities he looks for in great investors, how asset classes have evolved over his 30 years of investing, and how Scott recruited top talent to work at Notre Dame’s endowment. Scott is clearly on the Mt. Rushmore of institutional investors, and I’m lucky to consider him a mentor and a friend. I hope you enjoy this great conversation with Scott Malpass. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:54] - [First question] - Finding his way to investing and Notre Dame [00:06:11] - Key milestones of running their endowment for so long [00:07:58] - What an endowment model is and how it’s evolved [00:10:30] - The ingredients that unite their shared successes [00:11:46] - His philosophy on building a differentiated investing team [00:13:11] - How he approached talent identification when hiring new managers [00:15:39] - The importance of understanding who someone was before they became an investor [00:17:12] - Episode: Steve Mandel, Investing Behind Change [00:17:28] - Whether or not someone has a reliable and solid core [00:19:03] - Differentiating between self-confidence and an over-inflated ego [00:20:27] - Evaluating real investing skills in an individual [00:21:44] - The most memorable major early partner he brought on to the endowment [00:23:14] - What made Don Valentine and Sequoia so special [00:24:21] - Forcing good long-term incentive alignment with a firm [00:26:35] - What makes a GP exceptional in how they treat LPs [00:28:01] - How many managers actually have the ability to create alpha [00:29:24] - His thoughts on venture capital and how he’s seen it evolve [00:32:40] - The role private equity played in his success and how it’s changed over the years [00:34:36] - Why diversify when managing such a large pool of capital [00:35:58] - Public equity as an area of opportunity relative to private and venture capital [00:38:08] - Bonds in an endowment and high net worth family offices [00:39:32] - Whether or not equities are still appealing [00:40:20] - Lessons from investing in China so early in his career [00:42:59] - What he’s learned about effective leadership from leading the team at Notre Dame [00:44:54] - Advice on building your own basic portfolio [00:47:03] - Portable classroom lessons that lend themselves to effective teaching [00:48:28] - Why it’s important to do team-building exercises and off-sites [00:50:07] - His thoughts on cryptocurrency and how others should think about it [00:51:52] - Students that he’s most proud of across his career [00:54:56] - Ways you should spend your 20s if you want to become a great investor [00:55:49] - What’s on the horizon for him over the coming years [00:57:55] - The kindest thing anyone has ever done for him

My guest today is Mike Maples, co-founder and partner of Floodgate. As a child of the computer revolution, Mike was deconstructing calculators in grade school, writing video games in high school, and inevitably found himself building businesses in Silicon Valley after college. After his success as an operator, Mike eventually transitioned to become a full-time venture investor in the 2000s, and has since built a track record that includes Twitter, Twitch, Lyft, Octa, and a long list of successful tech businesses. I'm not sure I've recorded a conversation with more applicable ideas and advice for company builders. We discussed early insights and secrets, value hypothesis testing, customer development, growth, team orchestration, and a lot more. This is a masterclass from somebody who has seen it all. Also, do not miss his answer to the kindest thing question at the end of the conversation. I hope you enjoy this great talk with Mike Maples. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:08] - [First question] - His philosophy on the power of forcing a choice [00:04:43] - How he knows when he comes across a team that has an apple quality [00:07:39] - Exploring and hunting new inflections in ever-changing systems [00:10:37] - Why recognizing winning insights allows you to not have to predict the future [00:12:23] - Whether or not the evolving nature of the funding landscape changes his thinking [00:14:18] - An example of his insight framework and stress testing a team’s potential [00:17:21] - Practice reckless optimism [00:18:54] - Commonalities between teams and their ideas when they get inflections wrong [00:20:12] - What the value hypothesis is and how to test it [00:22:15] - Ways that effective startup teams operate compared to big corporations [00:25:36] - His involvement post-investment and where outsiders can be most helpful in a companies’ early days [00:28:34] - Lessons learned about finding, convincing, and marketing to their first customers [00:32:13] - An example of early customer selection done phenomenally well [00:34:09] - Why it was possible for companies like Justin.TV and Lift to pivot so dramatically from their original ideas [00:38:49] - Customer development and using good customers to your advantage [00:42:31] - Who went from founder to the best growth executive [00:43:05] - What he thinks his firm will need to do to continue offering an apple to founders [00:46:08] - The most useful stress tests his firm can offer founders [00:46:52] - Defining category design and what the process of category design looks like [00:50:33] - Inflections he’s currently paying the most attention to [00:52:07] - His experience with an HP35 calculator and how it shaped his life [00:54:41] - What venture capital may look like in the future [00:56:30] - The most difficult things he faces in his career [00:57:52] - Ways he’s learned to manage failure more effectively [00:59:06] - The kindest thing that anyone has ever done for him

My guests today are Renata Quintini and Roseanne Wincek, co-founders and managing directors of Renegade Partners. Before launching Renegade, Renata and Roseanne were partners at high-profile VC firms, Lux Capital and IVP. During our conversation, we explore their careers and what led them to launch Renegade. We cover what it means to invest at the “Supercritical Stage” in venture and dive into a variety of topics around this theme. We then discuss their investing philosophies more broadly, covering what best-in-class talent pipelines look like, what quality revenue means to them, and what worries them most in search of businesses with outsized potential returns. I think this episode highlights that even as competition in venture has intensified - the best VC partners can offer more than just capital. I hope you enjoy my conversation with Renata and Roseanne. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:57] - [First question] - What the process of starting a new investment firm was like [00:05:22] - Why the world needs another venture firm [00:06:48] - The biggest takeaway from Renata's experience at a start-up Venture firm [00:07:51] - The inspiration for Renegade [00:11:48] - The most common mistakes made in the early stages of a company [00:15:14] - Key items to look into first when evaluating companies [00:18:04] - Internal superpowers: helping a founder use their strengths [00:23:46] - Superforecasting: The Art and Science of Prediction [00:24:04] - What makes a good customer call [00:25:44] - How more than one Operating Partner changes the conversation and reveals more [00:27:59] - How businesses have changed in the past few years [00:30:31] - What companies that have good talent pipelines do to set themselves apart [00:35:36] - Lessons learned from working with Coda and its CEO, Shishir Mehrotra [00:38:12] - Lessons learned from working with MasterClass [00:41:21] - Differentiating between high and low-quality revenue when evaluating a company [00:47:39] - What scares them about investing in outliers [00:51:07] - Improvements made as investors and catalysts for those changes [00:53:48] - Building an organization that will disrupt itself [00:56:43] - The kindest thing anyone has ever done for them

My guest today is Max Simkoff, Founder and CEO of Doma. Max founded Doma in 2016 after experiencing the pain and manual process associated with title insurance and real estate transactions. With a background in predictive analytics, Max built Doma to bring a digital-first approach to a historically manual and labor-intensive process. In our conversation, we cover the history behind mortgage closings, where title companies fall into that process, and how Doma is using technology to improve the client experience. We also discuss Max’s formative experiences at his previous venture, Evolv, and the lessons he’s learned from taking Doma from an idea to a public company. There are many great lessons in this episode, and Max’s entrepreneurial energy shines throughout. Please enjoy this great conversation with Max Simkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:17] - [First question] - What Doma does and what they do for customers [00:04:38] - What Title is and why it sits at the center of such a large transaction [00:08:41] - Overview of the business economics of this space [00:13:55] - How the ecosystem works writ large [00:18:05] - The formative business experiences he had that led him to today [00:23:03] - What it means to be great at this whole process [00:26:53] - The thing Doma tries to predict and the inputs that allow them to do so [00:32:50] - Defining his biggest roadblocks and how they’ve changed over time [00:36:02] - Managing stakeholder expectations and perception [00:40:22] - Learning to walk to the line of having a large vision and communicating it [00:42:51] - What his loose screw is as a founder [00:45:06] - The square-peg-round-hole they encountered during the pandemic [00:51:20] - What the counterproductive byproduct of his genius is [00:53:35] - Figuring out where to take the company next [00:56:52] - The big lessons learned from interacting with capital markets [00:59:30] - Other entrepreneurs he feels are maniacs that he respects [01:00:55] - What will be the biggest contributing factors to their success over the next decade [01:02:44] - The key ingredients for building a winning team [01:04:34] - The kindest thing anyone has ever done for him

The intro music you just heard is from my guest today, Suzanne Ciani, an early pioneer of electronic music dating back to the 1970s. As a 5-time Grammy-nominated composer, Suzanne’s music can be heard on her solo albums as well as films, games, and countless commercials. Many have argued her Coca-Cola “pop and pour” changed the sound of advertising forever. During our conversation, we discuss what it means to be an artist, how to evolve away from the need for approval and validation, and the importance of mentors during the creative process. While many of our guests strive to be lifelong learners - Suzanne seems to take this a step further as a lifelong learner and a lifelong creator. I hope you enjoy my conversation with Suzanne Ciani. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 20,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:53] - [First question] - One of her proudest moments early in her life [00:05:18] - What she’s learned about originality and its role in the creative process [00:07:24] - Advice for breaking out of a derivative impulse and finding your character [00:09:27] - Going from a classically trained pianist to exploring modular synthesis [00:13:47] - Performing on David Letterman [00:17:55] - What the Buchla is and the sounds it can make [00:23:03] - How much of playing a modular synth is improvisational versus pre-made [00:24:36] - Ways she would design a creative system for other creatives [00:27:38] - What her interface allows her to do and the mechanics of it [00:29:07] - Describing what the core sound elements are that she manipulates [00:32:30] - The role of women in music and how it’s evolved over time [00:35:06] - What stands out from her mentorship with Ilse Bing [00:38:16] - Later career creative freedom and what it unlocks for artists [00:39:25] - Her thoughts on the creative process writ large and its components [00:42:10] - Commercial sound design and working with Coca-Cola and Atari [00:44:46] - Observations from a creative life that other artists could benefit from [00:46:11] - Unifying factors across her best performances [00:47:53] - What the future might hold for technology and music [00:50:18] - Where to start when exploring her discography [00:51:17] - The kindest thing that anyone has ever done for her

My guest today is Sameer Shariff, co-founder and CEO of Cambly. After starting his career at Google, Sameer founded Cambly in 2013 as an on-demand service to learn English. At the touch of a button, Cambly connects its global user base into a 1-on-1 conversation with an English speaker. During our conversation, we cover the origin story of the business, what Sameer views as the core functions of the two-sided marketplace, and how the team approached scaling a product that was international from day one. Once you hear Sameer talk, you quickly realize the size of Cambly’s market opportunity and why it may have been easy to overlook this problem. I hope you enjoy this great conversation with Sameer Shariff. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:05] - [First question] - What led him to the original concept of Cambly [00:05:21] - Beginning to learn the scope of the problem and what solving it unlocked [00:07:58] - What Cambly is and how they started tackling the problem [00:09:15] - Lessons learned about the challenges of building an alive marketplace [00:11:41] - Technical challenges and the enabling technologies that allowed it to happen [00:12:59] - Deciding on what to focus on first when it comes to students [00:15:24] - Figuring out the formula for unit economics and the pricing structure [00:17:02] - Learning what doesn’t work in their business model [00:18:07] - Setting up quality control measures and moderation [00:21:01] - Tools and services that will improve their experience in the future [00:23:18] - What the 11-star version of Cambly would look like in a decade [00:26:56] - Ways in which their software and concept could be applied elsewhere [00:28:30] - Setting themselves up for success and fine-tuning the matchmaking component [00:30:37] - Driving users to the platform and audience building strategies [00:33:46] - Making the platform feel native to each country it serves [00:35:59] - Surprising lessons learned around distribution and market penetration [00:37:13] - The biggest boss battles faced as a business [00:40:17] - Advice he would give to founders in a similar situation [00:41:32] - How he’s personally changed the most across this journey [00:43:32] - Ways he’s shifted to a state of letting go and trusting his team more [00:45:14] - Lessons learned from studying Airbnb [00:47:22] - The kindest thing anyone has ever done for him

My guest today is Sridhar Ramaswamy, co-founder and CEO of Neeva and Venture Partner at Greylock. After a 15-year career building Google’s ad business, Sridhar launched Neeva as an ad-free search engine with a focus on personalization and privacy. During our conversation, we dive into the early days of search and what led to Google’s dominance. Sridhar shares his view on the potential end state for ad-based search engines, and how all of his experiences led him to found Neeva. Beyond a great deep dive into the origins of search, this discussion is filled with great lessons about data-driven decisions, the value of partnerships, and balancing revenue opportunities against user experience. I hope you enjoy my conversation with Sridhar Ramaswamy. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:39] - [First question] - Major chapters of the history of search engine technology [00:09:21] - The early days of the page rank revenue model prior to ads [00:16:27] - Reputation and quality and how they were applied in Google’s early days [00:21:10] - Driving variables of Google’s ad model that will drive their business going forward [00:26:48] - Lessons learned about the importance of partnerships while at Google [00:33:26] - What is Neeva and what motivated him to start it in the first place [00:39:11] - Variables in building an ad-free search engine that can compete with Google [00:44:57] - Thoughts on tracking and privacy in the tech world today writ large [00:50:09] - Lessons he’s learned about pricing when it comes to software [00:52:58] - Figuring out finding customers when your addressable market is everyone [00:56:20] - What he’s learned about leadership over the course of his career writ large [00:58:05] - What he’s learned about identifying candidates and winning them over when it comes to recruiting new talent [01:00:27] - His philosophy on product development in general [01:02:19] - Framing problems in a way that allows you to reach milestones as you build [01:04:43] - His biggest professional mistake and what he learned from it [01:06:08] - The kindest thing that anyone has ever done for him [01:07:49] - What Bill Campbell brings to mind when he thinks about him

My guest today is Ernie Garcia, co-founder and CEO of online used car platform, Carvana. Ernie launched Carvana in 2012, and less than a decade later, the business commands a $60 billion valuation while selling a used car every other minute. Our conversation covered a lot of ground. We discussed effective decision-making, what it means to be a long-term thinker, and what Ernie sees as the defining features of attractive markets. We then went deep on Carvana itself, covering the original insight, logistics operations, and counter-intuitive decisions Carvana took as they set about building the brand. I think you’ll find Ernie’s insights and energy infectious. I hope you enjoy this great conversation with Carvana CEO, Ernie Garcia. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by SnackMagic. SnackMagic is the only 100% customizable snack and swag service that allows recipients to build their own snack stash. Whether you want to thank your global team, need goodie bags for your upcoming hybrid event or want to stock your office pantry, the menu of over 1,000 types of snacks and sips covers just about every preference. To learn more and get 10% off your first order with code Patrick at snackmagic.com/patrick. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:10] - [First question] - Defining average decision quality and he weaves it into his business [00:05:40] - How he would assess average decision quality in another company [00:07:04] - What company culture means to him and building it at Carvana [00:08:45] - Key features of a market that is desirable to step into as an entrepreneur [00:10:06] - Various levels of complexity faced in automotive retail [00:13:51] - Reality Has A Surprising Amount Of Detail; The genesis idea that led to Carvana [00:17:52] - Critically new things delivered to customers when buying a used car [00:20:43] - Dealership unit economics vs logistics platform economics and what drives gross profit per unit [00:24:47] - What is an IRC center, the hub and spoke model, and the skeleton of Carvana [00:28:44] - The size and scope of one of their fulfillment centers and cost savings involved [00:30:29] - How the spoke component works and ways it will be improved over time [00:32:39] - Defining what being a long term thinker means to him [00:35:50] - The story behind the Carvana car vending machine [00:39:49] - His thinking on the dual-layer nature of customer experience and communication [00:41:59] - Mistakes and failures made while learning to become good communicators [00:44:21] - Great companies get a lot done very fast [00:48:56] - Infrastructure set in place to maintain their pace as they scale [00:51:50] - The embedded formula used for teams to communicate what they want to do [00:52:50] - What it felt like as a leader going through the pandemic [00:58:24] - Whether or not COVID-19 has permanently impacted the consumer landscape [01:00:03] - Businesses, leaders, and things he’s studied that others could learn from [01:01:55] - Surprising new things arising in the automotive and transport industries [01:05:23] - The kindest thing anyone has ever done for him

My guest today is Karen Karniol-Tambour, Partner and Co-CIO for Sustainability at Bridgewater Associates. You will quickly understand why Ray Dalio described Karen as a “vacuum cleaner of learning” - our conversation covered a variety of market themes, and Karen goes deep on each of them. We touch on inflation, monetary policy, currencies, retail investors, ESG, and how each of these levers has become more important for investors to understand. Karen has a rare skill for making complex ideas seem simple, and I love the frameworks she uses to deconstruct big, important issues. She does such a good job of explaining what’s changed, why it matters, and what to do about it. I hope you enjoy my great conversation with Karen Karniol-Tambour. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:39] - [First question] - How Bridgewater invests and the experiences that led her there [00:06:47] - What working with Daniel Kahneman felt like and learning his perspective [00:08:09] - An example of holding herself to accumulating and stress testing data [00:10:17] - Important variables to consider when seeking returns in large-scale bets [00:14:18] - What we should be thinking about in terms of inflation as we look to the future [00:20:07] - How she thinks about inflation and how she defines it [00:22:57] - Relevant asset classes that can protect or help diversify against inflation [00:26:14] - What still largely confuses her about inflation and its many facets [00:28:05] - Her philosophy and model for understanding the system of currency [00:33:21] - How investors should think about the US dollar [00:35:50] - Whether or not owning an unhedged global equity index gives you currency exposure [00:37:07] - The fundamental nature of equity markets and household balance sheets [00:41:37] - Ways the growing wave of retail investors will impact prices and returns [00:43:53] - How she’s evolved her valuation approach given our new investor landscape [00:45:43] - The good and bad roles ESG might play for investors going forward [00:50:36] - Potential concerns around the growing trend of ESG writ large [00:53:51] - Thoughts on the 60/40 portfolio and whether or not it’s still worth using [00:55:32] - Designing a default diversified portfolio in light of markets today [00:57:45] - Aspects of the global market economy today people should be talking about more [01:01:15] - Ways she investigates a new topic and how it has evolved over time [01:04:14] - Variables that matter in investment teams and company cultures [01:06:53] - How she would approach cryptocurrency and what’s interesting about them [01:09:08] - A rosey and gloomy take of what the world could look like in a decade [01:12:37] - The kindest thing that anyone has ever done for her

My guest today is Sebastian Mejia, co-founder and president of Rappi. Founded in Bogota, Colombia in 2015, Rappi set out to create an on-demand convenience store and has expanded into nine countries and over 200 cities. In our conversation, Sebastian and I discuss what differentiates Rappi from US-based delivery apps, how the company evolved early by understanding their customers’ behavior, and how the business balances growth vs. unit economics. I loved hearing Sebastian’s views of the value of brands in an increasingly app-based world, the importance of being hyper-local for any delivery-based business, and how fungibility is a key characteristic of any rewards program. I hope you enjoy this great conversation with Sebastian Mejia. Before we transition to the episode, I also wanted to highlight our newest series, Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. Find more information on joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Dell Technologies. When you call a Dell Technologies Advisor, they’re focused on you - ready to give advice on everything from laptops to the cloud to keep your small business ready for what’s next. Call an advisor today at 877 ASK DELL, and do more with modern devices and Windows 10 Pro. ----- This episode is brought to you by Versett. Versett designs, builds, and scales digital platforms for some of the world's most ambitious companies. If you require a high-performance team to tackle a hard or ambiguous problem, then Versett is the firm to call. To check them out, visit versett.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:54] - [First question] - What the Rappi is their current scale and user base [00:05:30] - The early-stage problems they encountered when building their platform [00:08:43] - Building the initial network dynamics and unit economics of couriers [00:12:35] - Solving the data collection and integration needed to power Rappi [00:15:22] - Defining what local means and the difference between units and zones [00:17:33] - Other active companies that offer a similar service [00:18:27] - Thoughts on making money in such a diversified supply chain [00:22:57] - The moment they realized they were starting to feel scale effects for the first time [00:25:11] - Questions they’re asking themselves as they continue to grow [00:28:20] - Streaming consumer goods and how they’ll change consumer behavior [00:31:45] - Impacts on brands Rappi might have with larger user adoption [00:34:34] - Unique attributes and opportunities in Latin American markets today [00:38:45] - Observations of early investors and questions investors as him often [00:40:17] - The value unlock of having a subscription model akin to Amazon prime [00:44:47] - How crypto and blockchain technology might benefit Rappi users [00:47:16] - His perspective on crypto in Latin America today compared to the US [00:48:09] - Their work in financial services [00:47:30] - Possible reasons why Rappi might not succeed in the future [00:50:30] - The kindest thing anyone has ever done for him

Today’s conversation is one of my all-time favorites, with someone I’ve come to respect deeply in the field of investing. My guest is Carl Kawaja, who has served as a portfolio manager at Capital Group for decades. Capital Group is among the most respected shareholders in the world, with over $2T of assets, and listening to Carl, you’ll hear why. In our conversation, we cover Carl’s criteria for building conviction around long-term holdings, why he views uncertainty and ambiguity as healthy, and why tolerating failure is key to great investing career. Throughout our discussion, Carl connects his lessons through a variety of direct experiences, personal analogies, and broader frameworks. I love his ability to talk in the weeds about his investments in Vale and TSMC and then quickly shift to his broader thematic views like “The Empire Strikes Back.” I hope you enjoy this great conversation with Carl Kawaja. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:38] - [First question] - The two companies he has owned the longest and what they’ve taught him as an investor [00:16:37] - Discussing his investment style through the lens of simplicity [00:24:35] - A time where he worked to try and create a simplified equation but couldn’t [00:30:59] - Discussing his investment style through the lens of echolocation and ambiguity [00:36:03] - Thoughts on whether buying well or holding well is more difficult [00:40:40] - Capital Group’s history and his river-rafting analogy in regards to the company [00:47:48] - What he means by “The Empire Strikes Back” and relevant market themes [00:54:50] - A brief summary of “The Empire Strikes Back” [00:58:42] - Common reasons that he may have gotten something really wrong [01:03:34] - Impressions made on him by the poet Rilke [01:09:00] - The work of Brunello Cucinelli and the nature of quality [01:13:08] - Advice for new investors who want to step into the field and set themselves up for success [01:13:54] - The Visual Display of Quantitative Information [01:17:39] - What he’s learned about kindness [01:19:54] - The kindest thing that anyone has ever done for him

My guest today is Stewart Butterfield, founder and CEO of Slack. Stewart’s 2014 essay “Why We Don’t Sell Saddles Here” had a massive impact on my own business journey, which made this discussion extra special. During our conversation, we discuss the concept of owner’s delusion, how to frame the boundaries between product and market, and the challenge of changing people’s mental models and behavior when introducing innovative products. I hope you enjoy my conversation with Stewart. Before we transition to the episode, I also wanted to highlight our newest series Business Breakdowns. Each week, we do a deep dive into an individual business to understand what makes it tick. For more information go to joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:51] - [First question] - Discussing his essay We Don’t Sell Saddles Here [00:06:19] - Important contrast between innovation and the product [00:06:46] - Who Do You Want Your Customers to Become? [00:08:07] - His thoughts on marketing from both ends and how he’s gotten better at it [00:10:45] - What across Slack’s history has been the most successful market messaging creation strategy [00:13:43] - The 5K contest and how it taught him about the design unlock of limitations [00:17:44] - How limitations and constraints can power and incentivize innovation [00:21:21] - Why both of his attempts to build videogames ended up as consumer software [00:27:55] - Whether or not there is still white space in digital communication software [00:30:15] - The dynamic between effective communication and building communication tools [00:34:02] - A future of digital-first companies and what that might look like [00:40:15] - Leadership and Self-Deception and what self-deception means to him [00:43:39] - Examples of self-deception he underwent that he was able to learn from [00:46:59] - Mastery and its importance in the world of business [00:48:59] - Why hippies and APIs may have a tighter correlation than we think [00:54:01] - Whether or not technology is fundamentally amoral [00:56:10] - Interesting and open questions about the future that remain unanswered [00:58:33] - His current creative outlets that he engages with the most [00:59:24] - Yahoo Resignation Letter and why he wrote it the way he did [01:00:31] - Lessons for investors and builders that he’s learned from building Slack [01:03:07] - The kindest thing that anyone has ever done for him [01:04:27] - Why a philosophy primer would be beneficial for virtually everyone

My guest today is Steve Mandel, founder of Lone Pine Capital, one of the most successful hedge fund and investment firms of this generation. In our conversation, we discuss how the investing business has evolved since Steve’s start in the 1980s, why it’s so difficult to drive alpha by shorting stocks today versus 20 years ago, and why Steve still loves to get into the guts of a business. Steve shares his lessons through a variety of great stories, which made this such a fun experience. Please enjoy my conversation with Steve Mandel. Before we transition to my interview with Steve, I’d also like to highlight the newest Colossus show, Business Breakdowns. If you like Steve’s idea of getting into the guts of a business, this is the show for you. Please find a list of our episodes at joincolossus.com and subscribe to Business Breakdowns on your preferred podcast player. I hope you enjoy my conversation with Steve Mandel. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:36] - [First question] - His first encounter with Walmart [00:05:51] - What about Sam Walton made him worth idolizing [00:08:14] - The juxtaposition of business to management quality [00:10:57] - Why a career in retail influenced the lens he sees the investing world through [00:11:23] - What bad company culture in retail looks like [00:12:33] - Aspects of Walmart’s culture that could be applied to other companies [00:13:54] - Defining the core essence of retail company culture [00:15:02] - How long it used to take for a stock to properly reflect new information [00:16:40] - The nature of edge and what it looked like back then [00:21:09] - Investing behind change and assessing trends [00:23:06] - Scars and stories from just how vicious short markets can be [00:26:32] - Thoughts on building an enduring firm and how it’s evolved over time [00:32:14] - The process and decision to remove himself from the day-to-day operations [00:33:55] - Lessons learned over time about what separates good from bad analysts [00:34:42] - Where to start looking when getting into the guts of a business [00:36:31] - What is most exciting when you’re inside the guts [00:39:19] - Interesting aspects about payments today writ large [00:42:15] - Broad trends around change in consumer trends [00:43:02] - How he views software businesses looking forward as an investor [00:45:14] - Great managers and their emphasis on analyzing their competitive advantage [00:48:02] - Ways that pace as a variable has changed in importance [00:49:27] - What he thinks we’ll look back on as silly in how markets currently operate [00:50:33] - Whether or not all markets becoming 24/7 will be a good thing [00:51:59] - Big iconic business stories that newcomers should study [00:56:06] - Whether or not business building is an art form [00:57:38] - Key levers that typically always matter for a business [00:59:53] - Other major aspects of the world that are important to consider [01:01:13] - How his personal motivations morphed over the years and what has changed [01:02:55] - Valuable lessons learned about the inputs and outputs of education [01:04:15] - Advice for would-be future investment analysts [01:05:46] - The kindest thing anyone has ever done for him

My guest today is Spenser Skates, CEO and co-founder of Amplitude Analytics. Spenser founded Amplitude in 2012 with a thesis that building the best product requires, deep cross-functional understanding of customer behavior. During our conversation, we discuss Spenser’s long history in programming and how his early experiences tie into his work today. We also explore the nuances of equity compensation, how different VCs can play a role in the success of a startup, and Spenser’s desire to see more direct listings vs. IPOs. While many founders follow the path of others, it is clear Spenser takes time to challenge the status quo. Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. In this episode, you will hear how Spenser’s team worked with the meditation app, Calm, to optimize for customer growth. It was particularly interesting to hear this story after listening to the Calm breakdown. Find episodes of Business Breakdowns on your preferred podcast provider or on joincolossus.com I hope you enjoy my conversation with Spenser Skates. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Upgrade your business during Dell Technologies’ Black Friday in July event. Get savings up to 50% off AND take your office with you with Windows 10 Pro. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:15] - [First question] - How he won the Battlecode tournament at MIT twice [00:06:43] - A few key insights that helped him win the tournaments [00:08:34] - Lessons learned at MIT and the road to starting Amplitude [00:13:57] - A typical customer experience when using Amplitude [00:17:17] - How their platform extrapolates key data points in user data that others don’t [00:19:03] - His most productive mistakes made while building the company [00:21:10] - The strange history of equity and his thoughts on how it should be used [00:28:08] - The recent changes in the vesting schedule for newly issued equity [00:29:59] - Lessons learned from working with some of the best investors out there [00:36:20] - His thoughts on the IPO process and going public writ large [00:41:04] - The role the SEC plays and his perspective on SPACs [00:44:01] - Differences in direct listings compared to traditional IPOs [00:48:36] - His thoughts on dual-class structures and corporate governance [00:50:11] - Hopes for Amplitude as he looks five years into the future [00:52:03] - The potential value unlock of smart software for end-users [00:55:08] - The kindest thing that anyone has ever done for him

My guest today is David Sacks, General Partner at Craft Ventures and founding COO of PayPal. During our conversation, we explore what differentiates Enterprise SaaS from DTC subscriptions, what makes for a magical product launch event, and what key growth metrics David uses to measure success. David has written extensively on his idea of operating cadence, and we explore how that applies to the various functions within an organization. As time goes on, I am more and more impressed at the talent that existed within the original PayPal mafia, and I couldn’t help but ask David to highlight the superpowers for a few of his early partners. This was an incredibly informative conversation with fun threads throughout. Please enjoy my conversation with David Sacks. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:30] - [First question] - Defining what it means when a company can explode [00:05:39] - What it would look like if a company didn’t have what it takes to explode [00:06:17] - Key factors that make for a strong product hook [00:08:51] - Whether or not there has been a divergence at the early stage of B2B investing compared to B2C [00:11:36] - Reasons why products that make people collaborate are always stronger [00:14:14] - Nuances between team subscriptions and team product use [00:15:37] - Describing the burn multiple metric and how it can be applied to companies [00:18:18] - The gross margin problem and issues for businesses in this area writ large [00:22:34] - Common practices amongst sales programs that have and haven’t worked [00:24:22] - What about new founders makes him most excited [00:25:58] - Explaining cadence and why he groups product and marketing as one bucket and sales and finance as another [00:30:44] - The anatomy of a great product launch [00:32:17] - Ways in which external dependencies can be landmines for growing companies [00:34:06] - Whether or not he’s willingness to invest in a business with regulatory variables [00:36:59] - What he’s seen in company culture that breaks a company as they scale [00:39:55] - Things a founder actually does in order to reign in and tame their culture [00:42:08] - Unique traits of founders who are both investors and operators [00:44:12] - Peter Thiel’s superpower [00:44:57] - Max Levchin’s superpower [00:45:38] - Elon Musk’s superpower [00:46:07] - Roelof Botha’s superpower [00:47:15] - Reid Hoffman’s superpower [00:47:43] - Keith Rabois’ superpower [00:48:41] - What zones of change in the world have his attention writ large [00:51:43] - Why teams want to be pushed and how we can apply that to business [00:55:25] - The kindest thing anyone has ever done for him

My guest today is David Vélez, founder and CEO of Nubank, the world’s largest digital bank with over 40 million customers. In our conversation, David talks about his venture capital background at Sequoia and how that led him down an entrepreneurial path in Latin America. We also talk about the pros and cons of building a digitally native business and what gets him most excited about innovation and technology in emerging markets. Before we start the episode, I would also like to highlight our newest Colossus show, Business Breakdowns. Since launching in early April, we have published over 15 Breakdowns and continue to release a new episode weekly. To learn more, check out joincolossus.com. I hope you enjoy my conversation with David Vélez. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:55] - [First question] - Why Berkshire Hathaway took such an interest in Nubank [00:04:46] - Key differentiators between Nubank and other incumbent banks [00:07:11] - Onboarding user experience and overview of customer acquisition [00:10:38] - The original problem Nubank wanted to solve and how they approached it [00:15:32] - Lessons from working at Sequoia about great FinTech businesses [00:19:18] - What parts of his personality and life experience worked its way into NuBank [00:23:18] - Obstacles that needed to be overcome in order to serve the Brazilian public [00:27:52] - Transparency and patience needed to overcome a complicated problem [00:31:11] - Nubank’s business economics compared to other banks [00:34:46] - Overview of rewards programs and why customers like them so much [00:37:27] - Best questions asked that explained Nubank’s market opportunity [00:42:02] - Second layer unit economics of the company and where to look for them [00:45:51] - How far we are into the Latin American technological ecosystem’s development [00:47:24] - Lessons learned from some of the worst decisions he’s made as a founder [00:51:30] - What he’s most excited about for the future [00:54:19] - The kindest thing anyone has ever done for him

My guest today is Balaji Srinivasan, a serial entrepreneur and angel investor. Balaji is known to challenge conventional wisdom, and he lives up to his reputation in this conversation. We discuss a wide variety of topics, including advancements in health tracking, ways to evaluate your own information diet, and how technology is driving decentralization and what that could mean for countries, corporations, and individuals. Before we transition to the episode, if you enjoy this conversation with Balaji, I’d recommend the Ethereum episode on our newest show, Business Breakdowns. You can find that episode and more on your favorite podcast player or at joincolossus.com. Please enjoy my conversation with Balaji Srinivasan. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Marqeta, Oatly, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick". ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:30] - [First question] - Thoughts on information diets and how they influence individuals [00:21:37] - Ways to optimize your diet by reading the source material and consuming less news [00:26:40] - Understanding the informational supply chain and tracing data back to the origin [00:41:07] - Modern cities, the nature of a group of individuals, and what sovereignty may mean in the coming years [00:53:52] - Key ingredients and main components needed for a successful startup city [01:11:35] - Social impacts from everyone becoming an investor and how it ties into everything [01:25:49] - Recommendations and a personal prescription for longevity, health, and wealth [01:37:32] - The kindest thing anyone has ever done for him

My guest today Michael Mayer, is the founder and CEO of Bottomless, a company that automatically replenishes your coffee supply where I am both an excited investor and customer. Today’s conversation is about tactical lessons Michael has learned while building the business. We talk about identifying an addressable problem, how to avoid solving for bottlenecks that don’t yet exist, and how to iterate through problems before scaling. As yet another example of a self-taught entrepreneur, it’s inspiring to hear Michael’s mindset for problem-solving. I hope you enjoy my conversation with Michael Mayer. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Upgrade your business during Dell Technologies’ Black Friday in July event. Get savings up to 50% off AND take your office with you with Windows 10 Pro. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at https://www.dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA, or ISO 27001 reports at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - How he got into this space in the first place and found the problem Bottomless would eventually solve [00:08:43] - What he would do better the second time if he had to find a problem and narrow his focus all over again [00:09:49] - The most notable lessons learned about data legibility beyond the scale [00:10:15] - Seeing like a State: How Certain Schemes to Improve the Human Condition Have Failed [00:13:01] - Overview of building the first Bottomless hardware prototype [00:14:29] - First steps of physically assembling the first scale and learning fabrication [00:17:40] - Roughly how long it would take to build scales in the beginning [00:18:30] - How long the company was bootstrapped [00:20:41] - Making the pivot to seeking out investor support [00:29:03] - The often overlooked role of social capital as a startup founder [00:31:00] - Importance of following niches and passions [00:32:15] - His philosophy in successfully scaling the production side of the company [00:34:45] - Lessons learned from bottlenecks and their utility in founder growth [00:36:52] - The problem of supplier legibility and improving it [00:40:14] - Understanding USPS predictability as a product input [00:43:03] - Always problems to solve and the fractal nature of them [00:46:13] - Challenges of hiring staff in the tech space [00:50:15] - Lessons learned about personal bottlenecks and the need to evolve alongside your company [00:52:21] - Monitoring your informational inputs and their role in shaping your mindset [00:55:58] - Closing thoughts on the business boss battles founders face [00:57:38] - Why society writ large should perceive starting a company as status-enhancing [00:59:44] - What bottlenecks for Bottomless may present themselves in a year from now

My guest today is Silicon Valley icon, Marc Andreessen. Before co-founding the legendary venture capital firm, Andreessen Horowitz, Marc was an early pioneer of the internet. At age 22, he built Mosaic, the first widely adopted web browser and the technology that underpinned Netscape Communications. Marc was an early proponent of cloud computing, social networks, and the software business model. In each case, Marc seemed to be well ahead of the crowd. During our conversation, we explore how software is making the world better, how slow sectors like education, healthcare, and housing are eating the economy, and Marc’s vision of the future for A16Z. Please enjoy my conversation with Marc Andreessen. Before we transition to the episode, I wanted to highlight our newest series, Business Breakdowns. Each week we do a deep dive into an individual business to understand what makes it great. Find more information on joincolossus.com or search for and sign up to the Business Breakdowns feed on your preferred podcast player. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:04:10] - [First question] The ways in which software is eating the world [00:06:25] - The power of transitioning from atoms to bits and its impacts [00:09:57] - Potential downsides and credible concerns as we shift into an automated world [00:16:00] - Major impediments of productive growth over the coming decades [00:23:12] - Real change versus false change due to COVID-19 writ large [00:30:06] - Thoughts on the rising cost of post-secondary education in light of the internet [00:37:03] - Why doesn’t Google have their own university and if they might in the future [00:41:30] - Whether or not an entrepreneurial focus on generally slower sectors may produce excess returns [00:44:17] - Thoughts on hardware, its unit economics, and its role in shaping society [00:47:52] - How to think about investing in immensely complicated, large-scale projects [00:54:10] - What they’re building at A16Z, a new crypto fund, and where their sights are set [01:03:09] - East coast investing styles and things we can borrow from them [01:06:01] - Potential plans to step into the public equity space [01:11:09] - Defining why it’s time to build and the imperative it sets [01:15:13] - The kindest thing anyone has ever done for him

My guest today is Will Ahmed, founder of fitness wearable company WHOOP. What started as a business plan in 2011 has evolved into the 24/7 health-tracking device you’ll often see on athletes across professional sports. During our conversation, Will and I discuss how his own backstory ties into the founding of WHOOP, the key design decisions they made in the ultra-competitive wearables market, and how the company grew slowly before inflecting in recent years. Will shares awesome details on health tracking and what it might look like in the future as a preventative tool rather than simply a tracking tool. I hope you enjoy this great conversation with Will Ahmed. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - The founding story of WHOOP [00:05:45] - Narrowing in on the problem to focus on solving [00:08:58] - Overview of analyzing and quantifying recovery, strain, and sleep [00:15:52] - Downsizing the problem set to deliver an affordable solution [00:18:48] - What he’s learned about hardware product road mapping [00:21:43] - How many people wear their WHOOP all-day [00:22:05] - Early lessons from taking their wearable tech product to market [00:26:25] - Ways in which they landed their first high-profile athletic brand ambassadors [00:27:55] - Interesting methods that proved successful in their marketing tactics [00:32:06] - Observations of making the switch to a subscription service [00:34:00] - Why big apparel companies failed where WHOOP didn’t [00:35:20] - Changes in behavior from users who learn about their habits using WHOOP [00:40:18] - His philosophy on business partnerships and how he developed it [00:44:56] - How he ended up with a paddle from the Navy Seals [00:47:13] - Ways WHOOP stays ahead and upcoming trends in the wearable tech space [00:50:13] - Data beyond HRV that will become more accessible and affordable to track [00:51:09] - The extent that data and software relative to hardware are a key part of WHOOP [00:53:06] - Lessons learned about effective leadership on a personal level [00:56:13] - Notable differences in his leadership style from then compared to now [00:57:34] - Thoughts about business defensibility in such a competitive space [00:59:44] - Reasons behind why WHOOP products don’t have a screen [01:02:13] - Valuable lessons for other entrepreneurs when studying WHOOP’s story [01:05:03] - Systems in place that allow for their speed and pace of growth [01:06:31] - What makes a day of work fun for him [01:08:39] - Why we shouldn’t measure our steps [01:10:01] - What is the kindest thing anyone has ever done for him

My guest today is Howard Marks, co-founder of Oaktree Capital, a leading investment manager, and one of the world’s largest distressed debt investors. In our conversation, we discuss takeaways from the market selloff and rapid recovery in 2020, the importance of assessing both quantitative and qualitative factors in markets, and the benefits Howard has realized from a career of writing. I hope you enjoy this great conversation with Howard Marks. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:40] - [First question] - Ideas he has that he feels will stand the test of time [00:04:39] - Defining the difference between risk and uncertainty and a frame of mind to have around uncertainty as an investor [00:05:31] - Equity and debt investing as the businesses of what could go right or wrong [00:07:01] - How exciting equity up runs can lead to analytical blindspots [00:09:10] - Ways in which the last 18 months stacked up against his market experience [00:11:57] - Ways we can change our model of the world going forward to avoid a crisis [00:15:04] - Why psychology is important to consider over data during market extremes [00:17:46] - Reflections and lessons from discussing the concept of value with his son [00:27:33] - Spirited disagreements he and his son continue to have about markets [00:31:46] - What he’s learned about writing well and the utility of doing so [00:40:39] - Lessons that are better experienced in investing than reading about them [00:43:35] - Daring to be great and the willingness to be wrong, alone or different [00:50:24] - Embracing mystery and the joys it can bring [00:53:28] - The kindest thing anyone has ever done for him

My guest today is Christina Cacioppo, founder of Vanta, a security and compliance software business founded in 2017. In our conversation, Christina brings to life the idea of “finding a problem that exists and fixing it.” We dive into the experiences that led her to launch Vanta, the strategy she took to build, price, and distribute the product, and we touch on her lessons from running a growing organization. I always admire the drive that founders have when they set off to build something -- Christina fits that mold, and you will hear about how she embarked on a self-taught journey early in her career. I hope you enjoy my conversation with Christina. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:44] - [First question] - How she first found her interest in business [00:04:09] - Early days exploring business for the first time [00:07:09] - Lessons learned from USV that have been applied to Vanta [00:07:42] - The next stage of her learning journey after USV [00:09:20] - Making a massive pivot in life and teaching herself to code [00:10:53] - The four-year road that lead to building Vanta [00:12:39] - First encounters with the software security problem space [00:15:21] - Origins of SOC 2, what it means, and what it does [00:17:11] - What software security means writ large [00:19:32] - Who demands a SOC 2 and why [00:20:57] - How Vanta improved a broken process and productized it [00:23:33] - What V1 of Vanta looked like [00:26:30] - Understanding the value of using spreadsheets first [00:27:48] - From static to streaming and finding product-market fit [00:29:22] - Monitoring whether or not a company is SOC 2 compliant in real-time [00:32:19] - Auditors that still exist in the compliance space today [00:33:39] - The pace of onboarding new clients onto the Vanta software [00:34:53] - Figuring out a price point for the service Vanta offers [00:37:06] - Developing the business model and scaling it [00:39:18] - Lessons learned and innovations created about effective sales organization [00:41:52] - Hardest hills to climb in building Vanta [00:43:17] - Building competitive advantage into the framework of the business [00:46:07] - Overview of the frontier of software security [00:47:43] - General thoughts on competitive advantage as a whole [00:49:43] - Quality control of decision making in Vanta [00:50:40] - Downstream effects of structural and organizational business design [00:52:30] - Hard lessons learned going from being academic to pragmatic [00:53:36] - What the future could look like for Vanta based on its current trajectory [00:54:26] - What her information diet consists of lately [00:55:27] - Areas she’s interested in currently but learning more than being proficient [00:56:59] - Ways in which she’s become a better leader [00:57:46] - Unique factors about what makes Vanta tick [00:58:45] - Negative advice to would-be founders out there [01:00:22] - The kindest thing anyone has ever done for her [01:02:44] - Major insights learned from living in Rwanda, Thailand, and Uganda

My guest today is John Harris, Managing Partner of Ruane, Cunniff & Goldfarb, where the flagship Sequoia Fund has an incredible 50-year track record running a highly concentrated portfolio of equities. In our conversation, we cover John’s approach to finding businesses that can be owned for the long-term, what goes into their diligence process, and the importance of resilience for investors. I think many of the stock pickers will enjoy many of the points on good management, good businesses, and using imagination. I hope you enjoy my conversation with John. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:48] - [First question] - How markets undervalue long-duration growth of companies [00:07:21] - Why should one even do DCFs at all [00:10:01] - Defining homework when studying a business and what getting better as you do your homework tends to look like [00:12:24] - How the market still underestimates how the quality of a company reduces risk [00:15:09] - Reinvestment opportunity and risk and why they’re important for long term returns [00:17:14] - Lessons learned owning Google stock options for over a decade [00:22:02] - Skill versus luck when it comes to investing psychology [00:24:32] - Perspectives on big market cap companies in a portfolio when success often comes from smaller-cap non-linear growth [00:26:47] - Features of the current market landscape that he finds interesting [00:31:24] - What buying behavior looks like in the demand side of the business equation [00:34:10] - Discovering a company that served the customer and was a delight to discover [00:37:58] - Analysing getting one's hands dirty to get a competitive advantage in serving the customer [00:39:24] - The hardest episode of his investing career and what he learned from it [00:43:03] - Reasons why a company succeeded after doing a deep dive but not buying in [00:43:54] - One of the CEOs he finds most remarkable [00:47:20] - Examples of businesses where scale isn’t the driver of competitive advantage [00:49:50] - A company they owned that did well but didn’t have the strongest company culture [00:50:56] - His view on the investment industry today writ large [00:52:16] - Ways investors could expand their imagination when analyzing businesses [00:53:07] - The kindest thing anyone has ever done for him

My guests today are Florian Hagenbuch and Mate Pencz, co-founders of Loft. Based in Sao Paulo, Brazil, Loft is a digital platform designed to bring Latin American real estate into the e-commerce age. The 3-year-old startup scaled to over $150mm in annualized revenue in 2020 and is on track for multiples higher this year. We dive into the market opportunity in Brazilian real estate and how that differs from the US market, the value proposition for iBuying across the US and Latin America ecosystems, and touch on the potential for Loft to expand from real estate into adjacent services such as mortgages. Florian and Mate are second-time founders and have some great lessons shared throughout the episode. Please enjoy my conversation with Florian and Mate. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:52] - [First question] - Why Latin America currently presents such a unique opportunity for modern technology companies [00:04:38] - What the market looked like when they started Loft [00:07:20] - How they approached gathering data that wasn’t available or accessible in order to develop the company infrastructure [00:09:39] - How the process of buying a home used to be in São Paulo versus today [00:12:19] - What Loft’s hard work unlocks for consumers and home buyers [00:14:06] - What iBuying feels like writ large and more specifically in real estate [00:18:07] - Analysis of an iBuying real estate transaction from start to finish [00:20:09] - The role machine learning plays in property valuation and building that feature [00:22:50] - Defining their business model and being a fulfillment center aggregator [00:24:47] - Notable characteristics of the iBuying market in the United States [00:27:00] - How they think about the competitive advantage extensions of Loft [00:29:53] - Exciting opportunities for the FinTech broadly in Latin America [00:32:47] - Deciding on what it is they want to tackle next as they grow the company [00:34:13] - Thinking about the value proposition to customers and how they market it [00:35:50] - Lessons learned about building businesses early on that were applied to Loft [00:40:12] - What led them to finding their early product-market fit [00:42:48] - Calibrating and defining their ambitions for Loft out of the gate [00:45:05] - Important and interesting trends in the business world today writ large [00:48:43] - Further lessons and key challenges around building and scaling Loft [00:52:24] - The kindest things that anyone has ever done for them

My guest is Gabe Leydon, who is the co-founder and former CEO of MZ, also known as Machine Zone, the company behind huge games such as Mobile Strike and Game of War. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I have talked to in a long time. In our conversation, we cover why great design can be a bad sign that we’d run out of ways to innovate, the most important lessons from human psychology for building games and products, and why products which are busted or breaking but still booming can be great investment opportunities. This conversation rewired my brain on many levels, so I’m excited for you to listen. Take the red pill with us, and please enjoy my conversation with Gabe Leydon. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by Paxos. Paxos offers your customers crypto buying, selling, transferring, and more with easy to integrate APIs. Whether you’re a small fintech or a large financial institution, Paxos takes care of everything in the backend – from licensing and compliance to custody and exchange. You can start offering crypto to your customers within months. To learn more, visit paxos.com/patrick. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:59] - [First question] - Thoughts on the importance of design and the role it plays in capitalism writ large [00:07:26] - Huxley’s vision of the future versus Orwell’s - Amusing Ourselves to Death [00:10:49] - A question about game design in interviews that no one can answer well [00:18:27] - What about his early experiences that allowed him to be good at answering that question when others could not [00:26:35] - Another example to further explain the nature of meta software design mechanics [00:29:44] - Characteristics of what drives players to spend money in games [00:34:46] - Defining heroic spending and the group dynamics of spending gamification [00:38:18] - Skill set required to design an economy and what makes it so difficult [00:41:27] - Cosmetic purchases as a revenue stream in North American video games [00:43:56] - What he’s learned about human psychology through his design work [00:45:48] - How the technological infrastructure developed in building video games overlap in performance marketing [00:48:44] - His experience with the RT platform and some of the technologies he’s built [00:55:49] - Celebrity NFTs and a shift to becoming virtual manufacturers in the future [00:59:58] - What businesses can do now to prepare for and adapt to NFTs [01:01:03] - Why we need AI more than think we might [01:04:32] - What he plans to do with his skillset if the world becomes increasingly gamified [01:05:40] - Companies with poor design may be indicative of an attractive acquisition [01:08:11] - How differing cultural perspectives on video game design permeate into NFTs [01:08:46] - Defining the Chinese item box approach to in-game player rewards [01:11:24] - The kindest thing that anyone has ever done for him

My guest today is Assaf Wand, CEO, and co-founder of Hippo, a homeowner insurance startup founded in 2015. In March 2021, Hippo announced a SPAC merger, valuing the business at over $5bn. In our discussion, we cover how Hippo approached innovation in the highly regulated insurance industry, unique strategies for building brand trust, and how direct relationships with homeowners has opened up Hippo's business model to a wide range of opportunities. I was excited to speak with Assaf, given his experience as a serial entrepreneur, and he did not disappoint. Please enjoy my conversation with Assaf Wand. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad, to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:44] - [First question] - His philosophy on business [00:04:04] - His first experience in entrepreneurship [00:05:03] - Lawyers vs entrepreneurs [00:07:03] - Major lessons taking risk in entrepreneurship [00:11:14] - Importance of speed in business [00:15:02] - Increasing urgency into the business as a leader [00:18:59] - What the insurance sector was like at the start of Hippo [00:24:49] - Steps he took to bootstrap trust [00:27:03] - Convincing partners [00:29:04] - Building the products and distribution [00:32:49] - Thoughts on innovators dilemma [00:35:00] - Flaws within the insurance industry [00:34:57] - Vision for the firm [00:37:44] - Importance of culture in company building [00:41:19] - Storytelling as an essential piece of company building [00:41:50] - Building and managing a roadmap [00:43:19] - What does it mean to respect the customer [00:46:11] - Defensibility of the insurance industry [00:49:34] - Rewards of the trench warfare of entrepreneurship [00:53:33] - The feeling of getting wealthy [00:55:29] - Kindest thing anyone has done for him

My guest today is Dennis Lynch, Head of Counterpoint Global, where he oversees over $100bn in AUM and boasts one of the strongest track records of any public investor. In our conversation, we cover Dennis's unique approach to building a research team, how misclassification of companies often creates the highest upside opportunities, and how Dennis has adapted his investment process over the past 20 years. I think Dennis defines what it means to be intellectually honest, and you will hear that in his answers throughout our discussion. I hope you enjoy my conversation with Dennis Lynch. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. (for me- ) ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by MIT Investment Management Company (MITIMCo), the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:47] - [First question] - How he would teach potential students to be investors [00:04:26] - The Money Game [00:04:40] - Moneyball [00:05:59] - Pros and cons of volatility when investing [00:08:55] - Emotional response to volatility [00:12:44] - Training to have a better temperament [00:14:20] - What is his investing game [00:15:17] - The Ethical Algorithm [00:16:44] - How time horizon impacts their investment strategy [00:20:53] - Assessing a company’s earnings power [00:26:12] - Shifting business models vs. evolving within a business model [00:32:32] - Understanding how to invest in disruptive businesses [00:35:26] - Why he’s skeptical on Growth and Value investing strategies [00:38:42] - Expectations Investing [00:38:55] - How his view of assessing businesses has changed [00:43:56] - Defining unit economics [00:45:41] - Taking on uncertainty risk in the portfolio [00:50:38] - The business that taught him the most; Amazon [00:53:32] - Dealing with massive amounts of change [00:56:01] - The Big Short [00:59:46] - Interest in psychedelic research [01:01:02] - What has changed the most in investing from when he started [01:04:19] - Kindest thing anyone has done for him

My guest today is Henrique Dubugras, co-founder and CEO of Brex, an all-in-one finance account for businesses. Brex recently raised funding at a valuation of over 7 billion dollars despite being founded only four years ago. In our conversation, we cover Brex’s transition from a credit card for start-ups to the central account for businesses, why building that central account was orders of magnitude more difficult than expected, and the difference between building a business in Brazil and the US. We also discussed Henrique’s term horizon for building Brex and how that impacts his decision-making for the business. Please enjoy my conversation with Henrique Dubugras. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:53] - [First question] - The state of the B2B financial world before Brex [00:06:29] - How such a high margin space was generally underserved [00:08:24] - What the first version of the Brex card looked like [00:10:48] - How long it took to build and launch their infrastructure [00:11:13] - Why market penetration is so low for cards in B2B businesses [00:13:14] - How he thinks about this landscape in Brazil versus the US [00:14:55] - What interchange and high margins allows him to pass on to the consumer [00:16:23] - Brex’s first revenue event [00:17:38] - What the biggest hurdle was to overcome when they launched [00:19:02] - Key marketing strategy early on and what made it successful [00:21:16] - Continued distribution lessons they learned from their initial success [00:22:39] - Building an effective sales force to push their product [00:24:41] - What makes the current landscape so fertile for fintech businesses [00:27:12] - Analysis of their unique funding round dynamics [00:28:42] - Their second product and the insight that lead to that decision [00:31:05] - Darkest moments while trying to build their central account [00:31:50] - What their central account allows them to facilitate writ large [00:35:27] - Notable differences between entrepreneurship in Brazil versus the US [00:38:55] - Observations on inefficiencies in the US startup space [00:40:16] - Pros, cons, and costs of being largely remote [00:41:50] - Keys to building a successful hiring pipeline [00:44:05] - Lessons learned about decision making and optimization [00:45:39] - Developing an effective skill set to convince other people of anything [00:47:35] - What excites him about being a part of Brex lately [00:49:13] - What excites him about the future in general [00:50:39] - His business philosophy and the set of principles that guide him [00:52:03] - Nuances that make focusing on a single problem so attractive [00:53:51] - Long term infrastructure decisions that will pay off in the end [00:55:12] - Thoughts and hi perspective on cash flow in general [00:58:18] - The kindest thing anyone has ever done for him

My guest today is Justin Fishner-Wolfson, founder of 137 Ventures, a venture capital fund focused on providing liquidity solutions to founders, investors, and employees of private businesses. In our conversation, we discuss what early career experiences led Justin to start 137 Ventures, the counter-intuitive information asymmetry between public and private markets, and the interesting trend of digitization in the physical world. I hope you enjoy my conversation with Justin. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:47] - [First question] - Why he started 137 Ventures and what’s unique about it [00:05:31] - Overview of secondary equity markets in the tech sector [00:07:06] - Step by step process of how a secondary market investment works [00:09:37] - Scale of secondary transactions in markets today [00:10:19] - Valuations of secondary transaction rounds versus primary ones [00:11:37] - Defining great in private market investments and the competitive landscape [00:13:13] - Why there seems to be more information available in private markets [00:16:23] - How better capital allocation may result from less asymmetry [00:19:14] - What excites him about companies when meeting them for the first time [00:20:34] - Example of applying his philosophy of investing in a defensible business [00:22:20] - Counter positioning and inversion models to gain an advantage [00:24:17] - Lessons learned from Palantir about unlikely competitive advantage [00:25:57] - Building good businesses when selling them to the government [00:26:59] - What technology means in the current era [00:28:34] - Methods for evaluating potential sources of defensibility and a lack thereof [00:30:30] - Considering focus and expansion when scaling [00:32:52] - Shared qualities of entrepreneurs who build these types of businesses [00:33:50] - The business that individually taught him the most writ large [00:35:01] - Defensabilities that might appear beyond the seven powers framework [00:36:21] - Thoughts on what seems to be craziest in the world today [00:37:15] - What’s surprising on the low end of the valuation side [00:38:11] - Interesting business models and ones he’s averse to [00:40:31] - Constructing a portfolio with companies that have a customer focus [00:41:21] - Additional companies in their portfolio that aren’t of a similar model [00:42:08] - Lessons learned from SpaceX’s growth [00:44:46] - Watching a SpaceX launch in person [00:46:03] - Advice for entrepreneurs when seeking capital and capital partners [00:48:04] - Investors he finds most impressive that he knows well [00:49:26] - Defining the cost of capital and what it means to him as a venture investor [00:50:56] - Is giving entrepreneurs too much money dangerous? [00:54:14] - What great capital allocation looks like to him [00:55:29] - Accelerating learning curves with tighter feedback loops [00:55:57] - Useful metrics for customer acquisition and retention [00:57:06] - Whether or not investing firms can and should behave defensibly [00:59:13] - What is going in the world that has his attention lately [01:02:06] - Key factors that have allowed him and his firm to succeed [01:03:47] - What he thinks about when his mind isn’t focused on investing [01:04:08] - The kindest thing anyone has ever done for him

My guest today is Peter Reinhardt, co-founder and CEO of Segment, the market-leading data customer data platform that was acquired by Twilio last year. In our conversation, we cover the fascinating journey of Segment from an education feedback tool to the business it is today, Peter’s sales philosophy on meeting the customer where they are and not where you think they should be, and why revenue operations, or RevOps, is underrated for any business. This was an incredibly honest conversation on company building that any builder can learn a lot from. Please enjoy my conversation with Peter Reinhardt. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:47] - [First question] - What Segment currently does for its customers [00:03:37] - How this industry looked before Segment came along [00:04:30] - Overview of a simple data flow and the utility of capturing user data [00:05:55] - Insights that lead to developing the structure for a central data pipeline [00:07:52] - Why other companies don’t just build their own data collection API [00:10:04] - Early days of building the company and finding success outside their initial idea [00:12:29] - Pivoting from classroom software to providing software the world needed [00:16:17] - What Technology Wants [00:17:06] - Sign that validated becoming a B to B software company [00:19:49] - Challenging moments trying to scale Segment after bootstrapping the startup [00:24:58] - Getting customers to articulate your value proposition helps grow your sales [00:26:42] - Deciding what would be sold and what would remain open source [00:28:05] - Structuring and developing an enterprise sales team and sales model [00:30:23] - Overview of a 2 million dollar per sales person contract and how it’s allocated [00:31:38] - How it feels to be participant in the SaaS industry [00:34:02] - Lessons learned about revenue operations and how underappreciated it is [00:36:39] - Backwards efficiency and companies who use products to bootstrap scale economics [00:38:51] - Focusing on customer acquisition cost to maximize scale efficiency [00:40:52] - Potential disruptors to economies of scale [00:42:21] - Lessons learned from achieving massive scale and being acquired by Twilio [00:45:40] - Behind the curtain view of current data use trends [00:48:49] - His perspectives on the data privacy landscape and their implications writ large [00:51:48] - Legitimate businesses that will be hurt by changes in data privacy standards [00:53:11] - How data privacy standards may affect everyday merchants [00:54:03] - The worst advice he’s heard given to new entrepreneurs [00:56:20] - Impactful advice received along the way when growing Segment [00:56:47] - What has him most excited about the future [00:57:13] - Lessons learned about leadership from Jeff Lawson and his own experience [00:58:51] - The hardest changes he’s had to make as a leader [01:00:20] - The kindest thing anyone has ever done for him

My guest today is Brent Beshore. For those that don’t know Brent from his frequent appearances on this podcast, he runs Permanent Equity Fund and has been a close personal friend for the past five years. Brent and I revisit our conversation from the heart of COVID to touch on key lessons learned and where that leaves us today. Brent sits at a unique touchpoint of the economy, so I particularly enjoyed his anecdotes on inflation and how to operate around these dynamics. I hope you enjoy my conversation with Brent. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:52] - [First question] - Why last year ended up being so bullish [00:07:14] - Deal dynamics of the current landscape [00:09:54] - Lessons learned about managing a team through the pandemic [00:14:39] - Observations on the housing market and the pool industry [00:18:56] - Current labor force dynamics of trades [00:21:18] - Considering labor dependency when investing in new businesses [00:23:10] - His perspectives on the future of tech through his investment lens [00:25:50] - Seeking out traditional businesses that reinvent age-old frameworks [00:27:50] - Key stages of the art and science of evaluating and acquiring a company [00:31:45] - How much information he wants to know before making an initial offer [00:34:25] - Psychology of structuring and aligning incentives post-acquisition [00:37:41] - What defines a great deal negotiator [00:40:05] - His most creative act when structuring a deal that didn’t work out as well [00:42:17] - Hist most creative structuring act that proved useful for the upside [00:43:34] - Notable changes in large-cap private equity markets [00:45:41] - Skills he feels he can improve on over the coming five years [00:48:30] - Coaching small companies on how to recruit top tier talent [00:52:49] - How to effectively get people to say yes to job offers and openings [00:54:19] - Absolute and relative changes in the opportunity set of small to mid-cap markets [00:57:40] - Lessons learned from strong support networks and onramps of upward mobility

My guest today is Jeremy Cai, founder, and CEO of Italic, a subscription marketplace for consumer goods that works directly with manufacturers. I was introduced to Jeremy by my friend Blake Robbins and was dying to better understand the Italic business model. In our conversation, we discuss the Italic business model, the evolving role of manufacturers in supply chains, and the concept of building the next generation “everything store.” I love learning and discovering new business models, and this was fun to dig into. Please enjoy my conversation with Jeremy Cai. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:45] - [First question] - Overview of Italic’s business model [00:04:51] - Why comparing Italic to Costco isn’t completely accurate [00:10:06] - His initial experience with manufacturers and how that world works [00:15:21] - Direct to consumer commerce and the power of a brand’s story [00:20:06] - Where manufacturers find the cash to effectively manage their inventory [00:25:26] - How design and R & D are handled by manufacturers in the current era [00:29:36] - Educated consumers and emotional versus rational buying decisions [00:31:12] - Analyzing Italic’s five-step master plan and what needed to be built first [00:35:42] - Becoming more than just an aggregator and a platform [00:38:01] - Lessons learned from building Italic so far [00:39:02] - Other modern business models he finds interesting [00:43:26] - What Not Pot is and lessons learned from building it [00:44:51] - Observations about consumer behavior in his managed marketplace [00:48:07] - The kindest thing anyone has ever done for him

My guest today is Eli Dourado, economist and senior research fellow at the Center for Growth and Opportunity at Utah State University. In our discussion, we touch on the ongoing stagnation in labor productivity, the system constraints, and some of the innovative technologies that could reverse this trend. While Eli identifies as an economist, his wealth of knowledge on biotech innovation, alternative energy, and the space opportunity are sure to leave you craving more. I hope you enjoy my conversation with Eli. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:28] - [First question] - Why he’s interested the great stagnation [00:05:41] - Is a fair analog for total factor productivity technology? [00:07:29] - Leading theories for the stagnation in TFP [00:09:05] - Analysis of why growth is good, and stagnation is bad [00:10:19] - Rate limiters that are a key part of calculating stagnation [00:11:43] - Signs that we may be returning to a higher degree of TFP returning [00:12:24] - Exciting developments like MRNA in biotech that may lead to an explosion of innovation [00:16:16] - Functions of a protein and their role in advances in biotech [00:17:55] - What CRISPR is and what it unlocks for the future of humanity [00:19:31] - The pace of progression when rolling our clinical trials of cellular engineering [00:21:36] - How biotech may play a role in TFP as a proxy for progress and growth [00:22:51] - Interesting observations about potential innovation in the energy sector [00:24:10] - What currently requires energy that could be optimized if they had a lower energy cost [00:25:34] - Sources that could provide cheaper and more efficient energy [00:27:13] - Sage Geosystems and the future of the geothermal space [00:27:43] - The importance of batteries in the modern era [00:29:02] - Why energy should be a more pivotal focus in our future [00:29:41] - What’s interesting in the world of transportation writ large [00:31:02] - Boom’s story, supersonic air travel, and why concord shut down [00:34:55] - Mach 5 and March 12 supersonic air travel [00:36:19] - Second-order effects of reducing the time cost of air travel [00:38:19] - Liftoff, SpaceX, and the future of the space sector [00:43:07] - Other key players in space people could study; Blue Origin and Relativity Space [00:45:15] - What will we do in space once we can travel there cheaply [00:46:39] - What he’s most curious about in IT that could drive productive societal growth [00:50:07] - Ethereum and how a decentralized blockchain could change the world [00:51:19] - The kindest thing anyone has ever done for him

My guest today is James Reinhart, founder, and CEO of thredUP, an online thrift marketplace. thredUP’s online store is distinct in the way the company touches every product, processing every piece of clothing at their own facilities instead of focusing solely on being a marketplace connecting buyers and sellers. We talk about the competitive advantages of building processing plants from the ground up, how James turned thredUP from having negative gross margins to very strong unit economics, and the future of retail more broadly. I hope you enjoy this conversation with James Reinhart. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to by Dell Technologies. Dell Technologies and Windows can help you upgrade your business tech with its Small Business Month specials. Save up to 45% on PCs with Windows 10 Pro— plus business docks, monitors & more. To learn more, call a Dell Technologies Advisor at 877-ASK-DELL or check out the deals at dell.com/en-us/work/shop/deals. ----- This episode is brought to you by Eight Sleep. Eight Sleep's new Pod Pro Cover is the easiest and fastest way to sleep at your perfect temperature. Simply add the Pod Pro Cover to your current mattress and start sleeping as cool as 55°F or as hot as 110°F. To embrace the future of sleep and get $150 off your new mattress, go to eightsleep.com/patrick or use code "Patrick." ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:47] - [First question] - An overview of thredUP [00:03:44] - Origination of the idea [00:04:43] - Initial reactions to the concept [00:05:22] - Early days trying to acquire the first customers [00:07:32] - The evolution of their margins [00:11:04] - Providing convenience for the customer [00:13:01] - Lessons on working capital and inventory [00:14:27] - How consumers use the money they receive within the platform [00:15:47] - The evolution of the operations of the business and scaling [00:20:20] - When it’s time to shift from human capital to automation [00:22:00] - The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time [00:22:39] - Competitive Advantage: Creating and Sustaining Superior Performance [00:23:15] - Removing the hurdles for acquiring more buyers [00:27:19] - Convincing investors on this concept [00:30:44] - The most difficult time for him psychologically in creating the business [00:31:56] - How he thinks about capital allocation [00:32:12] - The Startup Way: How Modern Companies Use Entrepreneurial Management to Transform Culture and Drive Long-Term Growth [00:33:51] - Overview of the clothing landscape and what would surprise most people [00:38:00] - Expanding their business from here [00:40:36] - Improving how the raw material is sourced for apparel [00:42:45] - The nature of work [00:42:56] - Dustin Moskovitz Podcast Episode [00:49:04] - What he’s most excited about for the future [00:50:35] - Kindest thing anyone has done for him

My guest today is Andrew Sugrue, co-founder, and partner at Avenir Growth Capital. Avenir is a growth equity firm focused on backing category-defining businesses. In our conversation, we cover Andrew’s investing career, what he learned from Julian Robertson, how counter-positioning could drive unique distribution, and the difference between good and bad growth. We also spend time examining the business model of two of Andrew’s portfolio businesses, SavageXFenty and Latch. There are so many great lessons for investors and operators to take away from Andrew. Please enjoy my conversation with Andrew Sugrue. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by MIT Investment Management Company – MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo is also searching for an exceptional new teammate to join their internal investment team. Visit mitimco.org to learn more – click “Join” to learn more about the Global Investor Role on MITIMCo’s team or and click “Emerging Managers” to learn more about their emerging manager activities. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:31] - [First question] - His journey leading up to his current firm [00:05:55] - Lessons learned from time spent with Julian Robinson [00:07:54] - The chip on his shoulder that helped keep him driven [00:08:40] - Transforming his early motivators into a sustainable career-long fuel [00:10:46] - The first things in mind when approaching a new business or person [00:14:00] - Analysis of Savage Lingerie and learning about how that sector operates [00:20:27] - Amazon producing a one-hour special Savage infomercial [00:23:16] - Lessons learned from Savage that can be applied to other direct to consumer brands [00:25:04] - Having a celebrity at the forefront of your brand [00:26:41] - Levers and overview of apparel company income statements and how they can shape the way you grow and operate the business [00:30:08] - Apparel companies always being tied to identity [00:31:03] - Analysis of Latch and learning about the relationship between hardware and software [00:33:40] - How Latch works and why you might need it [00:38:56] - Other businesses that may benefit from understanding the events that drive demand and using it as an opportunity for customer acquisition [00:40:12] - The concept of density of demand and the power behind it [00:41:33] - Other areas of operations density of demand could be applied [00:44:11] - Shared components that unite Avenir’s portfolio companies [00:46:14] - How he thinks about the world of private investment, having lived such a diverse career [00:50:22] - Developing relationships growing such a concentrated portfolio [00:51:35] - Macro thoughts on the state of investing today [00:52:59] - Defining and identifying characteristics of bad growth [00:54:05] - The kindest thing anyone has ever done for him

My guest today is Alyssa Ravasio, co-founder and CEO of Hipcamp, a platform to discover and book your next camping trip. I was excited for this conversation as it combines two of my favorite passions – the outdoors and internet marketplaces. In our discussion, we cover how Alyssa bootstrapped demand in the early days of Hipcamp, the importance of creating not just great experiences but magical ones, and the evolution of Hipcamp’s business model. After listening to this episode, I’m sure the first thing you’ll want to do is get outside in nature. Please enjoy my conversation with Alyssa Ravasio. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers. If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:57] - [First question] - The original insight that led to founding Hipcamp [00:06:15] - What she studied in college and primary lessons learned there [00:08:18] - Specific features of studying the internet that influenced her trajectory [00:10:14] - Deciding what to attack first when developing Hipcamp’s infrastructure [00:14:12] - Dimensions and market size of the outdoor industry [00:15:48] - Organizing fragmented data into a useable schema and data set [00:18:24] - What customers cared about most in the early days of Hipcamp [00:20:00] - Managing focus and liquidity of the initial marketplace [00:22:58] - Helping landowners manage the logistics of their property placements [00:25:16] - Liability insurance in the outdoor industry [00:27:35] - The biggest challenge faced in developing an outdoor marketplace [00:30:03] - Amplifying and accelerating naturally grooved distribution [00:32:32] - Identifying the top correlates of making magic happen [00:34:55] - An ideal future for Hipcamp five years from now [00:38:28] - What bad supply looks like and creating quality standards [00:42:08] - Their business model and revenue stream [00:44:45] - Deciding on their take rate and the debate around booking fees [00:46:14] - Lessons learned along the way as a leader [00:47:42] - Unit economics from the host’s perspective [00:52:33] - The most interesting businesses built on top of Hipcamp [00:53:35] - Why is Hipcamp’s mission so important to her [00:57:11] - The kindest thing anyone has ever done for her

My guest today is Josh Buckley. Josh is the new CEO of Product Hunt and an investor in many breakout companies like Rippling, Lattice, Boom Supersonic, and Relativity Space. In our conversation, we cover how video game companies are at the forefront of new business models, what current companies can learn from video game companies, Josh’s investing philosophy, and the three things he looks for when trying to identify the next legendary startup. Josh’s long experience operating his video game business, Mino Games, gives him such an interesting perspective as an investor, and I really enjoyed exploring that with him. Please enjoy my conversation with Josh Buckley. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:56] - [First question] - His start as an entrepreneur in online game [00:05:09] - His parent's reaction to selling his first company at fifteen [00:05:57] - Starting a second video game company [00:07:40] - The video game industry being ahead of the curve in performance marketing, distribution, and operations [00:08:49] - Notable two year lag between gaming innovation and other consumer sectors [00:10:50] - What is happening today in gaming that may be a glimpse into the future [00:12:41] - Key elements for creating a great gaming experience [00:15:29] - Building a meta game on top of the game itself to maximize engagement [00:17:23] - Monetizing free to play games through in-game purchases [00:20:25] - The most portable idea from fifteen years in gaming that can be applied to business [00:22:02] - A future shift towards usage-based pricing models [00:23:03] - His overall investment philosophy and strategy [00:26:45] - Example of small a market with a high growth rate [00:27:38] - Key elements of system elements and design when evaluating a business [00:31:07] - What a flywheel looks like and investing in one such as Next Health [00:33:24] - Working core actions versus giving credit ones that aren’t yet working but may drive desirable outcomes [00:34:13] - Why don’t more investing firms have a flywheel? [00:39:04] - Product Hunt as a standalone business and part of a self-reinforcing ecosystem [00:40:17] - Emerging systems and ecosystem edges in the digital landscape [00:42:17] - Potential barriers for crypto becoming widely adopted in a variety of ways [00:44:29] - New frontiers and platform shifts like crypto that may unlock new doors for companies [00:45:13] - Which person has rewired his brain in his lifetime the most [00:47:13] - Weirdness around Stripe and Plaid when he first encountered them [00:48:37] - Meta games people in the industry are playing or should be playing [00:51:25] - Controversial ideas around the business world today writ large [00:54:01] - Implications of shifting primarily towards a digital world [00:54:14] - The kindest thing anyone has ever done for him

My guest today is Thomas Tull, the founder of Tulco LLC, an investment holding company that invests in businesses with high growth potential and helps them apply machine learning and data analytics. Thomas is also the founder and former CEO of Legendary Entertainment, the production company behind the Dark Knight, Hangover, Inception, 300, and many more iconic movies which he sold in 2016. In our discussion, we cover the movie industry’s value chain, the recipe for trying to make a successful movie and how Legendary pioneered the use of data analytics to improve those odds, and Thomas’ concept of the new physics of business and why it matters for what he’s now building at Tulco. Please enjoy my conversation with Thomas Tull. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:06] - [First question] - His overarching career philosophy and theme [00:04:07] - Attacking a previously established industry in a new way [00:05:20] - The origin story of Legendary and stepping into the film industry [00:07:56] - Stakeholders involved in producing a movie and pre-existing profit pools when Legendary was founded [00:12:44] - Topline and downstream revenue distribution of intellectual property from then versus now [00:19:46] - Lessons learned about intellectual property writ large [00:19:03] - What makes Chris Nolan such an exceptional storyteller [00:23:42] - Power and defensibility of cinematic universes and transmedia storytelling [00:22:21] - Applying quantitative data analysis to film production and marketing [00:25:55] - Competitive frontiers in movie studios and his advantageous skillset [00:28:10] - Potential investment opportunities in media or media adjacent businesses [00:29:26] - Interesting new tools that could be developed in entertainment technology [00:31:00] - His favorite mind-blowing and awe-inspiring movies [00:32:41] - Telling Jackie Robinson’s story in the film, 42 [00:35:30] - Jackie Robinson and Chadwick Boseman’s quiet dignity [00:36:56] - Building the holding company Tulco [00:39:02] - The new physics of business that can’t be ignored [00:42:40] - Modern velocity in the current era of business [00:46:03] - Interweaving an antifragile mindset into the company culture [00:47:55] - Who Tulco Labs is and what they do [00:49:12] - What gets him most excited about exploring a new business for the first time [00:50:48] - Unique characteristics he seeks out in a management team [00:52:31] - Trends that make him feel worried about the future [00:57:47] - Trends that make him feel optimistic about the future [00:58:49] - An important lesson learned from his career on a personal level [01:00:15] - The kindest thing anyone’s ever done for him

My guest today is Paul Enright, managing partner at Krainos Capital, his family office. Before running his own family office, Paul worked on the buy-side at Viking Global for over a decade managing their consumer and technology portfolios and before that at Morgan Stanley on the sell-side. I thought Paul would be the perfect person to help me demystify the world of high finance – explaining the difference between the buy-side and sell-side, how long/shorts differ from long onlys, and walking through the various jobs in the investing world. In addition to setting that foundation, we also cover the evolution of the buy-side, what makes someone a great researcher verse a great stock picker, and various portfolio construction methodologies. Paul brings such a wealth of knowledge and experience to the table. I think this episode will be enjoyable for investing novices and professionals alike. Please enjoy my conversation with Paul Enright. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:39] - [First question] - His history in both the buy and sell side [00:05:20] - Different types of roles on the buy side and sell side [00:06:48] - Interest sets that best align with being a buyer or a seller [00:07:57] - The emotional experience of being on the buy side and exposed to risk [00:08:53] - How the nature of buying and portfolio construction has changed [00:10;15] - What Regulation Fair Disclosure (Reg FD) is [00:12:46] - Key terminology and definitions of long-only and long-short funds [00:17:40] - Varying clusters of long-short funds and defining each type [00:21:48] - Differences in exposure between a platform model versus a traditional long-short stock picking sense [00:25:16] - Skill sets that are most important to have when navigating this space [00:29:03] - What is good and what is great when it comes to “digging” [00:31:20] - Why the quality of one’s analysis matters [00:33:10] - Having a potential edge when deciding based on someone else’s analysis [00:35:19] - Foundational building blocks of an effective pitch [00:37:20] - Finding wrongly identified stocks and reaping the rewards [00:40:49] - Overview of good portfolio construction and lessons learned over the years [00:44:06] - Why hedge funds tend to traffic heavily in T.M.T. and consumer sectors [00:45:53] - Elements that strike him as great in a business [00:48:05] - A business that once seemed great but has since faded away [00:49:22] - Why hedge-fund managers seem to always make the most money [00:53:50] - What a well run firm looks like [00:56:39] - Characteristics that may make you well suited for a career in fund management [01:00:23] - Why quality mentors and portfolio managers are so important when deciding where you want to work [01:01:38] - What interests him mosts in markets today [01:05:20] - Useful frameworks and formulas used when approaching a new business [01:08:15] - Interesting features about telecom businesses and what defines them [01:10:45] - The future of the modern world’s internet infrastructure [01:14:44] - Abundance vs zero-sum and fixed vs growth mindsets [01:18:12] - The kindest thing anyone’s ever done for him

My guest today is Trevor McFedries, the founder of technology startup Brud and the creator of virtual pop star Miquela, a Gen Z icon with millions of fans worldwide. Trevor’s background is fascinating - he worked as a DJ and producer, toured with Katy Perry, worked at Spotify, and done just about every interesting thing I can imagine. In our conversation, we discuss the music-industrial complex, the creation of Miquela, and what Web 3.0 will mean for creators and builders in the future. I hope you enjoy this conversation with Trevor McFedries. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:54] - [First question] - What unites the diversity of his career [00:03:39] - What inspired him to pivot away from football and step into creative arts [00:05:50] - Lessons learned from being a touring DJ and producer that apply to the creative tech sector [00:07:40] - A view of the music industrial complex from the inside [00:08:57] - How the internet deciding who becomes popular affected already established artists [00:10:57] - Interesting opportunities in the music landscape in 2021 [00:11:40] - Time spent at Spotify and the spark of insight that led to founding Brud [00:16:02] - The sequence of creating a digital artist like Lil Miquela [00:19:02] - What it feels like to be “othered” [00:20:24] - Embracing one's intersections and applying it to a business model [00:21:18] - The team behind Lil Miquela and her design process [00:25:49] - Ingredients required for building a great narrative [00:28:35] - What social media platforms matter today, and the state of the social landscape [00:32:21] - Expanding Lil Miquela’s world and digital media monetization [00:36:32] - Differences between web 2.0 and 3.0 that may directly affect creators [00:38:27] - Ways innovations like NFTs make spawn new network participants [00:39:49] - Programmable art and media experiences [00:41:03] - The most cutting-edge ideas in the digital persona space [00:43:21] - Technology that wasn’t available that had to be built to enable new experiences [00:45:49] - One of the hardest decisions he’s had to make in Brud’s history [00:47:16] - The furthest they’ve ever pushed the envelope [00:48:06] - What’s the thing that keeps him going every day [00:50:12] - Finding cultural white space and inventing a character that could speak to investing to inspire new generations [00:52:01] - Units of media contribution and creative container experimentation [00:53:27] - What has him the most excited about the future of his industry [00:54:32] - Missing technological components that could inspire new digital creatives [00:56:53] - Work ethic through the lens of developing a jump shot [00:59:00] - One business lesson that he believes in deeply [01:00:05] - The kindest thing anyone’s ever done for him

My guest today is Chris Dixon, a general partner at Andreessen Horowitz. Chris is a prolific investor and thinker, having been an entrepreneur, angel investor, and is now focused on investing in the crypto and blockchain space for Andreessen. Our conversation focuses on Chris's overall thesis for investing in the cryptocurrency space, the opportunities and limitations of blockchain applications, and why this is the most interesting area for investing and building over the next ten years. What's exciting to me is blockchain technology's ability to help us re-imagine old business models and catapult them into the 21st century – and we cover a lot of them. I hope you enjoy my conversation with Chris Dixon. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:56] - [First question] - His overall crypto investing philosophy [00:06:37] - New opportunities presented by blockchain technology [00:15:31] - Permanent limitations and shortcomings of blockchains [00:18:32] - Evolution of DeFi and crypto currencies [00:21:11] - Whitepapers: Bitcoin, Ethereum, MakerDAO [00:22:08] - How to take out a loan using the Maker protocol [00:23:22] - Utility of Dai and stablecoins [00:29:14] - How the DeFi network will reinvent the future [00:39:53] - Uniswap, tokens, and fundamentally redefining leverage [00:36:29] - The Company: A Short History of a Revolutionary Idea [00:38:00] - Developer and entrepreneurial incentives for building blockchain technology [00:39:46] - BitClout, Rally and the early days of social tokens [00:46:38] - Demand curve and value creation efficiency in a digital creator economy [00:47:24] - NFTs and a Thousand True Fans [00:54:49] - Polkadot, Solana, Cosmos and programmable blockchains [00:58:03] - The most exciting moment for him in the last year [01:00:19] - Decentralized autonomous organizations [01:02:46] - The single thing that has him most excited about the future of this space [01:05:18] - The Next Big Thing Will Start Out Looking Like a Toy

Welcome to the first episode of our newest show, Business Breakdowns, featuring deep-dive conversations on individual businesses. In each episode, we will dissect a new company with investors and operators that know it best. We’ve already released the first three episodes on Shopify, Chipotle, and Alibaba. Subscribe to Business Breakdowns through the podcast player of your choice: Apple Spotify Google Overcast Amazon Leave us a 5-star rating on Apple Podcasts if you like the show! ----- Today we will be diving into Shopify. Shopify was founded in 2004 by Tobi Lütke and Scott Lake around their original problem of why it's so hard to build an online business when they struggled to open an online snowboard equipment store. Today, Shopify's goal is to make commerce better for everyone, and it's used by more than 2 million merchants to run their online businesses. It's essentially an on-ramp for people looking to sell online. To help us break down Shopify, I'm joined by co-host Zack Fuss and our guest Alex Danco, who works on the Money team at Shopify. To really understand Shopify, you have to understand its different business units -- Core, Merchant Services, Ecosystem, and the new Shop platform -- and the role they each play in making commerce easier and better for merchants. We begin this breakdown by covering each of those business units and how they compare to Apple's business lines. We then dive deep into how Shopify makes money through the first and second derivative of their merchant success and how Shopify thinks about friction in e-commerce. We close with an incredible analogy of Shopify and StarCraft and the tools that Shopify has built into the still-nascent world of e-commerce. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Business Breakdowns is a property of Colossus, Inc. For more episodes of Business Breakdowns, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss Show Notes [00:04:03] - [First question] - What Shopify is as a product [00:05:58] - Product pillar 1: Core[00:07:58] - Product pillar 2: Merchant services[00:10:02] - Product pillar 3: Ecosystem [00:12:04] - Product pillar 4: Shop [00:14:08] - The evolution of commerce with the rise of the internet [00:21:01] - Differences between high and low trust commerce [00:25:48] - The role of friction and trust in stakeholder variety [00:30:18] - Overview of all four product pillars’ business models [00:33:10] - Shopify App Store [00:34:16] - How Shopify competes and partners with their competitors [00:36:53] - Shop Pay expands to Facebook and Instagram [00:38:49] - Key areas where Shopify will continue to grow across their product pillars [00:42:52] - Affirm, Klarna, Afterpay [00:43:56] - Potential pitfalls of having such a high self-imposed quality bar [00:45:12] - Conway’s law[00:45:12] - Aggregators versus platforms [00:53:35] - Unique marketing aspects for Shopify’s sales and marketing with their subscription model [00:56:37] - Shopify: A StarCraft Inspired Business Strategy

My guest today is Tony Xu, co-founder, and CEO of DoorDash. Tony started DoorDash 7.5 years ago, and today it is one of the largest food delivery and logistics platforms globally, with operations in the US, Canada, Australia. In our conversation, we discuss the initial problem that DoorDash set out to solve, DoorDash’s counterintuitive approach to building their product, and the surprising benefits of capital constraints in DoorDash’s early days. DoorDash’s business model is an equal parts logistics nightmare and a human coordination problem, or as Tony puts it, a human and math problem. After talking to Tony, I feel his personality makes him a great candidate to solve those problems. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:07] - [First question] - The catalytic moment that inspired Tony to build DoorDash [00:06:33] - Network density and its role in scalability [00:09:15] - Solving a math and sales problem simultaneously [00:11:33] - Becoming aware of multiple problem sets for restaurant owners [00:14:34] - Designing a team to quantify friction and turn it into useable data [00:16:49] - How to approach difficult problems and compartmentalize them in a practical way [00:18:38] - Accounting for high-level variance in long-term goals [00:21:54] - Factoring in time horizons for variance and planning for the future [00:23:08] - Slowing down an action process to minimize a high-consequence decision [00:26:48] - Generating demand after completing their software infrastructure [00:28:15] - Strategic choices between network health and unit economics [00:30:32] - Why DoorDash struggled to raise financing in their seed-stage [00:32:23] - Solving a small fraction of a larger logistics problem [00:35:00] - Differences between local commerce and distribution centers [00:36:44] - Creating the DashPass subscription service and how premium experiences influence user behavior [00:38:34] - Advantages and potential diminishing returns in servant leadership [00:40:41] - His broader philosophy on leadership and how it’s changed over the years [00:44:55] - Creating an incentive-aligned culture of ownership at scale [00:47:02] - The most surprising lessons learned about company building [00:50:38] - Unexpected positive outcomes that may emerge in other areas due to DoorDash’s growth in the coming years [00:53:44] - Will DoorDash’s presence change behavioral patterns in where people choose to live or start their business? [00:55:36] - What has him most excited for the future [00:56:55] - Kindest thing anyone has ever done for him

My guests this week are Jesse Jacobs and Mike Kerns, co-founders and partners at The Chernin Group, TCG, a multi-stage investment firm dedicated to building consumer businesses. Many think of TCG as some of the best media investors in the world, and in this discussion, you’ll quickly see why. In our conversation, we cover how TCG identifies creators that they can help build businesses with, how established companies should think about influencers and media today, and what innovations they are most excited for in the creator space. As I become more heavily involved in building new media properties, Jesse and Mike are always my first point of call for advice, and I’m so excited to share this with you. Please enjoy my conversation with Jesse Jacobs and Mike Kerns. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Coinbase, Roblox, Qualtrics and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by MIT Investment Management Company – also known as MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo doesn’t care how small, new, or un-institutional your firm is if you have the potential to generate amazing results that support MIT’s pursuit of world-class education, cutting-edge research, and groundbreaking innovation. Despite their willingness to invest early, they do not ask for GP economics, and they commit their initial capital for ten years. Visit www.mitimco.org and their new emerging managers page to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:32] - [First question] - The history of TCG [00:04:30] - iFilm (Discontinued) [00:07:08] - Full Screen [00:07:13] - Crunchyroll [00:10:46] - Uniting properties across all of TCG’s brands[00:11:14] - Barstool, MeatEater[00:12:00] - Headspace, Food 52, Hodinkee, Surfline [00:14:03] - Accidental businesses and pre-commercial success[00:14:53] - Exploding Kittens [00:16:05] - Evaluating the potential of a new pitch [00:19:12] - Testing, tracking and understanding media brand conversions [00:21:13] - The most important things happening in media in 2021[00:25:12] - Analysis of MeatEater from content to commerce [00:27:22] - First Lite [00:29:21] - Replacing your own sponsors with owned companies [00:30:11] - Analysis of Hodinkee from content to commerce [00:33:42] - What sparked the resurgence of interest in collectibles [00:38:05] - Hands on investing in the intersection of media, finance and tech [00:40:05] - Comcast [00:41:02] - Surprising discoveries in the sports collectibles space [00:43:06] - NFTs and their role in generating capital for media companies [00:44:25] - Sorare [00:45:22] - JPG File Sells for $69 Million, as “NFT Mania” Gathers Pace [00:47:23] - How to adapt to the NFT space as a business seeking equity [00:51:12] - The valuation landscape of today [00:55:25] - Defining success when working with an influencer [00:58:48] - Upcoming trends they’re most excited about in the world [01:01:40] - Roblox [01:02:00] - Mr Beast, Beastburger [01:02:47] - Pokemon Go [01:04:01] - The kindest things anyone’s ever done for them

Welcome to Business Breakdowns, a new Colossus podcast featuring deep-dive conversations on individual businesses. In each episode, we will dissect a new company with investors and operators that know it best. We believe every business has secrets and lessons to learn from, and these conversations are designed to deliver that content in an entertaining and narrative format. The series launches today with Shopify, so check out the links below and give it a listen. Subscribe to Business Breakdowns via: Apple Spotify Google Overcast Amazon Leave us a 5-star rating on Apple Podcasts if you like the show. With each new episode, we will be releasing full episode transcripts, show notes, and the best content we could find on that business from across the internet. Check out www.joincolossus.com for more.

My guest today is Jesse Pujji, the Founder & CEO of Gateway X, a holding company that builds, buys, and invests in companies that are driving the direct-to-consumer landscape. Prior to Gateway X, Jesse was the CEO and co-founder of Ampush, a performance marketing business helping power customer acquisition across some of the world's biggest brands. Jesse is my go-to person for all things performance marketing and customer acquisition, so we decided to record this episode to bring his incredible lessons to a wider audience. It also dovetails nicely into the series of episodes we are making called Primers, where we take our audience from a 0 to a 7 on just about any topic. In this Primer with Jesse, we dive into how revenue mechanics affect ad campaigns, why long sales funnels often offer the greatest opportunities for differentiation, and the various channels and strategies available for performance marketing. I hope you enjoy my conversation with Jesse Pujji. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2 report at a fraction of the typical cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:58] - [First question] - Overview of Jesse’s career and starting Ampush [00:12:11] - Red Ventures [00:13:11] - The four components of performance marketing [00:17:47] - Time and other variables in between impressions and revenue events [00:23:12] - Understanding the dimensions of a business and their offering [00:25:32] - Common misunderstandings businesses have about their marketing [00:27:17] - Major changes in the Facebook and Google digital marketing ecosystems [00:29:27] - Direct response marketing vs brand marketing[00:35:08] - The importance and impact of effective messaging [00:37:28] - The differences between good and bad conversions [00:40:56] - Does alpha still exist, is it worth looking for, and does beta have a place [00:43:25] - Fundamentals of a high performing marketing organization [00:50:04] - Attention aggregators of marketing agencies[00:50:18] - Nerdwallet - Thumbtack [00:51:22] - Product channel fit [00:52:11] - PebblePost[00:53:58] - Lessons learned from working with Uber [00:55:42] - Retention marketing [00:57:31] - Upcoming frontiers of performance marketing [01:01:15] - Overview of Nerdwallet [01:03:36] - How Jesse’s time at Ampush has shaped his investment lens[01:07:20] - Lessons from bootstrapping a business vs venture capital funding [01:17:05] - The entrepreneurial execution loop and operating cadence [01:29:20] - Kindest thing anyone has ever done for him

My guest today is Kanyi Maqubela, co-founder of seed-stage VC firm Kindred Ventures, which he started with his partner Steven Jang in 2019. Before founding Kindred Ventures, Kanyi was a general partner at Collaborative Fund. In our conversation, we discuss the parallels between today and the Roaring ’20s of the last century, the misunderstood risk curve of seed investing, and dive deep into how Kanyi evaluates founders and businesses at the earliest stage of company formation. We also discuss Kanyi’s experience teaching the Design Your Life class at Stanford and how some of those principles convinced him to take the leap to start his own fund. I hope you enjoy my conversation with Kanyi Maqubela. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:04:11] - [First question] - Understanding the roaring 20s and their potential resurgence [00:06:14] - Seed-stage investing today compared to a few years ago [00:09:02] - Lessons learned from studying the 1920s [00:11:52] - Supply chain infrastructure in the 21st century [00:14:49] - His investment philosophy and what influenced it [00:17:47] - Defining the risk curve and early-stage divergence [00:21:31] - Assessing risk in seed-stage investing [00:23:32] - Other moments that influenced Kanyi’s investment philosophy [00:26:50] - Assisting early-stage companies as a VC [00:29:31] - How he approaches VC differently than traditional US VCs [00:31:55] - Non-consensus ways and unique views when evaluating founders [00:35:19] - Domain insight and its importance [00:36:53] - What he looks for in a company when considering investing in them [00:38:17] - Assessing a team in whether or not they have characteristics of longevity [00:40:59] - Questions he most enjoys asking people [00:42:24] - What makes for a good problem space [00:44:26] - Early-stage crypto investing [00:47:27] - How the crypto space and NFTs will change and influence other sectors [00:50:37] - Emerging trends that are catching his attention [00:54:20] - The potential for upward mobility in the coming decade [00:56:30] - Teaching the Design Your Life course [01:01:21] - Advice for modern investor-operators [01:03:26] - If he could change one major thing in the industry [01:06:57] - The biggest lesson learned from Obama’s campaign [01:07:44] - The kindest thing anyone has ever done for him

My guest today is Roxanne Petraeus, co-founder and CEO of Ethena, a modern compliance platform for businesses. Roxanne’s background is pretty incredible, before starting Ethena she was a Rhodes Scholar, served in the US Army, and worked at McKinsey. In our conversation, we cover the lessons Roxanne ported over from her military career to building a business, how she’s trying to make compliance training not suck, and the woeful state of funding female founders in VC today and what can be done about it. Far from a boring conversation about compliance, this was an incredible discussion with one of the best founders I’ve met recently. I hope you enjoy my conversation with Roxanne Petraeus. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers. If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:29] - [First question] - What Ethena does [00:06:31] - Lessons from her military career [00:09:13] - Good and bad elements of leadership training from the military [00:11:35] - The problem of what sucks in compliance training [00:14:33] - The enablement of bad behavior among people with power [00:17:56] - The original idea for Ethena and bringing it to market [00:21:15] - Determining who is the right person to serve first [00:24:03] - Lessons for building good software [00:26:21] - How they have adapted to working in and around regulation [00:29:31] - Getting other companies to buy into the product [00:34:45] - Creating effective content and measuring that effectiveness [00:38:13] - Darker sides of growing the business and raising money [00:39:57] - How ‘the Motherhood Penalty’ Plays Out for Startup Founders [00:43:12] - Fixing the problems with bias in venture capital investing [00:46:57] - What is the outlook and long-term vision for the business [00:50:38] - What has her most excited for the future [00:51:53] - Most interesting about the Rhodes Scholar program [00:54:02] - Kindest thing anyone has done for her

My guest today is Jesse Walden, the founder of Variant, an early-stage venture firm investing in crypto networks and platforms building the ownership economy. With all the hype surrounding NFTs, I wanted to talk to Jesse about them, given his background in the music industry and his focus on the creator and ownership economy. The conversation did not disappoint. We discuss the basics of what an NFT is, what new creative paradigms they might unlock, and where we are in the NFT hype cycle. This episode is the first in what will likely become its own show we are calling Primers. Our goal for primers is to bring investors and operators from a zero to a seven understanding of a topic, concept, or industry. The goal here is for the education around these topics to be fast and entertaining. I hope you enjoy this discussion with Jesse Walden and hopefully the first of many Primers to come. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:04:19] - [First question] - Simple definition of an NFT [00:05:22] - What distinguishes NFTs from each other [00:06:24] - The value chain of a song, and who owns it [00:12:07] - Monetization and royalties on traded tokens [00:15:02] - Consumer incentives for purchasing NFTs [00:19:19] - Long-term passive income and media legos [00:22:23] - Technical breakdown of minting, hosting, and storing tokens [00:24:28] - Verification of token ownership on the blockchain [00:25:58] - NFT marketplaces and aggregators [00:27:06] - Opensea.io [00:27:21] - Foundation.app [00:29:46] - Innovations inspired by the NFT explosion [00:31:01] - Mirror.xyz [00:32:26] - NBA Topshot [00:32:57] - Crypto Punks [00:23:24] - Nifty Gateway [00:34:30] - Physical cultural assets in the digital landscape [00:36:02] - Legacy brands exploring digital goods and tokenized ownership [00:38:37] - NFTs becoming the port of entry of all media [00:39:39] - An ownership economy in second generation internet platforms [00:41:02] - Uniswap[00:42:41] - The “hype cycle” of NFTs and incoming market correction[00:44:18] - Lessons for investors in the NFT space [00:45:15] - Lessons for buildings in the NFT space [00:45:54] - Resources to continue learning about NFTs[00:45:54] - NFTs make the internet ownable by Jesse Walden[00:46:20] - NFTs and a thousand true fans by Chris Dixon[00:46:13] - A beginner’s guide to NFTs by Linda Xie

My guest today is Jonathan Goldberg, the founder, and CEO of Carbon Direct, a company focused on advising and investing in carbon removal at scale. Jonathan started his career in the commodities division of Goldman Sachs and then went on to start a commodity hedge fund, BBL Commodities. In our conversation, we cover the state of the carbon problem today, the importance of global carbon standards and carbon taxes, and the future of carbon capture and removal technologies. This was a masterclass on all things carbon-related. Please enjoy my conversation with Jonathan Goldberg. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by DigitalOcean. DigitalOcean provides founders and creators with the platform they need to get their website and apps off the ground, all with low-bandwidth pricing to save them money over other cloud providers. If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:25] - [First question] - Overview of his career [00:06:02] - The start of his commodities trading strategy and its evolution [00:09:08] - Key strategies for making money as a commodities trader [00:10:41] - Opportunity to trade commodities today [00:11:39] - Making the shift to carbon capture work [00:15:04] - Range of consequences for elevated carbon emissions and biggest buckets of carbon [00:18:52] - An outline of the Paris Climate Accord and other agreements on climate change [00:20:26] - Ways to remove carbon from the atmosphere [00:23:46] - The technology to remove carbon and incentives to invest in this technology [00:26:19] - Corporate participation in the carbon trade [00:28:35] - Balance of natural vs man-made solutions [00:31:53] - Making money without the altruistic goals [00:33:43] - Trends in the fossil fuel industry [00:36:41] - Convenient ways for consumers to switch to clean energy products [00:39:57] - The geopolitical will to shift towards cleaner energy [00:41:58] - Primary consequences of not making this shift [00:44:25] - The important role of regulation [00:46:01] - Thinking through the investing side of combating climate change [00:48:59] - Kindest thing anyone has done for him

My guest this week is Marissa King, a professor of organizational behavior at the Yale School of Management. I was fascinated by Marissa's work after coming across her book, Social Chemistry: Decoding the Elements of Human Connection, earlier this year. Our conversation covers the three types of social networking styles, the surprising impact of COVID on social networks, and what her research tells us about building high-performing teams. This episode covers many topics I haven't explored before that I find fascinating. I hope you enjoy my conversation with Marissa King. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:04:04] - [First question] - Origin of her career and topics she is focused on [00:04:06] - Social Chemistry: Decoding the Patterns of Human Connection [00:04:09] - Priya Parker Podcast Episode [00:05:41] - Why the focus on Autism and some of the trends around it [00:08:07] - Prevalence of mental health and substance abuse vs. raised awareness [00:09:16] - The eureka moment for her in this research [00:10:16] - Pattern in growing large social movements [00:11:43] - The Expansionists group and their role in large social movements [00:14:31] - Acid test for the Brokers group [00:15:35] - How she developed the categories of people that drive social movements [00:17:35] - Most memorable moments of discovery in the development of these categories [00:18:58] - Important categories for overall network science [00:20:20] - Behavioral changes we can make to improve the nature of our social connections [00:23:21] - The pitfalls for each group and how they can invest in their own network [00:25:29] - Conveners and what they need to improve [00:26:34] - Downside of being a broker [00:27:58] - The attachments styles of secure, anxious, or avoidant [00:30:07] - Velocity of interactions possible today and what it means for research [00:32:02] - How men and women develop networks differently [00:33:55] - What is unique in organizational behavior through the lens of her research [00:36:19] - Best practice for creating high output interactions [00:37:33] - Putting together the perfect team [00:38:42] - Largest pitfalls in putting together a good team [00:40:00] - Role of conversation in effective network building [00:41:15] - Being a great listeners and distractions [00:42:47] - Eric Maddox Podcast Episode [00:43:41] - Good policy for running a network, being attentive to the network [00:46:40] - The power of touch [00:48:39] - How movements become societal and what role technology has played [00:52:46] - How this applies to a business [00:53:34] - Biological underpinnings of Dunbar’s number [00:57:13] - Kindest thing anyone has done for her

My guest this week is Jonathan Neman, the co-founder and CEO of Sweetgreen. Sweetgreen is a fast-casual restaurant chain that Jonathan co-founded in 2007 during their senior year at Georgetown when he realized they couldn't find a healthy, affordable, and convenient place to eat. Today, Sweetgreen operates in 11 markets and will have about 160 restaurants across the US by the end of 2021. In our conversation, we cover the origins of Sweetgreen and how it builds a direct relationship with its customers, how Jonathan thinks restaurants should work with marketplaces like DoorDash, and the economics of operating restaurants. While Sweetgreen is primarily a restaurant concept, Jonathan brings a tech-first mindset to the food industry, focusing less on single-store economics and more about customer lifetime value and the importance of owning the relationship with the customer. I hope you enjoy my conversation with Jonathan Neman. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Klaviyo. Klaviyo is the ultimate marketing platform for e-commerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo is trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial, check out klaviyo.com/founders. ----- This episode is brought to you by LinkedIn Jobs. With LinkedIn, you get access to an active community of professionals with more than 722 million members worldwide. LinkedIn is the easiest place in the world to post a job and message qualified candidates. Getting started is easier than ever, and now you can do this all from your mobile device. When your business is ready to make that next hire, find the right person with LinkedIn Jobs. And now, you can post a job for free. Just visit linkedin.com/fieldguide to post a job for free. Terms and conditions apply. ----- Founder's Field Guide is a property of Colossus, Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:04] - [First question] - The origins of Sweetgreen [00:05:47] - Something they did from a position of naivete, working their supply chain [00:07:18] - Most common reason restaurants go wrong [00:08:35] - Building the first restaurant and lessons along the way [00:12:22] - Effective menu building [00:14:36] - The Sweetgreen network and how they view the restaurant as a network [00:21:05] - What their digital business means compared to other restaurant businesses [00:23:55] - How they have improved at converting people into their ecosystem [00:27:40] - Creating win-win partnerships [00:29:12] - The pros/cons of the marketplaces in the food industry [00:32:58] - The general economics of a restaurant [00:36:58] - Allocating capital differently when the focus is the customer and not the store [00:39:36] - How tech trends aimed at improving personal health plays into Sweetgreen’s plans [00:45:11] - Their focus on sustainability for the business [00:47:56] - The core values of ‘Add the Sweet Touch’ and ‘Live the Sweet Life’ [00:50:18] - Kindest thing anyone has done for him [00:51:38] - Never Eat Alone: And Other Secrets to Success, One Relationship at a Time

My guests today are Josh Wolfe and Tony Thomas, better known as T2. Josh is the co-founder and General Partner at Lux Capital. T2 is now a venture partner alongside Josh at Lux Capital, after serving for almost 40 years in the US military and becoming a 4-star general and the 11th Commander of US Special Operations Command. Our conversation focuses on the technology frontier in defense as well as the geopolitical threats that the US faces. We talk about everything from semiconductors and autonomous weapons systems to the moral dimensions of investing in defense technology. I hope you enjoy this fascinating conversation with Josh Wolfe and Tony Thomas. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ------ This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by MIT Investment Management Company – also known as MITIMCo, the endowment office of MIT. MITIMCo seeks to find people who are focused on achieving exceptional long-term investment returns, partner with these firms early, and stick around for the very long term. MITIMCo doesn’t care how small, new, or un-institutional your firm is if you have the potential to generate amazing results that support MIT’s pursuit of world-class education, cutting-edge research, and groundbreaking innovation. Despite their willingness to invest early, they do not ask for GP economics and they commit their initial capital for ten years. Visit www.mitimco.org and their new emerging managers page to learn more. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:46] - [First question] - Overview of Tony Thomas’s career [00:06:36] - His focus on the information wars and truthiness [00:08:50] - How Josh and Tony met [00:12:27] - Experiencing the slow pace of technology growth within the Department of Defense [00:15:51] - History of businesses selling to and engaging with the government [00:23:52] - Consensus of the threats we face today [00:28:55] - Most important competitive frontier today [00:35:09] - The lessening of kinetic warfare [00:46:51] - State of the drone technology and industry [00:52:56] - Mapping the arctic and the geopolitical ramifications [00:54:31] - The frontier of space [00:59:26] - What shouldn’t be unmanned technology [01:02:31] - The cutting edge of simulation technology [01:06:50] - The most important thing to know about the future of semiconductors [01:11:36] - The moral lens of working with and investing in defense companies [01:20:53] - Traits of the most exceptional soldiers he’s served with [01:23:53] - Kindest thing anyone has done for Tony

My guest today is Matteo Franceschetti, the founder and CEO of Eight Sleep, a smart mattress company. I’m a customer of Eight Sleep and this was one of the most unique founder conversations I’ve had on the show, in both the focus on the product and the exploration of sleep. We talk about which biometrics matter, how hard it is to start a hardware company and launch manufacturing overseas, how Matteo manages his own sleep, and the massive potential for preventative health companies like Eight Sleep may have in the future. I hope you enjoy this conversation with Matteo Franceschetti. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:36] - [First question] - Origins of the Eight Sleep business [00:03:21] - Designing and testing the original product [00:04:17] - Goal of the product [00:05:19] - How temperature can improve sleep [00:06:28] - Accuracy of the sensors in this product [00:08:30] - Valuable inputs for health that they measure, HRV (heart rate variability) [00:09:59] - Amount of research on the variables they measure and impact on health [00:11:45] - Hardest data for them to measure in their mattress [00:14:03] - Early challenges to launching the business [00:15:27] - Lessons from the early manufacturing process [00:16:50] - Working through the potential business models [00:17:56] - Goal of less sleep and reducing light sleep [00:19:45] - Behavior changes he’s made as a result of understanding his sleep more [00:21:08] - How alcohol/caffeine impacts sleep [00:22:01] - How food impacts sleep [00:23:01] - Why glucose spikes are bad for sleep [00:23:40] - Challenges in the business after the crowdfunding stage [00:25:34] - Marketing lessons from a high price point and infrequently purchased product [00:26:42] - Most exciting day in the researching phase [00:27:48] - Turning an infrequent purchase into a frequent sale [00:28:54] - What it’s like to work with his wife [00:30:03] - Future of the quantified self-movement [00:31:23] - The hardest challenge in the business [00:32:13] - Most valuable things he’s learned as a fan of Formula 1 racing [00:33:41] - Future of the mattress business [00:35:28] - Other businesses he has learned from [00:36:40] - Lessons from the data part of the business [00:38:26] - Collecting more data from their customers without being intrusive [00:39:56] - What he’s learned through Apple Health [00:41:39] - What has him excited for the long term future of Eight Sleep [00:42:32] - Kindest thing anyone has done for him

My guest today is Jack Clark, head coach of the University of California Varsity Rugby team. Jack has one of the highest winning percentages not only at the collegiate level but in sports history, winning an incredible 90% of games since his start as a coach in 1984. That includes a 98 game winning streak from 1990 to 1996 and a 115 game winning streak from 2004 to 2009. In our conversation, we dive into how Jack builds high-performing teams, the shared vocabulary he creates across his organization, and his work with companies applying what he's learned on the field to operating businesses. Please enjoy this conversation with Jack Clark. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ------ This episode is brought to you by MIT Investment Management Company. MITIMCO is the endowment office of MIT. New and small investment funds listen up. MITIMCO is looking to find investors starting funds today. MITIMCO is partnership-driven, long-term focused, and has an extensive history of backing investors early in their careers. These partners are key in delivering the outstanding investment returns required to support MIT's pursuit of world-class education, cutting-edge research, and groundbreaking innovation. MITIMCO is focused on finding and partnering with the best investors across the globe, no matter the market environment. No firm is too small, too young, or too non-institutional. If you or someone you know is currently in the process of starting a fund or recently launched, please email partner@mitimco.org or discover more on their website at mitimco.org/partner. ------ Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:44] - [First question] - Overview of his playing and coaching career [00:06:02] - The importance of creating a set of values for a team [00:07:53] - Why selflessness is such an important trait he looks for in teams [00:09:20] - Examples of selflessness in the teams [00:10:06] - The Winner Within: A Life Plan for Team Players [00:10:24] - Lessons on gratitude and entitlement [00:11:34] - Being a meritocracy on the team [00:12:55] - Rewarding merit as a coach [00:14:18] - Improving a team today, the power of the basics and fundamentals [00:15:29] - Defining toughness for players and teams [00:17:29] - Mark Bingham, the epitome of toughness [00:18:33] - Why he created and how he uses a glossary [00:22:09] - Creating a high rate of conversion in recruiting [00:25:01] - What qualities did the teams that beat him share [00:27:22] - Take on pride and something he is exceedingly proud of [00:29:17] - Translating the concepts from the court into the business world [00:32:20] - Where companies have room to improve [00:33:16] - Changing a company culture [00:34:21] - Coaches he has learned from [00:36:00] - The power of non-cognitive grit [00:38:45] - Advice for companies creating a value set [00:40:40] - Kindest thing anyone has done for him

My guest today is Ryan Petersen, founder and CEO of Flexport. Flexport is a technology platform for global trade. In this conversation, Ryan takes us through the fragmented world of international freight shipping, and we dive deep into the history and inefficiencies of the system. We also cover how shipping containers were standardized, how new protocols get adopted internationally, and the challenges of doing business in the “no man's land” of international waters. Ryan is the type of entrepreneur I enjoy talking to most: he has incredible domain knowledge, high energy and is tackling an enormous global problem. I hope you enjoy my conversation with Ryan Petersen. For the full show notes, transcript, and links to mentioned content, check out the episode page here. If you are looking for the best place to build web apps or API backends on robust infrastructure, DigitalOcean is the place for you. They provide a fully managed solution that handles your infrastructure, operating systems, databases, and other dependencies, on their new App Platform product. App Platform makes it easy to build, deploy, and scale apps. Get started for free at do.co/founders. ----- Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:24] - [First question] - Overview of what Flexport does [00:04:49] - His introduction into the world of shipping [00:06:49] - Difference between parcel and freight [00:08:53] - Market cap of the overall shipping industry [00:12:52] - Worst parts of the shipping world [00:15:34] - Improving the tech behind the shipping container [00:19:06] - Why the shipping container changed the world [00:19:07] - The Box: How the Shipping Container Made the World Smaller and the World Economy Bigger [00:21:27] - Teams and outsider perspectives in solving problems [00:22:34] - How their business could make shipping more efficient and reduce costs [00:25:24] - Where the margins and profits are made in shipping [00:25:49] - Poor Charlie's Almanack: The Wit and Wisdom of Charles T. Munger [00:27:11] - The finance side of shipping [00:28:56] - Maritime law and the ocean [00:30:57] - How much is left in the digitization of shipping [00:32:48] - The perfect state of shipping using Flexport [00:38:19] - Investing in hard assets to expand the business [00:41:03] - Lessons about building a business and global coordination [00:43:15] - Multidisciplinary thinking among their team [00:44:04] - Global supply chain issues in light of Covid and ocean policing [00:44:15] - Peter Zeihan Podcast Episode [00:47:59] - Testing out demand in the beginning [00:50:28] - The process of testing out new ideas and killing off losers [00:52:33] - Important lessons/themes for founders [00:54:51] - Hardest learned lesson, fundraising [00:58:06] - Other opportunities in shipping [00:59:47] - Lessons for creating a new standard [01:02:22] - Using their standardization to improve global relief work [01:04:40] - Creating synchronicity in a company [01:07:09] - What he’s excited about for the future [01:07:53] - Kindest thing anyone has done for him

My guest today is Jeremy Grantham. Jeremy is the Long-Term Investment Strategist and Co-Founder at GMO. Jeremy has an encyclopedic knowledge of the history of markets, which made it such a pleasure to have him back on the show. In this conversation, we discuss the three key signs of a bubble, why Jeremy believes we are in a bubble right now and how it’s being led by retail rather than institutional investors. We close with the important role that demographics and productivity will play over the next few decades across the world. Please enjoy my conversation with Jeremy Grantham. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Koyfin, one of the fastest-growing fintech startups. I discovered Koyfin earlier this year when I asked Twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com. ------ This episode is brought to you by MIT Investment Management Company. MITIMCO is the endowment office of MIT. New and small investment funds listen up. MITIMCO is looking to find investors starting funds today. MITIMCO is partnership-driven, long-term focused, and has an extensive history of backing investors early in their careers. These partners are key in delivering the outstanding investment returns required to support MIT's pursuit of world-class education, cutting-edge research, and groundbreaking innovation. MITIMCO is focused on finding and partnering with the best investors across the globe, no matter the market environment. No firm is too small, too young, or too non-institutional. If you or someone you know is currently in the process of starting a fund or recently launched, please email partner@mitimco.org or discover more on their website at mitimco.org/partner. ------ Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:03] - [First question] - His view on the markets today [00:03:07] - Jeremy Grantham’s Podcast Episode [00:08:00] - Proliferation of SPAC’s and how he views them as a potential bubble [00:10:20] - Could SPAC’s help to improve the IPO process [00:14:30] - How he viewed the Gamestop story through his historical context [00:18:24] - Is investor education possible [00:19:50] - How the increasing role of retail investors impacts bubbles [00:24:15] - Attitudes towards market bears in bubbles [00:28:52] - Long term view on the economy and the forces pushing it higher [00:41:50] - Returning to a hard money standard for the US economy [00:49:39] - Would a finite supply of money change market trajectory [00:51:02] - Best ways to improve the infrastructure of the economy and people’s willingness to work [00:53:52] - What should one do if they believe we are in a bubble [00:58:14] - What he is excited about in his green investments [01:02:28] - Advice to young investors

My guest today is Carlos Brito, CEO of Anheuser-Busch InBev. AB InBev is the world’s largest brewer of beer and maintains a portfolio of hundreds of beer brands across the globe. Our conversation focuses on AB InBev’s culture of ownership, how Carlos balances organic growth with acquisitions and managing disruption as an industry incumbent. I loved hearing about Carlos’ story from growing up in Brazil to now running one of the largest businesses in the world. I hope you enjoy my conversation with Carlos Brito. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ----- This episode is brought to you by NetSuite. NetSuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly.Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at netsuite.com/invest. ----- Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:12] - [First question] - His career path and how he got to where he is today [00:11:02] - Culture building lessons throughout his career [00:14:52] - Maintaining ownership of company culture as businesses grow [00:16:47] - How and why they avoid wasted resources [00:18:49] - Why conserving resources is so beneficial for a company [00:21:18] - Spreading culture into new members of a team [00:25:26] - Lessons from managing a large portfolio of different brands [00:27:58] - Biggest mistakes he has seen within brands [00:29:38] - Navigating changes/threats in the beer industry, starting with craft beers [00:32:56] - Lessons from the production and distribution side of the business [00:36:02] - How to assess and decide to move into a new market [00:37:12] - Role of data in deciding how to allocate resources and capital [00:40:34] - The evolution of marketing over his career [00:44:32] - Implementing the meritocracy to keep the right people in the company and move them around [00:47:59] - Feedback he needed to hear [00:49:16] - How other leaders can decide on whether to focus on inorganic or organic growth [00:51:41] - What he’s most proud of from his career [00:53:13] - Passion for the product [00:54:12] - Most memorable beer in his life [00:54:56] - Kindest thing anyone has done for him

My guest today is Scott Belsky. Scott was the co-founder and CEO of Behance, the world's largest creative network, and a prolific angel investor, having made early-stage investments in Pinterest, Uber, Carta, and Airtable. His company was acquired by Adobe in 2012, where he is currently the chief product officer. In this conversation, we cover the importance of focusing on the first mile of a customer's experience with your product, why every user is (at first) either lazy, vain or selfish, and what the rise of creativity tools means for creators and investors in the future. We also cover the major trends that Scott thinks will dominate for the next decade. This was one of those conversations where I was left with 10 great lessons that will stick with me for a long time. Please enjoy my conversation with Scott Belsky. For the full show notes, transcript, and links to mentioned content, check out the episode page here. Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:24] - [First question] - Philosophy for building great products [00:04:52] - Starting the journey of building a great product [00:06:08] - Making the first mile better [00:08:12] - Understanding user progress in product building [00:10:25] - Getting to awareness and attention and interest in a product [00:12:41] - The concept of window dressing [00:14:24] - Taking an idea and turning it into a high-value product [00:14:42] - The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture and Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality [00:16:49] - Keeping rewards structure in place for teams to stay engaged [00:19:56] - Using his knowledge in product building to invest in other companies [00:24:00] - The concept of object model [00:25:52] - User psychology concepts they keep in mind when designing a product [00:27:51] - Implementing all of these strategies into a product [00:29:25] - The era of eduployment [00:31:05] - How this will impact colleges [00:33:27] - The evolution of the talent/audience relationship [00:35:32] - Decentralization and the companies of 1 [00:37:44] - How that decentralization will impact his investment thesis [00:39:21] - How increased productivity tools could help with more creativity in the workplace [00:42:04] - Training people to be more creative in the workplace [00:44:33] - Future of user interfaces [00:44:58] - The Interface Layer: Where Design Commoditizes Tech [00:48:10] - Good design principles [00:49:51] - The future coming out of Covid [00:52:09] - Kindest thing anyone has done for him

My guest today is Matt Mullenweg, co-founder and CEO of Automattic, the company on top of the open-source project WordPress that Matt helped start. Today, WordPress powers 40% of all the websites in the world. Our wide-ranging conversation covers the state of the internet when Matt first started WordPress, the symbiotic relationship between open source and proprietary projects, and how the most successful companies are really master world builders. I hope you enjoy this great conversation with Matt Mullenweg. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. All you have to do is log in. Visit tegus.co/patrick to learn more. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founder’s Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:15] – [First question] – What the internet felt like when he first started building Wordpress [00:05:11] – What was wrong with his impression of the internet then [00:06:50] – Being a connoisseur of things overlooked [00:08:34] – How permission less publishing and open source software shaped the internet [00:12:30] – Balance between centralization and decentralization and where we are in the cycle [00:14:08] – The cycle between direct-to-consumer and having intermediary [00:16:32] – New opportunities and challenges of the internet today [00:18:49] – Potential of cryptocurrency to enable big changes on the internet [00:21:22] – The idea of distributed work via the internet and the utopia of it [00:21:38] - Sam Harris podcast with Matt Mullenweg [00:24:31] – Advantage of having a team distributed across geographies and timezones [00:26:46] – What he learned from the Amazon’s API mandate [00:29:12] – Landmines of distributed work [00:31:13] – Interesting lessons learned building Wordpress [00:34:55] – Company building as world building [00:35:52] – Lessons from Microsoft on platform building [00:38:53] – Key ingredient to world building within your company [00:41:09] – Lessons from Wix and Shopify [00:42:23] – How to decide what to do next in resource and capital allocation [00:47:00] – How to engage with other stakeholders in a platform business [00:50:06] – The continued connectivity created by the internet [00:53:14] – Kindest thing anyone has done for him

My guest today is Michael Dempsey, General Partner at Compound. Michael invests in a broad range of areas but has a unique talent for combining brand building and direct customer relationships with technically demanding sectors. Our conversation covers the rise of virtual influencers, robotics, and how to best identify key inflection points in the evolution of new technologies. I hope you enjoy my conversation with Michael Dempsey. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Koyfin, one of the fastest-growing fintech startups. I discovered Koyfin earlier this year when I asked Twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com. ------ This episode is brought to you by MIT Investment Management Company. MITIMCO is the endowment office of MIT. New and small investment funds listen up. MITIMCO is looking to find investors starting funds today. MITIMCO is partnership-driven, long-term focused and has an extensive history of backing investors early in their careers. These partners are key in delivering the outstanding investment returns required to support MIT's pursuit of world-class education, cutting-edge research, and groundbreaking innovation. MITIMCO is focused on finding and partnering with the best investors across the globe no matter the market environment. No firm is too small, too young, or too non-institutional. If you or someone you know is currently in the process of starting a fund or recently launched, please email partner@mitimco.org or discover more on their website at mitimco.org/partner. ------ Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:02:54] – [First question] – Early stages of his career [00:05:13] - What are inflection points and how he views them as a source of opportunity [00:07:40] - Real vs fake inflection points [00:12:19] - Creativity as a key component of inflection points [00:12:33] - On Inflection Points [00:15:01] - Generative Adversarial Networks [00:18:02] - History of animation and the innovation we are seeing there today [00:20:12] - Animation is Eating the World [00:24:11] - The concept of a digital celebrity and their scale [00:29:17] - Characteristics of digital celebrity creators [00:31:12] - Longevity and consistency of these personalities [00:33:11] - Future of gaming and potential for investments in the space [00:37:49] - The landscape for robotics and what has him excited [00:41:07] - The exploration of space and the opportunities there. [00:44:35] - Computational biology and the investment potentials. [00:48:11] - How 2020 has changed the ability to solve scientific problems [00:51:32] - The idea that Cyberpunk is now [00:53:32] - Sam Hinkie podcast episode [00:53:51] - Kindest thing anyone has done for him

My guest today is Dustin Moskovitz, co-founder and CEO of Asana, a team-centric product management tool used by over 1.3 million users around the world. Dustin started Asana in 2008, 4 years after co-founding Facebook. In this conversation, we dive into Dustin's belief about the diminishing returns of hard work, the shocking amount of productivity lost in doing "work about work", and Dustin's philanthropic investment strategy around leverage and maximizing ROI. I hope you enjoy my wide-ranging conversation with Dustin Moskovitz. For the full show notes, transcript, and links to mentioned content, check out https://www.joincolossus.com/episodes/88012555/moskovitz-eliminating-work-about-work ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. Visit https://www.tegus.co/patrick to learn more. ----- This episode is brought to you by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. ----- Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide, go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up at https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:03:19] – [First question] – Balancing hard purposeful work and too much work that leads to burn out [00:05:41] – What led to this way of thinking [00:06:54] – Regulating hard work through culture [00:08:25] – False tradeoffs and how Asana represents this [00:09:43] – Origins of Asana [00:13:22] – Organizing the chaos of a project [00:18:09] – Change vs discipline of the mission [00:19:55] – Transferring good ideas from one company to another [00:23:19] – Instilling leverage as a concept in an early company [00:25:21] – New learning curves in building Asana [00:26:52] – Hardest boss battle during his time at Asana [00:28:43] – The role of the work graph [00:31:46] – The proliferation of the work management space and the overall landscape [00:32:56] – The idea of radical inclusiveness [00:36:31] – Best reasons to start a new company [00:37:47] – What will lead to Asana’s continued success [00:38:59] – Lessons building the product [00:41:13] – Work with the Open Philanthropy Project [00:43:44] – Work on pandemics and biosecurity [00:46:11] – Where he sees the future of artificial intelligence [00:50:47] – Kindest thing anyone has done for him

My guest today is Chamath Palihapitiya, the founder and CEO of Social Capital, whose mission is to advance humanity by solving the world's hardest problems. I didn't know where this conversation would take us given Chamath's wide-ranging activities and interests but I think it provides an interesting glimpse into some of his core beliefs and the source of his drive. In our wide-ranging discussion we cover potential paths to closing the income inequality gap, how to manage one's personal psychology, his perspective on "value investing", and tackling climate change. I hope you enjoy my conversation with Chamath Palihapitiya. For the full show notes, transcript, and links to mentioned content, check out https://www.joincolossus.com/episodes/33654465/palihapitiya-the-major-problems-facing-the-world. ----- This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked Twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com. ----- This episode is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Affirm, Teladoc, Roblox, or almost any company of interest. Visit https://www.tegus.co/patrick to learn more. ----- Invest Like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best, go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up at https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:03:13] – [First question] – His experience with debt and how he approaches personal finance [00:09:13] – Attacking the problem of perpetual income inequality [00:12:06] – Reaching the right people to fix the problem [00:15:04] – A for profit business to solve the problem of income inequality [00:19:18] – Traps he has beaten and hasn’t beaten in his finances [00:22:15] – Chamath’s focus on family, friends, memories, and legacy [00:25:01] – Big issues of our time; inequality, climate change, improving education [00:29:28] – Lessons learned from Social Capital 1.0, allocating funds for himself and others [00:32:33] – The balance between data and the qualitative analysis of companies [00:35:26] – Insights into businesses beyond the investments he makes [00:40:29] – Absurdities in the value investing style [00:43:32] – Benefits of SPAC investing and opportunities for late-stage entrepreneurs [00:45:06] – Traits in managers that he invests in [00:47:20] – What he’s learned about combatting climate change [00:51:40] – Thoughts on the supply chain, specifically as Americans [00:54:35] – Company life cycles and innovation [00:57:15] – What is most broken in the capital markets system [00:58:58] – Fixing healthcare [01:01:36] – Fixing climate change as President for a day [01:02:06] – Messaging effectively [01:03:14] – Is he a “main character” in the investing world [01:04:06] – Tweeting a picture of himself as a kid [01:04:42] – Kindest thing anyone has done for him

My Guest today is Ali Ghodsi, founder and CEO of Databricks, a data analytics platform for data scientists and developers. He's also the founder of Apache Spark, the open-source project that Databricks is built on, and is an accomplished researcher at UC Berkley's computer science department. Our conversation ranges from the origins of distributed computing to modern data infrastructure, how companies can leverage their massive datasets, and the transformation of Databricks through its phases of growth as a business. While technical, it's exactly the kind of conversation I like to have on this show. I hope you enjoy my conversation with Ali Ghodsi. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/4919706/ghodsi-the-past-present-and-future-of-big-data This episode of Founder's Field Guide is sponsored by Klaviyo. Klaviyo is the ultimate marketing platform for ecommerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo's trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial check out https://www.klaviyo.com/founders. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:02:48] – [First question] – What is Databricks [00:03:34] – History of distributed computing [00:05:35] – Hardware that made this all possible [00:07:20] – Early challenges in building out these systems [00:09:43] – What has made networking technology better [00:10:35] – Doing something in storage vs with memory [00:11:45] – Origins of Hadoop [00:12:42] – Use cases of distributed data in 2010 that weren’t possible in 2000 [00:13:35] – Origins of Spark [00:15:25] – Early Spark and then the transformation into Databricks [00:16:50] – Early uses cases [00:17:37] – Their relationship to the open-source project [00:21:07] – What customers need in order to work with Databricks [00:23:11] – Their customer interaction [00:26:27] – How they think about making investments [00:28:24] – Their competitive advantage [00:30:13] – Other companies in moving the needle in building distributed computing industry [00:32:10] – Walls that need to be broken down today [00:34:02] – Best practices for companies when it comes to their data [00:34:13] – Jeff Lawson Podcast Episode [00:38:47] – Lessons being a CEO [00:39:53] – Working at the University of Berkeley’s AMPLab [00:41:56] – What excites him about the future [00:43:29] – Kindest thing anyone has done for him

My guest today is Joost van Dreunen, an investor in the gaming space, professor at NYU's Stern School of Business, and former CEO and co-founder of SuperData Research, a data-driven gaming firm that was acquired by Nielsen. He also recently authored One Up: Creativity, Competition, and the Global Business of Video Games, a great book on the business game industry and why I reached out to speak with him in the first place. Our conversation covers the rise and decline of GameStop, what parts of the value chain actually make money in video games, the evolution of video game business models from Nintendo to Fortnite, and what other industries can learn by studying the video game industry. I hope you enjoy my conversation with Joost van Dreunen. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/14574831/van-unlocking-value-in-gaming This episode of Invest Like the Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. Invest like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:02:38] – [First question] – First chapter of the modern gaming business [00:06:28] – The product era of video games [00:10:11] – The different pieces that take place in creating and selling a game [00:12:25] – The story of GameStop [00:18:45] – The transition to digital platform-based gaming [00:22:55] – How the breakdown of platforms has changed [00:27:35] – Free-to-play vs free-to-win in digital gaming [00:31:27] – How the revenue models are changing the type of games that are made [00:35:07] – Socializing games and the future there [00:38:14] – Who is making money in the modern gaming world [00:43:33] – The zones of opportunity to invest in within gaming [00:47:12] – Why the business models can be more powerful than new tech [00:53:52] – Strategies from gaming that the non-gaming industries can learn from [00:57:05] – Kindest thing anyone has done for him

My guest today is Ilkka Paananen, Founder and CEO of Supercell, a mobile game developer based in Finland. Supercell has built hugely successful games like Clash of Clans and Clash Royale that have reached over 100 million daily active users. What interests me most about the company is Supercell's unique culture built on decentralized, autonomous teams with nearly total creative control. Ilkka and I talk about how Supercell hires and designs teams, why they incorporate as little process as possible, and the rise of global, social games. I hope you enjoy my conversation with Ilkka. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/72273479/paananen-superpowering-teams This episode of Founder's Field Guide is sponsored by Klaviyo. Klaviyo is the ultimate marketing platform for ecommerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo's trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial check out https://www.klaviyo.com/founders. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:02:51] – [First question] – Why he is the “least powerful CEO in the world.” [00:04:03] – His career prior to Supercell [00:07:53] – Lessons from his prior career that he brought to Supercell [00:11:49] – What he looks for in identifying and recruiting the best people [00:13:46] – The funnel of getting great people into the business through the rest of the team [00:15:44] – The Supercell recruitment team [00:17:33] – Interviewing and screening applicants [00:18:39] – Building teams and how they are the driving force behind the company [00:21:29] – The culture of trust throughout the company [00:24:13] – Ensuring teams know when to kill a project [00:26:11] – Celebrating after a project gets shutdown [00:28:15] – Why retention is such an important focus of the company [00:30:40] – How reach and depth lead to a game’s success [00:32:21] – The teams outside of development and how they operate [00:33:36] - LOST & CROWNED | A Clash Short Film [00:34:53] – His day-to-day [00:35:49] – Biggest surprises within Supercell since its founding [00:36:38] – What makes for a good game [00:37:59] – The notion of infinite games [00:39:28] – Kindest thing anyone has done for him

My guest today is Claire Cormier Thielke, Managing Director of Asia Pacific for Hines, the largest private real estate investment, development and management firm in the world with over $144 billion in assets under management. Claire responsible for acquisitions, development, and new business generation for Hines APAC and was also recently appointed to the board of Zillow. I was first introduced to Claire two years ago and have wanted to have her on the podcast ever since. Her personal story is fascinating - Claire finished Stanford undergrad in 2.5 years and now teaches there - on the intersection of tech and real assets, she was a professional track and field athlete - competing for USA Track and Field, and she's run a marathon on Everest, which we discuss. Aside from her personal story and some of her amazing achievements, in the episode, we dive into the world of real estate investing including how to use pattern recognition to unlock real alpha in real estate, the ingredients that make a city special, and the surprising ROI of public art. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/72331821/cormier-the-future-of-cities-and-real-estate This episode of Invest Like the Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. Invest like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:03:01] – [First question] – Overview of her career and her passion for real estate [00:05:32] – The impact of Gerry Hines on her life [00:07:30] – Her theory of and what she thinks about cities [00:09:47] – Cities rhyming with each other [00:12:03] – How the highway act led to growth in cities [00:13:31] – How cities compare around the world [00:15:42] – Airplanes as time machines [00:18:42] – Overview of a building project and how it differs from investing in equities [00:23:15] – Rebuilding a city from scratch [00:25:45] – Major real estate changes we’ll be seeing in the US [00:28:30] – Real estate trends that fascinate her in Asia [00:30:10] – Real estate plugging into other industries [00:32:11] – Trends in Asia that could be ported to the US [00:34:08] – Where to see the best of cities today (post-pandemic) [00:37:28] – The ROI on public art [00:38:33] – Her time in track and field [00:41:59] – The concept of tomorrow time [00:42:49] – Cultivated other part of her training [00:45:07] – Her marathon on Mount Everest [00:46:26] – Replicating the extreme performance piece of herself in a professional setting [00:48:18] – Lessons from being a professor [00:49:53] – Joining Zillow’s board, what she wants to bring and get [00:52:17] – Her childhood and her parents, how that influenced her [00:56:26] – How one person can be actionable [00:58:30] – Brad Gerstner and Rich Barton podcast episode [01:00:32] – Kindest thing anyone has done for her

My guest today is Oliver Hughes, the CEO of Tinkoff, the leading online commercial bank based in Russia. I found this conversation fascinating and think it will be essential for anyone who wants to understand online financial services or the next generation of fintech. Our conversation touches on how Tinkoff used direct mail campaigns to become the largest online banking provider in Russia, their last-mile delivery platform that combines couriers with door-to-door salesmen, and how they build profitability into every aspect of the business. I hope you enjoy my conversation with Oliver Hughes. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/72486324/hughes-the-secret-fintech-giant This episode of Founder's Field Guide is sponsored by Klaviyo. Klaviyo is the ultimate marketing platform for ecommerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo's trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial check out https://www.klaviyo.com/founders. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:02:44] – [First question] – The origins of Tinkoff [00:06:18] – How they started and stayed profitable, and lessons learned [00:08:18] – Bringing Visa to Russia and what he took with him to Tinkoff [00:10:02] – Overall Credit card and Tinkoff's specifically business model [00:12:35] – Running an effective direct mail acquisition campaign [00:15:45] – Branching off from the original core credit card business into other spaces [00:18:45] – How he thinks about when to make competing investments [00:21:00] – Embedding into new businesses and how it goes wrong [00:24:50] – How they became a large door-to-door business in Russia [00:27:55] – Why that door-to-door business makes it hard to compete with them [00:29:38] – Challenges in the payments business [00:32:25] – Using content to help them grow their business [00:35:29] – Competitive frontiers for Tinkoff and how often they shift [00:38:45] – What the future of Tinkoff might look like and the Russian business environment [00:41:55] – State of the market in Russia today [00:45:27] – Recruiting talent and building culture [00:47:55] – What he enjoys most about his job [00:49:14] – Failures and lessons from them [00:52:00] – Kindest thing anyone has done for him

My guest today is Zach Fuss, an investor at Continental Grain, a 200-year-old family owned business that is focused on investing and operating businesses throughout the food and agriculture ecosystem with assets across the US, Latin America, and Asia. Prior to his work at Continental, Zack was an analyst at Tiger and Citadel. This is a must listen for those interested in any aspect of the food ecosystem but also understanding value chains more generally. In our conversation we cover where profits tend to sit in a specific value chain, how legacy food businesses are creating their 2nd acts as digital businesses and explore what makes Domino's Pizza so interesting and special. I hope you enjoy my conversation with Zach Fuss. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/93129089/fuss-breaking-down-the-food-ecosystem Invest like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:03:42] – [First question] – Key components of the food management business [00:05:12] – The most defensible businesses in the food chain [00:07:51] – Law of conservation of attractive profits in the food business and food delivery [00:11:05] – Legacy food businesses and ones that have adapted well to changes today [00:15:42] – Dark stores and cloud kitchens [00:17:11] – Breaking down the Domino's Pizza business [00:19:45] – Being a Domino's Pizza franchise owner [00:21:03] – Why they offer such high returns to franchise owners [00:23:22] – The tech company aspect of Domino's Pizza [00:25:25] – Same store economics for an owner [00:28:15] – When Domino's Pizza realized their food was not great [00:29:45] – Why Domino's Pizza owns the delivery and won’t go on other platforms [00:32:47] – Most portable pieces of Domino's Pizza business [00:34:03] – Parts of Domino's Pizza history that are intriguing [00:35:51] – Build once, sell many times [00:40:09] – Lessons from the best retail businesses [00:43:26] – Has it become harder for smaller companies to win with larger ones being more nimble [00:46:39] – Watching the alternative meat companies flourish [00:49:49] – Interesting trends in the food space [00:51:22] – Global trends in food that we can learn from [00:54:04] – Impact of Covid on the food industry [00:57:44] – Businesses outside of stores that he finds fascinating [01:00:08] – Why he’s impressed by Chipotle [01:01:48] – Approaching buying a franchise [01:05:30] – Creating a new QSR business and differentiating from the pack [01:07:58] – Frontiers that he’s interested in today [01:10:17] – What he is saying in the competitiveness in public equities [01:13:48] – Kindest thing anyone has done for him

My guest today is Carlos Cashman, co-founder and co-CEO of Thrasio an acquirer of third-party Amazon sellers. In a surprising departure for a high growth company, Thrasio has been profitable since its founding in 2018 and was most recently valued at $1 billion. In our conversation we discuss the full spectrum of the Amazon third party seller ecosystem, the effects of globally commoditized manufacturing, and the terms of Thrasio's acquisitions of Amazon businesses. I hope you enjoy this great conversation with Carlos Cashman. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/28372673/cashman-lessons-from-the-amazon-ecosystem This episode of Founder's Field Guide is sponsored by Klaviyo. Klaviyo is the ultimate marketing platform for ecommerce. With targeted segmentation, email automation, SMS marketing, and more, Klaviyo helps you create your ideal customer experience. See why Klaviyo's trusted by more than 50,000 brands, like Living Proof, Solo Stove, and Nomad to help them grow their business. For a free trial check out https://www.klaviyo.com/founders. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:02:44] – [First question] – Origin of Thrasio [00:07:27] – The types of business they work with [00:11:19] – Challenges for smaller businesses selling on Amazon and when they need a Thrasio [00:15:31] – How the Amazon ecosystem has changed since they started [00:18:14] – The capital sourcing side of their business [00:19:49] – Future of the ecommerce space that has them excited [00:27:20] – What makes the major online powerful so powerful for DTC companies [00:32:18] – How edge erodes on spend when people crowd into a platform [00:34:46] – Building the recognition of the Thrasio brand [00:44:06] – His history as an entrepreneur and what was the common thread in these businesses [00:45:47] – Getting customers early on [00:46:47] – Knowing when something will fail [00:48:48] – Downside of MBA’s [00:50:07] – The importance of people in building a company [00:51:01] – Effectively hiring people [00:52:37] – What has to remain with the founder [00:52:50] – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success [00:53:53] – Other places in ecommerce that fascinate him [00:56:36] – What are the risk factors that he worries about [00:59:12] – Kindest thing anyone has done for him

My guest today is Ram Parameswaran, founder of Octahedron Capital. Ram started Octahedron this year after more than 5 years as a partner at Altimeter Capital where he made investments in Square, Bytedance, Pinduoduo, and Udaan. In our conversation we cover the potential for internet scale businesses, explore the common characteristics of these businesses, and then go through a rapid-fire round of the most important qualities for 8 business models. This conversation was a blast of energy and could have gone on for 2 more hours. I hope to have Ram on again and can't imagine what his conversations are like at the dinner table with his wife and former podcast guest, Anu Hariharan. Please enjoy this awesome conversation with Ram Parameswaran. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/22392883/parameswaran-internet-scale-businesses This episode of Invest Like the Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. This episode is brought to you by the MIT Investment Management Company (MITIMCO). MITIMCO is always on the looking for promising investment managers with the potential to compound our capital for a decade or more. If you think your firm is too small, too young, or too non-institutional, you might just be exactly what we are looking for. Check us out at https://mitimco.org/partner/ or e-mail us at partner@mitimco.org. Please also see our new page for emerging managers https://mitimco.org/emerging-managers/. Invest like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:03:45] – [First question] – The opportunity of the commercial internet [00:11:18] – Identifying the companies that will take advantage of this shift to online commerce [00:18:30] – How businesses build scale, in particular internet vs non-internet businesses [00:23:09] – How Amazon Wins: By Steamrolling Rivals and Partners [00:24:19] – The Carvana playbook [00:30:11] – Using frequency of use as a factor in valuing a business [00:33:55] – Evaluating ByteDance and what can others learn from them [00:40:52] – Finding success in an experiment [00:43:32] – How online commerce business will grow globally, with India in focus [00:55:28] – How they approach and evaluate online advertising businesses [00:54:50] – Evaluating direct content subscription online businesses [00:55:42] – Biggest challenges in building ecommerce online businesses [00:58:31] – The lens to evaluate online marketplace businesses [00:59:43] – What distinct things matter for on-demand online businesses [01:01:56] – The competition in the online payment space business [01:06:35] – Rake/Take rates outside of the US [01:08:25] – Things that matter for consumer software [01:10:25] – How that compares to enterprise software [01:11:44] – Evaluating developer companies [01:11:51] – Jeff Lawson Podcast Episode [01:13:53] – Advice to help people be successful early in their investing career [01:17:22] – Kindest thing anyone has done for him

Dylan Field is the co-founder and CEO of Figma, a collaborative, online design tool which has taken the world by storm. With a most recent valuation of more than $2B and bakers like Andreessen Horowitz, Sequoia, Kleiner Perkins, and Greylock, Figma has been one of the most successful companies building tools for creators. In our conversation, we dive into the principles Figma is built on, how they created multi-player for design tools, and the growing importance of design in business. I hope you enjoy this conversation with Dylan Field. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/375923/field-the-growing-importance-of-design DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [00:2:04] – [First question] – His decision to and application for the Thiel Fellowship [00:3:23] – What makes his co-founder Evan so good [00:4:15] – The Thiel Fellowship interview process [00:5:26] – Creating better opportunities for open ended learning in education [00:6:12] – Why Software Is Eating The World [00:7:48] – Importance and types of independent thought as they built Figma [00:10:00] – Early stages of forming Figma [00:12:03] – The market of designers and what Figma does [00:15:57] – His principles of good design [00:17:36] – Bret Victor - Inventing on Principle [Youtube] [00:17:49] - Up and Down the Ladder of Abstraction [00:18:12] – Future of design tools [00:19:45] – Design as a multiplayer concept and surprises that have come from it [00:21:40] – Threshold to know when product-market fit occurred [00:24:11] – Lessons for pricing something effectively [00:25:48] – Biggest challenge growing the business for him [00:26:58] – What he’s learned as a manager since starting Figma [00:28:38] – Lessons in effective recruiting [00:31:49] – Payoff of hiring the right partner [00:33:01] – The chapters/stages of Figma [00:34:38] – What has led to success in terms of the distribution of Figma [00:35:56] – Hardest thing to copy about Figma [00:36:47] – Dealing with customer support and unhappy users [00:38:08] – Their Communities platform and why it’s important for the business [00:39:02] – Learning about and from their competitors [00:41:50] – The landscape of software design tools [00:43:43] – Interesting creator tools [00:44:31] – What would be the key levers that lead to explosive growth for Figma [00:45:57] – Global trends he is most curious in [00:47:21] – Creating a more private digital world [00:49:33] – Thoughts or advice for people building something new [00:50:57] – Kindest thing anyone has done for him

My guest today is Tracy Graham, founder and managing principal of Graham Allen Partners, a private equity firm that specializes in acquiring and building technology-enabled businesses. In our conversation we discuss how Tracy ended up playing football at Notre Dame, the key lessons he learned from famed coach Lou Holtz, why Graham Allen believes that businesses in secondary or tertiary US markets are undervalued, and why technology represents a great way to improve old businesses. I hope you enjoy my fun conversation with Tracy. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/86798473/graham-investing-in-overlooked-businesses. This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more. This episode is brought to you by the MIT Investment Management Company (MITIMCO). MITIMCO is always on the looking for promising investment managers with the potential to compound our capital for a decade or more. If you think your firm is too small, too young, or too non-institutional, you might just be exactly what we are looking for. Check us out at https://mitimco.org/partner/ or e-mail us at partner@mitimco.org. Please also see our new page for emerging managers https://mitimco.org/emerging-managers/. Invest like the Best is a property of Colossus Inc. For more episodes of Invest Like the Best go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here at https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [3:35] – [First question] – Tracy’s origin story [7:17] – Lessons from Lou Holtz [8:58] – Why Lou was so good as a leader [10:32] – His early experience as an entrepreneur [15:45] – Investing principle at Graham Allen and how it was shaped by his experience [18:41] – Types of companies they target for investment [23:09] – Defining a unique and interesting data set [27:14] – Mispricing data sets and the fools gold [29:19] – Overview of a Midwest manufacturing company [31:50] – How data is being generated in manufacturing businesses [36:57] – Data to improve marketing [41:13] – Using data to dissect distribution [45:59] – Valuation of the companies in terms of multiples they are looking at [47:31] – Business values he strongly believes in [50:54] – Significance of Kenneth Allen in the firm [52:23] – Kindest thing anyone has done for him

Zach Perret is the founder and CEO of Plaid. Plaid helps companies build fintech solutions by creating APIs that allow people to connect their financial data to apps and services. In this conversation, we dive into Zach's philosophy on building products, how the financial system works today, how the financial system needs to be updated, and the trends Zach is seeing from the next wave of fintech companies launching on Plaid. I hope you enjoy this conversation with Zach Perret. For the full show notes, transcript, and links to mentioned content check out https://www.joincolossus.com/episodes/39328476/perret-the-future-of-financial-services DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com. Founder's Field Guide is a property of Colossus Inc. For more episodes of Founder's Field Guide go to https://www.joincolossus.com/episodes. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here - https://www.joincolossus.com/newsletter. Follow Patrick on Twitter at @patrick_oshag Follow Colossus on Twitter at @JoinColossus Show Notes [2:00] – [First question] – The notion of Great Challenges he got from his parents [3:34] – How it was instilled into him [4:26] – Default Consumptive State and constantly asking questions [5:33] – Origins of Plaid [8:57] – An overview of the Plaid product [11:10] – The early challenges of building Plaid and creating trust with all of the stakeholders [15:57] – First big break for Plaid [18:06] – Convincing Venmo to work with them [20:12] – What helped build relationships with customers [21:30] – How money is moved and their place in the chain [24:34] – How convenience helps to create larger markets and opportunities [26:39] – Usage base vs recurring revenue models [28:03] – Maintaining their systems as the landscapes and customers shift [29:56] – What is he seeing on the financial services frontier [32:34] – Building relationships with developers [35:07] – Lessons from building a business he’s learned along the way [37:44] – Successful techniques in recruiting [39:52] – What’s working well in this current landscape [41:41] – Business models that interest him [43:14] – Advice for other startup founders [44:49] – Things he doesn’t understand today that he wishes he did [45:46] – What he attributes Plaid’s success too [47:55] – Kindest thing anyone has done for him [50:09] – How you know when you’ve found a great challenge

My guest today is Mario Cibelli. Mario is the managing partner of Marathon Partners Equity Management, a long-biased, concentrated investment firm that he's run for over 20 years. In our conversation, we discuss how his firm figured out Blockbuster's DVD volume and told Reed Hastings and Netflix about their numbers, why visiting a company's distribution center can be an edge for investors, Mario's interesting foray into the world of tequila, and how a few "cornerstone" investing insights have led to many of Marathon's long positions. I hope you enjoy my conversation with Mario. This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:34) – (First question) – Doing a deep dive into the early days of Netflix (2:43) – Netflixed: The Epic Battle for America's Eyeballs (6:50) – What was impressive about Reed (7:34) – Visiting Netflix’s distribution centers early on and the lessons of those visits (10:44) – Lessons learned from other distribution centers (17:52) – What helps create good luck for a company (19:17) – Why tequila was fun to investigate (25:09) – Why tequila is different from other hard liquors (27:40) – Finding the cornerstone insight in a company (29:20) – What he’s learned about media-driven personalities and WWE (34:30) – Lessons in starting a media company and developing IP (39:00) – Having to battle activist shareholders in business (42:43) – How the rate of return in deep investigations has changed over his time (45:08) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today, Bob Pittman, has had one of the most interesting careers I’ve ever come across. Today, he’s the CEO of iHeartMedia, the country’s largest operator of radio stations and podcasts. Bob also created MTV, was the CEO of Six Flags and 21 Century Real Estate, and the COO of AOL and AOL Time Warner. He’s the Dos Equis man of business. In our conversation we discuss why convenience is king for consumers, his lessons from building MTV into one of the most iconic brands and media properties in the world, the rise of user-generated content platforms, and the future of media. We also discuss what qualities make for a great host, a topic that given my current position, is always fascinating. Please enjoy my great conversation with Bob Pittman. DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com. This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:56) – (First question) – His personal interest that unites all of his business ventures (4:09) – His philosophy on the consumer (7:43) – Biggest quality mistakes business leaders make (9:31) – Respecting convenience in consumer preferences (11:08) – Founding insight to build MTV (16:23) – Fred Seibert on Math in Magic Podcast (17:14) – How the music video concept evolved with MTV (22:37) – Role of hosts vs guests in the media world (25:13) – Quality that increases the odds a host works (30:15) – Why everyone needs to know how to tell a good story (31:53) – Peak of his time at MTV (37:51) – Lessons for new media from his experience (43:46 – The largest uncertainty in the media landscape amid the rise of user generated content platforms (49:27) – Where he finds inspiration outside of business (55:40) – What Other People Say May Change What You See (56:16) – Different ownership structures and how they changed his behavior (59:09) – Finding and respecting your audience (1:02:11) – Lessons from time at Six Flags (1:02:24) – Most interesting thing about podcasting (102:52) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Sam Hinkie. Sam worked for more than a decade in the NBA with the Houston Rockets and then as the President and GM of the Philadelphia 76ers. And now, after years of personal investing, he has launched his own venture capital firm, Eighty-Seven Capital. Every conversation I have with Sam is alive with insight, and this one is no different. We explore the idea of studying the "breadcrumbs" that someone leaves behind as a way to track their progress and trajectory, finding and attracting the right people into one’s orbit, and the lessons from the NBA that most shape his investing career. Sam has taught me the most about the topic of building trust, which we cover here as well. I am excited to share my conversation with Sam with all of you. Please enjoy! For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:48) – (First question) – Conducting a good interview (5:58) – Drilling into topics to learn more about people (7:49 – What percentage of people are actually worth spending time with for Sam (9:29) – People who think in a strange way that intrigues him (10:36) – Interest in digital breadcrumbs and how to follow them (14:02) – Building context around founders vs analyzing their pitch decks (17:20) – A real world example of the bread crumb strategy, Houston Rockets GM (21:25) – How successful people evolve with the erosion of their pre-established edge (23:07) – Shifting to a people-first focus (24:50) – Creating an atmosphere that attracts the best talent (26:50) – Tailoring things to someone else’s incentive structure (28:24) – Most amazing thing someone did in early days of working with Sam (30:18) – Lessons from sports that he carries with him (32:31) – Exceptions to relationships being a key to success (33:03) – Have people gone soft? (34:58) – Knowing whether founders are on the right path (36:07) – Avoiding transactional type people (37:04) – Most effective lessons he brought to sports from the investing world (40:01) – Ideas from the sports world he is bringing to the investing world (44:11) – How the size of the team can impact the success of the team (45:48) – Designing the game for himself (50:33) – Lessons learned from watching them build trust (52:26) – Market areas that have his attention (54:13) – Fascination into API’s (58:05) – Keeping your focus on your expertise (59:45) – Strangest things he’s seen in early stage investing (1:01:26) – Playing the long game (1:04:29) – Calling it Eighty-Seven Capital. (1:04:42) – Means of Ascent (The Years of Lyndon Johnson) (1:05:49) – Increasing his chance at a GM job (1:06:52) – What can Caro teach us about the long game (1:08:26) – Lessons of power (1:10:39) – Quality in leaders he respects most (1:11:17) – The Passage of Power: The Years of Lyndon Johnson (1:12:58) – The power of breadcrumbs and how people can start to lay them out Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Michelle Zatlyn. Michelle is the co-founder and COO of Cloudflare, a now $25 billion dollar business which she helped take public last year. Cloudflare helps businesses make their websites faster and more secure, and over 25 million websites are running Cloudflare today. In our conversation, we discuss the catalyst for starting CloudFlare, explore the layers of the internet and the future of distributed storage and computing power, and discuss how and why Cloudflare operates its network across 200 cities globally. We close with the importance of finding and working with great co-founders and partners as you build a business. I hope you enjoy our conversation. DocSend is a document sharing platform that enables companies to share business-critical documents with ease and get real-time actionable analytics. With DocSend’s security and control, startup founders, investors, business development executives, and financial professionals can drive business outcomes that have a lasting impact. Start for free at www.docsend.com. This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:52) – (First question) – Project Honeypot and how it started (3:39) – What question was Honeypot solving (4:59) – Working through the idea maze of Cloudflare (7:30) – The first iteration of Cloudflare (8:15) – An overview of the cybersecurity market and why more leaders need to pay attention (10:33) – First big break for the company (12:50) – Risks they help mitigate (16:42) – Cyber weapons that Cloudflare protects against (20:14) – Hardest part of the building process (24:06) – Effective marketing lessons (25:41) – The sharks vs mosquitoes concept (27:53) – How do decide where to focus next (31:34) – The Cloudflare workers program (36:33) – Their scale vs other cloud providers (42:21) – The finance side of Cloudflare and their relationship vs Wall Street (42:40) – John Collison Podcast Episode (44:47) – Relationship with their founding partners (50:46) – What about the future is most excites them (52:32) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Danny Meyer, the founder and CEO of Union Square Hospitality Group, which compromises some of the most acclaimed restaurants in New York like Gramercy Tavern and Union Square Café. He’s also the founder and chairman of Shake Shack, which began in New York City but is now a publicly traded company with hundreds of locations worldwide. Our conversation focuses on how great hospitality leads to a great business, regardless of what sector its in. We discuss why hospitality is the starting point for Danny’s business philosophy, why first impressions matter, Danny’s concept of ABCD - always be connecting dots, how to scale hospitality, and how to build a business with essentialism and soul. The other day, when my young son went ice skating and fell a lot he said to me “well you learn from your mistake so you try to make as many of them as you can.” You’ll hear Danny say something powerfully similar late in the conversation. It’s a lovely thought, then, that I found out my son, my firstborn, was a boy in one of Danny’s restaurants, in a reveal orchestrated by his incredible team. I really hope you enjoy our conversation. This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you’d want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more. This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:41) – (First question) – His experience as a tour guide in Italy (8:17) – Why hospitality is the center of business focus (8:19) – Setting the Table: The Transforming Power of Hospitality in Business (11:50) – Early lessons at creating an environment of hospitality (15:17) - His strategy ABCD and learning from a trout fisherman relate and relate to hospitality (20:45) – Scaling hospitality (24:56) – What kind of people make a hospitality business work (29:34) – How to be an effective leader (33:00) – Handling mistakes well in the role of hospitality (36:28) – Creating the spark in the early part of entrepreneurial ventures (40:32) – When its time to start something new vs expand something you are already doing (45:52) – The excellence reflex and an example of this in his career (50:25) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Zac Bookman. Zac is the Founder and CEO of OpenGov a budgeting and financial management software for local governments. Before he founded OpenGov Zac was an Advisor to U.S. Army General H.R. McMaster in Afganistan, a law clerk on the Ninth Circuit Federal Court of Appeals, and earned a Fullbright Fellowship studying corruption in the Mexican government. This conversation is one of the most unique and wide-ranging of any I've had on the show. We cover how Zac built a world-class sales organization, the power of selling momentum, and the role capital efficiency still plays in building great companies. We also dive into the details on how local government works from mayors down to school board meetings. Please enjoy my conversation with Zac Bookman. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode of Founder’s Field Guide is also brought to you by NetSuite. Netsuite allows founders to centralize their payment systems, ditch old spreadsheets and Quickbook tools, and finally gain visibility and control over their financials, HR, inventory, eCommerce - all in one place, instantly. Whether you are doing a million in revenue or hundreds of millions in revenue - see why over 22,000 companies are using NetSuite today. Schedule your free product tour at https://www.netsuite.com/invest. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:56) – (First question) – His career leading up to OpenGov (5:45) – Experience in Afghanistan and lessons from his time there (8:54) – Aligning a large group on a strategy (9:56) – Aligning the team at OpenGov when getting started (11:54) – Levels of government that matter and what their systems looked like when he was getting started (15:24) – Role of budget and how money flows in in government operations (18:55) – How technology can fix the bureaucracy of government (21:40) – Can technology help the public’s relationship to government (24:20) – Defining vertical SaaS products (27:02) – Picking the right products/customers to build your product well (28:33) – Their purpose when building their first product (30:23) – Building a company in a highly regulated space (32:14) – Selling in this space and lessons learned (34:04) – Building a machine to distribute enterprise software (37:03) – Getting the technical, political, and commercial processes aligned (39:40) – Staying up to date on the market and fending off your competition (42:18) – Competency within public governments (44:03) – Metrics that he uses to understand the health of OpenGov (46:07) – The importance of charging the right price for professional services (48:36) – Hardest episode in developing OpenGov (50:17) – Valid early criticisms of the company (52:34) – Advice to new entrepreneurs entering the vertical SaaS space (54:06) – The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers (57:04) – Engineering momentum among teams (59:00) – Personal improvement as a leader (1:01:55) – The study of death and why it’s important for him (1:04:19) – What people can get spending time in the mountains (1:06:53) – Role of capital efficiency in his work (1:09:11) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Daniel Gross. Daniel is the founder of Pioneer, an extremely unique company which he describes as a “fully remote startup generator” that helps talented people around the world figure out if their idea has legs. You can learn more about it at pioneer.app. Our wide-ranging conversation covers the art of asking great questions, the use of predictive modeling and psychometrics to identify talent, and why psychometrics are probably overrated and not that scientific. We then dive into exciting new frontiers for tech investing ranging from GPT-3 to satellites. I really enjoyed this conversation and I hope you will too. This episode of Invest like the Best is brought to you by Tegus. Tegus has built the most extensive primary information platform available for investors. With Tegus, you can learn everything you'd want to know about a company in an on-demand digital platform. Investors share their expert calls, allowing others to instantly access more than 10,000 calls on Square, Snowflake, or almost any company of interest. All you have to do is log in. Visit https://www.tegus.co/patrick to learn more. This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:15) – (First question) – His passion for Crank and Whiplash and why movies are great screeners for interviews (6:15) – Overview of Pioneer (7:56) – Defining talent (10:02) – The equivalent page rank when it comes to people (14:10) – Psychometrics and matter to him (18:13) – The importance of persistence (20:23) – The concept of insecure overachievers (22:48) – Fast twitch vs slow twitch capitalism (24:31) – Importance of memes as it relates to human behavior today (26:14) – The landscape of the type of businesses being formed (29:25) – Overview of GPT3 (33:33) - The Power of Ten Playbook (38:08) – Technologies going from a frontier to a utility (42:45) – Why something like a Starlink can’t be regulated (44:58) – Seed vs leech ratio in capital funding (49:10) – Give and Take: Why Helping Others Drives Our Success (49:15) – Dissecting Patrick’s usual closing question and good questions for screening people (52:56) – What questions help him get to the bottom of (55:58) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Emmett Shear, founder and CEO of Twitch. Twitch is the world's leading live streaming platform for gamers, which was acquired by Amazon in 2014. We talk about how Twitch empowers streamers to monetize their audience, the necessity of picking a customer early in a business, and the lessons Emmett learned scaling Twitch from an online reality TV show to a global brand inside Amazon. We also discuss how Twitch has helped create a new language in the internet age with emotes, a topic I am fascinated by. I hope you enjoy this conversation with Emmett Shear. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also brought to you by Solo Stove. There's simply no better way to create good moments this holiday season than around a fire with a Solo Stove Bonfire. Complete with 30-day return policy and a lifetime warranty, the unit is made entirely of stainless steel, and at just 20 pounds, the Solo Stove Bonfire is easy to transport for a perfect evening in the backyard, at the campground, or on the beach. Get $5 off with code Patrick5 before December 31st 2020. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:52) – (First question) – History of interactive entertainment (4:10) – Interactivity from the clubs in Vienna and what he learned from that (5:16) – Origins of Justin.TV and when gaming became the focus for Twitch (8:59) – What he enjoyed about video streaming games early on (10:21) – Interactive experience between creators and community (12:28) – Emotes on twitch and how they came to be (14:45) – Business of emotes and the affiliates (16:27) – How these features are proliferating out on the internet and changing it (17:21) – How far we are in the streamer-influencer phenomenon (20:00) – Building an effective platform for fans (23:07) – Evolution of the just chatting piece of Twitch (24:58) – Favorite parts of Twitch from followers: Chess (26:45) – Running a business within a larger business (28:09) – Most interesting trend in the market today (30:40) – Effective ways for recruiting the team (31:35) – Most curious about what is happening on the internet today (33:06) – Advice from the early days of Twitch (35:55) – Ira Glass video taste and making things (36:34) – Focus on strategic mission (38:06) – Identifying the customer (40:40) – Starting small (41:45) – Investors focus on potential market size (43:00) – Most common reasons talented people fail (43:47) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests today are Raju Rishi, Nikita Singareddy, and Jason Black of RRE Ventures. RRE is a New York-based VC firm investing in early-stage start-ups with more than 400 investments over its 25 year history. Raju, Nikita, and Jason focus their time in the world of healthcare investing, a topic I haven't explored much personally or on this show. We discuss the current landscape for healthcare investing, the variety of stakeholders in the healthcare value chain, the opportunities for founders and investors in the space, what excites them most about the future of the space, and the impact COVID has had in shaking up the industry. I hope you enjoy my conversation with the RRE team. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com Ladder Teams is a modern personal training experience with expertly designed workout plans, 1x1 access to some of the best coaches in the world, and the power of community, all delivered to your phone. If you’re looking to switch up your fitness routine at home or if you are back at the gym and looking to refresh your training plan Ladder Teams has a program for you. Check out https://ladder.fit/Patrick to download the app and get started. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:34) – (First question) – How the team think about attractive investment concepts (7:13) – The current landscape for healthcare investments (8:53) – Complications in pricing healthcare and where it needs to change (17:45) – Catastrophic Care: Why Everything We Think We Know about Health Care Is Wrong (17:55) – The major stakeholders and where the innovation is coming from (18:22) – The Patient Will See You Now: The Future of Medicine Is in Your Hands (24:43) – How Covid is changing the healthcare sector (28:43) – Cutting edge of remote patient monitoring (37:03) – Passive monitoring and future tech of healthcare (39:38) – Improving the clinical trial process (44:54) – Doctors being lost in the shuffle and improving the experience for them (50:20) – Excites them most about the future of the space (56:17) – Kindest thing anyone has done for them Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Nick Kokonas, the co-founder of the 3 of the best restaurants and bars in America - Alinea, Next, and The Aviary as well as the co-founder and CEO of Tock, a comprehensive booking system for restaurants. This was one of my favorite conversations in the history of the show. Nick is a philosophy major turned derivatives trader that is now one of the most well-known names in the restaurant and hospitality industry. We cover so many topics I can’t list them here, but I’ll remember it for why it's so important for a business to really know what it's selling and then actually sell it. Nick also pulls back the curtain on why restaurants and even book publishers can be great businesses if you do them in the right way. I felt like this conversation could have gone on for hours and I hope you enjoy it. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also brought to you by Solo Stove. There's simply no better way to create good moments this holiday season than around a fire with a Solo Stove Bonfire. Complete with 30-day return policy and a lifetime warranty, the unit is made entirely of stainless steel, and at just 20 pounds, the Solo Stove Bonfire is easy to transport for a perfect evening in the backyard, at the campground, or on the beach. Get $5 off with code Patrick5 before December 31st 2020. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:02) – (First question) – Why he thinks it’s so important to own something (4:35) – Make decisions that have outcomes (7:00) – His interest in the restaurant business (8:54) – Why restaurants are so tough (12:05) – How their business mindset changed their running of the restaurant (14:35) – Words they would avoid in the restaurant (16:19) – Asking the right questions in the restaurant business (20:40) – Importance in taking the right risks (22:02) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing (30:08) – Can dynamic pricing be extended to other businesses (31:20) – Origin of Tock (36:17) – Early days of Tock and identifying the right customers/challenges (41:33) – Importance of the first customer (44:22) – The typical restaurant business model (49:23) – Lessons from Tock and the importance of knowing what your selling (53:47) – Lessons from publishing (55:44) – Other aspects of business that people know but do nothing about (1:00:19) – Their response to Covid and lessons learned (1:07:43) – The real impact to the food delivery companies (1:09:24) – How businesses communicate their end processes to their customers (1:14:07) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Niki Scevak, co-founder and partner at Blackbird Ventures. Blackbird is a leading VC firm in Australia and New Zealand and has invested in companies like graphic design platform Canva and autonomous vehicle company Zoox. Our conversation covers the types of wild ideas Blackbird invests in, the landscape of venture and start-ups in Australia and New Zealand, and everything Niki knows about gross margins and customer acquisition. We also introduce a new concept on the show I'm calling Breakdowns, where we dive into a single business, what it does, how it operates, and what makes it tick. I hope you enjoy the conversation. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:39) – (First question) – Defining a wild heart (3:38 – How you identify someone doing their life’s work (4:30) – Defining a wild idea (6:13) – Origin of Blackbird and importance of small teams (7:05) – Investing in companies and not rounds (09:57) – Signs of a good story and storyteller (11:37) – Any places he disagrees with the majority of thinkers in the tech investing space (13:11) – The sleepy firms backing high growth companies (16:02) – The products of an investment firm (18:17) – What he likes to see in a startup after their initial investment and gets him worried (20:21) – Unique characteristics of the New Zealand and Australian markets (23:36) – Trends he’s seeing in companies he’s backed recently (24:46) – Everything he knows about gross margins (25:36) – Range of gross margins in software companies and the quality of the business (27:00) – Lessons on customer acquisition (28:23) – Unique way a company acquired customers early on (29:23) – Customer retention (31:12) – Finding the best product thinkers (32:30) – Question he is trying to answer (34:01) – Lessons from his investing career (35:40) – Business breakdown of Canva (38:36) – How Canva gets to its customers (41:25) – Figuring out the monetization model (44:42) – Canva’s moat (46:08) – Most delightful feature (46:41) – Positive portable lesson from Canva (49:13) – Best way to learn more about the company (49:24) – How I Built This with Melanie Perkins (49:27) – This Week in Startups with Melanie Perkins (49:41) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Todd McKinnon, co-founder and CEO of Okta, the leading provider of identity management for enterprises. Todd started Okta in 2009 after realizing that enterprises would need a robust solution for identity management in a world where everything was quickly moving to the cloud and today counts over 7,000 enterprises as customers. Our conversation focuses on how Todd decided to leave Salesforce to start Okta, the painful early years of growing the business, how companies can create and define a new market, the different roles he's had to play as the company grew and went public, and the frameworks he's put in place to continue to innovate and test new things as public business. I hope you enjoy our conversation. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:19) – (First question) – Best slide in his presentation for starting Okta (5:21) – The early days of Okta and what they were trying to do (8:36) – Challenge of building the company from an engineering perspective (10:32) – First version of the Okta product (11:03) – An overview on identify management (13:55) – The major innovation in the early days of the product (16:11) – The early struggles of starting a company (18:49) – Becoming a default mode solution (20:39) – Most interesting ways the company has grown its services (22:10) – Future of platform businesses (24:24) – Expanding into an infrastructure business (25:59) – Important shifts that they are paying attention (28:21) – Future of our digital identity and Okta’s potential role (32:20) – The chapters of Okta’s story so far (35:03) – Challenges they had to overcome in growing the company (37:31) – Recruiting the right talent and fostering it early on (39:12) – Biggest mistakes he’s made with the business (41:06) – Benefits of extreme focus vs having a broader view of the problems (43:35) – Innovating within Okta (46:02) – How software businesses define cost of revenue and cost of goods (48:23) – Lessons they’ve learned about selling the services of a small company into the largest company (49:54) – Lessons from working with bad clients/customers (51:06) – Their inside view into the future of business today (51:10) – Jeff Lawson podcast Episode (52:36) – Best way to maintain the growth of Okta over the long term (53:30) – Lessons he would give to business students today (54:51) – Being scared as a founder (55:27) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests today are Jason Karp and Rohan Oza. Jason is the founder and CEO of HumanCo, a holding company focused on building businesses that help people live healthier lives. Jason formerly ran the hedge fund Tourbillon Capital and was an audience favorite when he was on the podcast several years ago. Rohan is the co-founder of CAVU Venture Partners, one of the fastest-growing venture funds in the CPG space. Before Cavu, Rohan focused on supercharging brands like Vitaminwater and Smartwater at Glaceau which was acquired by Coca Cola for over $4b dollars. You may also recognize his name as a recurring Shark on ABC's Shark Tank. Our conversation covers how to think about investing in brands, what makes for a great brand, how partnerships with influencers and celebrities can turbocharger a brand, how brand ultimately gives you pricing power, and how Rohan and Jason try to add, in their words, sizzle, to the brands they work with. I really enjoyed this conversation with two of the smartest people I know on brands and brand strategy and hope you will too. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com Ladder Teams is a modern personal training experience with expertly designed workout plans, 1x1 access to some of the best coaches in the world, and the power of community, all delivered to your phone. If you’re looking to switch up your fitness routine at home or if you are back at the gym and looking to refresh your training plan Ladder Teams has a program for you. Check out https://ladder.fit/Patrick to download the app and get started. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:58) – (First question) – Exploring the early part of Rohan’s career with Mars (4:53) – First time changing a brand’s image (6:40) – Jason’s transition since his last appearance on the podcast (9:47) – What parts of a brand excite Rohan as an investor (11:33) – The marketing machine once you find a brand (13:13) – Options in the retail strategy (19:07) – Biggest errors early in a brands lifecycle (21:04) – The shift where consumers care more about the makeup of a product than just the brand (26:20) – Finding the fanatical few in the early part of a brands lifecycle (31:03) – How the role of celebrity has changed in shaping brands (33:01) – The importance of how a brand makes consumers feel (36:15) – Will distribution drive market changes in the future (38:17) – Driving revenue multiples for products (48:33) – Categories in health and wellness ripe for disruption (52:20) – How scalable health and wellness brands are as public companies (55:00) – Challenges that older brands have in today’s environment (56:46) – Kindest thing anyone has done for Rohan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is John Chambers. John was the CEO of Cisco from 1995 to 2015 where he helped grow Cisco from $70 million to $40 billion in annual revenue. In this conversation we discuss the best business lesson he learned from long time GE CEO Jack Welch, his key lessons from acquiring over 180 companies with Cisco, pattern recognition and playbooks, capitalizing on market transitions enabled by new technologies, the value of team offsites, and a lot more. I was immediately drawn into John's magnetic personality and it's easy to see how he was so adept at running a 40,000 person company for 2 decades. I hope you enjoy this great conversation with John Chambers. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:04) – (First question) – Why companies need a near death experience (6:37) – The way his leadership changed between 1999 and 2003 (11:34) – His career before and leading to his time joining Cisco (17:51) – What Cisco was like when he joined (21:02) – Role that pattern recognition plays in his management (24:16) – Lessons learned from the spate of acquisitions they took on under his tenure (30:46) – Pricing deals and using Cisco’s scale to be successful (33:09) – Lessons he learned in terms of distribution (35:10) – What he learned from his relationship with Shimon Peres (42:08) – His role in helping young entrepreneurs (46:00) – Transformation on his team building trips to Alaska (50:42) – Transitions in the world he is focused on right now (52:542) – Kindest thing anyone has done for John Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Anu Hariharan. Anu is a partner at Y-Combinator's Continuity Fund where she focuses on growth investing. Before YC, Anu was an Investment Partner at Andreesen Horowitz where she worked with portfolio companies Airbnb, Instacart, Medium and Udacity. In this conversation, we discuss growth stage businesses and their business models, how her background as an engineer impacts her investing style, the most interesting international markets for tech start-ups, and how much opportunity there still is for investing in tech and e-commerce startups. This conversation left me thinking about how much digital transformation there still is in front us and the exciting opportunities ahead. Enjoy this great conversation with Anu Hariharan. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:45) – (First question) – How she thinks about growth stage businesses through their business models (5:00) – Her views on the winner-take-all business goal (9:53) – How to prioritize the stakeholders when building a network business (12:19) – Priorities in growth stage businesses vs those seeking Series A funding (18:25) – Most interesting international markets (21:44) – Risks in investing in international tech startups (24:54) – Assessing a hardware-based tech company vs software business (30:22) – How her background as an engineer impacts her investing style (36:11) – Lessons from the various growth strategies she’s observed (40:05) – How valuation impacts the company and her decision to invest (45:45) – How far along are we into the global digital transformation and what opportunity is left (48:15) – Sectors that are still primed for more digital transformation (52:50) – How the tech investing landscape has changed during her career (57:45) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Laura Behrens Wu, co-founder and CEO of Shippo. Shippo started in 2014 after Laura realized with her own e-commerce start-up that shipping was an incredibly difficult task for most merchants, so she set out to fix the problem for everyone. Shippo let's merchants small and large use its dashboard or APIs to simplify the shipping and tracking process. Our conversation focuses on Laura's background prior to Shippo, how Shippo's business and business strategy have evolved, the inherent challenges of building a shipping platform, and the intersection of the physical and digital worlds. I hope you enjoy our wide-ranging conversation. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:57) – (First question) – The story of Popout and how it led to Shippo (7:40) – Challenge of working in a huge and crowded market (10:36) – How Shippo changed shipping for small businesses (12:30) – First big break in their favor (13:39) – Their master account with the major shipping companies (14:39) – Why is the shipping industry so complex (16:25) – Most painful part of building Shippo (18:20) – Advice for people in early company building (19:26) – Pricing software in early days (20:32) – The early days of Shippo and getting it to where it is today (23:17) – Going to market and targeting new customers when they’re mostly small businesses (25:48) – Partnering with a larger company, in their case Shopify (27:52) – How they think about their long-term planning (30:48) – Competing in a world where companies can own their own infrastructure (32:39) – How often they think about other competitive advantages (34:20) – Worst question an investor asked her: what if Amazon tries to copy them (35:17) – Her superpowers as a founder (36:41) – API vs dashboard and the difference in their customer bases (38:52) – What businesses that need shipping today need to know (40:14) – Changes in how businesses are being built today (41:28) – What excites her most about the future of this business (43:28) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests today are Rich Barton and Brad Gerstner. Brad is the founder of Altimeter Capital and is one of my favorite active investors. Brad and Altimeter were one of the largest investors in Snowflake in its earlier days and continue to invest in iconic modern businesses with an extreme focus. Rich has one of the most impressive resumes in the business world. He founded Expedia, Glassdoor, and Zillow; He’s a longtime Netflix board member, since before they went public; he’s a venture partner at Benchmark Capital; and he give back through the Barton family foundation. Our conversation covers Rich’s “power to the people,” strategy, Brad and Rich’s perspectives on taking companies public through SPACs vs. IPOs, and their perspectives on how to build a great company. This one is so fun, we even discuss how to come up with company names, talk about the importance Wizard of Oz, and explore the importance of big hairy audacious goals. I really enjoyed this conversation with two of the smartest people I know, and I hope you will too. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:59) – (First question) – How Brad and Rich met (5:57) – The instant click between them (7:21) – The power to the people perspective (7:29) – Brad Gerstner Podcast Episode (10:21) – Delivering information to consumers (11:31) – The investing perception of data-delivery businesses (13:54) – How they use SPACs (17:38) – How entrepreneurs view SPACs (20:17) – Lessons from their involvement in Altimeter Growth Corp (23:57) – Defining value add investor in the public and private markets (26:36) – The Wizard of OZ and Pygmalions (30:41) – Leadership mold at businesses and big audacious goals (30:44) – No Rules Rules: Netflix and the Culture of Reinvention (36:05) – Frank Slootman’s leadership style (36:12) – Amp It Up (46:13) – TAPE SUCKS: Inside Data Domain, A Silicon Valley Growth Story (38:11) – Courage in leadership (41:33) – Physical businesses vs digital only businesses (43:34) – Getting companies fit (45:39) – Lessons around talent density (48:28) – State of the world and markets today since the inception of the pandemic (53:46) – Making up words for companies and fertile ground (56:45) – Go to market model vs business model (58:50) – Early days of product market sales (1:03:03) – Advice to early investors and entrepreneurs for the future of their careers (1:08:10) – The board challenge (1:12:06) – What question are they working hard to answer right now (1:16:09) – Kindest thing anyone has done for Rich Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Jason Citron, founder and CEO of Discord. Discord is one of the largest and fastest growing social networks in the world. It started as a place for gamers to congregate online, but thanks to how easy it makes it to create a community of any type and its offering of text, audio, and video as means of communication, it has expanded far beyond gaming. It has the potential to become the default digital “third place” that we go to find belonging in a variety of online communities. With over 100 million users, it’s also one of the most interesting communications service businesses since the original social networks rose to power. Our conversation focuses on his background prior to Discord, Discord’s founding and growth, its business model and how it has evolved over the past 8 years, and what the future holds for Discord. As we talked, I had this sense that I’d be willing to go work for Jason, and I think you’ll see why. I hope you enjoy our wide ranging conversation. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:17) – (First question) – Lessons from his time as a video game developer (7:58) – Going from game developer to game development platform (12:23) – From his first startup to Discord (16:33) – Expressing the hypothesis of discord (20:10) – How to know what signal to build upon (22:11) – Early adoption of Discord (26:17) – Getting the word out about Discord in the early days (30:43) – Creating more than just a platform, but creating a third place for people to congregate (32:38) – The Great Good Place: Cafes, Coffee Shops, Bookstores, Bars, Hair Salons, and Other Hangouts at the Heart of a Community (32:55) – The evolution and expansion of the types of community using their platform (37:27) – Discord’s business model and how it’s evolved (41:32) – Enhancing communication through Nitro (45:05) – Big principles for company building at Discord (51:22) – His thoughts around competitive advantage for the platform (52:55) – Creating a holistic experience for the users (55:45) – What bothers him the most when hiring (57:47) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests today are Ben Gilbert and David Rosenthal. Ben and David are investors but also the duo behind the Acquired podcast, which is one of my favorite podcasts that dives deep into business history and famous acquisitions. I recommend you check it out. In this conversation, we review of some of the greatest corporate acquisitions of all time and also discuss investing lessons Ben and David have learned across their careers. I hope you enjoy my conversation with Ben and David. This episode is brought to you by Koyfin, one of the fastest growing fintech startups. I discovered Koyfin earlier this year when I asked twitter for the best Bloomberg alternative, and the overwhelming winner was an intriguing new product called Koyfin. Koyfin has tons of high-quality data, powerful functionality, and a nice clean interface. If you’re an individual investor, research analyst, portfolio manager, or financial advisor, you should definitely check them out. Sign up for free at koyfin.com This episode of Invest Like The Best is also sponsored by Assure. Assure is changing the way investors manage private transactions. With Assure, investors can eliminate nearly all the admin cost of private investment. On top of that, they handle all the backend, legal, taxes, accounting, and compliance. All of it, with a straightforward one-time fee. Learn more and try Assure for yourself at https://www.assure.co/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:29) – (First question) – What they look for in new founders based on more experienced managers they’ve worked with (5:07) – Difference between emerging vs legacy market (9:17) – Research steps to determine if a market can get big enough to invest in (12:08) – Working with other firms for doing an initial investment round (15:42) – Recent trends in the supply of capital and number of founders in the VC space (18:56) – Lessons they have learned studying corporate transactions (24:13) – How do startups transform once they are acquired to increase their multiples so much (28:10) – What they learned from deliberations that take place within the acquiring company (30:39) – Most interesting deal for them to unpack (32:44) – What are features of a business that is difficult for others to replicate (35:52) – Any company that are intimidated to go up against (37:37) – Who would they follow (38:52) – Blake Robbins Podcast Episode (39:09) – Missing pieces in their skill set (41:43) – Early green shoots (44:40) – Lessons from Alaska Airlines acquisition and the value of scarcity (47:07) – Kindest thing anyone has done for them Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Leore Avidar. Leore is the co-founder and CEO of Lob, a company which makes it easy to send direct mail programmatically. He’s also the founder of a new company focusing on sports card collectibles, Alt, which is how we originally connected. Our conversation ranges from building Lob, buying a Lebron James rookie card, starting a 2nd business while operating his first and how Leore tries to create and sell superpowers. Like my conversation with Rahul Vohra from Superhuman, I think this conversation will inspire entrepreneurs out there to start building aggressively. Please enjoy. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:55) – (First question) – Origin of Lob (6:14) – Creating and selling superpowers to other people and its value proposition (7:23) – Defining an API in his words (8:44) – Early breaks for Lob (10:45) – Early lessons in responsible growth (12:19) – Physical infrastructure behind Lob (14:14) – Surprises in mail delivery (15:00) – Progression through their pricing models (18:10) – Leaders in the world of making the world programmable (19:07) – Their interest in the physical world (19:45) – Hardest part of scaling a physical business (21:09) – Building a culture that keeps people around (23:13) – Why he is fascinated by negotiations and what he’s learned from it (25:20) – Scarcity, time, and leverage impact’s on negotiations (26:35) – His interest in collectibles and the formation of Alt (30:18) – Size of the alternative market he focuses on (30:54) – The focus on cards (32:18) – An overview of collectible cards industry (33:19) – What is the API of card collection and trading (35:51) – Competitors in the space (37:19) – Buying a Lebron James card (38:21) – Building a fund around the collectibles and the strategy (39:45) – What it means to be a technology company (40:23) – Collectibles beyond sports (41:30) – Defining a good investor (43:32) – Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts (43:43) – Qualities he looks for in investors (45:03) – What does the collectible universe look like over the next 5-7 years (45:43) – Cultural value of assets (48:50) – Managing his time while launching two businesses (49:51) – What he’s most excited about over the next 6 months (51:45) – Consolidation of API businesses (52:19) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Jacqueline Novogratz. Jacqueline is the founder and CEO of Acumen, a non-profit global venture fund that uses entrepreneurial approaches to solve the problems of poverty. Our conversation touches on how Jacqueline left Wall Street and ended up starting a micro finance bank in Rwanda, how she thinks about investing in character, how creating dignity plays such a major role in her investments, and how governments and businesses can work together to solve the world's toughest problems. It is a bit of a departure from my normal investing conversations but contains powerful lessons for many investors and builders. I really enjoyed our conversation and hope you will to. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:29) – (First question) – Where the concept of the blue sweater came from for her book. (2:44) - The Blue Sweater: Bridging the Gap Between Rich and Poor in an Interconnected World (4:29) – Every child has a humiliated experience and the impact on their life (6:55) – The origin of Acumen (10:42) – Why character is such an important investing filter for her (11:59) – How the markets have changed through the lens of Acumen (16:59) – The challenges of getting started (17:04) – Manifesto for a Moral Revolution: Practices to Build a Better World (19:46) – Embracing the idea of being uncomfortable and an example for her (21:50) – The space between government action and market action (26:11) – The concept of conformity traps (29:29) – The lens of moral imagination (30:32) – The importance of brining dignity to others (35:09) – Entrepreneurial skills she sees outside of the US that we lack here (39:38) – Biggest problems across the globe she is interested in tackling (42:48) – Impediments to investing in global problems (49:11) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Justin Singer, the founder and CEO of Caliper Foods and Stillwater Brands, two leading companies in the cannabis industry. We start our conversation with a fascinating discussion on how regulation creates or destroys business and investing opportunities, and then go on to discuss the ins and outs of the cannabis industry in detail. You’ll be able to tell quickly how high-quality Justin is as a thinker and operator, and you’ll learn a ton about this nascent business. Please enjoy our conversation. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:51) – (First question) – How changes in regulation create market opportunities (5:38) – Why VC’s need to pay attention to regulatory changes (6:50) – Story of Section 230 of the communication decency act (8:54) – Relationships between rules, laws, and free markets (11:56) – How regulatory changes impacted recent business ventures (13:30) – His initial interest in the cannabis space (17:28) – How the industry participants have changed over time (21:04) – An overview of the cannabis industry and different pieces of the chain (25:51) – What has led to delays in the legalization of the marijuana industry (28:52) – How the dosage of the product impacts the business (31:34) – CBD vs THC industry differences (32:53) – How much of this industry is left to be unlocked and potential timing (35:55) – Business and investing opportunities in the space (38:16) – Competitive frontier in cannabis (40:37) – The timeline and pending changes coming (43:03) – Margins and business factors of his business (45:51) – First big break for the business (49:47) – What he learned working under Tim Wu (50:34) – Why we are in the golden error for fraud (52:11) – Avoiding fraud (55:12) – What he wants to learn more about in the cannabis space (56:50) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Jesse Livermore. I’ve worked with Jesse as part of our research partners program at O’Shaughnessy Asset Management for years now. Whenever there is a huge, important, and complex issue to be studied, I believe he’s among the best minds in the world to tackle it. He did that recently on the topic of what he calls “upside down markets,” which is the topic of this conversation. We seek to answer the simple question: against a horrible economic backdrop, how can the stock market be near all-time highs? Jesse explains in detail the impact that fiscal policy has had on the market and may have in the future. Please enjoy this master class in upside down markets. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:29) – (First question) – What is Upside Down Markets (5:44) – Overview on monetary easing and the fed’s role in the markets (9:42) – Why fiscal policy is such an important lever and the impact it has on the economy (15:07) – The impact of stimulus on public companies’ fundamentals (19:25) – The mix of assets in the market due to stimulus (22:13) – What made 1929 so different to how we are reacting today (26:14) – Negative concerns: too much money in the system and the risk of inflation (32:43) – Will the pendulum swing back to labor and higher wages (37:23) – How these changes could impact specific companies or sectors differently (41:34) – How he is applying all of this to his personal investment philosophy (44:25) – Biggest risks still out there (49:51) – Most interesting gap in his knowledge putting together this piece Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

Today’s episode represents a new chapter for Invest Like the Best, so requires a longer introduction than normal. Starting today, I’ll be bringing you two episodes per week on the same feed. On Tuesday’s, I’ll focus on investors, and on Thursday’s, I’ll host builders—founders, CEOs, and operators from all different fields. We call this new Thursday series Founder’s Field Guide. There’s nothing more interesting to me than how great businesses get build, and how investors can identify those businesses at the right time. We’ve already recorded with founders build companies in food, technology, infrastructure, shipping, collectibles, and many more categories. The goal each weak will be to have a builder share what they’ve done, how they’ve done it, and what they’ve learned along the way. We view this as a critical next step in furthering our mission: to capture and openly share the world’s best knowledge on business and investing. Onto the kickoff episode with Rahul Vohra. Rahul is the Founder & CEO of Superhuman, an extremely popular product for managing email. Rahul describes himself as a Computer Scientist, Gamer, Entrepreneur, and Designer. You’ll see quickly why it’s the intersection of these areas that sets Superhuman apart. We discuss why emotion matters when building products, and how other entrepreneurs can learn from his experience. Please enjoy the very first episode of Founder’s Field Guide, and stay tuned in future weeks as we host leaders from Nike, Cisco, Twitch, and so many more…listen in as we explore the world of cannabis, baking (not that kind), manufacturing, hardware, software, and more. Let’s dive in. This episode is brought to you by Microsoft for Startups. Microsoft for Startups is a global program dedicated to helping “enterprise-ready” B2B startups successfully scale their companies. If you’re a founder running a B2B company targeting the enterprise, you should definitely check them out. This episode is also sponsored by Vanta. Vanta has built software that makes it easier to both get and maintain your SOC 2 report, at a fraction of the normal cost. Founders Field Guide listeners can redeem a $1k off coupon at vanta.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (3:56) – (First question) – His interest in game design and emotion in software creation (5:15) – Key elements of game design (6:23) – Toys in digital software creation (8:48) – Finding success in boring software solutions (11:19) – Getting confidence while building when there are no real customers (14:08) – How they landed on their final product (15:40) – The Superhuman Product/Market Fit Engine (20:46) – Determining software price (21:55) – Positioning Your Startup is Vital — Here’s How to Nail It (23:09) – Positioning: The Battle for Your Mind (24:13) – Monetizing Innovation: How Smart Companies Design the Product Around the Price (26:36) – First big break for the business (29:04) – How technology companies actually grow (32:15) – Branding a software (33:57) – How he evaluates a company brand as an investor (36:07) – Questions to ask founders when considering an investment (37:35) – How the distribution of Superhuman worked so well (41:25) – Most common question asked by VC’s about Superhuman (43:00) – Why they do manual onboarding of customers (43:05) – Daniel Ek Podcast Episode (45:10) – Cost structure of a busines looking to reach the billion-dollar valuation (47:18) – Designing for flow in software business (51:21) – His design philosophy and their joy formula (58:03) – His superpower (1:00:46) – The power of therapy (1:02:50) – Why he invests in other companies (1:05:05) – Trends in the technology space that have him excited (1:07:28) – The future for Superhuman (1:10:26) – Kindest thing anyone has done for him

Before getting to this week’s guest, an announcement: starting Thursday we will be introducing a new series of interviews. Be sure to check this same podcast feed in two days to learn more. My guest this week goes by the pseudonym Modest Proposal. He’s both a close friend, and one of the most respected thinkers on financial twitter. I field more inbound questions about him than just about anyone, and you’ll see why in this episode. We discuss many of the biggest themes in today’s stock market, from consumer to technology to marketplace and local home services. As always, Modest brings specific insight and general frameworks to the discussion. I talk to him as often as I can because I learn something new every time, and this discussion was no exception. Please enjoy my conversation with Modest Proposal. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:37) – (First question) – How investing is about underwriting the future (5:42) – Essential tools to underwrite the future (7:59) – Michael Mauboussin base rate book (9:02) – Increasing returns to scale as the most important tool (11:36) – Example of silly investments (14:00) – Ideas of consumer signal and non-linear beahvior (16:30) – Why he was blown away by ibuyer.com (19:08) – How businesses are targeting facilitating transactions (23:11) – Ecommerce and digital penetration in business (25:42) – Gavin Baker podcast episode (26:00) – Modest proposal last podcast appearance (27:56) – His thoughts on the extinction of so many businesses as a result of the pandemic (32:26) – Chart tracking Product to service against homogeneous to heterogenous (33:41) – The Perfect Store (33:49) – eBoys (43:51) – Other features of business that fascinate him (46:29) – Ideas that pique his interest right now (51:20) – Case study: IAC/InterActiveCorp (59:36) – Barry Diller’s superpowers (1:01:17) – Why he’s spent so much time exploring IAC/InterActiveCorp (1:02:56) – Related companies to explore Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Lauren Taylor Wolfe. Lauren is the co-founder and Managing Partner of Impactive Capital. Prior to founding Impactive she spent 10 years at Blue Harbour Group, a $3 billion activist investment firm. Our conversation is on the modernization of the activist investor playbook—how investors engage with companies to make them better and improve long term outcomes. We discuss the entire activist toolkit, focuses on what has changed the most in recent years. I’m also very excited to announce a new initiative. After years of building, operating, and investing in software, we are launching Positive Sum, a new early stage equity investing firm. You can read a bit more at positivesumadvisors.com. Now, please enjoy my conversation with Lauren Taylor Wolfe. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:31) – (First question) – Her background and how she landed at Impactive Capital (6:25) – Impactive’s strategy vs the stereotype of the activist investor (10:55) – Potential candidates for what they do (13:26) – How they view the small cap tech world as the space is dominated by huge companies (15:24) - How capital allocation has evolved over her career (15:30) - The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success (17:38) – Best capital allocation strategies and mistakes that most companies make (18:48) – The levers activists pull: cap structure; capital allocation and operating structure (22:00) – Major lessons from earlier in her career (23:25) – Major changes in Governance as part of the ESG strategy (26:13) – The issue of dual-class in the space (27:35) – Features of a pristine healthy board (28:40) – Board’s role setting incentives and objectives for management (29:55) – How she thinks about the E&S in ESG and how it helps shareholders (32:56) – Applying her strategy in a real-world example (37:40) – What they look for in a business when it comes to sum of the parts (40:29) – Businesses that are misunderstood and what she looks for in that category (41:39) – How she manages relationships with the boards (45:11) – What she has learned transitioning business models (47:08) – The rise of employee activism (50:02) – What she’s seeing in terms of diversity and inclusion in board rooms and C-Suites (53:32) – Best practices and ways to disrupt hiring (57:48) – Something she doesn’t understand well today that she wishes she did (58:59) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Rory Sutherland. Rory is the Vice Chairman of Ogilvy & Mather Group, which is one of the largest and most renowned advertising agencies in the world. He’s also the author of one of my favorite recent books called Alchemy: The surprising power of ideas that don’t make sense. In this conversation, we explore many of his counterintuitive ideas about business. Rory makes you think as much as anyone, so I hope you enjoy this conversation. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:12) – (First question) – Why spreadsheets and logic kill magic (5:42) – What a product/service is vs how it’s delivered and makes people feel (regular moonshot vs psychological moonshot) (13:22) – Psychological anomalies - doing things faster, better, cheaper (Red Bull vs Coke) (19:54) – Swiss army knife that companies should avoid (22:50) – Don’t design for average (24:39) – How do people approach improving their business through marketing (27:30) – Case for direct mail (29:22) – Turning your weaknesses into a strength (34:29) – The seven deadly sins and how useful they are as guideposts (37:38) – Most powerful sin for marketing (39:14) – Reaching intelligent answers from dumb questions (43:25) – Why the opposite of a good idea can sometimes be a good idea (47:30) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Michael Seibel. Michael is a Partner at Y Combinator, and the CEO of YC's startup accelerator. He was the cofounder and CEO Justin.tv, which eventually became Twitch, and Socialcam. In this conversation, we discuss all Michael has learned reviewing thousands of applications to YC, interviewing countless new entrepreneurs, and watch young companies begin to grow and, occasionally, find product market fit. Listeners will also enjoy when Michael traps me big time in my thinking about AirBnb and his framework for great problems to solve. Enjoy this great conversation with Michael Seibel This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:22) – (First question) – Emerging trends among founders (6:00) – The long-term impact of Covid on business (7:16) – What an application to YC looks like and what stands out for him (11:46) – What he wants to learn in the interviews (13:54) – Poise in the interviews (15:40) – How the YC experience has evolved and improvements they’ve made (18:38) – How he defines technology (18:50) – Every Company is Becoming a Software Company (21:12) – His thoughts on non-software companies and how they play into what YC does (23:48) – Why frequency and intensity of the problem matter to him (28:32) – Serving the supplier and building the demand (30:38) – Bravery in founders (36:07) – Partnerships and collaboration in venture capital investing (37:58) – Second time founders focus on distribution (39:23) – Coaching the psychological component of being a founder (44:16) – Learning as a founder vs the education system (46:08) – Customer vs investor focus of founders’ mindset (48:16) – How teams know they are really onto something (52:38) – His being a founder trainable or innate (54:08) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Michael Mauboussin, the head of consilient research at Counterpoint Global. Michael is an all-time favorite guest here on the show, and this is his fourth appearance. We discuss one of the biggest topics in the world of investing: the shift from public to private markets that has taken place over the last several decades. We explore the reasons for this shift, the biggest overall changes in capital markets, and what the future may hold. Along the way we explore other fascinating topics like the rise of intangible asset investments, employee-based compensation as a form of financing, and more. If you enjoy this conversation I urge you to read Michael’s paper on the topic which will be linked in the shownotes. Please enjoy this conversation with Michael Mauboussin. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:27) – (First question) – Motivation for writing the book from public to private equity (2:28) – Public to Private Equity in the US: A Long-Term Look (3:02) – The Incredible Shrinking Universe of Stocks (4:48) – Size of the public vs private markets (7:20) – History and changes in the public to private markets (12:00) – Public market vs venture capital returns (16:48) – Persistence of returns (20:01) – Role of price and EBIDTA on the returns of a buyout (23:31) – How buyout forms are sourcing the debt (29:31) – Transition to businesses relying on intangibles (29:42) – Capitalism without Capital: The Rise of the Intangible Economy (30:13) – Endogenous Technological Change (30:36) – Should Intangible Investments Be Reported Separately or Commingled with Operating Expenses? New Evidence (34:18) – Explaining the Recent Failure of Value Investing (36:21) – Superstar firms and increasing returns (42:38) – Role on monopolies in creating network effects (4:52) – The allocators perspective in these investments (49:16) – How does this all impact public market active management (51:54) – Advice to young people getting into the investment industry (52:30) – Jeremy Grantham Podcast Episode (53:30) – Other areas he is researching/looking into (55:44) – How investment work and Santa Fe research influence eachother (56:54) – Investors to learn from (57:15) – John Collison Podcast Episode Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guests this week are Jeremiah Lowin and Chetan Puttagunta. Jeremiah is the founder of Prefect.io, an open-source software company where my family and I are investors, and Chetan is a partner at Benchmark Capital. Both are past guests and good friends. I asked them on to help the audience understand the open source software business model. I’ve been fascinated with this model in which companies give a huge chunk of their work and value away for free to a community of developers, and then make money by building additional tools, functionality, and services on top of their free and open platform. While this may strike you as a wonky discussion on a niche software topic, I think it is valuable for everyone because the ideas can be applied to more than just code. I view much of my own activity as open-sourcing investment research and knowledge. It is also important because much of the world’s technology is built on top of open source projects. I hope you learn something new about this emerging category. Please enjoy. This episode of Invest Like The Best is sponsored by Canalyst. Canalyst is the leading destination for public company data and analysis. If you’re a professional equity investor and haven’t talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:40) – (First question) – Originator business in open source software; Redhat (5:51) – Why open source is valuable in building a business (7:40) – Examples of the benefits of open source projects (10:27) – Open source business models that produce the best results (17:04) – Defensibility of open source companies (25:02) – Mentoring younger founders on using open-source (30:54) – The benefits of launching open-source (36:41) – Building a digital community (41:31) – Lessons from Open Source that can be applied to other businesses (50:04) – The opportunity sets available in the open source space (53:33) – Future of open source (56:31) – Tobi Lutke Podcast Episode Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Katrina Lake, the co-founder and CEO of Stitch Fix. Stitch Fix is a multi-billion-dollar public company which has brought an entirely new model to retail apparel by combining data science, technology, and personal stylists to create a unique shopping experience tailored to the individual consumer. I first met Katrina through past guest Bill Gurley and have been excited to host her since that first meeting. In our conversation, Katrina and I discuss all aspects of Stich Fix—its history, business model, innovations, and its future. Please enjoy this great and thought-provoking conversation with Katrina Lake. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:19) – (First question) – Where E-Commerce stands and what the future might hold (4:37) – Why personalization makes Stitch Fix stand out from the others (9:34) – Why data science is foundational to their business (12:15) – What makes for a good augmented human and hiring stylists (14:34) – Stakeholder value and creating a great partnership with suppliers (18:10) – Their emphasis on stakeholder focus and social justice (19:28) – The capital efficiency of their business in the early days (24:46) – Her superpower of recruiting (29:46) – Her strengths in building Stitch Fix (31:56) – Transparency vs authenticity (32:59) – Big break for the business (37:15) – Exclusive brands to Stitch Fix (39:01) – The next act for Stitch Fix (41:43) – Lessons learned in pricing services (44:24) – Future trends in retail apparel (48:02) – Hardest thing to copy about Stitch Fix (49:59) – Lessons for putting data science at the center of your business (53:37) – Moments during her journey she’s felt most alive (55:23) – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Brian Armstrong, the co-founder and CEO of Coinbase. The topic of our conversation is the future of cryptocurrency and decentralized finance. Its been a while since I checked in on the world of crypto and while prices are still below the 2017 highs, there’s been a ton of additional work and infrastructure laid. We discuss the major events of the past decade and what might happen in the 2020s. Perhaps most interesting, we cover the potential benefits of a modernized financial system, which Coinbase hopes to help usher in. As I’m trying to do more in conversation with CEOs, we also discuss the lessons he’s learned building a business. Please enjoy my conversation with Brian Armstrong. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:23) – (First question) – Most important developments in cryptocurrencies (3:00) - What happened in crypto over the last decade (3:01) – What will happen to cryptocurrency in the 2020s (4:01) – Long term vision for Coinbase (6:57) – Why should we be aiming towards an open financial system (11:41) – How crypto improves the movement of money (14:22) – Creating sound money and currencies (16:21) – Why economic freedom is an important variable in what he’s trying to do (19:44) - How economic freedom can happen with various regulators around the world and in different countries (22:49) – How Coinbase attracted its first users (26:33) – The December 2017 madness of cryptocurrencies (29:50) – How he thinks about recruiting teams and motivating them to be productive (33:40) – Mistakes with people he’s learned from (34:56) – Steering a product roadmap and creating a successful business (37:17) – What do the non-Bitcoin currencies offer that Bitcoin doesn’t (41:19) – Innovation in cryptocurrency that excites him: DeFi (43:40) – Interesting geographic locations and their impact on crypto (45:29) – How his thoughts on company building has changed over the years (46:47) – Battling any loss of confidence as a founder (51:01) – Improving decision making as a leader (53:54) – Aspects of the job that he loves the most today (56:25) – Largest impediments to mass adoption of crypto (58:25) – His curiosity for scientific research and bioengineering (59:19) – Advice that helped him that he would offer others (1:01:38) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today, Matthew Ball, is a long time coming. He’s the former head of strategy at Amazon Studios, an investor, and probably my favorite business essayist writing today. In fact, I can’t think of another author whose work I read as quickly once a new essay drops. Read his latest on the past and future of Nintendo and you’ll see why. Our conversation is all about the past and future of media. We discuss movies, music, television, video games, and the metaverse. When I re-listened to this episode I couldn’t believe how much information was in Matthew's head and how easily he covered so many topics in depth. Please enjoy this great conversation. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:20) – (First question) – Compulsive interest of how people entertain themselves (4:19) – Changes of intellectual property and trademark in media (9:12) – Cross media world building and Netflix’s strategy (11:47) – Competing with the major power players at the top (16:54) – Fate of movies in the new media landscape (20:38) – Fate of music in the new media landscape (25:40) – Age and gaming in this media transition (26:20) – Gavin Baker Podcast Episode (29:50) – Legacy of the Marvel Cinematic Universe (34:48) – How he defines the notion of a metaverse (39:53) – Creating a more interoperable version of our digital world (47:37) – What is not included in the metaverse and investing in one (52:14) – Tim Sweeney’s role in Epic Gaming (58:12) – The unreal engine (1:07:46) – What should investors be thinking about when it comes to gaming worlds (1:12:43) – Opportunities in the gaming space for investors (1:19:59) – Cloud gaming’s impact on the space (1:26:54) – Will other media platforms have to copy the gaming industry (1:30:51) – How interactivity and feedback loops plays into his investment decisions (1:33:07) – Ease of creating a new media business today (1:35:20) – Trends media storytelling (1:38:50) – What makes for good IP in media content (1:42;14) – Why he wants to explore payment platforms and block chain (1:44:56) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Kat Cole, the COO and president of North America for Focus Brands, which owns famous companies like Cinnabon, Carvel, Jamba, and more. Kat’s story and career trajectory are remarkable, as are the lessons she’s picked up along the way which she shares with us all in this conversation. We discuss negotiation, distribution, brand building, brand extension strategies, and leadership. I always enjoy having a true operator on the show, so I was very excited to discover Kat and her thinking. Please enjoy this great conversation. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:13) – (First question) – Her call to prayer (2:16) – Kat Cole on Pomp’s podcast (5:20) – Her positivity lens (7:59) – Applying that positivity lens in business (13:34) – How to show positivity in early interactions with someone (17:37) – Overview of Kat’s career (21:03) – Lessons learned building brands (27:11) – Changing relevance or differentiation within a brand (32:34) – Keeping a brands dominant position in people’s minds (36:00) – The power of franchising and shared commitment (40:50) – How her experience makes her a better investor (42:55) – Lessons around distribution (46:24) – Effectively negotiating and getting your fair share in a partnership (52:49) – Attributes of a brand that get Kat most excited (56:34) – Transferring her brand lessons to software and tech companies (59:09) – Biggest lessons in leadership she’s learned (1:04:13) – Checking In: the power of intention, reflection, and action to be your best and help others do the same (1:05:18) – Most effective questions in her check-ins (1:06:29) – Personal check-ins vs professional check-ins (1:10:44) – Balancing gratitude and ambition (1:14:37) – The kindest thing anyone has done for Kat Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Eric Vishria, a general partner at Benchmark Capital. Eric joined Benchmark after spending the first part of his career as an operator and CEO. The topic of our conversation is the past, present, and future of software businesses. We begin by explaining why public software companies trade at such incredibly high multiples today. We then explore the several different generations of these businesses and why the future remains so bright for companies building software as their primary product. I’d go one step further and suggest that the information in this episode is even more valuable for non-software businesses and investors, because its crucial to understand the impact that these products will have on the overall business landscape. COVID has accelerated the long-running transition to digital across the corporate world, and Eric serves as the perfect guide. Let’s dive in. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:29) – (First question) – His take on public markets, and specifically as it relates to SaaS businesses (4:04) – Why these companies trade so high (7:53) – Peter Zeihan Podcast Episode (11:19) – The competitive frontier in the digital markets (14:02) – The API competitive frontier (14:22) – Chetan Puttagunta Podcast Episode (18:36) – Every Company is Becoming a Software Company (20:10) – John Collison Podcast Episode (22:54) – Charging in an API business model (24:09) – Describing the different generations of SaaS, starting with Gen 1 (28:15) – Gen 2 SaaS businesses (31:52) – Being an investor in SaaS (36:55) – Gen 3 and importance of traditional SaaS companies to get into API (38:06) – Other problems software can solve (44:19) – Why more money isn’t going into SaaS (46:48) – Lessons from the investment universe and how it could apply to SaaS (47:26) – The Hierarchy of Marketplaces — Introduction and Level 1 - Sarah Taval (51:49) – Lessons about scaling (57:51) – Cross customer strategy (1:00:01) – Energy and Civilization: A History (1:01:28) – Qualities of an interesting investor (1:03:52) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Turner Novak, a partner at Gelt VC. Many of the largest companies in the world today are consumer social companies, so Turner and I discuss the past, present, and future of those businesses. When executed right, they are often the fastest-growing companies in history, and the rise of TikTok and some other companies we discuss makes it clear that there may always be more room at the top. The network effects that support these companies make them unique beasts to analyze, and Turner’s writing has been among my favorite content on the topic. Please enjoy our detailed conversation on this important are of public and private markets. This week’s episode is sponsored by Bottomless. Bottomless is a smart coffee subscription which automatically re-orders coffee for you based on your consumption habits. Bottomless is offering one month and your second bag of coffee for free at bottomless.com/patrick. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:18) – (First question) – History of consumer social companies (3:28 – The importance of quality growth over rate of growth (4:43) – Importance of friends and identity in a social network (6:21) – Major markers he analyzes in new social networks (7:59) – The meteoric rise of TikTok and how it compares to other social networks (8:08) – The Rise of TikTok and Understanding Its Parent Company, ByteDance (13:38) – How TikTok deals with user friction (17:28) – Why TikTok copies is a waste (21:08) – Advising companies to build a media arm in this environment (24:18) – Business models beyond advertising for social networks (30:44) – His thoughts on Pinduoduo and the opportunity for a similar company in the US (37:36) – What Snapchat is doing (43:51) – How social eCommerce could be a competitor to an Amazon (46:31) – His review of Zynn (46:36) - Attack of the Clones: TikTok’s Rival Kuaishou Lands in the US (52:22) – The geopolitical battle of social networks (53:36) – Creating social commerce companies (54:27) – Fantasy draft portfolio (59:18) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Charlie Songhurst, the former head of strategy at Microsoft and a prolific investor, having personally invested in nearly 500 companies throughout his career. I met Charlie at an event hosted in New York and you can tell within one minute of meeting him that his mind is sparkling with ideas and curiosity. Its no wonder he’s been among the most commonly requested guests when I asked several top investors and CEOs who I should have on the show. We discuss the lessons he’s learned about business, investing, and people from such a large sample size of companies. I won’t reveal any more here, I highly recommend you just listen to Charlie and learn. Let’s dive in. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:25) – (First question) – Stack ranking the vices of power, money and fame (2:41) – Memorable response to the stack ranking question (3:13) – Best scenario to explore this stack ranking concept (3:55) – Other ways to rank founders (4:44) – Quick look at this career (5:16) – Time at Microsoft (6:03) – Features he looks for in startups (10:55) – Managing the declining curve of productivity (14:55) – Why founders are often unique people (14:57) – Jeff Gramm Podcast Episode (15:04) – Aliens, Jedi & Cults (19;43) – How early entrepreneurs need to make recruitment a serious part of their work (23:06) – How successful founders win the best candidates (25:27) – The East Coast vs. West Coast investment strategies (30:40) – When it’s time to bring in quantitative factors into early stage investing (34:36) – The markers that pop up in companies that hit (37:22) – Boring but successful investments (39:28) – Investor aesthetics (41:29) – Characteristics of investors that he believes are important to success (42:57) – Impacts of Covid and some of the permanent changes that have happened as a result (47:49) – Investing opportunities in the local community (49:13) – His take on cryptocurrencies (53:47) – Most mis valued asset in the world (55:16) – Investing opportunities in Europe (57:34) – Make up of his 483 investments (57:58) – Matt Clifford Podcast Episode (59:17) – Curation as a skill (1:01:54) – Timing and startup success (1:05:11) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Blake Robbins, a partner at Ludlow Ventures. We talk about all things video games, including the major companies in the industry, how games monetize, how in-game economies work, how e-sports has evolved, and much more. This is a fast-growing segment of consumer attention and interest, I believe we are in the very early days of gaming going mainstream. I also have a favor to ask. My team and I have built a small survey for Invest Like the Best listeners and if you’ve enjoyed the podcast, I’d deeply appreciate it if you took 5 minutes to fill it out at investorfieldguide.com/survey. It will help shape the future direction of the show, which I intend to keep improving in the years to come. Thank you, and now please enjoy my conversation with Blake Robbins. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:35) – (First question) – Overview of the gaming industry and how folks may get involved as an investor (3:46) – Some of the biggest players in the space (5:30) – The monetization methods of these gams (9:22) – How do these games respond to real currencies (14:49) – The landscape of e-sports/e-gaming as a whole (19:57) – His involvement with 100 Thieves (25:52) – The media landscape and the role of influencers (29:05) – When he invests and what the opportunities are out there (33:07) – The engines behind a lot of this; Unity and Unreal (34:58) – Other investors that get this trend (37:43) – Other interesting areas of investment for him, including the creator economy (41:25) – Opportunities to build out and invest in the infrastructure of the creator economy (45:37) – Infrastructure opportunities that need to be built (48:08) – Advice for younger professionals (49:04) – Investment allocation he is most proud of (50:08) – A unique skill he couldn’t teach or train in others (52:27) – Something in gaming he doesn’t understand or wants to learn more about (54:08) – The kindest thing anyone has done for Blake Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club and new email newsletter called “Inside the Episode” at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest today is Brad Gerstner, the founder and CIO of Altimeter Capital, a multi-billion dollar technology-focused investment firm. Brad and his team are known for a deep expertise in internet-enabled businesses, including Expedia, Facebook, Uber, and many more. We discuss the evolution of opportunity in this style of investing, including the important shift to private investing, where so much of the value creation now happens. I won’t soon forget our discussion of consumer intent on the internet and how it has shifted, the role that essentialism plays in Brad’s business and life, and the rise of the Chinese internet giants like Bytedance. Please enjoy this great conversation with Brad Gerstner. This episode is brought to you by the MIT investment management company (MITIMCO) Reach out or learn more: Email: partner@mitimco.org Website: https://mitimco.org/partner/ MITIMCo 10 year Letter: https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure: https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:32) – (First question) – Overall investment philosophy at Altimeter (5:12) – Most interesting thing in the landscape today (11:16) – Disrupting the tech giants moving forward (13:56) – The investing opportunity in the backend of the internet (16:42) – His take on old line businesses and how technology could shift his view on them (18:56) – Lessons from company founders whose platforms rely on consumer discovery (21:32) – Running his business on essentialism (21:40) – Essentialism: The Disciplined Pursuit of Less (26:11) – Tactical applications of essentialism (29:46) – Applying essentialism outside of business (31:16) – What travel has taught him about business (33:43) – What we should know about the Chinese internet market (37:11) – The emergence of bite sized transactions across the web (39:22) – Bite sized work (42:43) – How early on can you figure out what company would win a vertical (45:36) – What problem space would he tackle today (48:49) – Collaborating in the private markets (57:27) – Pricing businesses as a key component of his investment choices (1:02:47) – Fascination with life sciences and software (1:04:12) – What about the future excites him (1:06:48) – Kindest thing anyone has done for Brad Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is John Collison, the Co-Founder of the digital payments company Stripe. Stripe’s mission is to increase the GDP of the internet, a lofty and deeply interesting pursuit. John is clearly a voracious learner across business and investing, which you’ll hear instantly. He started Stripe with his brother Patrick when he was just 19 years old, and has grown it to, at last valuation, a $36B business. In our conversation, we discuss conglomerates, the internet economy, the power of writing, and why board members are like Pokémon characters, each with different powers. It’s a lively and wide-ranging conversation with one of the entrepreneurs I’ve most enjoyed speaking with. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:30) – (First question) – Interest in industrial conglomerates (9:10) – Their thinking on acquisitions vs starting new companies (11:42) – How the payment landscape looked when Stripe was started (15:55) – View on the internet economy (20:09) – Exciting possibilities for the future of the internet economy (22:11) – The forces of size vs speed among startups (26:53) – Driving reasons why employees choose Stripe starting with clear communication (28:55) – Tips for better internal communications (30:09) – The importance of rigor in Stripe’s corporate culture (32:15) – Investors and investing styles that are most intriguing to him (36:02) – Teaching vs experiencing business lessons (37:56) – Lessons from going to market with new ideas (50:58) – Allowing teams to explore new ideas at Stripe (44:11) – Best startup companies to study to understand the history of this space (44:52) – Softwar: An Intimate Portrait of Larry Ellison and Oracle (48:18) – Cable Cowboy: John Malone and the Rise of the Modern Cable Business (48:43) – Infrastructures of internet businesses that are missing (52:03) – Does general accounting practices need to change to capture the true value of a company like Stripe (1:01:53) – Shared playbooks in Silicon Valley (1:02:02) – The transition to the no code movement (1:08:22) – Other businesses that pique his interest outside of software (1:10:21) – Future trends that excite him (1:11:10) – First memory when he felt like he was participating in the tech economy (1:12:46 – The role of board members (1:15:48) – Kindest thing anyone has done for him (1:18:49) – Advice for young people Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Jeremy Grantham. Jeremy is the co-founder and chief investment strategist of Grantham, Mayo, & van Otterloo (aka GMO). GMO, which manages more than $60B for clients, was a firm that helped educate me early in my investing career. They’ve long published thought-provoking research, most of which came from Grantham himself. He is regarded as a highly knowledgeable investor in various stock, bond, and commodity markets, but is particularly noted for his prediction of various bubbles. In this conversation we discuss the current crisis, which he calls the fourth major event of his long and storied career as an investor. As he says, this one is the most uncertain. We also discuss unique topics like commodity-based companies, and how opportunity often lies between fields of expertise. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:37) – (First question) – What keeps him going in investing (2:54) – Changing approaches to managing money over the decades (7:27) – Their investment forecast for major allocations and how that has evolved (10:06) – How to markets compete with FAANG stocks (16:06) – More opportunity for active investors and where (30:55) – How he talks to clients about major stock market events (34:09) – His interest in natural resources/commodities (47:07) – Long term argument for the three natural resources: oil, metals, and food (47:10) – An Investment Only A Mother Could Love: The Tactical Case (52:01) – Specific case for particular metals (56:46) – Areas in the future that excite him or that he wants to learn more about (1:03:42) – Advice for people interested in investing (1:05:15) – Kindest thing anyone has done for Jeremy Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Ben Thompson. Ben is the author of my favorite business strategy newsletter called Stratechery. He’s also the host of the exponent podcast, and now the Dithering, a podcast he recently launched with John Gruber. I think Ben is among the most interesting business analysts in the world, and I’ve learned from and directly applied many of his ideas. We cover many of the major concepts he’s introduced over the years, including his well know aggregation theory. I think that to understand how the internet has changed the business world for good, you must read Ben and follow his thinking. I’m excited to finally have him as a guest on the show. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (01:26) – (First question) – Companies that are built for the next disruption (1:32) – The End of the Beginning (9:58) – Aggregation Theory and the Smiling Curve (13:18) – Steps to creating an aggregator (19:46) – Pattern of successful aggregators or luck? (24:34) – How aggregators interact with suppliers and consumers (30:49) – Taking on other aggregators (34:09) – Platform vs aggregator in the scope of Shopify vs Amazon/Walmart (40:55) – The Moat Map (46:16) – Value chain thinking and profitable business models (51:58) – Future of media and independent content creator’s vs bundles (56:07) – Bundling independent creators (1:00:37) – The infrastructure layer of technology and software companies (1:02:35) – His thoughts on gaming platforms (1:06:13) – The atoms vs the bits in the tech world (1:12:18) – What he’s learned from covering Netflix (1:13:46) – Kindest thing anyone has done for Ben (1:15:56) – Stratechery Podcast Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Shishir Mehrotra and the topic of our conversation is the bundle: offering access to multiple products, services, or providers for a single bundled price. This topic is full of incorrect pre-conceived notions, and as it turns out, the bundle is one of the most powerful ideas in business. Properly harnessed it is good for everyone involved. Shishir explains the ins and outs of bundles in this conversation. Shishir ran product at YouTube for years and sits on the Spotify board of directors. He founded and now leads Coda (which is “A Doc” spelled backwards) in 2014, to bundle together productivity apps like docs, spreadsheets, databases, and applications. I love this wonky, detailed conversation which has me thinking differently about many businesses and business strategy. Please enjoy. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:08) – (First question) – The arc of his career (3:32) – Why he has an interest in bundling (7:45) – The concepts of superfan, casualfan, and nonfan businesses (11:05) – Using Spotify as an example of bundles (13:24) – The first myth of bundling: Bundling is bad for consumers (17:53) – The second myth of bundling: 1st vs 3rd party providers and the bundlers (23:03) – Low usage but high Marginal Churn Contribution (MCC) business (24:26) – How insurance fits into these models (26:37) – Myth 3 of bundling: How this impacts consumers (32:12) – How marginal costs play into the thinking of bundling (34:54) – Myth 4: Bundling things that have nothing to do with each other (39:51) – How bundling companies can apply this into their product development (43:21) – Strategic advice to companies building bundles (49:01) – How price and pricing power play into advantages for certain bundlers (54:16) – How does bundling play into his investing thesis (56:47) – Most interesting bundles he’s observed (58:44) – Eigenquestions: The Art of Framing Problems (59:14) – What the future of this trend is (1:02:24) – What is an eigenquestion (1:06:29) – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Hamilton Helmer, the Co-Founder and Chief Investment Officer of Strategy Capital and the author of one of the best business books in history called 7 Powers, which is the topic of much of our conversation. He has spent his career as a practicing business strategist: advising companies, investing based on strategic insights and teaching strategy. In the last three decades, he has also utilized his strategy concepts as a public equity investor. In this conversation we cover all seven business powers, from counter-positioning to scale economies, and how companies earn and keep those powers. Any investor or businessperson should understand these concepts, and 7 Powers is the best work I’ve seen that explains them in depth. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:31) – (First question) - What power means to him (5:05) – Benefits being more common than barriers in the power equation (6:28) – How early-stage companies develop their barriers (11:23) – The power of counter positioning and how he’s seen it applied (14:47) – The product side of counter positioning (16:39) – Daniel Ek Podcast episode (17:27) – Applying the idea of counter positioning to yourself (20:40) – A cornered resource (23:49) – A look at google as a cornered resource (27:12) – Unique power of network economies (31:18) – What subtleties disqualify network effects (32:54) – Nuances of scale economies (35:56) – Learning economies and who can scale it better (37:07) – Building a switching cost and barrier into your business (40:10) – Branding as power (44:27) – Defining process power and how it differs from scale economies (46:40) – The notion of the time lag and cash flow (50:42) – Why is so much power concentrated in technology businesses (52:07) – What does power mean for customers (53:43) – Developing power as an art vs science, and the best power artists (55:08) – The kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Tobi Lutke, the co-founder, and CEO of Shopify. This is both a timely and evergreen conversation. Timely, as the world as moved aggressively digital in the past two months, and Shopify powers so much of digital commerce. Evergreen, because while we touch on Covid and the Shopify business, this is much more a conversation on business and personal principles, learning, design, and growth. Tobi is one of the CEO’s I look up to most for the type of company he is building and for the way he conducts himself. We discuss business focus, why video games help you learn the power of attention, what design means for products and organizations, and much more. Please enjoy my conversation with Tobi Lutke. This episode is brought to you by the MIT investment management company (MITIMCO) Reach out or learn more: Email: partner@mitimco.org Website: https://mitimco.org/partner/ MITIMCo 10 year Letter: https://mitimco.org/wp-content/uploads/2017/03/MITIMCo-Alumni-Letter.pdf MITIMCo brochure: https://mitimco.org/wp-content/uploads/2019/01/MITIMCo-Brochure_web_2018-12-05.pdf For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:35) – (First question) – The launch of the new Shopify shop app (2:44) – Daniel Ek Podcast Episode (2:45) – Jeff Lawson Podcast Episode (4:56) – Having the right focus and growing a good business (9:06) – Marketplace business model vs the merchant driven business model 9:16 – Bill Gurley Podcast Appearances - 162 | 144 | 137 (11:47) – His role as a decisionmaker as CEO of the company (14:07) – What does he mean when he talks about quality (18:28) – His thinking on design and quality (18:32) – Zen And The Art Of Motorcycle Maintenance (19:59) – The Design of Everyday Things (21:06) – Friction as a force in business and manufacturing (26:04) – His thoughts on systems and being free of process (26:08) – The Systems Bible (30:01) – The game of Factoria and how it relates to systems (32:16) – Transfer Learning (34:33) – What Real-Time Strategy games have taught Tobi (38:30) – Building context inside of a company and making it scale (41:17) – Personality typing (46:22) – The Tobi Blueprint (46:04) – Why he likes The Guide to the Good Life and stoicism (55:38) – Raising kids and the impact of Covid (1:03:16) – The kindest thing anyone has done for Tobi Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is popular past guest Ali Hamed, who joins us for an update on private credit. We discuss what has happened so far, what parts of the market are frozen, and where opportunities may lie. We also talk about how the world has shifted digitally since the beginning of the COVID pandemic. Please enjoy my conversation with my friend Ali Hamed. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:41) – (First question) – World of private credit in the pandemic age (4:50) – Bag of uncertainty (6:27) – Important levers in private credit (9:15) – Scary scenarios and systemic risks in this world (13:21) – General trends in the credit data (15:30) – Are investors factoring government response properly (17:02) – Defining advanced rates (20:18) – Focus on quality vs rate of return now (22:26) – Pockets of opportunity as uncertainty declines (26:06) – Online ecommerce platforms, like the YouTube economy (29:40) – Non advertising driven ecommerce platforms (31:54) – How venture capital is responding (38:19) – How junior debt could be am opportunity (40:17) – Trends he’s thinking about; redefining small businesses (43:07) – Ali Hamed Podcast Episode Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today for a flash update is Chris Bloomstran, the founder and CIO of Semper Augustus and a popular past guest on the show. We talk about his view on the state of the public equity market, why it will be hard for the market to deliver great returns for the next decade relative to the last, and where opportunities may lie. Please enjoy. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:42) – (First question) – Adjustments to his portfolio in the age of a pandemic (6:41) – Chris Bloomstran Podcast Episode (9:36) – The Federal Reserve Act (12:32) – Surprising action in the markets during the crisis (13:08) – 2020 Investment Letter (15:02) – Why we won’t see the same performance in tech over the future as we’ve seen the last decade (21:00) – The carnage in energy sector and return potential (30:06) – Berkshires activity since the crisis started (35:48) – Where sectors are valued in the current market (41:12) – Expectation for deflation over inflation (48:54) – Characteristics to look for in businesses to own over the next 10 years (52:05) – Economic factors they are focusing on Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Josh Kopelman, the founder of famed venture capital firm First Round Capital. Prior to starting First Round, which has invested at the earliest stages in companies like Square, Uber, and Roblox, Josh was a three-time entrepreneur, so our conversation spans early-stage investing, business building, and entrepreneurship. I’ll not sure forget his analogy distinguishing between navigators and cartographers, nor the rest of the interesting ideas he shared after seeing and investing in so many great businesses. We also discuss how First Round has bucked the trend to build what I’d call a platform adjacent to the core investing business which does a lot for their entrepreneurs and is a model for other professional investing firms, both in venture and elsewhere. Please enjoy my conversation with Josh Kopelman. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:05) – (First question) – How pandemic has impacted their investing strategies (3:54) – How this stressful environment impacts founders (6:23) – His early career as a founder and how startup culture has changed (10:15) – Most important lessons from his entrepreneurial career and building from just an idea (11:50) – How to analyze a founder (14:05) – Common disagreements when it comes to deciding on an investment (15:33) – How many opportunities they evaluate in a meeting (16:16) – The curvy road to their investment in Roadblox (17:52) – Whether the concept for a platform is overused (19:36) – Founders asking what google search they should build on (20:46) – Solving existing or forecasted problems (25:39) – How the startup scene is impacted by the huge legacy tech companies (30:28) – What makes a great early stage investor (32:19) – Do they focus on founders or themes (33:19) – Where will valuations and returns come back to after the pandemic (36:30) – How are business models evolving in technology entrepreneurship (36:31) – Matt Clifford Podcast Episode (39:40) – The Dorm Room Fund (43:02) – Whether investment funds should have their own platform (47:31) – Product mistakes in software building (51:52) – What he’s most excited about for the future (54:05) – The kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Manny Stotz, the founder of Kingsway Capital. Manny is one of the leading investors in Frontier Markets, investing in equities in countries like Egypt, Bangladesh, and Pakistan. We discuss the opportunity in these markets from all angles: demographics, valuations, sectors and beyond. It is important to note that we recorded this conversation before COVID, and these markets have fallen 30% without a similar rebound in prices that we’ve seen in the U.S. As you listen you’ll hear why this may be relevant for the companies Manny focuses on and may accentuate the opportunity in Frontier Markets even relative to the numbers quoted in this conversation. Listeners will know my interest in Frontier Markets runs deep, so I was excited to have one of the categories leading investors join me. Please enjoy my conversation with Manny Stotz. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:07 – (First question) – How Kingsway was conceived, their focus on frontier emerging markets, and his career path 11:57 – What are the best company builders good at when it comes to fostering a brand 18:30 – How country-specific factors impact the tailwind 25:43 – How markets are faring in these special circumstances 32:09 – Building a book in many of the markets they trade-in 37:10 – Understanding your edge in frontier markets, showing up 39:59 – Importance of solid distribution for the companies he invests in 42:12 – Concentration in various markets 44:10 – Moving beyond consumer brands in these markets 47:14 – Some of the most interesting countries they are looking into and the country business model 47:42 – Guns, Germs, and Steel: The Fates of Human Societies 47:44 – Civilization: The West and the Rest 47:46 – Why Nations Fail: The Origins of Power, Prosperity, and Poverty 53:21 – New topics he’s excited to learn about that will impact his business over the next 10-20 years 55:37 – Best way for people to get involved and invest in these markets 58:17 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest this week is Sarah Tavel, a general partner at Benchmark, working alongside past guests Bill Gurley and Chetan Puttagunta. Sarah has a long history as both an investor and as an operator. She was an early product leader at Pinterest before joining Benchmark. Sarah has become one of my go-to resources for topics like networks, consumer technology, and marketplaces among many other topics. I’ve used her framework for how to think about client engagement, company data, and marketplace liquidity and quality over and over again in my business life. I’m so excited to finally have her on the show. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:24 – (First question) - Lessons learned from watching the food delivery space 5:44 – Hip camp and how they are thinking about the space rental sector 5:45 - The a16z Marketplace 100 7:47 – Valuing private companies vs public companies 9:37 – Building marketplaces 14:24 – Tipping a market 14:30 – Bill Gurley Podcast Episode 18:09 – How to incorporate reputation scores into a network 19:55 – Search ranking as a tool for marketplaces 21:00 – Size of marketplaces vs their competitors 22:15 – Niching of marketplaces 22:21 - Chetan Puttagunta Podcast Episode 23:26 – State of the consumer social sector 27:50 – The LinkedIn problem and how she would build a social platform 30:42 – Things that are piquing her interest in the consumer space 32:20 – Lessons learned about scaling while working at Pinterest 38:42 – Pricing and the marketplace 41:25 – Identifying and optimizing a Core Action in a digital business 44:18 – Accruing benefits and mounting losses as part of the product design 47:48 – Her investment in Reci 52:18 – How should companies gather the best data from their business 56:03 – Lessons to SaaS investing 56:29 – Kindest thing anyone has done for Sarah 57:45 – Most interesting philosophy lesson 58:09 – Creating a Kingdom of Ends Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

In the midst of the worldwide quarantine, my friend Boyd Varty decided to begin an adventure he has been considering for a long time: a 40 day and 40 night stay in the African wilderness. I’m releasing this short conversation with Boyd to pique your interest in his daily dispatches. He will be taking short audio journal-like recordings and sharing them with the world as he goes. As of today they are several that you can listen to by subscribing to the Track Your Life podcast on Spotify or wherever you get your podcasts. Please enjoy this short chat with my good friend Boyd Varty. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (0:31) – The start of his 40-day trip (1:42) – Origin of the word quarantine and how it led to this journey (3:07) – History of this idea (6:14) – The logistics of this 40-day venture (9:59) – His experience doing this before and how it changed his psyche (12:07) – What is he most fearful of (13:22) – How he feels about sharing this experience when he returns (15:47) – The mental preparation to this journey (15:48) – Priya Parker Podcast Episode (15:49) – The Art of Gathering: How We Meet and Why It Matters (17:33) – How can outsiders make a connection to Boyd while he’s in this isolation (19:55) – How can people actually follow him on this journey (20:23) – Track Your Life with Boyd Varty Podcast – Apple Podcasts | Spotify (20:33) – Instagram - @boyd_varty (20:36) – boydvarty.com (20:43) – 40daysand40nights.com (21:05) – The story of the 17 lions Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is with past guest Gavin Baker, the founder and CIO of Atreides Management, LP. We discuss investing during a bear market and the major ways in which the COVID19 outbreak has dramatically altered the investment landscape. Please enjoy my second conversation with Gavin Baker. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (1:40) – How he sees the markets right now (3:06) – How he handles information uncertainty and the value spreads (5:53) – Trading in today’s market and the volatility (9:45) – How the economic activity squares with the amount of stimulus being pumped into the market (13:11) – Market Wizards: Interviews with Top Traders (13:56) – Asset tests for individual companies in this environment (19:09) – This Time Is Different: Eight Centuries of Financial Folly (20:45) – His take on software companies during the crisis (28:57) – Fast pace of change during extreme times of duress (35:14) – Space as a service (39:52) – Attention and time inside digital universes and how investors can take advantage (46:17) – Why chaos is a ladder (50:42) – It Was a Very Good Year: Extraordinary Moments in Stock Market History Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is D.A. Wallach, one of the more interesting investors I’ve come across. He is the former lead singer of the group Chester French and the former artist-in-residence at Spotify, where he was also an early investor. While he’s also an early investor in companies like SpaceX, his focus the last 5 years has been on early stage health care investing, which is the topic of this conversation. We discuss the entire life sciences and heath care investing ecosystem. This was recorded in the very early days of the Coronavirus outbreak so while we touch on it briefly it isn’t the primary focus, and I intend on returning to more traditional episodes like this one in the coming weeks, meant to be evergreen conversations. Please enjoy my conversation with D.A. Wallach. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:31 – (First question) – Where is interest in healthcare started 4:04 – How to categorize health services 5:13 – The product of medicine 6:56 – How medicine is changing in 2020 10:17 – What is enabling innovation in medicine 12:41 – Manufacturing of solutions, gene therapy example 17:16 – Using CRISPR 19:47 – Pros and cons, and the morality of gene intervention 23:44 – How progress is being made in medical breakthroughs 26:51 – What is the business and investment world seeing on the longevity side 30:15 – What is next in the wearable medical tracking trend 33:04 – The personalization of medical treatments 34:31 – How he thinks about all of this from an investing standpoint 36:37 – Exiting these companies 39:41 – How he thinks about founders in this space 42:35 – Drug prices 42:46 – The Paradox of Pricing 46:45 – What will lead to a change in the pricing of drugs 49:05 – The delivery side of healthcare 51:09 – Investments that could improve the delivery side of healthcare 53:33 – Thoughts on the anti-interventionist line of thinking in the medical world 57:50 – Lessons from his health portfolio 1:02:33 – Other frontiers that pique his interest, including gut biome 1:06:46 – His career in music 1:08:20 – Lessons he learned during his time in the music industry 1:10:19 – Opportunities in the music industry as an investor 1:12:29 – Kindest thing anyone has done for DA Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Chad Cascarilla, here to discuss some of the tail risks in the economy and markets as of March 24th in the midst of the Coronavirus pandemic. Chad was one of the most successful investors during the global financial crisis with a specialty in the banking and finance systems. He now runs Paxos, a trust company which trades and custodies unique products like pax gold, bitcoin, and other tokenized assets including simple pax dollars. I feel it is important to avoid confirmation bias in times like this and not just talk to people are optimistic or long, and while I still believe this is ultimately a positive and optimistic conversation, Chad acknowledges and outlines scenarios that few are talking about yet in the markets. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes (2:04) – (First question) – Today’s market and the porridge scenario (7:38) – Risks to the market that people aren’t focused on (10:54) – What lessons from 2008 do we need to heed this time (13:07) – How does he think about inflation on the other side of this crisis (16:02) – What does a too cold recovery look like (20:35) – Benefits of nationalizing the banks vs pumping liquidity (24:13) – What does the just right recovery look like (25:24) – Assets that might be ideal to hold in a too hot or too cold scenario (29:00) – His take on how Bitcoin has performed during this crisis (31:53) – The US’s inherent strengths compared to the rest of the global economy (34:50) – Advice for people (38:59) – Paxos.com (39:48) – What is he monitoring to see which way things shake out Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My conversation today is with my close friend Brent Beshore. Brent is a private equity investor who owns and interacts with many small businesses, which have been hit especially hard by COVID. We discuss the various impacts that COVID has had and may have on both small business and the private equity investing community. Brent also proposes some policy actions which he thinks may help those most in need. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:13 – (First question) – What Brent sees as the current landscape for small businesses 3:25 – The real problem for small businesses right now 6:02 – How long can small businesses survive these freezes 9:14 – Ideas to help businesses stay afloat during a global shutdown 11:01 – The cost of restarting businesses on the other side of this 13:41 – Policies that could help 14:30 – government co-paying some business expenses 16:05 – Suspending payroll taxes 16:17 – The small business bond 18:00 – Wider latitude for banks 20:03 – How effective would Brent’s ideas actually be at lessening the pain 22:41 – A look at how things look in the private equity complex 25:39 – What are the potential opportunities out there 29:24 – What is a balance sheet product 32:00 – How this is personally impacting Brent 34:20 – How this is personally impacting Patrick 35:45 – Importance of relationships for personal health Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest this morning is Dan Rasmussen of Verdad Capital. Like me, Dan and his firm focus on quantitative research. Just a month before the COVID crisis hit markets, they completely and published a study on investing during periods of market crisis, which is the topic of this conversation. We discuss what works and what doesn’t during and after acute periods of panic in markets. I think you’ll find it extremely informative. Because Dan’s firm and my own share many beliefs about investing and conduct similar flavors of research, I try to offer devil’s advocate questions throughout. Please enjoy. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:54 – (First question) – What he sees in the markets today given the atmosphere right now 4:26 – An overview of their study: Crisis Investing: How to Maximize Return During Market Panics 8:38 – How things get more predictable during crisis 11:15 – The length of these crises and assets they focused on 12:40 – What happens to bonds and credit during these times 15:50 – Geography of crises 18:14 – How does this impact the philosophy of just index investing 20:40 – Positioning of value in this market 27:50 – Lessons from other crises 32:21 – Importance of a blended factor approach 35:44 – Role of momentum 38:10 – What else he is paying attention to during this crisis Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guests today are Bill Gurley and Chetan Puttagunta, both partners at benchmark capital. We review the early stage investing world in the face of coronavirus in a very timely conversation, which is one that will remain valuable once this crisis is done. We discuss enterprise and consumer, funding and growth, and the entrepreneurial spirit in the face of a crisis. Please enjoy. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:44 – (First question) – Landscape for venture capital ecosystem 6:47 – The experience in 2009 and the entrepreneurs that tend to rise to the top 8:24 – The relationship between early stage companies and public investors 10:45 – How this crisis impacts enterprise businesses vs the broader corporate sector 14:46 – Advice for early stage companies in a period like this 18:23 – What Chetan was doing during the last downturn and what he learned during it 20:27 – Early stage vs late stage companies in this environment 22:57 – On the Road to Recap 23:00 – Benefits of being small in a period like this 25:22 – How portfolio companies are responding and pivoting during this period 29:33 – Best practices for remote companies 31:39 – Themes that stand out during this period 34:51 – Closing thoughts Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest in this flash podcast is Bryan Krug of Artisan partners. We discuss what has happened so far in the corporate high yield and investment-grade credit markets, and the loan market. We compare today’s environment to the financial crisis and other past crises with lots of nuances that I hope will be helpful to bond and equity investors. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:08 – (First question) – An overview of what he covers in the corporate credit markets 1:52 – How things have changed in the last couple of weeks 3:56 – Composition of the high yield market 7:07 – Major sectors of the high yield market outside of energy 8:39 – How do they price the risk in securities right now 11:21 – How do they handicap a great unknown 13:00 – Risk for broader contagion in the overall credit markets 14:49 – What’s the downside potential here 16:31 – Potential for upside 18:33 – How does he view companies that are drawing down on their entire line of credit 19:44 – An overview of the loan market 20:42 – What warning signs equity investors should be watching for in the bond markets 21:57 – What do credit spreads look like today compared to before this crisis Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

This week, I’ll be recording and immediately releasing a series of conversations on business and market reactions to the spread of coronavirus. The conversations will be on oil and gas, corporate credit, and the reaction within the venture capital community. Today’s conversation is with Matt Smith, Ian Singer, and Kobi Platt of Deep Basin Capital. We are investors in Deep Basin, and they were past guests on the podcast. We discuss the new price war in the oil markets and the impact it might have on equities and especially on U.S. oil producers. Please enjoy. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:59 – (First question) – An overview of the global oil market and demand 3:37 – Supply and demand shocks we’ve seen lately 6:22 – What happened this weekend with Russia and Saudi Arabia and why the outcome was so shocking 9:45 – The knock-on effects of this activity on equities 14:24 – Impact on US energy production 18:29 – What other industries will feel the effect of reduced production in the US 20:35 – Defining a price war and how victory is defined 27:53 – Saudi Arabia’s calculus in this energy fight. 31:11 – How does all of this change what factors they use to analyze companies 35:43 – What it actually looks like within the commodities markets to trade energy 40:01 – What uncertainty is most intriguing to each of them 43:00 – The long-term interest in investing in the energy sector Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest this week is Peter Zeihan, the author of a new book, the Disunited Nations. Peter was an extremely popular guest on the show last year and after reading his new book, I knew we had a lot to discuss in round 2. In this conversation, we discuss two ways of ruling the world, the coming American disinterest in global affairs, and which country are poised to do well int eh future. We explore military and non-military technologies, political changes, and up and coming alliances like that between the United States and Mexico. As with last time, peter packs more information into an hour than just about anybody. Please enjoy our conversation. This episode is brought to by Koyfin. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:57 – (First question) – What makes for a successful country 6:02 – Five first-tier countries that are well positioned 7:14 – Ruling the world, US carrot model vs British stick model 9:39 – How other countries will use these models in the future 12:59 – The surprising reliance of Iran and Russia on the US 15:24– Key points of his research on the Middle East 18:36 – Advice for how those operating in the US should think about future business investments 23:05 – The future of manufacturing partnerships with the US and the focus on Mexico 27:30 – What Coronavirus has taught us about the world economy 30:01 – What the primaries and election are teaching us 35:09 – What role does Africa play in the future 38:36 – Strong and weak players in Europe and how Brexit has impacted things 44:41 – The future for nuclear power 46:27 – The outlook for South America 50:42 – The trends and future in military technology 55:03 – Non-military technology that will have a major impact 58:26 – Skills young people should focus on for the future 1:00:07 – Coronavirus as a dress rehearsal for large scale disruptions to the world Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest this week is Jeff Lawson, the Founder, and CEO of Twilio. Twilio is a 15-billion-dollar company offering a cloud communications platform to its customers. Twilio is used by customers like Lyft, Twitch, and Yelp to make communications in their products easy. Jeff and I talk about why it pays to be a platform, how to be a platform, and how to sculpt a company culture. This is a must-listen for anyone building a business whether it’s a tech business or not. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:18 – (First Question) – Company vowels and draw the owl 5:26 – Significance of API’s 12:14 – How non-software businesses can transition into the space 17:50 - Agile way of working at ING Belgium (video) 18:38 – How they strategize their product build 23:27 – The idea of asking your developer and why it’s so important to them 33:02 – How they codified their business culture 45:12 – Parting advice for people building platforms 48:13 – Kindest thing anyone has done for Jeff Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

Niko Canner is the founder of Incandescent where he and his team help the leaders of large companies in the areas of strategy and innovation. He was also the founder of Katzenbach Partners and a member of Bridgewater’s management committee. Niko is a fantastic writer, and I highly recommend you check out his blog “On Human Enterprise,” which has posts on many of the most interesting aspects of business and personal purpose. This conversation was inspired by many of those posts. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:17 – (First Question) – The story of Doctor V 3:24 – Aravind and the Choice of Great Achievement 4:00 – Becoming the perfect instrument 6:05 – What is Niko planning to be the perfect instrument of 8:18 – How should individuals think about finding what they can be the perfect instrument of 8:59 – Brett Victor – Inventing on Principle 10:59 – How do businesses apply this principle 13:20 – Making choices easier 16:43 – Era’s to a company and when it’s time to start a new one 19:52 – How can business culture be cultivated and useful 22:53 – Cultures at the tail end of a distribution 24:33 – Can hierarchy be fluid, or does it need to be a dedicated corporate structure 27:47 – My Unlikeliest Favorite Business Book 28:03 – The Millionaire Real Estate Agent: It's Not About the Money...It's About Being the Best You Can Be! 30:46 – The Red Test and how it can be used by businesses 36:54 - Ten Principles for How to Run a Company 42:25 – Dealing with the sponsor owner brief in the software world 45:24 – How does one choose customers 46:32 – Bill Hubbard passage – A Theory for Practice: Architecture in Three Discourses 49:09 – Kindest thing anyone has done for Niko Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals 5:27 – What conditions would they add debt down the road after investing in a company 6:52 – What business sectors are most intriguing for Morgan to invest in right now 6:57 – Trent Griffin Podcast 9:34 – Why no HVAC businesses if it’s such an attractive sector 13:56 – thoughts on rolling up similar businesses and horizontal scale 16:04 – Another industry Brent would focus on 18:02 – Difference between property management in larger cities vs smaller metro areas 18:51 – What role does profit margin play when Brent is evaluating a business 22:46 – The appeal of a hyper cyclical business 22:52 – Brent Beshore Podcast Episode 27:27 – Favorite counter cyclical business 28:14 – How they judge assets, tangible vs intangible assets 33:58 – How does he think about wage inflation when considering the cost of a business 37:21 – His fascination with pet crematoriums 38:57 – History of the permanent equity fund and the changes by having a larger pool of capital 43:48 – Pitching investors on a new structure for the business 46:14 – How will this business model scale Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is a good friend and a business mentor of mine. Chetan Puttagunta is a general partner at Benchmark Capital and has a remarkable track record of investing in early-stage software businesses, including several like Mulesoft, MongoDB, and Elastic that went on to be public companies. Chetan has been my key guide for understanding the world of enterprise software as we at O’Shaughnessy Asset Management have built an investing platform called Canvas. His advice has been critical to our early success. In this episode, we explore the history of software and software investing, and go into the details on how to build and grow new software businesses. We discuss product, sales and marketing, recruiting, scaling, and everything in between. Please enjoy this great conversation with one of my favorite business and investing thinkers. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:34 – (First Question) – How Chetan found MongoDB and decided to invest in it 8:01 – The evolution of databases in the growth of technology 16:19 – Market penetration of this space and what investors should be thinking about 21:46 – Advice how companies can build software effectively 25:12 – Tactics to effectively implement empathy led product building 30:33 – Companies asking users what to build vs telling users what they want 34:26 – The need for the right capital, and patient capital in particular 37:55 – Creating the perfect customer experience 44:37 – Common reasons they don’t invest in a company 48:48 – Lessons on scaling, especially in sales and marketing 52:47 – Best recruiting pipeline strategies 59:56 – Pitfalls of unit economic traps 1:00:23 – The Dangerous Seduction of the Lifetime Value (LTV) Formula 1:01:34– The Hierarchy of Engagement 1:02:18 – What has changed for Chetan in his time working with the team at Benchmark 1:06:009 – Later stage life cycle business considerations and Amazon’s AWS 1:13:29 – The business model of open-source software 1:15:54 – Being default open 1:17:53 – Kindest thing anyone has done for Chetan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Rebecca Kaden, a partner at famed venture firm union square ventures. USV is known for thesis-driven investing, which is the topic of our conversation. Rebecca walks us through the evolution of USV’s thesis into its third generation, and from there we explore many of the most interesting and exciting areas of business, technology, and learning. Please enjoy our conversation For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:11 – (First Question) – An overview of Union Square Ventures Thesis 3.0 7:49 – Core changes that can help any community 9:59 – Ways to fix the broken education system 13:41 – Gap between job preparedness and the education system 14:44 – Companies creating education systems to prepare people for careers in their field 18:49 – Most unique technological solution for people to educate themselves 22:00 – Ways to improve access to capital 26:49 – The distribution problem in capital markets 28:19 – How does she assess an early-stage company and its team’s ability to assess their ability to maximize distribution 30:56 – Digital marketing and why it could be broken 34:22 – Examples of masterful marketing 36:07 – How they are focused on improving wellbeing, their first focus on healthcare 39:35 – Wellbeing on their focus on community 41:29– The Art of Community: Seven Principles for Belonging 45:30 – Her thoughts on mentorship 48:23 – What she has learned in her time at USV 51:50 – Kindest thing anyone has done for Rebecca Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest today is Matt Clifford. He’s the co-founder of Entrepreneur First, the world’s leading talent investor. They invest “pre-company” by helping the best people in cities around the world find a co-founder, develop an idea, and start a company. So far, they’ve helped 1000 people start 200 companies worth a combined $1.5B. This conversation covers their entire ecosystem and holds lessons for anyone building a business. I especially loved Matt’s ideas on the history of ambition. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:20 – (First Question) – An overview on talent investing 4:37 – The history of ambition 10:08 – How do they search for ambitious people 12:21 – What happens early on for these formed teams 17:43 – Assigning an idea to a talented team 20:52 – Opportunities in deep technology 27:16 – A closer look at the hardware and machinery of the deep technology changes 30:54 – The geographical focus of venture capital investments 37:16 – Problems with the way early-stage investment world works 41:22 – People who are creating value in a management company and how they manage their investments 55:12 – Advice to people creating investment companies and pricing power 1:00:31 – The power of cities 1:02:46 – Topics they cover in their newsletter; technological sovereignty as one example 1:04:11 – Experience and thoughts on China 1:06:51 – A.I. Nationalism 1:12:03 – Kindest thing anyone has done for Matt Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Peter Buffett. Peter is a musician, composer, author, and philanthropist. Peter is an Emmy Award winner, New York Times best-selling author and co-chair of the NoVo Foundation. We discuss music, community, philanthropy, and finding one's note in life. This is a very different episode much more about life in general, with no business or investing discussed. Like his father Warren, Peter has the gene for phrasing ideas in memorable ways, and I think you’ll find many great phrases in this chat that will stick with you. I’ve been thinking about Peter's idea making sure those in your life are safe, seen, and celebrated ever since our chat. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:27 - (First Question) – Welcome and small talk 1:35 – Why Peter is in Kingston and how it plays into his foundation work 4:01 – How moving from the city to the country changed Peter 6:27 – Seeing connections vs living abstractions 7:30 – What is the Nova Foundation 11:03 – Historical points that inform his views 13:51 – Identifying qualitative negative side effects and which ones they are attacking 17:51 – What makes for effective community 20:22 – Linkage between consumption and individualism 23:55 – The cultivation of work ethic, curiosity, and education 23:57 – Life Is What You Make It: Find Your Own Path to Fulfillment 27:22 – Early exploration of his curiosity 32:26 – What has music taught Peter about music that is unique to that experience 34:26 – Most memorable question a person has asked Peter at his concert and conversation series 36:46 – What makes for good relationships, in particular marriage 42:03 – What keeps people from putting in the work into a relationship 45:11 – What he has learned about being a good friend 46:29 – How does one person have a relationship with a large community 49:21 – Dark sides of the philanthropic world 49:54 – The Charitable-Industrial Complex 53:21 – Dignity: Seeking Respect in Back Row America 55:55 – What one spot would he send everyone to learn 57:48 – Traumas and helping people find their note 57:49 – The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma 1:00:38 – How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence 1:02:24 – What is he most interested in right now: how to best use Nova’s funds 1:04:45 – Lessons from family 1:07:22 – Kindest thing anyone has done for Peter Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Ben Savage, a partner at Clocktower ventures. Ben is focused on financial technology, fintech, investing which is the topic of our conversation. I’ve been making the fintech is rounds of late, and plan on making a few of these conversations public. Ben is the first in what may be a mini-series because of the sheer amount I learned in our discussion. We cover all aspects of the fintech ecosystem. I hope you enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 (First Question) – The market portfolio and how technology will move us away from liquid markets 7:24 – Businesses that are making assets that weren’t investable, investable 9:11 – Ryan Caldbeck Podcast Episode 12:03 – Most interesting places where technology is creating investment opportunities 18:33 – Assets that are likely to tap into new sources of beta 23:46 – How well are investors prepared for the changes that are coming 28:35 – Trends in asset management with technology 33:05 – View on cryptocurrency and blockchain 36:45 – Places where startups can reduce costs/fees and create efficiencies 40:17 – Views on private equity markets and their future 45:40 – Privilege of access problem 48:50 – Verticals in fintech that are interesting to him 59:53 – The importance of focus and niche 1:02:26 – Kindest thing anyone has done for Ben Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Jeff Ma. Jeff was on the famous MIT Blackjack team from the book Bringing Down the House but has spent his career in an around fields of analytics and data science. He’s studied sports betting and analytics, built companies for analyzing human capital, and ran the data science and analytics group at Twitter. Here are links to his book, blog, and podcast. Our discussion is about a number of fascinating ways data is being used to make decisions in the worlds of sports and business. Please enjoy! For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:20 - (First Question) – How quantitative analytics have evolved in sports and how they’re being used 4:26 – Best role of humans in the analysis process 8:38 – Sports that are most interesting to observe through analytics 10:26 – How does luck play into sports analysis 11:54 – Team analytics vs better analytics 12:38 – Concentration of success among sports betters and their moats 14:58 – Favorite lessons learned from professional gamblers 16:45 – How analytics got introduced into gambling 19:21 – Understanding one’s own biases 24:04 – How he became VP of analytics at Twitter 28:37 – Primary lessons from the work evaluating human capital and talent with analytics 28:59 – Niel Roberson Podcast Episode 31:40 – How to model people for success when hiring 33:29 – How to hire the right data scientists’ team 37:54 – Most interesting problems they tackled at twitter 42:31 – Responsibility of social platforms to police itself 45:34 – Areas that would interest him in the future as an investor 49:24 – Kindest thing anyone has done for Jeff 51:50 – Values instilled in him by his parents. Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Vaughn Tan, who studies quality, innovation, and organizational behavior. His resume is bonkers. He’s a PhD from Harvard, Was an infantry signals logistician in the Republic of Singapore Army, then worked at Google on advertising, Earth, Maps, spaceflight, and Fusion Tables. He’s also been a wood sculptor. But the topic of our conversation is how to foster quality and innovation in ourselves and inside of companies—lessons he learned in part by studying inside some of the world’s best restaurants. If you enjoy this conversation, I recommend you also check out his new book, The Uncertainty Mindset Innovation Insights from the Frontiers of Food. Please enjoy my conversation with Vaughn Tan. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:33 - (First Question) – Interesting ways to identify high quality 5:06 – The current problem with the way we think about the world 8:56 – How people think about their careers and college 11:21 – Uncertainty vs risk, and productive discomfort 19:08 – Cultivation of discomfort for an individual 24:05 – Successful innovation cultures 32:25 – Analyzing quality and restaurant bread 37:43 – The Slug idea 40:43 – His research project where he observed restaurants 45:44 – How do people mandate their own structure in the face of uncertainty 53:46 – How employees should approach this rent-to-buy hiring structure 57:17 – Example of someone who took advantage of uncertainty time 1:00:05 – Playful adults 1:00:07 – Jerry Neumann Podcast Episode 1:03:10 – Other changes companies can make to their culture to be more innovative 1:08:19 – The difference between simplicity and complexity 1:11:12 – How he applies his thinking into several different ideas, like Cannabis 1:16:17 – Asking the right question 1:19:05 – Andy Rachleff Podcast Episode 1:20:19 – Kindest thing anyone has done for Vaughn Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Gavin Baker, the founder, and manager of Atreides Management. I met Gavin in the same way I meet many of the most interesting people, on twitter. His focus is on consumer and technology growth investing, which is the topic of our conversation. We discuss many of the largest trends in these sectors, several fascinating investment cases, and also explore the videogame industry in detail—which I found especially interesting. Please enjoy my conversation with Gavin Baker. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:16 – (first question) – His unique view on the markets 4:00 – Distilling Apple as a growth investment 6:44 – What is the most important lever for Apple looking forward 9:01 – His view on Intel 11:03 – Most important technological changes that may dictate his investing strategy 16:20 – How do you look at a big idea, like AR, and then apply to an individual business 18:21 – Fortnite isn't a game, it's a place 18:26– Fortnite Is the Future, but Probably Not for the Reasons You Think 18:56 – His insight into video games and their ability to control attention 28:36 – How do you invest in the gaming sector 40:06 – Favorite video games 32:07 – Why gaming and customer sector allows him to find Alpha richness 34:17 – Being in the top 1% of knowledge before investing in a company 36:24 – His view on value investing today and, in the future, 41:15 – Increase of regulatory capture 42:01 – Headwinds to the tech companies today 43:50 – Thoughts on the Chinese internet market and how it impacts US markets 45:36 – How often companies look at China for ideas 46:21 – Role of alternative data in his process 49:36 – Big trends today we should be paying attention to 54:20 – the most interesting company he does not own 58:48 – Advice for new investors 1:00:17 – Non-obvious tech resources - TechMeme 1:00:50 – Favorite sci-fi character 1:01:19 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag All opinions expressed by Patrick and podcast guests are solely their own opinions and do not reflect the opinion of O'shaughnessy asset management. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of O'shaughnessy asset management may maintain positions in the securities discussed in this podcast. Clients of the podcast guest’s firm may also maintain positions in the securities discussed in this podcast.

My guests this week are Kevin Systrom and Mike Krieger, the co-founders of Instagram. I met Kevin and Mike a few months ago over a shared interest in business and investing. I have found them both to be extremely good people who have a rare talent for finding and solving interesting problems. Indeed, problem-solving and jobs-to-be-done is a big part of our conversation. I realized walking into the podcast that Kevin and Mike have a rare set of experiences: having both built and sold an extremely successful product from scratch, but then also operated and scaled inside one of the largest businesses in the world. This means they have unique knowledge to offer just about anyone interested in business and products. We dig into all those lessons here. I am working on hosting more founders and CEOs on the podcast, and can’t think of a better pair to show you why I want to do so. Please enjoy my conversation with Kevin and Mike. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:38 – (first question) – Projects they’ve been working on since leaving Instagram 5:22 – How they can apply what they are learning in machine learning 7:18 – Most interesting experience diving back into data and machine learning 8:42 – How startups compare today to when they founded Instagram 13:23 – Judging founders and whether they know how to use their data effectively 14:26 – The jobs-to-be-done framework 19:14 – Laying out a vision vs solving problems that pop up 25:20 – Developing and sharing the principles of the company with the team 30:48 – Creating a community when it includes almost the entire world 39:03 – The most popular ways people used the platform 41:24 – What was the jobs-to-be-done rational behind the stories feature 44:15 – Interesting things that they saw as Instagram entered the developing world 46:40 – Their thoughts on how Instagram shaped culture and if they focused on those 52:58 – The new waves that they are observing right now 55:11 – How their thinking on leadership and teams changed during their time at Instagram and Facebook 1:03:23 – The pillars of a good business, including humility and confidence 1:06:06 – Focus on growth and distribution in a startup 1:10:01 – How early were they thinking about monetization on this free platform 1:13:43 – How do they think about how they invest their money and allocate resources 1:17:36 – Mentors for Kevin and Mike 1:20:30 – Their passion for learning to fly and the someday/maybe list 1:23:01 – Their interest in coffee 1:26:24 – Advice for everyone else 1:30:00 – Kindest thing anyone has done for them Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Daniel Ek, the founder and CEO of Spotify. In my conversations with Daniel, I’ve found him to be one of the most interesting and thoughtful business leaders in the world. You’ll see what I mean as you listen to our conversation. We talk about Spotify plenty, but what I so enjoy about Daniel is his way of thinking in systems and frameworks. He is committed to evolution, innovation, and growth for both himself and for Spotify and is on my shortlist of CEOs to emulate. This was one of my favorite conversations on the podcast, I hope you enjoy it. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:21 – (first question) – Management lessons from a Dubai chocolate maker 4:54 – Trends shaping the business landscape today: globalization, automation, and digitation 7:51 – How he thinks about the vertical integration of his business and scale 10:37 – Are companies doing a good job adjusting to the changes in the global business landscape 14:44 – How does Spotify view scale moving forward 17:59 – What trends has he seen among creators as a result of the Spotify platform 20:32 – The community benefit that has been created by the platform 23:47 – Intimacy of audio 25:31 – Creating an environment that continues to spur innovation 29:12 – Star vs constellation business strategy 32:21 – Measuring network health 35:12 – Spotify Originals and what his competition in the video market is doing 39:36 – How podcasts play into the growth strategy 43:04 – How did he solve the problem of competing with free 47:21 – Is their strategy repeatable, going after fractured suppliers 49:02 – Role of the CEO in a startup 51:22 – Others who have taught him great business lessons 53:18 – Kindest thing anyone has done for Daniel Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is George Rzepecki, the found and managing partner Raba, an Africa focused investment firm. George is making investments across Africa in early-stage companies. Africa represents a fascinating opportunity: a huge and diverse population and enormous room for per capita GDP growth. We cover all aspects of investing in the continent, including unique potential rewards and risks. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:18 – (first question) – Interest in emerging markets and the tech landscape in Africa 4:57 – Similarities across all of the different metro markets across Africa 8:05 – Why has the continent lagged behind the rest of the world 10:49 – What is the history and landscape of capital in the African continent 13:32 – The market opportunity given the demographics 15:44 – US investment/involvement in Africa 18:06 – Kinds of companies that he likes to invest in 23:26 – Initiatives and investments that could help lift the population out of poverty: finance 29:33 – The public marketplace landscape in Africa 31:49 – Capacity on the private side 34:24 – How the valuation of deals compares to other markets 36:13 – Unique risks in the investments they are making 38:28 – Most exciting trends or changes he is seeing 40:22 – The professional investor environment 43:25 – How to learn more and get involved 43:49 – China Africa Research Initiative 44:17 – China Africa Project 44:38 – Factfulness: Ten Reasons We're Wrong About the World--and Why Things Are Better Than You Think Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Chad Cascarilla, the CEO and co-founder of Paxos, which describes itself as a financial technology company “mobilizing assets at the speed of the internet.“ Thanks to more than 20 years of investing and financial services experience, Chad has a unique perspective on integrating blockchain technology with traditional systems. He also has one of my favorite bitcoin origin stories, which we explore. Before Paxos, Charles co-founded institutional asset management complex Cedar Hill Capital Partners in 2005 and its blockchain-focused venture capital subsidiary, Liberty City Ventures (LCV). Our conversation is less about cryptocurrencies and more about the history, current state, and potential future states of our financial system. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:32 - (First Question) – His work in the finance world before crypto’s 5:12 – Experience navigating the subprime mortgage trend and what it taught him about blockchain 9:59 – The levers that matter in the financial services industry today vs when he first started 14:07 – Open vs closed money in financial services 19:16 – How slowdowns are different in the modern era 23:06 – What would lead to a major winding down of global debt 27:09 – What would be his focus as a traditional investor 29:21 – How he first got involved with bitcoin 29:47 – Elliott Wave Newsletter 31:53 – His measured view of Bitcoin and living through the volatility of it 32:03 – Bitcoin: A Peer-to-Peer Electronic Cash System 35:57 – Allocation of a portfolio which includes crypto 36:54 – His involvement and feelings on gold 37:56 – The formation of Paxos and the problem it exists to solve 41:34 – How Paxos is impacting the space 44:12 – Advantages of a private blockchain 43:59 – What is Pax Gold and how does it work 48:53 – Bad ways and situations to own gold 52:12 – Using a stable coin 56:00 – Biggest problem they are working on now 57:23 – What should people be paying attention to in the crypto currency space 59:23 – Coindesk Research Archive 59:39 – Has the influx of interest in crypto helped in other spaces 1:02:11 – Other lessons people should learn from his career 1:04:53 – Kindest thing anyone has done for Chad Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Bill Gurley, general partner at Benchmark Capital. Our conversation is about one specific issue that has popped up as a topic of interest in the investing community in recent months: the comparison between bringing a company public through a traditional IPO vs. what’s known as a direct listing. As a third party observer with no real dog in the hunt (as we don’t buy IPOs at O’Shaughnessy Asset Management), I thought this was a small and nuanced issue. I’ve therefore been surprised by the strength of opinions on both sides of this issue as I’ve explored it behind the scenes this past week. It feels almost like I’ve encountered a political third rail, where one side throws a lot of vitriol towards the other. To be clear, this episode is very much in favor of direct listings instead of traditional IPOs. For those that want a good discussion of the IPO process and its upsides, check out episode 173 of the Exponent podcast with Ben Thompson. Now please enjoy my very interesting conversation with Bill Gurley For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:22 - (First Question) – His view on the IPO process 5:42 – Will now be the turning point for IPO’s 6:40 – The engagement between a new company going public and their counterparty and the IPO process 13:38 – The math of capital costs 18:18 – Banks that underprice the IPO’s 20:45 – The psychology of IPO’s 23:14 – The pop in the IPO and the media 24:54 – The value that shareholders give vs VC’s 25:37 – The Green Shoots 28:17 – The lock-up 31:40 – Direct listings vs IPO’s 36:07 – Spotify’s CEO Reveals Why He’s Not Doing a Traditional IPO 38:23 – The capital raised in an IPO and diluting the company 40:18 – Privilege access and buy-side firms 43:33 – What will actually lead to changes in the IPO space 44:48 – Why he became so interested in the IPO space Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

My guest this week is Albert Wenger, a managing partner at Union Square Ventures and the author of the book World After Capital. Albert studied economics at Harvard and earned a PhD in information from technology, but if you’d asked me to guess before looking those up, I’d have guessed that he studied philosophy because of how widely he has thought about the world and the impact of technology. Our conversation is about how technology is changing the world from an Industrial Age to a knowledge age. We explore how cryptocurrencies, low cost computing, and regulation will impact our future and why the transition may require delicate care. I loved this conversation because of my obsession with the concept of scarcity. We explore what has been scarce through time and what may be scarce in the future. Albert is one of the most interesting thinkers I’ve come across and was a pleasure to speak with. I hope you enjoy our conversation. Hash Power is presented by Fidelity Investments For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Links Referenced World After Capital Show Notes 2:16 – (First Question) – Defining what it means to be human 2:58 – World After Capital 3:56 – Trans-humans vs neo-humans 4:37 – The concept of Qualia 5:25 – Albert’s investment philosophy= 8:27 – How Albert began his exploration into cryptocurrencies 12:59 – Most exciting things blockchains could enable 14:27 – How does Albert view blockchain technology from the view of an venture capital investor 17:00 - Why Albert thinks that the dominate cryptocurrency of our time may not exist just yet and what he is looking for in protocols that will become the leader in the space 20:16 – What are the central functions that will be important in cryptocurrencies 21:22 - The state of regulation in the cryptocurrency space 27:37 – What has Albert most excited for the future of blockchain 29:10 – The idea of universal basic income 32:26 – How do you solve the problem of giving money value in a world of universal basic income 35:00 – How scarcity has changed over time 39:01 – Role of financial capital in the last 200 years of civilization 42:39 – Are we as a society only capable of solving problems once they become an immediate threat 44:15 – Explaining the idea of attention as a scarce resource 47:56 – The two key drivers of change; zero marginal cost distribution and universality of computational power 53:13 - What should we as investors and inventors be focusing on as the new objective function 57:24 – Scariest aspect of this transition into the knowledge age 59:45 – Three basic freedoms we all seek; informational, economic, psychological 1:02:13 – Fermi’s paradox and the scarcity of attention 1:02:56 – How Albert thinks about his own day and wellbeing given all of this information 1:05:01 – Kindest thing anyone has done for Albert Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week are Matt Smith and Ian singer of Deep Basin Capital, a hedge fund specializing in the energy sector. I first met Matt almost 10 years and, in that time, I’ve grown to respect him as much as any investor that I’ve ever met. Now having spent time with Ian, who specializes in oil and gas field exploration companies and the rest of the Deep Basin team, I have similar respect and admiration for all of them. Deep Basin does almost the exact opposite of what us quants do. In fact, their entire goal is to build a portfolio of mostly idiosyncratic or stock specific risk, the very thing us quants mostly remove from portfolios. Deep Basin positions the portfolio to make a series of carefully constructed bets, long and short, without taking market risk, style-factor risk, or even commodity risk. They use a hybrid fundamental and quantitative process which we explore in detail. This is definitely another good example of who we are all up against in public markets. What makes this story unique is that we are investors in Deep Basin’s management company and so have a clear interest in their ongoing success. Listeners know that I want to be as transparent as possible on this podcast so we event spend a little time telling the story about how it all came together a few years ago. I have learned a ton about investing from my countless hours with this team and hope that this conversation gives you a glimpse into what is happening at the cutting edge of investing in the world of hedge funds. Please enjoy my conversation with Deep Basin For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Books Referenced Expectations Investing: Reading Stock Prices for Better Returns Show Notes 2:47 – (First Question) – Looking at the universe of the energy space that they are focusing on 7:48 – Breaking down the important components and their labels in this space 10:27 – What makes energy companies distinct from the broader market. 12:52 – How the isolate unique value creation 14:58 – Ian’s take on the upstream part of the business where he has spent a lot of time 18:35 – How does Deep Basin use data and what edge do they derive from it. 21:31 – What insight are they looking for from updated well data 23:59 – How do they use combine the business value that they measure with the market price that is being forecasted 24:40 – Expectations Investing: Reading Stock Prices for Better Returns 29:34 – How do they build an actual portfolio 31:51 – Their systematic approach to energy investing 37:53 – What are their thoughts about using leverage when making investments in the energy space 40:53 – A look at the changes to the hedge fund industry over the entirety of their careers 45:46 – Defining the culture of Deep Basin 49:15 – The story of how OSAM and the O’Shaughnessy’s came to be investors in the Deep Basin 54:13 – Kindest thing anyone has done for each of them Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Pat Dorsey, who was the longtime director of equity research at Morningstar, where he specialized in economic moats: sources of sustained competitive advantage that allow a few companies to deliver huge returns over time. Several years ago he left Morningstar to form his own asset management firm, Dorsey asset management, and build a portfolio of companies with wide moats like those he studied at Morningstar. And while moats are critical, equally important is how companies allocate the capital generated--or made possible--by the existence of the moat. A special thank you to Brian Bares who introduced me to Pat, and to Will Thorndike--an earlier guest on the show. In the vast majority of conversations you hear on this show, I'm meeting the guest for the first time. I mention this to encourage you to connect me with anyone whose story or way of looking at the world might resonate. Always feel free to contact me with ideas. Pat and I begin our discussion with the key differences between the sell side and the buy side, and then discuss all aspects of moats and capital allocation. For comprehensive show notes on this episode go to http://investorfieldguide.com/dorsey For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:23 – (First question) – Transition from the sell side to the buy side and the biggest surprise 3:40 – What is a moat 5:16 – What part of the stock market universe has a moat 6:57 – Pat’s framework for identifying moat, starting with intangibles 8:32 – The power of brands 9:44 – what chance does an upstart have to come in and usurp a well-established brand 12:24 – Switching costs as part of the framework for identifying a moat 14:55 – The third component of identifying a moat, network effects, and what businesses should do to effectively build one 17:29 – Last component, cost advantages/economies of scale 19:29 – How do you analyze these four components into an investing framework that can be built into an actual strategy 21:13 – How does Pat think about this from a mis-pricing standpoint 23:37 – How does Pat incorporate current price of a company in consideration for future returns when pricing a moat 25:39 – How should a company with a moat operate to protect that characteristic, especially when it comes to their capital allocation 26:51 – Which characteristic of a moat does Pat find most intriguing 30:35 – What makes for good and smart capital allocation 35:58 – What is Pat’s process for identifying the best investment opportunities 38:38 – What are good economics when looking at a company 41:03 – If Pat could take any business, but have to swap leadership, what would he choose. 44:13 – Back to his process of finding investment opportunities 46:05 – Kindest thing anyone has ever done for Pat Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag Read more at https://investlikethebest.libsyn.com/pat-dorsey-buying-companies-with-economic-moats-invest-like-the-best-ep51#oBGdOp1br4EMtORd.99

My guest this week is Joe McLean, the founder of Intersect Capital, which provides financial advisory services to a variety of clients, including a number of NBA players and other professional athletes. What I loved about this conversation was the weaving of sport, coaching, and finance into a cohesive whole. There’s so much to take from this discussion—from the importance of service and low self-orientation to the impact of strict standards for who you work with, to common mistakes we all tend to make with money. Please enjoy my conversation with Joe McLean. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:18 - (First Question) – His backstory and the combination of athleticism and finance 2:43 – His time in Ireland 3:29 – Moving away from basketball and into finance 6:08 – What the Intersect business is today and his early lessons 7:55 – Most important coach/mentor 8:59 – Where the name Intersect came from 10:22 – Setting high standards early on 12:35 – Biggest mistakes he saw in his early clients 14:04 – Developing his value proposition to clients 14:24 – Michael Kitces Podcast Episode 16:57 – Process when he’s working with a client signing a new athletic contract 19:53 – The concept of a Pro’s Pro and Top 50 Reasons Professional Athletes Remain Wealthy 22:40 – Managing clients’ interest in creating businesses off their brand 24:20 – The role media plays in athletes’ long-term strategies 25:40 – Getting early clients into compliance with his strategy 28:24 – Daily maintenance role he plays with clients 32:24 – What has impressed him most from his young clients 33:36 – What makes for a great coach 34:50 – The meaning of “all in” to Joe 35:54 – His assessment of the financial services industry today 37:32 – Where his value in service came from 39:05 – Longer term vision for his business 40:33 – Unique ways he finds himself helping his clients 43:49 – Watching his client’s mentor the next generation 45:10 – Historical players and teams he personally admires 46:22 – Athletes and venture capital investing 47:38 – Who makes up his trust network 49:09 – What he’s most excited about for the future of the business 49:46 – Kindest thing anyone has done for Joe 50:24 – Biggest impact a coach had on his life Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week’s guest is, Zack Kanter, the founder and CEO of the Stedi. Zack and I decided not to talk much about his business on this podcast and opted instead to explore more generally, so a bit of an introduction to what they do may be helpful here for some extra context. Stedi is a platform for exchanging and automating 300+ types of business-to-business transactions - transactions like purchase orders, invoices, etc. It’s a modern take on an archaic protocol called EDI - electronic data interchange, something I’d never even heard of until several months ago. Learning about EDI is a bit like finding out about the Matrix - every physical object you come across, from the food you ate for breakfast to the clothes you’re wearing and consumer electronics you use - anything with a barcode on it - was likely touched by EDI, often dozens of times before making it into your hands. Stedi is the first update to this messaging later in decades. Our conversation in this podcast is about business in general, starting with Zack’s fascination with Walmart and Amazon. I should also not that my family is a recent investor in Stedi, and I’m thankful to have learned a great deal from him over the past few months. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:52 - (First Question) – Interest in Walmart and Amazon 4:02 – Sam Walton: Made In America 4:49 – What from their success can be applied elsewhere 11:07– The idea of tempo with a business 17:17 – Ability for a business to expand laterally 24:33 - Magic of Amazon as a constitution 26:24 – The concept of the OODA loop 26:40 – Boyd: The Fighter Pilot Who Changed the Art of War 31:51 – Orientation within software businesses 32:24 – The Systems Bible: The Beginner's Guide to Systems Large and Small 38:03 – Lessons in building software 38:37– Certain to Win: The Strategy of John Boyd, Applied to Business 41:51 – Setting a common vision for a company 44:14 – Changing the dynamic of teams and how different size teams can accomplish different things 48:00 – How leaders should think about build vs buy 51:07 – The different types of value propositions 53:07 – Utility for companies 57:31 – Concept of network health and the best question from VCs 1:04:04 – Massive projects are less frequent in a world where we can do a lot quickly 1:04:08 – Wait but Why 1:09:37 – Just in time vs just in case learning framework 1:11:55 – His favorite question 1:13:39 – Why is most commonly heard advice wrong 1:18:06 – Kindest thing anyone has done for Zack Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Chris Bloomstran, the president and chief investment officer of Semper Augustus Investments Group. He became famous in investing circles a few years back for his incredibly detailed investigations of Berkshire Hathaway. While we do cover Berkshire towards the end of the conversation, we spend most of our time talking about what makes for a quality business. I loved some of his angles on the current landscape, including our discussion of companies like Richemont and Disney which are actively taking distribution back in house. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:18 - (First Question) – Largest investing error 4:52 – Defining quality investor and their investment strategy 11:48 – Incremental return on capital and other themes that they focus on with investments 15:33 – Importance of unique business models 22:58 – Ownership of the customer relationship 28:06 – Bringing distribution back in house 29:55 – Doing something unique with owned distribution 32:40 – His thoughts on growth and value 32:42 – Chuck Akre podcast episode 37:12 – History of his interest in Berkshire Hathaway and he characterizes the business 53:29 – How is Berkshire protected into the future 59:17 – Most important trends in adjustments 1:08:00 – Which sectors or industries would he focus on 1:10:02 – Most intriguing business he’s unlikely to own 1:11:44 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Brian Christian, the author of two of my favorite recent books: Algorithms to Live By and The Most Human Human. Our conversation covers the present and future of how humans interact with and use computers. Brian’s thoughts on the nature of intelligence and what it means to be human continue to make me think about what works, and life, will be like in the future. I hope you enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:11 - (First Question) – Summarizing his collection of interests that led to his three books 2:59 – Biggest questions in AI 3:43 – Defining AGI (Artificial General Intelligence) and its history 5:18 – Computing Machinery and Intelligence 7:54 – The idea of the most human human 9:59 – Tactics that have changed the most in learning to be the most human human 16:10 –Tests for measuring AGI and updates made to them 20:12 – Concerns for once we have AGI 26:06 – Self-awareness as a threshold for AGI 31:58 – Skeptics’ take on AGI 37:14 – Advice for people building careers and how AGI will impact work 38:16 – Explore/Exploit trade-off 44:57 – How to explore/exploit applies to business concepts 49:16 – Impacts of AGI on the economy 52:40 – Highlights from his second book 57:39 – Kindest thing anyone has done for Brian Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Eric Sorensen, the CEO of Panagora asset management, which manages more than $46B for clients across a variety of strategies. Eric began his career serving in the Air Force as both a pilot and instructor in high-performance jet aircraft. He then accumulated 40 years of quantitative research and investment experience, with a Ph.D. along the way. Please enjoy our conversation on the changing landscape of quantitative investment strategies. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – His background in the Air Force 1:23 – Boyd: The Fighter Pilot Who Changed the Art of War 3:18 – Training people on high-performance machines 4:47 – Traits that made for better pilots 5:51 – The evolution of quantitative equity research and its stages 7:56 – How his research led to becoming a practitioner 9:10 - The early feature sets in his research 10:44 – Tradeoffs in the spectrum of interpretability 12:08 – Early days of his practitioner career 13:24 – Risk Premia and the 5 C’s 14:28 – Quantitative Equity Portfolio Management: Modern Techniques and Applications 17:13 – Applying the 5 C’s to value investing 18:38 – Knowing when a strategy/signal is broken 21:24 – What does this strategy plan mean for his firm today 24:56 – Mixing expert systems and portfolio construction 30:07 – Natural language processing 32:00 – The cultivating the power and creativity to ask good questions 35:13 – The concept of a research graveyard 37:45 – State of risk premia today 40:04 – Active equity process 46:37 – Frontiers of research that he’s excited about 48:53 – Safe havens for non-quantitative investors 52:16– Advice for young quants 54:36 – Quants on the buy-side that he admires 55:41 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on Twitter at @patrick_oshag

Jane McGonigal, PhD is a world-renowned designer of alternate reality games — or, games that are designed to improve real lives and solve real problems. She is the Author of Reality is Broken: Why Games Make Us Better and How They Can Change the World and is the inventor and co-founder of SuperBetter, a game that has helped nearly a million players tackle real-life health challenges such as depression, anxiety, chronic pain, and traumatic brain injury. Our conversation is about how to design useful games, how games effect us and our kids, and what the future might hold. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:22 - (First Question) – Her take on the history of gaming and studying the players themselves 3:44 – Where her passion for gaming really started 4:55 – Her take on flow states 7:47 – Kids and gaming 10:32 – Advice for parents when it comes to the role of games 11:06 – SuperBetter: A Revolutionary Approach to Getting Stronger, Happier, Braver and More Resilient--Powered by the Science of Games 13:53 – Types of games that develop the right skills for kids 16:20 – Four things all games share in common 16:23 – Reality Is Broken: Why Games Make Us Better and How They Can Change the World 20:50 – Her take on Carse’s theory about infinite gaming 21:04 – Finite and Infinite Games 26:28 – How to understand gaming culture if you’ve never played a game before 28:28 – Amazon and gaming 31:18 – How fun makes anything more enjoyable 34:55 – How game designers calibrate feedback loops 39:14 – The good and bad of gamifying life 45:01 – What is the superbetter app 52:43 - Why powerups and bad guys are so important in games 57:03 – Secret identity 59:04 – Playing with boundaries 1:00:36 – Most worried about in the gaming world, and most exited about 1:07:32 – Kindest thing anyone has done for Jane Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Bill Gurley, a general partner at Benchmark Capital and one my favorite investment thinkers. As you’ll hear, despite enormous success through his career, Bill is clearly still in love with business and investing. Where many might discuss past glories, I’ve been incredibly impressed with how both Bill and his partners emphasize the current portfolio and market landscape. I’m thankful to have had the chance to speak with him in this format. I hope you enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:13 - (First Question) – The idea of increasing returns 1:21 – Competiting Technologies, Increasing Returns, and Lock-in By Historical Events 2:07 – Complex Systems Theory – Santa Fe Institute 4:35 – Markers that could be a sign of network effect in a company 6:27 – The opportunities for companies to capture network effect 8:46 – Are there certain teams/leaders that are more conducive to leading a network effect company 11:55 – Liquidity quality 13:35 – How important is the revenue model at the beginning 15:59 – Fascination with Nextdoor 17:56 – Paradox of Choice 18:39 – Finding opportunities 20:17 – Potential marketplaces and assets that could be commoditized 20:20 – All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces 21:39 – Usage yield on the world’s assets 23:50 – Has technology changed the world of value investing 26:28 – Hyper niche marketplaces 27:52 – Challenges of labor marketplaces 30:12 – User generated content businesses 32:44 – People who are capable of building UGC businesses 33:16 – His interest in Discord 34:31 – Factors of a healthy marketplace 37:57 – Fools’ gold in marketplace businesses 39:04 – How influx of cash is impacting the marketplace business landscape 40:43 – All Revenue is Not Created Equal: The Keys to the 10X Revenue Club 43:20 – How does the influx of money into the space impact him 46:44 – Spending money to attack top brands 50:32 – Regulatory capture 53:36 – His thoughts on the IPO market 57:49 – How did he realize this was his passion 1:00:42 – Qualifying his passion 1:01:52 – Favorite thing about working with entrepreneurs 102:48 – Honing your craft 1:04:33 – Making yourself a good mentor 1:05:56 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week I have a very special guest years in the making. Like another favorite episode, with anonymous guest Modest Proposal, this conversation is with one of the stars of the financial twitter universe who writes anonymously and goes by the pseudonym Jesse Livermore. I met Jesse 6 years ago after reading his unbelievably unique investing research, which tackled all the big and interesting issues in markets. He now also works with me as a research partner at OSAM, where’s he’s used our data to continue to his search for truth in markets. Despite being one of the brightest minds I’ve encountered he is also as humble and unassuming as they come. I’m at least a slightly better person because of trying to emulate how he conducts himself. I get to have many conversations with him that go from 0-100 fast, and I’m thrilled to be able to share one of those with you. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:33 - (First Question) – Jesse’s origin story for investing 4:37 – Exploring his ways of problem solving starting with intuitive 7:53 – David Epstein Podcast Episode 11:46 – Looking at the analytical way of problem solving 15:42 – Statistical inference 24:45 – Should we opt for simplicity in the investment process 25:26 – Does his own investing include all three, intuition, analysis, and statistics 26:09 – The evolution of his research, process, and thinking on various investment factors. 31:38 – Thoughts on inflation and its impact on market valuation 40:05 – The Earnings Mirage 46:25 – Free Cash flow and valuations 50:51 – What should investors take away from this research 53:01 – Thoughts on trend as an interesting market signal 59:00 – The problems with trend 1:00:34 – Post on “The Single Greatest Predictor of Future Stock Market Returns” 1:11:15 – His work into understanding factors 1:15:36 – Looking at momentum 1:18:16 – His curiosity into the current market cycle 1:20:04 – Lessons learned from his time in the military, an effective way to create an environment where people can safely disagree with their co-workers 1:30:10 – The concept of progress in meaningful work 1:33:08 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Chuck Akre, a now widely famous investor who founded Akre Capital Management in 1989, which now manages approximately $10B dollars. We discuss his investing style and his “three-legged stool” for evaluating companies. Please enjoy this great conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:06 - (First Question) – Advantage of being in Middleburg, Virginia 2:11 – What a day looks like for Chuck 3:06 – Why imagination is more important than knowledge 3:38 – Difference between curiosity and imagination 4:38 – The origins of the Nirvana Three-Legged Stool concept 10:14 – First leg of the stool, Extraordinary business and ROE’s with a focus on Bandag. 14:36 – How his evaluations of value has changed over the last 10-15 years 16:10 – A look at recent businesses that he’s bought and why they are interesting 19:56 – Why they keep things simple 21:35 – Second leg of the stool, the people involved and characteristics of managers he has invested in 23:20 – Role of capital allocation in the people he focuses on 28:03 – Favorite biographies 28:22 – 100 to 1 in the Stock Market: A Distinguished Security Analyst Tells How to Make More of Your Investment Opportunities 29:34 – Third leg of the stool, reinvestment 21:09 – How does he think about diversifying across an investment area 33:32 – Great businesses wrapped in a bad balance sheet 37:35 – What would cause him to sell 38:52 – What does he look for in people 43:27 – How curiosity has impacted his interest in land conservation 43:51 – Advice for investors, especially younger ones 46:14 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Jerry Neumann. Jerry is one of the most thoughtful early stage investors that I’ve encountered, and his writings at reactionwheel.net are my favorite on this topic. He applies an incredibly structured way of thinking to a notoriously mysterious investment category. This is our second conversation, in which we cover why investing with one’s gut is a bad idea and why some of the popular edges in startups, like network effects, may be picked over. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:17 - (First Question) – His take on the venture landscape and the type of investments new VC’s are making vs what they should be making 3:44 – Most important implications of excess VC firms 5:32 – Misalignment of incentives in the VC space 8:19 – What he does differently from angel investors or VC’s 10:11 – The notion of risk and the types of risk the people he invests in takes 14:33 – Protections that he thinks about when it comes to the ideas he invests in 19:37 – Is there an area of expertise that provides an edge for startups 20:11 – Network effects are picked over 21:35 – IP protection 23:08 – One of the two most interesting things for VC’s to go after, brands 25:13 – The other most important thing, the value chain 27:42 – A current example of a disruptive value chain 29:14 – Innovation as the source of profit 29:16 – Schumpeter on Strategy 31:50 – Efficiency innovation vs value innovation 31:52 – Energy and Civilization: A History 35:50 – Efficiency investments he’s made 37:13 – Investment in Unsupervised and the machine learning landscape 41:25 – Investment in Sila 43:14 – Investment in Edmit 44:44 – investing on gut 50:32 – Black boxes and their value in investments 53:23 – Metrics about the predictive level of whether people are going to succeed 54:45 – What defines good people worth backing 57:50 – Advice for LP investors in this space and how they should evaluate VC’s in this space Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

I came across this week’s guest thanks to the overlap of three passions of mine: data informed investing, value creation, and basketball. Sam Hinkie worked for more than a decade in the NBA with the Houston Rockets, and then most recently as the President and GM of the Philadelphia 76ers. He helped launch basketball's analytics movement when he joined the Houston Rockets in 2005, and is known for unique trade structuring and a keen focus on acquiring undervalued players. Today, he is also an investor and advisor to a limited number of young companies in which he feels his experience can improve outcomes. Please enjoy this unique episode with Sam Hinkie. Show Notes 3:24 – (First Question) Advantages of having a long view and how to structurally harness one 6:08 – Using technology to foster an innovative culture 6:18– Empire of the Summer Moon: Quanah Parker and the Rise and Fall of the Comanches, the Most Powerful Indian Tribe in American History 10:16 – Favorite example of applied innovation from Sam’s career 11:34 - Most fun aspect of doing data analytics early on the Houston Rockets 13:38 - Is there anything more important than courage in asymmetric outcomes 14:29 – How does Sam know when to let the art of decision making finish where the data started 16:29 - Pros and cons of a contrarian mindset 17:26 – Where he wanted to apply his knowledge in sports when first getting out of school and how his thinking is best applied in the current sports landscape 21:39 – How does he think about trying to find the equivalent of mispriced assets in the NBA 23:12 – Where tradition can be an impediment to innovation 25:07 – What did the team and workflow of the team look like in the front office 27:03 - The measure of truth in a sports complex 29:10 – What were the early factors coming out of the data that helped to shape NBA teams 30:42 – Best tactics for hiring 33:59 – Process of recruiting spectacular people 35:39 – Thoughts on fostering a good marriage 37:57 – Picking your kids traits in your spouse 38:02 – Selfish Reasons to Have More Kids: Why Being a Great Parent is Less Work and More Fun Than You Think 40:45 – What kind of markers does he look for when evaluating long term investment ideas 42:44 – His interest in machine learning 45:55 – What’s more exciting, the actual advances in machine learning or the applications that can be imagined as a result 47:15– International Justice Mission 48:11 – How he got started teaching negotiations and some of the points he makes in that class 49:16 – Effective techniques for negotiating 50:03 – Is negotiating contentious, do you need empathy 50:41 – A Rorschach test of Sam based on his reading of Lessons of History (book) 53:01 – Biggest risk Sam took in his career 54:37 – Biggest risks Sam took while with the 76ers 58:09 – Do people undervalue asymmetric outcomes in the NBA 1:00:11 – The players Sam has enjoyed watching over the years 1:02:45 – Why Robert Caro is a favorite author of his 1:04:30 – Kindest thing anyone has done for Sam

My guest this week is David Epstein. David is a writer and researcher extraordinaire and the author of two great books. His second, Range, is out today and I highly recommend it. We discuss the pros and cons of both the generalist and specialist mindsets in detail and go down many interesting trails along the way. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:12 - (First Question) – What he uncovered in “The Sports Gene: Inside the Science of Extraordinary Athletic Performance” that led him to his latest book 2:38 – Debate with Malcolm Gladwell (YouTube) 4:12 – What did the public pay most attention to and what did they gloss over 7:56 – How his views on nature vs nurture shifted during the process of writing The Sports Gene 10:05 – Blending practice with your nature 13:04 – His process of reading 10 journal articles a day as part of his research 19:06 – Exploring his new book “Range: Why Generalists Triumph in a Specialized World”, and his idea of Martian tennis 23:03 – Idea of the cult of the head start and how we set up our own feedback loops 28:58 – What does his research say about the nations education system 30:42 – The Flynn Effect chapter 33:54 – Hacks for learning 37:52 – The concept of struggle and harnessing the power of it 46:31 – Personality changes and how to drive those changes in a positive way 52:00 – Using the outside perspective in businesses for more productive outcomes and how it applied to Nintendo 52:59 – Josh Wolfe Podcast Episode 1:04:45 – Other examples of using withered technologies, 3M 1:09:00 – The arc of his work and how it has evolved 1:13:54 – Taking a different view on problems 1:17:52 – Ending Medical Reversal: Improving Outcomes, Saving Lives 1:18:04– Anyway to change these bad trends with new strategies Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week I’m hosting an investor retreat and so thought it fitting to release this conversation with Priya Parker on the art of gathering. I’ve been interested in the topic of community and gathering for some time and along with the book The Art of Community, Priya’s book on the art of gathering is by far the best I’ve read. It is both conceptually interesting and extremely practical. In the book there is literally a table for how big a gathering space should be per person, sorted by the type of vibe you are after. We had a time constraint but I could have talked to Priya for much longer. I hope you enjoy our conversation as much as I did, and that it inspires you to do something new and different with friends, family, or colleagues. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:23 - (First Question) – Overview on what she does as a conflict resolution facilitator 1:38 – The Art of Gathering: How We Meet and Why It Matters 4:45 – Lessons about structuring a gathering from her early very difficult work and the idea of sustained dialogue 7:43 – First event she facilitated 9:38 – Importance of a good opening for any gathering 12:30 – Identifying a good purpose for a gathering 15:06 – Why being specific on rules/code of conduct leads to more success 18:54 – Do rules help facilitate more creativity in groups 21:22 – Segregating a good from bad purpose 24:34 – Identity and good/bad gatherings 26:50 – Purpose and the guest list for a gathering 31:03 – Community building is line drawing 32:27 – Dreams from My Father: A Story of Race and Inheritance 34:29 – Importance of well crafted invitations 35:17 – Making the middle of gatherings interesting 39:21 – Exploring risk at gatherings 41:28 – Patterns of Transformation 41:43 – The hero’s journey 46:54 – Making a meaningful transition out of these gatherings 52:39 – Kindest thing anyone has done for Priya Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week’s conversation is about artificial intelligence and interplanetary travel. Its about content creation, thinking from first principles, and death progress units. Its about brain machine interfaces and why it is crucial that you be a chef and not a cook. My guest is Tim Urban, along with his business partner Andrew Finn. Tim is the most entertaining writer I’ve come across in years, who explains complicated and interesting topics to his millions of dedicated readers on the website “Wait, But Why.” As an example, Tim’s last post on Elon Musk’s neurlink venture is 40,000 words long, roughly the length of a short book. It explains almost all of human progress and our potential future using drawings and cartoons. Its impossible to stop reading. While this conversation is wildly entertaining, it is also chock full of metaphors and lessons that will be useful to anyone doing creative work or building a company. I hope this leaves you as energized as it left me. I called this episode Grand Theft Life because that is the name that Tim and Andrew give to their worldview, which I think will change the way you behave, too. Please enjoy my conversation with Tim Urban. For comprehensive show notes on this episode go to http://investorfieldguide.com/urban For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Books Referenced Superintelligence: Paths, Dangers, Strategies Links Referenced The Cook and the Chef: Musk’s Secret Sauce Wait But Why Neuralink and the Brain’s Magical Future Wait But Hi YouTube Channel Kurzgesagt – In a Nutshell Show Notes 1:50 – (First question) – Explaining his concept of planets 1, 2, 3 and 4 and understanding the human colossus 5:46 – Tim’s favorite idea of the human knowledge compounding 7:52 – Die Progress Units (DPU) 9:45 – Different stages of AI and the positives and negatives of each stage 14;04 – What happens when AI gains breadth and general intelligence 16:23 – The idea of a cook vs a chef and how Tim had the chance to interview Elon Musk 17:48 – Why you should reason from first principles instead of reasoning by analogies 25:19 – Why it’s possible to turn a cook into a chef 30:08 – Why being a chef is the safer route in a world with AI and what Tim has changed in himself as to why. 31:22 – Looking at the discovery process 34:39 – Superintelligence: Paths, Dangers, Strategies\ 40:01 – Being the person who creates the metaphor vs being the people who simply using them 43:41 – YouTube Channel Kurzgesagt – In a Nutshell 44:54 – Most fun that Tim has had researching a topic 46:08 – Musk model for attaining your goals 53:43 – Why not caring what people think is one of the world’s best superpowers, grand theft life 56:50 – Neuralink – what is it and how did Tim come to research it 1:02:38 – Elon Musk’s concerns about AI 1:14:28 – What then if the Neuralink concept works out 1:18:02 – Kindest thing anyone has done for Tim Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Stephanie Cohen, who is the chief strategy officer for Goldman Sachs and a member of their management committee. Prior to her current role, she spent the majority of her career in the investment banking and M&A divisions at Goldman. We discuss lessons learned from her career in M&A and the many initiatives she now leads at the firm. I really enjoyed her perspective on how a big, established firm like Goldman can balance innovation with improving existing businesses. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – Motives on both sides for doing M&A 3:26 – Most difficult deal she worked on 4:50 – Biggest value add she brought from her seat on the Fiat deal 5:59 – Biggest changes since she started to today 8:31 – Smartest ways for companies who want to be acquired to be prepared 10:14 – Best M&A banker she’s seen 11:13 – What should businesses looking to make an acquisition be thinking about 15:16 – What does a strategy from her perspective mean 17:16 – Tension between innovation and change 19:46 – Difference between bottom-up and top-down components of strategy 22:15 – Exploration vs exploitation 26:28 – Submission process within accelerate 29:37 – Next step after you see a good idea 31:05 – Her take on FinTech and Industrials and their collision 35:15 – Lessons from elite early stage investors 37:21 – The origins of the LAUNCH program 40:06 – Important pieces beyond just the capital 42:42 – How they market to women starting business 44:56 – Lessons that she has learned about narrative and communications 47:07 – How she handles developing talent internally 49:28 – Managing her time 59:28 – Biggest concerns about OKR’s? 52:09 – Kindest thing anyone has done for Stephanie 53:07 – Kids in the area of competing Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week’s guest is Will Thorndike, an author and investor whose book The Outsiders is an all-time favorite of mine. Our conversation is in two parts. First, we dive deep into the lessons of his 8-year research project studying CEOs who were master capital allocators. These CEOs include Henry Singleton, John Malone, Tom Murphy, Katherine Graham, and Warren Buffett. We discuss how these CEOs tended to be contrarians on topics like dividends, buybacks, acquisitions, and the use of debt. As we go through each of the tools in the capital allocators toolkit, you’ll hear several useful lessons for running or evaluating a business. In the second part, we cover Will’s career in private equity. Will founded and continues to run Housatonic Partners, investing in buyouts, recaps, and search funds. Will has been one of the most active search fund investors for decades, and given how much time I’ve spent in past episodes on the searchers or operators in the micro-cap, permanent equity space, it was great to get the perspective of an experienced LP. As always, we also take time to survey the dangers and opportunities in today’s private equity market. For comprehensive show notes on this episode go to http://investorfieldguide.com/thorndike For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag

My guest this week is Josh Wolfe, co-founder and managing partner at Lux Capital. I had Josh on the podcast last year which was one of the most popular episodes in the shows history. This is a continuation of our ongoing conversation about investing in the frontiers of technology. My favorite thing about Josh and the way that he invests is the mosaic that he and his team at Lux are constantly building to understand the world and where new companies may fit in. We cover a crazy variety of topics from business model innovation, roles of a CEO, the military, the death of privacy, and arrows of human progress. Please enjoy round two with Josh Wolfe. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:22 - (First Question) –Ability to tackle massive scale problems 4:05 – Key roles of leaders and his checklist for evaluating them 5:55 – Common traits among founders that make them incredible storytellers and leaders 10:22 – The concept of ill-liquidity 14:53 – Thoughts on the types of companies going public 16:41 – Most innovative business models 19:14 - Advice for LP’s 23:51 – Common devil 24:01 – The True Believer: Thoughts on the Nature of Mass Movements 25:09 – Big internal debates at his firm, starting with price discipline 28:45 – The value debate internally 33:34 – CRISPR from an investment standpoint 36:50 – Edge cases they are looking at 46:52 – How they target ideas in a single concept 50:01 – The Coast of Utopia: Voyage, Shipwreck, Salvage 51:04 – New theses that they chase 56:31 – Recent adventure with special operations guys Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Katherine Collins, who is the head of sustainable investing at Putnam Investments, a portfolio manager on two of Putnam’s sustainable investing funds, and the author of the book The Nature of Investing: Resilient Investment Strategies through Biomimicry. Our conversation is on the ins and outs of ESG and impact investing, a young but increasingly common topic in the investing world. This is challenging ground for me as a quant, because the data available is so new and limited—so Katherine’s perspective was very helpful as we continue to learn. Given the importance of this topic, I’m also searching for more guests with both positive and negative views on the role of ESG in an investing framework, and welcome suggestions for future guests. Please enjoy my conversation with Katherine Collins. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:29 - (First Question) –Mechanical vs human judgement processes 4:21 – ESG, and the non-utility portion of it. 7:11 – Data behind the objective function that is different from returns 12:34 – What are the most interesting data sets 16:04 – How does she determine what factors to target 19:31 – Why do we know that diversity of experience/opinion/background is good for a company 21:30 – The social vertical and how it plays into her investing system and better returns 25:51 – Corporate Sustainability: First Evidence on Materiality 27:00 – Environmental factors and the issues that jump to mind 29:48 – Importance of signing the UNPRI and is it just box checking 32:33 – Data for companies on the solution oriented companies 34:53 – Why doesn’t the market recognize the Alpha 36:17 – LP interest in ESG investing 38:25 – How other groups of investors approach ESG 40:03 – Best practices at business making an impact in ESG 44:01 – Unique or interesting tactics in environmental 46:33 – Who is the biggest opponent or position in opposition of ESG 47:37 – Most interesting edge 48:20 – Playbook for business managers thinking about social for the first time 49:59 – Measurements vs principles/values 51:21 – Advice to quants trying to use ESG in how they gather data 53:04 – Most memorable encounter with a company through the lens of ESG 53:53 – Where to learn more about ESG 54:50 – How much role regulation plays in the future of business sustainability 56:30 – Any more lessons from her research into natural systems 57:05 – Kindest thing anyone has done for her Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week Geoffrey Batt and the topic of our conversation is how to earn transformational returns in very hard markets. In his case, that means Iraqi equities which we cover in detail. He now runs a large pool of capital in Iraqi stocks through his firm Euphrates, but the journey was arduous to say the least. This is one of my favorite boots on the ground contrarian investments stories thus far on the podcast. I hope you enjoy the story and the lessons that Geoff has to offer. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – What does it take to earn transformational returns 4:43 – How he deals with LPs, especially given the volatility of the market he invests in 10:26 – Why LPs have to think about the other investors in a fund 1:17 – How Geoffrey got interested in the Iraqi market 16:15 – Factors he was considering when exploring Iraq 16:53 – Harvey Sawikin Podcast Episode 19:20 – Visiting companies in Iraq 22:30 – Most memorable meeting with a company on his first trip 27:18 – Size and nature of Iraqi market when he first got interested 30:44 – A specific allocator in Iraq 34:37 – Does price reflect the work over there 37:51 - What does he perceive as his role in the changes to Iraq’s equity market 40:12 - How do Iraqi equities look today compared to when he started and is the opportunity still interesting 44:14 – How businesses perceive him now that the market has opened up more 47:28 – Scale of potential return and where it comes from 49:51 – Advice for younger aspiring investors exploring frontier markets 52:16 – Kindest thing anyone has done for Geoffrey Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Brian Singerman, a partner at the venture capital firm Founders Fund. Founder’s Fund is widely considered one of the top VC firms and its partners are known to have diverse investment strategies. Brian invests across industries and focuses on backing exceptional founders. You’ll hear right off the bat that he cares about moat, market, and strong execution. I love his point that the only way to become a good investor is to do a lot of investing. He describes himself an investor who uses his gut a lot, which took me a while to get used to in our conversation. But I have to say that at the end of this episode I felt refreshed and generally excited to keep putting in reps in my own way, both in the podcast and the quant research settings. I hope you enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notesd 1:28 - (First Question) – What Brian looks for when evaluating companies 2:38 – What a moat looks like in investing 3:11 – Most memorable initial moat 4:17 – How he evaluates a potential market 5:28 – Attributes they look for in founders 6:24 – Most significant technological changes and how they have impacted his investment strategy 8:57 – The sourcing of his deals 13:00 – Qualities he likes at various stages of deal sourcing 13:46 – How he evaluates the teams he may fund 15:17 – His take on the pricing landscape for deals 16:13 – How he allocates his time as a board member 17:16 – Thoughts on long term stock exchange 18:26 – How much research does he do on an industry in order to stay on top of his investments 20:10 – Outside information he follows 21:20 - Other investors he’s learned a lot from 23:12 – What values does Peter Thiel instill in the partners 24:05 – Process of StemCentrics 26:03 – Other places holding his interest today 26:57 – His interest in e-sports 31:44 – Interactions with LP’s 32:51 – What they look for in recruiting new partners 34:32 – How geography impacts the opportunity for new ideas 36:24 – Opportunities in public companies and other investment types 37:57 – Aspects of overseeing a startup venture 39:26 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week for the third time is Michael Mauboussin. If there is a major question about markets and investing, Michael has usually written one of the best pieces of research on that topic. Today’s conversation is a mix of several of his research pieces, but focuses on the sources of alpha. The framing of the conversation is the brilliant question “who is on the other side” of a given trade. If you are buying, who is selling, and why? Knowing the answer to this question is one key to understanding where excess return comes from. As is usual with Michael, we also explore tons of other interesting ideas that will serve as food for thought. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:23 - (First Question) – An outline of the syllabus for the course he teaches 4:02 – What are smart people missing when it comes to decision making 5:33 – Why Michael went down the path of defining major investing concepts 7:41 – On the impossibility of informational inefficient markets 9:14 – Beware behavioral finance 12:03 – What are the behavioral errors that people can take advantage of in a trade 15:14 – Timing opportunities 17:25 – Modest Proposal Podcast Episode 17:47 – Where the analytical edge comes from 21:16 – Is there an advantage to exhibit time arbitrage 23:53 – Technical arbitrage 29:34 – What impact do flows into ETFs play on the market 32:25 – Informational edge and how you source that edge 36:39 – Biggest changes that he has seen on the buy side 43:18 - How would Michael apply this as a sports GM 48:35 – His views on stock buybacks 51:02 – The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success 52:55 – EBIT to EBITDA paper 54:43 – What Does a PE Multiple Mean? 59:28 – The concept of benign myths 1:02:06 – What the future holds of Michael 1:04:17 – The Myth of Capitalism: Monopolies and the Death of Competition Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is with Annie Duke, and the topic of our discussion is how to improve decision making. We break decisions down into their component parts: values, beliefs, decisions, randomness, and outcomes. After diving into each, we discuss how to make better decisions, how to work in group settings, and how to harness power of tribes and identity to improve our behavior. Annie has thought about this as much as anyone, and her various tricks for getting us to think in probabilities and to stop evaluating decisions based on outcomes that have been tainted by randomness will be useful for anyone listening. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:23 - (First Question) – Why people don’t take the best investing advice 2:11 – Investing tribes 4:21 – Jay Van Bavel twitter 6:34 – Rule setting as a way of crafting an investment strategy 11:13 – How much control do we have in choosing our values 15:52 – Anatomy of a decision 19:28 – Her concept of resulting 26:47 - How beliefs impact your decision making 34:28 – Tact’s for making the best decision 42:40 – Ego and decision making 47:06 – People who are exceptional at changing their decision making 48:18 – How often do people who change their decision making, stick with the rules of the game 50:07 – Finite and Infinite Games 50:28 – Psychology of making decision that involves other people 59:20 - Never close doors on other people 1:01:57 – Best decision that Annie made 1:04:24 – Kindest thing anyone has done for Annie Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is unique and so requires a short story. I met our guest Michael Mayer because of twitter. I followed and enjoyed one of several pseudonymous accounts that he maintains to experiment with ideas. His various accounts have wide followings. I think many of the best accounts on twitter are anonymous or pseudonymous, and I’ve always made a point to get to know the ones I like best. As it turns out, Michael was also an entrepreneur. He’d been building a new company and was raising a small amount of outside capital. I didn’t invest personally, in part because he raised it so quickly after I spoke with him. Ever since, I’ve gotten to know him better and followed his company, Bottomless, with interest. You know that I am always hyper transparent about any potential conflicts of interest, so it’s worth noting that while I am not an investor in this company, I expect to be at some point in the future. The topic of our conversation is both his social media activity and his company. I am a coffee fanatic, and the problem he is solving is one I live. I order a weekly bag of coffee beans, but I often have too much coffee or run out. Bottomless solves this by shipping you a simple scale which you keep wherever you store your coffee, connect to your Wi-Fi, and set your bag of coffee on. It automatically orders new coffee for you at the right time. Thus the name: Bottomless. If you like the conversation, check out bottomless.com With this podcast, all I’m really trying to do is find, meet, and learn from interesting people. Michael certainly qualifies. I hope you enjoy this unique episode. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:06 - (First Question) – Why he writes under a pseudonym online 2:58 – Positive impacts of writing this way 3:45 – His background 5:02 – Habits he improved upon 7:03 – Where did his exploration into technology and start-ups come from 7:33 – Algorithms to Live By: The Computer Science of Human Decisions 10:32 – Elements of business that interest him most 13:26 – Building social capital vs the current state of education 17:06 – What information does he like to consume 18:17 – Zero to One: Notes on Startups, or How to Build the Future 18:34 – Jerry Neumann blog Reaction Wheel | Podcast episode 18:39 – Kevin Simler’s blog Melting Asphalt| Podcast Episode 21:01 – Why the current education system is busted 22:54 – Formation of his business 24:04 – Importance of making things legible 25:54 – On demand delivery vs subscription business models 30:16 – Early day in developing the scale for his business 33:50 – What he learned about coffee roasters 35:29 – thoughts on supplier power 36:17 – The customer relationship 39:50 – Best objections to his business 41:58 – Biggest operational/emotional challenges 42:56 – Best moment 44:39 – Time at Y combinator 46:28 – His unique co-founder story 49:47 – Marketing strategies and acquisition costs 51:37 – The idea of a commercial loop 53:27 – Discarded ideas, such as spaced repetition social networks 57:38 – Having a long-term plan vs reformatting a business into success 1:00:35 – What works on twitter based on his experience 1:03:09 – Most controversial opinion 1:05:59 – Kindest thing anyone has done Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Peter is a geopolitical strategist who combines expertise in demography, economics, energy, politics, technology, and security to assess an uncertain future. Before founding his own strategy firm, Peter helped develop the analytical models for Stratfor, one of the world’s premier private intelligence companies. I came across Peter via his books the Accidental Superpower and the Absent Superpower. We discuss America’s changing place in the world and four additional countries poised to do well in the future. Spoiler alert: he believes the U.S. is particularly well positioned. While we don’t discuss equity markets per se, all of what we talk about will obviously impact companies across the world for the remainder of our careers. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:32 - (First Question) – His model of the world 4:05 – What makes for a strategically advantaged country 5:35 – History of the Bretton Woods agreement and the order that it created 8:47 – The security apparatus that has made globalization of manufacturing possible 12:04 – The US’s pullback from being the naval police of global trade 12:08 – The Absent Superpower: The Shale Revolution and a World Without America 14:57 – How energy has played into America’s disinterest abroad 21:52 – Moving towards global disorder 24:55 – Characterizing factors that will impact countries in any collapse 27:38 – How this manifest in physical conflict 32:44 – How the new world order will end the ease of innovation we are accustomed to today 34:13 – What gets the US to reengage before this new world order 38:08 – Demographics that make a country prepared for this, Japan as an example 40:57 – A look at China 43:59 – What the story is about Argentina 45:52 – How North America fares based on their geography and relationships 49:50 – The trader wars that are currently ongoing 52:17 – US political system 56:15 – Most important policy issues moving forward 58:27 – His view on American infrastructure 1:00:33 – Technologies that interest him the most 1:02:55 – What he is watching most closely in his research, starting with media 1:05:59 – What are and should be the countries of the future 1:06:55 – Kindest thing anyone has done for Peter 1:07:32 – Favorite places he’s been Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Michael Kitces, who is one of our industries go-to experts on all things financial advise and financial planning. We discuss the past, present, and future of financial advise, financial technology, and investing. If you are a financial advisor or use one, this conversation is full of great history and perspective. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:08 - (First Question) – History of financial planning/advice model 5:26 – Fee changes in the 1970’s 10:01 – The start of the AUM model 10:44 – Value proposition for financial advisors beyond trading vs robo-advsiors 11:49 – Why Robo-Advisors Will Be No Threat To Real Advisors 18:20 – Why are humans still dominating the space 23:58 – Future of advisor fees 32:50 – Viability of the human driven flat fee model 37:50 – The dominance of flat fee models 43:13 – What services are financial advisors offering to justify their fees 47:17 – Dimensions to divide potential customers 52:20 – Exciting updates on the investment side that will help differentiate managers 55:37 – Any investment function beyond the basics that is intriguing to him 58:45 – Most interesting problems to be solved on the investing and non-investing sides 1:04:52 – Advice for young advisors 1:09:24 – How does he invest his own money 1:11:31 – Kindest thing anyone has done for Michael Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Alex Danco. Alex is a member of the Discover Team at Social Capital, has a background in biology, and has written about all things tech and business. While Alex is only 30, it seems like he has spent decades thinking about all the topics that we discuss, from changing business models, to railroads, to the shift from products to functions, and the rise and fall of asset bubbles. I hope you enjoy this wide ranging conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – A look at his day job on the discover team 2:20 – 40 problems doc 4:27 – How companies get on the list and the turnover 5:21 – Hardest problem they are looking at…housing 11:37 – The investment component that fixes housing 15:35 – Where we are in the technology cycle in the view of abundance vs scarcity 20:54 – Change in distribution and the business vs utility business idea. 28:40 – Bifurcation of small and larger businesses 32:48 – New forms of scarcity today 38:31 – The trend of massive company incumbency 41:07 – The utility of bubbles 49:08 – His favorite bubble 51:18 – Challenges and nuances of bubbles 53:35 – Zero to One Notes on Start-Ups, or How to Build the Future 1:02:22 – Future for VC funding in Silicon Valley 1:04:07 – Advice for business builders 1:08:23 – The Three True Outcomes 1:13:04 – His background in biology and innovation in that space that is coming 1:19:46 – Company examples that are of interest to him and that encapsulate his way of investing 1:24:56 – Kindest thing anyone has done for Alex Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Keith Wasserman, co-founder of the real estate investment firm Gelt. This was my first fully dedicated conversation on direct real estate investing, so we cover many different topics, including the pros and cons of different types of real estate, current valuations, risk vs. reward, tax protection, and the most interesting emergent areas. You can tell Keith is an entrepreneur at heart so I enjoyed his energy and all that he has learned. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – Their interest in apartments and mobile homes as investments 2:32 – The returns spectrum for different classes of real estate 4:03 – His early entrepreneurial ventures and the start of Gelt 7:45 – Don’t be afraid of negotiating 8:34 – Going through early deals in real estate 11:57 – How he determines when it’s time to sell a property 14:13 – How do they think about taxes in their investment offerings 16:57 – Depreciation strategies in real estate investing 18:27 – The evolution of the types of real estate properties they’ve invested in 21:41 – Most important factors when evaluating a building to invest in 23:50 – Barriers to entry 25:41 – Changes in his cost of capital 28:51 – Cost of debt and deciding how much to put into a building 30:33 – A look at the competition 34:51 – Effective marketing strategies 37:07 – How demographics impact their strategies 39:11 – The co-living space 40:34 – Cloud kitchens and how he would invest in these 46:11 – How autonomous vehicles will impact real estate 47:52 – Pros and cons of developing new properties vs buying existing ones 49:59 – Early stage investing interest 53:48 – Favorite business/entrepreneur story 55:10 – Advice for younger entrepreneurs 57:09 – Kindest thing anyone has done for Keith Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub

My guest this week is Alex Mittal, co-founder of Funders Club. Following past guest Jeremiah Lowin, Alex is my second elementary school friend to appear on the podcast—a trend I hope continues. Funders club is a unique venture firm, because it is build around a network of investors and entrepreneurs who submit deals for consideration and invest together. But as you’ll hear, Alex and his co-founder Boris aren’t just building an open platform for early stage investing: they also then take a very traditional venture approach, making investing decisions themselves when it comes to building a centralized portfolio. Our conversation is about what Alex has learned investing in almost 300 early stage companies over the past 7 years. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:30 - (First Question) – Inception of the Founder’s Club 1:36 – Jeremiah Lowin Podcast Episode 3:59 – How the process of their platform works 5:40 – Role of the network in Founders Club setup and success 8:26 – What he has learned from all of the data he has access to 16:00 – Early stage investing and finding the sweet spot 22:17 – What makes a really intriguing bad idea 25:23 – Why he remains so excited about Ethereum 31:18 – More bad ideas 31:55 – Apoorva Mehta on How I Built This Podcast 37:15 – Thoughts on retail and logistics and how they fit his Venn diagram of boring and crazy 43:13 – Chip and electronic design 45:47 – Companies that are not just increasing efficiencies but actually making foundational changes 45:54 – Energy and Civilization: A History 52:34 – What does he look for in founders 55:26 – Pivot or Fail 57:05 – Kindest thing anyone has done for Alex Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week, Eugene Wei, has one of the most interesting backgrounds of anyone I’ve had on the podcast. He worked at Amazon early in its life, was the head of product at Hulu and Flipboard, and head of video and Oculus. Our conversation is about the intersection of technology, media, culture. We discuss Eugene’s concept of invisible asymptotes: why growth slows down (for both companies and people) and how some can burst through. I’d list more of the topics, but we covered so much that you should just listen. Finally, I’ll say that after spending a day with Eugene (including a wildly interesting dinner with Eugene, past podcast guest Sam Hinkie, and future podcast guest Kevin Kwok) that he is the type of uniquely interesting and kind person I am always searching for and one that I wish I could bet on somehow. If you know more people like this, reach out and suggest them for this podcast. Now, enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:38 - (First Question) – Idea of cuisine and empire 1:52 – Cuisine and Empire: Cooking in World History 4:20 – Key takeaways from the Defiant Ones Documentary 8;25 – Being convinced to buy a sports coat 11:10 – The concept of invisible asymptote 17:43 – How the medium shapes the messaging and the impact of cameras everywhere on society 17:48– Invisible asymptotes 17:56 – Selfies as a second language 22:57 – Proof of work in building a social network 32:51 – Magnification of inequalities in digital networks 34:01 – The Lessons of History 36:47 – His thoughts on the media industry’s impact on society as a whole 39:42 – His time at Hulu 44:48 – Places where video could replace text 47:30 – The need for media for any business looking to grow 49:35 – Amusing Ourselves to Death: Public Discourse in the Age of Show Business 53:08 – Personal asymptotes 57:19 - Habit building and goal setting 1:00:29 – Travel recommendations 1:03:24 – Movie recommendations 1:08:16 – Product recommendations and what makes them indispensable 1:10:44 – Creation: Life and How to Make It 1:13:23 – Thoughts on the art of conversation 1:14:59 – The Most Human Human: What Artificial Intelligence Teaches Us About Being Alive 1:18:30 – Kindest thing anyone has done for Eugene Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Michael Duda, and the topic of our conversation is the role that brand plays in business and investing. Michael has worked on and invested in a wide-range of brands including Birchbox, Casper, Harry's, Citibank, DirecTV, Google, TripAdvisor, Under Armour and vineyard vines. His background in advertising made this a unique and interesting conversation. please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:11 - (First Question) – Mission of Bullish 2:15 – Typical relationship they have with companies 3:01 – Defining brand 4:35 – Ryan Caldbeck Podcast Episode 5:51 – A dive into how brands make people feel 7:54 – Does the emphasis on brand still matter to consumers and if so, where 10:01 – Process of building up a brand 14:53 – What has changed most in the planning of a brand strategy 18:35 – How does his thinking impact his investing strategy 21:48 – Where does he differ from the rest of the market 23:34 – Advice he would give to companies in general 26:18 – How advertising has changed in the current landscape 28:35 – The screening process for picking potential investments 35:16 – How they analyze valuation 37:31 – Unusual traits he likes in founders 40:12 – Categories most ripe for young companies to disrupt 44:03 – Most interesting marketing channel for direct to consumer businesses 46:45 – Marketing piece he is most proud of 49:23 – Companies that embody the best of what has been discussed 52:31 – His love for people in business 53:41 – Kindest thing done for Michael Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Over the summer. I spent time with Abby Johnson, who is the chairman and CEO of Fidelity Investments and several other business leads at Fidelity to understand how a very large firm like theirs is navigating change in our industry. What follows is a condensed version of my various conversations with Abby and her team. We discuss the big buzzwords like blockchain and machine learning, but also thoughts on leadership, client centricity and measures of success. I hope you enjoyed this exploration For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:16 - (First Question) – [Abby] A look at the early part of Abby’s career 2:45 – Analyzing the skill of capital allocators 3:27 – A look at the asset management world of today and what to focus on today 7:23 – A set of decision-making principles that guide Abby 12:55 – Their strategy around the digitization of the world 16:07 – Balance between robo-advisors and humans and the markers of a good relationship 18:24 – What is the future of the role of the human in these relationships 20:15 – Their interest in emerging technologies like Blockchain 24:50 – Will crypto be its own asset class in the future 25:58 – [TOM] State of the business and the most interesting points of change 28:14 – Who is winning the battle for the next generation of investors 29:24 – How much of the change in financial business is cyclical 30:17 – What are businesses doing right to bridge that generational gap 31:01 – What does the future of the asset management industry look like 32:13 – What technologies could impact the asset management business the most 33:44 – The difference between machine learning and AI in this format 35:26 – In what way will AI impact these processes and replace humans 36:41 – What has him most excited about the future 37:54 – Advice for people thinking about pursuing a career in financial services 39:20 – Markers of a business that would be attractive for the next generation to consider working for 40:33 – The importance of brand when thinking about their business and those they work with 41:57 – Ways of engendering trust from a branding prospective 43:20 – Kindest thing anyone has done for Tom 44:28 – [VIPIN] Building a team around AI 45:21 – Markers for a good data strategy 47:25 – Kindest thing anyone has done for Vipin 48:58 - [ABBY] – How Fidelity thinks about data as an investing initiative 50:24 – Differentiating attributes of good analysts and if they’ve changed 51:34 – Investor she has always enjoyed learning from 52:37 – Favorite Peter Lynch story 53:17 – Business lessons that people could take away from Abby 54:59 – The role of women in financial services and what can be done to improve the situation there 57:35 – Trends that Abby is most excited to explore 1:00:22 – Positives and negatives of being part of a family business 1:01:46 – Kindest thing anyone has done for Abby Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology. One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode. We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:35 (First Question) – A look at his investing philosophy 3:16 – Favorite examples of his own investment history 4:40 – 7 Powers: The Foundations of Business Strategy 5:07 – Understanding what is anomalous in a given investment 7:07 – How much a secret needs to be protected within a business 11:51 – Why accumulating advantage with data is of interest to Keith 15:12 – Digital health companies and ideas that he finds compelling 16:17 – Nuance around financial services that investors should be mindful of 17:56 – How do they evaluate managers ability to recruit talent 19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career 24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.” 27:04 – Is problem identification a specific skill set 28:29 – Objection with experimentation/iteration 30:02 – Bad ideas in venture 31:36 – What he likes about Apple 31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs 32:26 - Interview questions for identifying great talent 35:41 – Elements of good design 37:14 – Impact of platforms on opening new opportunities 38:42 – His take on valuation in the early stage environment 40:33 – Advice he would give people early in their careers 43:58 – Do high growth companies get beat by established larger businesses 45:25 – Popular narratives that he thinks are just wrong 48:22 – His thoughts on how people should learn, balancing experience vs information gathering 50:00 – Other investors that are taking a unique approach to investing 51:57 – Reflecting on the entrepreneur as a client model of private equity 55:04 – Books that he recommends that is least known 55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It 56:30 – Kindest thing anyone has done for Keith Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest today is Bryan Krug, who manages the Artisan Partners Credit Team and overseas more than $3B in high yield credit investments for the firm. This was my first conversation on high yield, so I took it as an opportunity to get an overview on the investment universe and home in on the tools used for analysis and security selection. As an equity investor, I think one of the most fruitful areas of research is into ways that companies fail or go wrong, and credit investors focus almost entirely on this potential for impairment. My guess is that all equity investors will learn something useful from this conversation. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:11 – Overview of the high yield debt markets 5:05 – Why should investors consider this investment class 7:11 – How analyzing a company’s debt is different from what equity analysts look for 8:42 – Primary factors when exploring a company’s ability to de-lever 9:43 – What is their alpha vs others in the space 12:02 – Deep dive into the quantitative factors for them to look into a deal 14:25 – Benchmarks he uses 16:08 – Portfolio construction 17:15 – Their preference for broadband providers over cable tv networks 20:01 – What piques his interest about spreads 21:50 – The ratings of debt 25:40 – A recent example of an opportunity and how the mispricing was identified 29:17 – Most valuable data sets in this world 31:51 – Favorite part of this process 32:26 – Most surprising new learning 33:01 Maintaining your advantage 34:49 – The biggest pools of error in this industry 48:00 – What industries interest Bryan 40:50 – Dedication to this market 41:45 – Evolution of his healthy skepticism 42:38 – Can things in the debt market help to project what will happen in the equity markets 44:56 – Current view of the world based on what is happening in the credit markets 45:51 – Categories of convenience that he cares about 49:15 – Anything that has him worried in high yield markets 50:38 – Kindest thing anyone has done for Bryan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Maureen Chiquet, the former longtime CEO of Chanel. Maureen also spent much of her career at the Gap, growing Old Navy from scratch, and serving as the president of Banana Republic. The topic of discussion is her experience running large businesses and of finding one’s way in a career and as a leader of others. I hope you enjoy this unique conversation and that it encourages you to, among other things, travel somewhere new and interesting in the coming year. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:15 - (First Question) – The importance of being able to put yourself in other people’s shoes 3:05 – Scott Norton Podcast Episode 4:36 – Most memorable sale from her early career 5:03 – The intersection of facts and emotions in sales 6:40 – Most important emotions in business 7:30 – The importance of identity as part of the selling/marketing of sales and products 9:10 – Difference in strategy for luxury brands vs others 9:21 – The Luxury Strategy: Break the Rules of Marketing to Build Luxury Brands 10:55 – Striking a balance between tradition and innovation 13:46 – Advice for new brand company related to rarity 14:59 – Importance of being organic with your brand purpose 15:01 – Wild Company: The Untold Story of Banana Republic 16:26 – Maureen’s purpose over the years 18:44 – How to harness your purpose for your job 20:53 – Her process for writing and desire to do TV 24:01 – Her time with Micky Drexler 27:40 – As a leader, guiding people to succeed. 32:33 – Strategy for shifting culture at a company 37:54 – The importance of courageous conversations we should all be having 43:45 – Markers of courageous conversations 46:43 – How she thinks about introspection 50:12 – What draws here to certain locations 55:15 – Advice for younger people starting out their career 57:11 – Kindest thing anyone has done for Maureen Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Hunter Walk, the co-founder of Homebrew, a unique venture capital firm. Hunter is a tool builder, having spent his career before venture at companies like Google and YouTube. The topic of our conversation is the intersection of creative expression, technology, human behavior, and problem solving. We discuss his time at the company behind the video game Second Life, building tools for creators at YouTube, and why a very hands-on style of early stage venture investing represents an interesting use of his skillset at this stage of his career. Please enjoy my conversation with Hunter Walk. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:24 - (First Question) – Background on Second Life and what role Hunter had there 6:10 – The virtual currency system at use in Second Life 9:51 – Measuring how people behaved in this virtual world 12:21 – How closely is the Second Life world mimicking real life 15:13 – The market for platforms that lets people take on creative ventures 17:58 – Investments that interest Homebrew 20:21 – Lessons learned while working at YouTube 28:34 – The idea behind Homebrew 33:44 – How to best describe good problems to solve for 36:10 – The Shadow economy and investing in companies operating there 42:17 – Monetization of attention 47:22 – His interest in fintech companies 54:03 – Major trends of change he’s observed over his first three funds 1:04:13 – What is there take on the state of returns for VC’s 1:09:52 – What is the most common way that founders need help and what advice is more helpful 1:14:35 – Kindest thing anyone has done for Hunter Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

[REPLAY] Modern Monopolies: What It Takes to Dominate the 21st Century Economy, which explores the platform business model (Uber, Airbnb, Github). Alex is also the founder and CEO of Applico, a company that he started in his dorm room that is since grown into a huge enterprise that helps startups and Fortune 500 innovate with platforms. Alex and I talk about history and future of businesses and different types of business models. There’s a lot in here for investors, entrepreneurs, and historians. Please enjoy! For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag Books Referenced Modern Monopolies: What It Takes to Dominate the 21st Century Economy The Systems Bible: The Beginner's Guide to Systems Large and Small The Master Switch: The Rise and Fall of Information Empires Zero to One: Notes on Startups, or How to Build the Future Links Referenced Failed Color App Applico Show Notes 2:39 – (first question) – Exploring the history of business models from linear to platform. 5:46 – A look at the share of overall business platform companies have taken over 7:06 - Modern Monopolies: What It Takes to Dominate the 21st Century Economy 7:48 – The potential for platform businesses over the next 20 years 9:18 – Detailing the difference between a linear and a platform business 12:08 – Exploring transaction costs and core transactions across different business models 19:49 – Is the platform business model good for investors and VC’s since so many can get crushed when there’s a sole victor, or is it just for the founders and entrepreneurs. 24:35 – How the self-driving car is going to deliver more opportunity for consumer consumption 27:15 – Untapped supplies as the opportunity for new platforms and where we could see new openings 30:24 – How consolidated will things become across all platforms 33:16 – How do platform companies create a moat to keep others from replicating their business strategy 37:03 – Are there platform strategies that specifically don’t work 37:40 - Failed Color App 38:45 – Why complex systems typically don’t scale up and you should think small and easy to get started 38:47 – The Systems Bible: The Beginner's Guide to Systems Large and Small 40:02 – How the origin of so many larger companies started out small and localized, and why it makes investors more comfortable 41:37 – How Alibaba had to tweak their business model to accommodate the Chinese market 44:07 – Why are the modern monopolies better for consumers 47:52 – Exploring platforms that are asset heavy 49:00 – What do you look for as a VC to determine 52:05 – Alex’s take on whether a platform based company like Uber should be more asset heavy 54:31 – Exploring some lesser known platform businesses that Alex finds interesting 56:18 – If there is a demand in the secondary markets for a product, why don’t the primary suppliers simply raise their prices 57:03 – What Alex’s portfolio of platform-based businesses would look like 58:48 – A couple of most influential books Alex has read 59:12 – The Master Switch: The Rise and Fall of Information Empires 59:38 – Zero to One: Notes on Startups, or How to Build the Future and other Peter Thiel books 59:53 – Looking at Applico, how it started and how it become so focused on the platform business model 1:03:56 - Most memorable day for Alex 1:05:13 – Kindest person to Alex in his life 1:06:10 – What platform opportunities could exist in the financial world Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Cliff Asness, the managing and founding principal at AQR Capital Management. 20 years after its founding in 1998, AQR manages $226 Billion dollars across a number of quantitatively based investing strategies. Cliff was an original quant researcher and he has long been one of the financial writers and thinkers that I look to for education and for inspiration. I distinctly remember reading one paper in particular—value and momentum everywhere—somewhat early in my career and thinking: this is the kind of research I want to do forever. You can always tell when talking to Cliff or hearing him speak that he just loves researching markets. There is a deep intellectual honesty in his work, and a respect for thinkers at different ends of the market spectrum, from Gene Fama and Ken French, to Jack Bogle, to Dick Thaler and Robert Shiller. Our conversation is about all things quant—past, present, and future. Cliff touches on many of the big issues facing quant investing and tells some great strong along the way. I hope you enjoy our discussion. Let’s dive in. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:47 - (First Question) – Favorite superhero 2:43 – Why ‘Ka nama kaa lajerama’ is part of his twitter profile. 3:38 – How portfolios have shifted the way they use factors in a portfolio 10:15 – What are good questions clients are asking right now 13:24 – Contrarian Factor Timing Is Deceptively Difficult 15:40 – Does technology impact investing strategy 22:14 – When to share information vs keep it proprietary for clients sake 26:40 – How their research process is governed 31:14 – How they will incorporate machine learning into their process 34:21 – What they will do when red flags show up 37:01 – Wackiest question from a client 41:47 – The Three Sharpe Ratio Strategy 41:53 – Liquid Alt Ragnarök 48:10 – Does his thinking change when it comes to asset allocation vs portfolio building 50:17 – Parallels Between the Cross-Sectional Predictability of Stock and Country Returns 53:01 – Sin a Little 57:14 – Trends in fees and pricing 1:02:43 – Thoughts on private equity markets 1:11:03 – Common attributes of really good researchers 1:13:21 – What is he most curious about right now 1:15:43 – What excites him outside of finance 1:17:00 – How much he discusses his work with his kids 1:18:35 – The Devil in HML’s details 1:19:36 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

[REPLAY] My guest this week is Peter Attia, M.D., whose mission is to understand and improve human lifespan and healthspan (or quality of life). Reading Peter’s research, you find that there are many similarities between health and investing—ideas like compounding—which we explore in detail. We spend a lot of time on mind, body, spirit and performance as it relates to living a better life. Of particular interest is the strategic problem that we face when studying longevity. As Peter puts it in our conversation: we are the species of interest, but we can’t conduct the kinds of experiments on humans—randomized trials, with control groups—that we apply to solve other big problems. So we have to back our way into a better understanding of longevity and quality of life. To that end, we discuss what we can learn from studying centenarians, the problem of progress in science, a drug called Rapamycin (which Peter believes could be revolutionary), eating, the importance of muscle mass, and the idea of distressed tolerance. We emerge with a framework for thinking about health and well-being which can hopefully help us all live longer, better lives. Please enjoy! For comprehensive show notes on this episode go to http://investorfieldguide.com/attia For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag Posts From Peter Attia That You Should Read Do Calories Matter How You Move Defines How You Live 2016 Update Long List of Questions Answered: Part 1 and Part 2 Links Referenced The Scientific Method-Richard Feynman Knowing Versus Understanding-Feynman again Books Referenced Barbarians at the Gate: The Fall of RJR Nabisco Diffusion of Innovations Good Calories, Bad Calories Show Notes 2:31 – (first question) – Getting Peter to define the concept of wealth and how it might have changed in his life 5:01 – How do you increase the number of really good people in your life. 6:50 – Looking at the relationship between healthspan and lifespan and a chart that Peter created on this specific topic. 11:11 – Drilling down into the different dimensions and aspects of this chart that could be most important for people, especially how compounding plays into our health. 16:57 – The difference between strategies and tactics that will help you extend lifespan 17:54 – The Scientific Method-Richard Feynman 21:41 – Different types of intermittent fasting 28:59 – What role does repair play in health 34:17 – Barbarians at the Gate: The Fall of RJR Nabisco 36:01 – Looking back, what health trends today will look absurd 36:19 – Diffusion of Innovations 39:24 – What are the primary benefits of weight lifting 40:21 – The importance of glucose disposal 45:07 – Good Calories, Bad Calories 46:31 – What is the state of progress in the scientific community 52:14 – Peter is asked about how he guards against getting too attached to old beliefs 1:01:51 – A look at how performance relates to healthspan 1:03:34 –Peter’s first great auto-racing experience 1:09:17 – Looking into Peter’s medical practice and understanding his thinking that goes into helping people 1:18:11 – The most memorable day in Peter’s career 1:22:31 – The kindest thing anyone has done for Peter Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Ryan Caldbeck, a private equity investor who wants to bring quantitative rigor to the private markets. Ryan is the CEO of Circle Up, which uses a system it calls Helio to identify attractive investments in early stage consumer brands. While I am of course a fan of quantitative investing, I also know from experience how much harder private markets are than public markets when it comes to the transactions themselves. We discuss this and many other potential roadblocks to bringing models to private markets. Using many individual companies as examples, Ryan explains some of the major predictive factors they’ve uncovered in their research. We also discuss which parts of the private markets might be infiltrated by quant processes first, and which may never be. I expect many more to go on a journey similar to Ryan’s in the years to come. They serve as an interesting example for ambitious investors out there. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:39 - (First Question) – Formation of Helio 6:57 – How they handle the relationship building needed to make investments in private markets 10:26 – Why consumer and retail are interesting spaces to apply their quantitative approach in private markets 12:54 – Searching for new relevant data 16:14 – How do they stay ahead of the commoditization of uniqueness 16:21 – Pattern Recognition and Machine Learning 17:24 – Sam Hinkie Podcast Episode 18:00 – Dominant predictive factors in this world 21:05 – Which is more important, relative value or rate of change 21:48 – What does the data say about online sales vs offline (being in a store) 23:30 – Variable that consumer investors think matters but it doesn’t 24:53 – Valuing companies and accounting for mispricing’s 25:36 – Michael Recce Podcast Episode 26:41 – Goes through the process using Liquid Ivy as an example 28:46 – Most interesting sub-categories 29:33 – Future for this model 32:10 – Albert Wenger Podcast Episode 35:19 – Other categories outside consumer and retail interest Ryan 36:28 – Biggest challenges for CircleUp as a business 38:46 – Handicapping their earnings expectations 41:36 – Take on the VC/PE landscape 43:03 – The types of models that are most interesting to the team 45:05 – Quantitative elements of brand that are most interesting 47:30 – Most unique brand and distribution strategy he’s come across 53:27 – Who has influenced Ryan the most 54:37 – His personal values 55:51 – More people who had an influence on Ryan 56:05 – The Innovator's Dilemma: The Revolutionary Book That Will Change the Way You Do Business 57:07 – Thoughts on goal setting at the company 59:29 – Unchangeable factors that shape their long-term vision 1:02:01 – Most interesting individual conversation as part of this journey 1:04:02 – If he could only keep one dataset, what would he keep 1:05:09 – kindest thing anyone has done for Ryan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week aspires to be the Larry David of investing, and we discuss why. Howard Lindzon is hard to categorize. He’s primarily an early stage investor right now, but he’s participated in all types of investing. He describes himself as a trend follower and always has a unique take on popular topics. In this conversation, we cover his investing history and his take on the fintech investing landscape. What I’ll remember most is the idea that we should focus on what is happening versus what we think will happen or might happen. There is a Peter Lynch like quality to some of Howard’s thinking, and a willingness to embrace the weird that I find very appealing. The few times I’ve met Howard, I’ve smiled or laughed most of the time, which is about as nice a thing as I could say about someone. He’s a good example of why I like this podcast format. His investing style bears literally no resemblance to my own, but it got me thinking about a lot of new things. I hope you enjoy our chat. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:42 - (First Question) – Why he wants to be the Larry David of investing 2:00 – Why his investing style is best described as trend following 4:05 – The biggest inspirations/influencers on Howard’s investing 6:39 – What made his second mentor, Fred Wilson such a great investor 9:52 – Formation of Wall Strip 12:33 – Why weird is so important in his investment philosophy 14:56 – Understanding his investment philosophy through his investment in Rally Road. 21:02 – His assessment of the fintech space 28:54 – Why fintech pushes away from human nature 30:50 – Major trends in fintech that have his attention 35:02 – What stands out about the teams at these companies he invests in 36:37 – Thoughts on fractionalization plays 36:44 – Capital Allocators podcast episode 36:54 – Venture Stories Podcast 40:03 – Any major trends that are changing and worth attention 42:06 – The Tipping Point: How Little Things Can Make a Big Difference 43:26 – His take on the media landscape 45:10 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guests this week are Ali Hamed, Brian Harwitt and Marc Porzecanski who work together at CoVenture Credit. When I first had Ali on as a podcast guest, we discussed the many aspects of what his firm does, ranging from venture, to crypto, to credit. We glossed over the lending side of the business, but having since learned a lot from them on the topic, I was excited to get the chance to talk with members of their credit team for today’s longer exploration of esoteric high yield lending. I am always proselytizing the value of investor education, s this week we have a podcast first. The CoVenture team has prepared a long series of posts that correspond to our conversation and go even deeper into the topic of credit investing. You can find them in the shownotes at investorfieldguide.com/credit This is entirely differently from any conversation I’ve shared before, so I hope you learn as much as I did. Please enjoy my discussion with team CoVenture Credit. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:42 - (First Question) – The formation of their unique credit business 7:09 – Their advantage in seeing both the equity and credit side of their investments 10:23 – Looking at the Returnly deal as an example 14:07 – How they view these deals and are able to sustain them as long-term investments 18:09 – Their interest in payroll deduction lending 20:08 – Finding unique types of default risk 21:31 – What stands out in a platform that makes CoVenture want to take a deeper look 26:43 – Most interesting types of problem they have come across that they have yet to do a deal in 31:35 – What is going to change to make for more thoughtful underwriting of subprime lending 35:51 – Major structures of asset backed lending 39:49 – Whether the home serves as an interesting playground for credit opportunities and whether people will own anything again 42:44 – Mark’s experience working at a huge firm vs his experience at CoVenture 44:31 – How does the current credit cycle impact their view 47:04 – Lending against bitcoin 50:06 – Who is interested in these loans against bitcoin 50:57 – How to set interest rates against a weird asset like this 53:00 – What are the key determents of success in this business 1:02:27 – Kindest thing anyone has team for the team 1:03:52 – How to treat people that you pass on Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Saifedean Ammous, author of the book the Bitcoin Standard. This was one of the more interesting conversations I’ve had in the world of cryptocurrency, primarily because we don’t talk about Bitcoin or Crypto until 25 minutes into the talk. Instead, we focus on history, economics, sound money, low time preference, and gold—all interesting topics. Saif’s thinking on cryptocurrencies other than bitcoin—which is that they are worthless—is unique and thought provoking. His reasoning around why gold shouldn’t be compared to the returns generated by assets like equities was also compelling. If you’ve followed my Hash Power episodes, this is a new a differentiated interpretation of Bitcoin as a technology for the store of value use case. Please enjoy our conversation. Hash Power is presented by Fidelity Investments For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:10 - (First Question) – Explain Sound Money 4:25 – Examples of hard vs easy money 7:36 – the even money trap 9:36 – The benefits of hard money vs today’s standards 14:05 – Why this interests him 14:16 – Gold Wars: The Battle Against Sound Money As Seen From A Swiss Perspective 14:56 – Democracy – The God That Failed: The Economics and Politics of Monarchy, Democracy and Natural Order 16:17 – Correlation between time preference and people’s ability to succeed in life 19:59 – How money markets worked in the late 18th century vs today 27:57 – How he came across Bitcoin and how he thinks of it as a digital gold 35:42 – How will the world transition to a sound money standard 42:15 – The impacts of hyperinflation on crypto currencies 45:04 – The idea of a orderly upgrade of the world currency 48:20 – His thinking on alternative coins 54:05 – What it takes to compete with bitcoin 1:01:43 – How he diversifies 1:04:35 – Stalling bitcoins demand 1:06:11 – Does he apply his thinking of lower time preference elsewhere in his life 1:07:09 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is one of my best and oldest friends, Jeremiah Lowin. Jeremiah has had a fascinating career, starting with advanced work in statistics before moving into the risk management field in the hedge fund world. Through his career he has studied data, risk, statistics, and machine learning—the last of which is the topic of our conversation today. He has now left the world of finance to found a company called Prefect, which is a framework for building data infrastructure. Prefect was inspired by observing frictions between data scientists and data engineers, and solves these problems with a functional API for defining and executing data workflows. These problems, while wonky, are ones I can relate to working in quantitative investing—and others that suffer from them out there will be nodding their heads. In full and fair disclosure, both me and my family are investors in Jeremiah’s business. You won’t have to worry about that potential conflict of interest in today’s conversation, though, because our focus is on the deployment of machine learning technologies in the realm of investing. What I love about talking to Jeremiah is that he is an optimist and a skeptic. He loves working with new statistical learning technologies, but often thinks they are overhyped or entirely unsuited to the tasks they are being used for. We get into some deep detail on how tests are set up, the importance of data, and how the minimization of error is a guiding light in machine learning and perhaps all of human learning, too. Let’s dive in. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:06 - (First Question) – What do people need to think about when considering using machine learning tools 3:19 – Types of problems that AI is perfect for 6:09 – Walking through an actual test and understanding the terminology 11:52 – Data in training: training set, test set, validation set 13:55 – The difference between machine learning and classical academic finance modelling 16:09 – What will the future of investing look like using these technologies 19:53 – The concept of stationarity 21:31 – Why you shouldn’t take for granted label formation in tests 24:12 – Ability for a model to shrug 26:13 – Hyper parameter tuning 28:16 – Categories of types of models 30:49 – Idea of a nearest neighbor or K-Means Algorithm 34:48 – Trees as the ultimate utility player in this landscape 38:00 – Features and data sets as the driver of edge in Machine Learning 40:12 – Key considerations when working through time series 42:05 – Pitfalls he has seen when folks try to build predictive market investing models 44:36 – Getting started 46:29 – Looking back at his career, what are some of the frontier vs settled applications of machine learning he has implemented 49:49 – Does intereptability matter in all of this 52:31 – How gradient decent fits into this whole picture Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

This week, to mark the two-year anniversary of the podcast, I offer a quick summary looking back and forward.

My guest this week is Kathryn Minshew, the co-founder and CEO of the Muse, and the co-author of The New Rules for Work: the Modern Playbook for Navigating Your Career. I’ve learned in business is that the quality of people and the culture they create dictate outcomes. Having made plenty of mistakes hiring, and having had many enormous successes, I am always interested in best practices for finding and successfully recruiting the right people. Given that Kathryn runs a jobs marketplace and has written a book on the topic, she is the perfect person to explore some the core concepts around pairing people with the right positions. We discuss how companies should market to prospective employees, how employees should represent themselves to employers, and the most common mistakes she sees across the hiring landscape. Please enjoy our conversation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:31 - (First Question) Largest changes in the nature of work and how people approach finding the right job for them 3:27 – Can this work be jammed into a formula 5:18 – What strategies is she sharing with employers when it comes to hiring 8:31 – How long should the process take 9:33 – Biggest mistakes employers make in this process 10:39 – Besides the usual stuff, what can perspective employees do to bolster their chances 12:50 – How much more efficient will matching technology get in the years to come 16:00 – What will be the largest changes to work itself 19:09 – Will we move away from full time work into parsels of work units 20:50 – Most successful piece of content or content strategy the Muse has employed 22:34 – Advice for early stage entrepreneurs 26:24 – Kindest thing anyone has done for Kathryn Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

I intentionally avoid the world of quantitative investing on this podcast. The whole point of this format is to learn about many different fields, and the vast majority of my time is already spent in quant world. Occasionally I’ve broken this rule because of something unique, including this week’s conversation with Richard Craib, the founder and CEO of Numerai. If you listen to the podcast often you’ll have heard me reference Numerai, a hedge fund which blends quant investing, cryptocurrencies, crowdsourcing, and machine learning — talk about a PR company’s dream. One important note: Numerai is both incredibly open and very secretive. You may sense a bit of frustration on my part, but that is only because, as a fellow quant who loves details about data and modeling, we couldn’t go deeper into the details on the record. We discuss how Numerai has created an incentive structure to work with data scientists around the world in an attempt to build better investing models. The idea of having data scientists stake cryptocurrency in support of the quality of their models is fascinating. Like many hedge funds, Numerai doesn’t share its track record, so we don’t know if this works—but I hope you, like me, use this conversation as inspiration for how different technologies can intersect. Hash Power is presented by Fidelity Investments Please enjoy my conversation with Richard Craib. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:32 - (First Question) – How he came up with Numerai and how its related to his background 4:08 – How he works with and models the data for his system 5:24 – Describing machine learning as it relates to his work, and specifically linear regression 7:11 – The important stages in his sequence 8:46 – How the scale in the number of data scientists they use is different from other areas 11:30 – Which is the most important aspect of creating alpha; their data, algorithm work, proprietary ensembling of those algorithms. 14:30 – The idea of staking in blockchain 17:30 – Does the magnitude of the stake matter in blockchain 19:10 – Understanding the full incentive structure for both staked and unstaked work 21:07 – How is the prize pool determined 22:29 – Philosophy on how to source interesting data 26:11 – His thoughts on the crowd model and the wisdom of crowds 27:12 – The size of stakers for Numerai 27:51 – Interpreting the models and knowing when something is broken 30:03 – How they think about people not submitting their models 31:48 – Their model building 32:39 – Most interesting set of things they are working on to improve the overall process 35:38 – The Market for "Lemons": Quality Uncertainty and the Market Mechanism 37:11 – How people can come along with their own data 39:00 – His thoughts on the quantitative investment community 40:44 – What else is interesting him in the hedge fund world 44:03 – Building a marketplace and staving off competition 46:16 – Kindest thing anyone has done for him Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week has a fascinating background. He has a PhD in biology but has split his time as both an investor and an operator. As an investor, he’s involved in companies like Airbnb, Coinbase, Instacart, Opendoor, Stripe, Square, and Pinterest—not too shabby. As an operator, he helped both Google and Twitter scale their businesses, in the case of Twitter from 100 employees to 1500 over two years. He’s just written a book about these experiences called the High Growth Handbook. Our talk centered on what makes for a good investment and more specifically how Elad identifies an interesting market. Operators and early stage investors will find lots of nuggets in this fun conversation. Please enjoy. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:31 - (First Question) – Process for evaluating a young business 2:43 – Andy Rachleff Podcast Episode 3:09 – Data factors for evaluating a business 5:08 – Reference checks 6:42 – Advice for companies that are reliant on product cyclicality 7:01 – Where to Go After Product-Market Fit: An Interview with Marc Andreessen 7:31 – High Growth Handbook 9:30 - Lessons learned from marketing and growing companies 12:09 – How do you hire the best people to improve your distribution 13:16 – How does he think about lifetime customer value vs customer acquisition cost 15:57 – Should companies just focus on the high margin power users 16:35 – Best ways to organize a company hierarchy 19:16 – His interest and background in the area of longevity research 21:52 – Changes he has made in his own life as a result of this longevity research 22:56 – Most effective use of a CEO’s time 24:58 – How he evaluates or identifies interesting markets for potential businesses 28:03 – Any markets that fit his criteria that are underappreciated by investors 30:02 – Worst practices for businesses 32:19 – Kindest thing anyone has done for him 33:20 – What would be the topic of his next book 34:40 – Biggest lessons he’s learned about markets Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

For the 100th episode, I’ve brought back my good friend Brent Beshore. Brent was the 10th guest on the podcast, after we met because of a mutual interest in capital allocation. I quickly learned that Brent was one of the most unique and thoughtful investors around. He was an entrepreneur from the moment he left school, trying many different things before finding a fit buying smaller business with the intention of owning them forever. What amazes me about Brent is his encyclopedic understanding of business and the nuances of different business models and deal structures. This comes from reps. He and his team have looked at about 12,000 deals over the years, at every kind of business that you could imagine. I’ve been with him when he goes through this process and it’s fun to hear what makes certain businesses stand out from others, which is largely the topic of this conversation. You all know transparency is key for me, so it’s important to know that my family and I are investors in a fund called permanent equity, run by Brent and his firm Adventure.es. To commemorate this milestone episode, I can think of no one better than Brent, because he exemplifies what has made this podcast so fun for me: learning from other people who are willing to share what they themselves have learned through fun, blood, sweat, and tears. Please enjoy our conversation, and thank you so much for coming along on this journey. I can’t tell you how much it means to me. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:02 - (First Question) – How does he think about optimizing risk in terms of the capital stack when looking at deals 5:27 – What conditions would they add debt down the road after investing in a company 6:52 – What business sectors are most intriguing for Morgan to invest in right now 6:57 – Trent Griffin Podcast 9:34 – Why no HVAC businesses if it’s such an attractive sector 13:56 – thoughts on rolling up similar businesses and horizontal scale 16:04 – Another industry Brent would focus on 18:02 – Difference between property management in larger cities vs smaller metro areas 18:51 – What role does profit margin play when Brent is evaluating a business 22:46 – The appeal of a hyper cyclical business 22:52 – Brent Beshore Podcast Episode 27:27 – Favorite counter cyclical business 28:14 – How they judge assets, tangible vs intangible assets 33:58 – How does he think about wage inflation when considering the cost of a business 37:21 – His fascination with pet crematoriums 38:57 – History of the permanent equity fund and the changes by having a larger pool of capital 43:48 – Pitching investors on a new structure for the business 46:14 – How will this business model scale Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Today’s conversation is a continuation of my discussion on applying the lessons of tracking animals in the wild to tracking in your own life. I encourage to listen to that episode first. In this second part, Boyd’s sister Bronwyn joins and offers perspective on business and life. Given that Boyd and Bron grew up in this wild place, their perspective on the world is refreshing and very different. We discuss a wide range of things, But the section on restoration near the end is just phenomenal stuff. Please enjoy part two of my conversation with the Varty family. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:21 - (First Question) – Concept of shame and the role it plays in the lives of the people that visit 3:11 – Bron’s take on shame and if this is uniquely male issue 5:15 – How the Varty’s think about the concept of presence, and time with Nelson Mandela 13:34 – Selfishness as an impediment to presence 20:26 – Tending the cup 20:37 – Life is not a zero-sum game 23:15 – How they run the reserve as a business 30:18 – Importance of motivation as a business 33:55 – Cultivating a culture that makes a business a family 40:15 – How they help other family businesses 45:29 – The idea of restoration as a business and legacy 51:23 -Restoration model in investment 53:49 – The age of restoration will be born on the age of information 54:48 – Places that have given Varty’s deep connections (other than Africa) 1:00:46 – Kindest thing anyone has done for Bron Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

An interesting question that I think about a lot: how do you balance exploring the new with savoring what you already know and love? Most of the time I prefer to explore, but the best part of this podcast experience for me has been meeting people who become close friends. For episodes 99 and 100, I’m bringing back two of the most popular past guest who are both now dear friends. This week’s episode is split into two parts, today and tomorrow. Today’s episode is with Boyd Varty and tomorrow is with both Boyd and his sister Bronwyn. The incredible Varty family hosted me in South Africa, so you’ll hear birds and elephants in the background as we talk. This conversation with Boyd is about our shared experience called “track your life” which I couldn’t recommend more highly. We tracked animals on foot for five days, and learned a lot from the environment itself. While we discuss our time together, this is much more about how to live. My original conversation with Boyd had a huge impact on me, and this continues the exploration of Boyd’s idea that we should all be going our own way, in the right way, instead of simply following well trodden paths. I hope you enjoy this conversation with Boyd and check back tomorrow for another conversation with the Vartys. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 1:55 - (First Question) – Encounter with five wild dogs 10:19 – The idea of a perfect day on the track 15:59 – The importance of silence 19:42 – Why we could all benefit from the power of silence 21:37 – Side effects of being on the track 23:49 – Following the smaller paths 25:20 – How culture can keep us from forging our own path 29:34 – The stress he puts on the watch at night 33:34 – The power of going from alert to rest and back again 35:11 – Why Zebras Don't Get Ulcers 38:25 – Disconnecting from the modern world and reconnecting with your life’s purpose 41:42 – How much does skill play into finding your life’s calling 43:23 – Common objections to what they do 49:58 – Importance of end of day on the track 52:33 – Silence and feeling of thousands of years of time passing through hallucinogenic 56:22 – His experience with bees Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Ryan Selkis - The Crypto Barbell and Token Curated Registries - [Invest Like the Best, EP.98] This week’s conversation is for those interested in the nitty gritty of cryptocurrencies and for those who, like me, are fascinated by that world but more than a bit skeptical of the investing prospects for the many cryptocurrencies now in existence. My guest is Ryan Selkis, who I met at an event hosted by Union Square Ventures and Blocktower Capital. At that event, in a crowd of many brilliant people, Ryan was consistently asking hard questions and raising counterpoints. I love his perspective because he is both passionate, but realistic, excited about crypto, but worried about many aspects of the ecosystem. We discuss many new topics like his barbell analogy for thinking about different kinds of coins, token curated registries, and the need to better transparency around decentralized projects. Hash Power is presented by Fidelity Investments Please enjoy our conversation. March for the Fallen Want to meet other curious investors, get in good shape, and support a fantastic cause? Consider joining a great group to hike 28 miles in honor of those who have fallen in defense of our nation. Learn more and sign up at alphaarchitect.com/mftf. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:55 - (First Question) – how he best explains blockchain technology 4:12 – How does he categorize each cryptocurrency 9:11 – How Numeraii is valued 10:04 – Explaining token curated registries (TCR) 12:58 – How Token Curated Registries are being applied 15:05 – Innovations that will protect against nefarious actors in the crypto space 16:37 – How do you convince investors to commit to TCR’s 18:40 – Biggest headwinds to this industry 22:12 – What are the quality filters to root out the bad actors 25:42 – Thoughts on the ICO market as an alternative to capital raising 29:23 – Litmus test for who should use an ICO to raise capital 34:28 – What is unique about creation of a token vs the normal exchange of cash to determine if a company needs a token 36:21 – How many ICO projects are really necessary 38:28 – How should people form an investment opinion about this space 41:35 – Core mission of his company 44:28 – What are some of the reasons his goals won’t happen 49:30 – Lessons learned while working at Coindesk 49:58 – What is he most excited about for the future of this space 52:56 – Kindest thing anyone has done for Ryan Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

My guest this week is Cathie Wood, the founder of ARK invest. Cathie and her team believe that disruptive innovation is the key to long-term growth and, therefore, alpha in the public markets. Because their style of investing is entirely contingent on what will happen and change in the future, it is about as different a style as exists from the quantitative approach to investing, which relies on what is currently knowable about stocks and businesses. The future is notoriously hard to predict, so I am always interested to hear about investing approaches which try to model or handicap the future and build portfolios against that work. In this conversation, we explore all the most interesting and exciting technology trends at play in the world today—and how those trends may play out for investors. We discuss genome sequencing, blockchain, software 2.0, mobility as a service, automation, and more. We also discuss Cathie’s take on building a bridge between the worlds of finance and Silicon Valley, and why starting with a benchmark is anathema to their process. It is hard to deny Cathie’s passion and enthusiasm, and I credit her for building a unique firm culture that emphasizes openness and collaboration. Please enjoy our conversation on investing in innovation. For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Show Notes 2:30 - (First Question) – Cathie’s idea of bringing open source to Wall Street 4:47 – Deep dive into the platform 6:09 – White Paper on Bitcoin – Could Bitoin serve as the role of money 7:43 – Why disruptive innovation is so inefficiently priced 10:04 – How well does the market discount cash flow of disruptive businesses 14:09 – A look at their investing strategies, starting with top-down. 16:10 – How they picked their 5 categories of technological change, starting with foundational 19:42 – Changes in energy 21:53 – Robotics 24:17 – Excitement over deep learning 28:03 – How they express their top-down ideas from the bottom up 36:06 – Mobility as a service as a key area of focus 45:25 – The power of public mistakes 46:39 – What she looks for when hiring 51:14 – her philosophy on building and maintain a portfolio 56:38 – Behind the growth of the company 1:04:01 – Most exciting area for her right now 1:07:52 – Kindest thing anyone has done for Cathie Learn More For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

I’ve often heard that good investors are a bit like journalists: doggedly collecting evidence and building an understanding of how all the pieces of a company or investment fit together. My guest this week is one of my favorite writers and journalists, Bethany McLean. Across her career, Bethany has covered many of the most interesting stories in business and investing, including Enron (which became the famous book and documentary, the Smartest Guys in the Room), Valeant, Wells Fargo, SAC Capital, Fannie Mae and Freddie Mac, the great financial crisis, and most recently, fracking and the energy revolution. Given how deeply she has investigated all of these topics-- and thought about the common threads across them all--this was an amazing conversation. When talking to her, you can feel how much she cares and how diligent and fair she is when analyzing a topic. In addition to all of the great stories already listed, we discuss the art of persistence and other lessons she has learned about businesses and people gone bad. I especially loved her evolving take on housing in America. Please enjoy my conversation with Bethany McLean For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag Links Referenced The Hunt for Steve Cohen Books Referenced Free Radicals: The Secret Anarchy of Science Saudi America: The Truth About Fracking and How It's Changing the World Twilight in the Desert: The Coming Saudi Oil Shock and the World Economy All the Devils Are Here: The Hidden History of the Financial Crisis Show Notes 2:22 - (First Question) – Differences and similarities between investors and journalists 3:19 – What has more of an impact on business practices, exposing negatives or reporting positive 4:57 – first story that got Bethany intrigued with finding bad behaviors 6:19 – The process of getting to know the people who know more than the market 7:43 – Mindsets: Optimism vs. Complacency vs. Pessimism 8:18 – First short seller that garnered her interest 8:57 – The process that led to The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron 10:36 – How to ask questions 12:18 – Importance of preparation 14:20 – Difference between a visionary and a fraud 15:42 – Free Radicals: The Secret Anarchy of Science 16:23 – Any standout frauds that told a really compelling story 17:33 – Looking into Valient 19:32 –Writing about the #MeToo movement 19:34 - Disgraced ex-BofA exec raises uncomfortable questions about #MeToo 21:49 – Thoughts on the spectrum of chasing this story 23:26 – Ways journalist can fairly impact this movement 24:14 – The romance of owning a home in America and what it has meant for the market 24:34 – Shaky Ground: The Strange Saga of the U.S. Mortgage Giants 28:27 – What has changed on her thinking about housing 30:24 – What role does Fannie and Freddie have in the market today 31:13 – Her desire to look into energy 32:26 – Saudi America: The Truth About Fracking and How It's Changing the World 35:05 – What have been the changes in energy market in the US 34:40 – Twilight in the Desert: The Coming Saudi Oil Shock and the World Economy 37:01 – Where are we in the life cycle of energy production 38:29 – Technologies that shaped industrial revolution in America 41:10 – Why is Peter Elkin the best investigative journalist 42:24 – Most relentless she has ever been 43:58 – Who is doing it right 44:38 – All the Devils Are Here: The Hidden History of the Financial Crisis 45:36 – Her take on reporting the The Hunt for Steve Cohen story 49:01 – How her views have evolved over her career and lessons learned 50:40 – Are there ways to prevent success from leading people down a bad path 53:48 – The role of empathy in her career 55:13 – Kindest thing anyone has done for Bethany’s career