Invest Like the Best with Patrick O'Shaughnessy

My guests today are Rick Ruback [https://www.hbs.edu/faculty/Pages/profile.aspx?facId=6543] and Royce Yudkoff [https://www.hbs.edu/faculty/Pages/profile.aspx?facId=589675]. Rick and Royce are Harvard Business School professors who teach their students how to search for, acquire, and run small business directly after graduation. It has been almost a decade since our first conversation, and unlike many past interviews that have become outdated due to technology or market changes, the core principles they shared about entrepreneurship through acquisition remain remarkably relevant today. They explore fascinating developments in the search-fund ecosystem, including the bifurcation between funded searchers targeting larger companies and self-funded entrepreneurs finding success with smaller businesses. Rick and Royce share their accumulated wisdom on what makes a company worth buying, why the "magic is in the multiples," and how their students consistently achieve impressive returns through patient, value-oriented business acquisition. Please enjoy my conversation with Rick Ruback and Royce Yudkoff. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ here.⁠ [https://joincolossus.com/episode/entrepreneurship%E2%80%A6ough-acquisition/] ----- This episode is brought to you by⁠ Ramp⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to⁠ Ramp.com/invest⁠ [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by⁠ AlphaSense⁠ [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at⁠ Alpha-Sense.com/Invest⁠ [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠ Ridgeline⁠ [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to⁠ ridgelineapps.com⁠ [https://www.ridgelineapps.com/] to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠https://thepodcastconsultant.com⁠ [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:23) Changes in the Small Firm Acquisition Space (00:06:52) The Impact of SBA Loans on Acquisition Entrepreneurship (00:08:55) The Evolution of Entrepreneurship Through Acquisition (00:10:09) Risk and Return in the Search Fund Model (00:13:38) The Role of Investors in Funded and Unfunded Searches (00:19:33) Criteria for a Good Acquisition Target (00:28:36) The Growing Popularity of Self-Funded Searches (00:43:21) Challenges and Red Flags in Small Firm Acquisitions (00:49:47) Exploring Margin Expansion and Growth (00:51:02) The Impact of Practical Teaching in Business Education (00:52:12) Keys to a Successful Business Class (00:53:30) The Role of Theory in Practical Business Education (00:55:29) Challenges and Rewards of Teaching Business (00:57:46) Capital Allocation in Small Businesses (01:00:50) Advice for Aspiring Business Searchers (01:03:45) Value Creation and Business Lifecycle (01:08:20) Deciding to Leave Private Equity (01:11:20) The Future of Higher Education in Business (01:16:06) Ongoing Relationships with Former Students (01:18:45) Favorite Business Cases to Teach (01:24:46) Encouraging More People to Pursue Business Ownership

My guest today is David Senra [https://x.com/FoundersPodcast]. David is the host of Founders podcast and a dear friend. This is our third time doing Invest Like the Best together and we have conversations like this one all the time. In today’s episode, David distills wisdom from 400 entrepreneur biographies into a single word: focus. He reveals why exceptional builders like Todd Graves and James Dyson create billion-dollar empires through obsessive dedication to simple ideas—whether perfecting chicken fingers or designing vacuum cleaners—while rejecting conventional growth timelines and investor pressure. David challenges us all to find the one thing we’d pursue even without recognition or reward, or what I like to call your life’s work. We discuss the concept of “anti-business,” raising capital as a founder, and decades-long commitment. Please enjoy this discussion with David Senra.  For the full show notes, transcript, and links to mentioned content, check out the episode page here. [https://joincolossus.com/episode/the-focused-few/] ----- This episode is brought to you by Ramp [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. –  This episode is brought to you by AlphaSense [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by Ridgeline [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com [https://www.ridgelineapps.com/] to learn more about the platform. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:43) The Essence of Focus in Entrepreneurship (00:09:20) The Value of Long-Term Commitment (00:17:41) The Importance of Simplicity and Mastery (00:37:11) The Miracle of Entrepreneurship (00:44:56) James Dyson's Journey to Success (00:47:03) The Importance of Passion in Business (00:49:12) Critique of Modern Consumerism (00:52:18) The Value of Craftsmanship (00:56:36) The Drive for Excellence (01:04:06) The Importance of Hiring Top Talent (01:09:54) Creative Financing Strategies (01:19:35) Defining a Founder

My guest today is Cliff Sosin [https://x.com/CliffordSosin]. Cliff is the founder of CAS Investment Partners, a fund he started with $5 million in 2012 and has grown to $1.7 billion as of the last reported numbers at the end of 2024. At the time, CAS had only four positions. This conversation is different to our typical episodes. We start by talking about Cliff's investing philosophy but the bulk of this long discussion is a case study into his remarkable investment in Carvana. Cliff is one of the biggest investors in the business, which had a market cap over $60 billion in 2021, then fell 99%, survived, and now has a market cap approaching $50 billion again. While I hosted Carvana's CEO, Ernie Garcia, last year to get the inside perspective on managing through such turbulence, today we hear the investor's side of this extraordinary story. It is a singular episode and there are so many lessons in this rare opportunity to hear a major investor describe his decision-making process at every stage of the journey. Please enjoy my great conversation with Cliff Sosin. For the full show notes, transcript, and links to mentioned content, check out the episode page here. [https://joincolossus.com/episode/investing-in-carvana/] ----- This episode is brought to you by Ramp [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com [https://www.ridgelineapps.com/] to learn more about the platform. –  This episode is brought to you by AlphaSense [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:32) Early Career and Discovering Investing (00:06:49) Starting the Firm and Initial Challenges (00:08:41) Investment Philosophy and Market Realities (00:11:07) Building the Firm and Investor Relations (00:12:23) Defining a Good Business (00:17:31) Contained vs. Uncontained Businesses (00:20:30) Mental Models and Market Insights (00:35:13) The Role of ESG in Investing (00:39:26) The Carvana Investment Story (00:46:43) Carvana's Real Estate and Logistics Network (00:49:12) Reconditioning and Selling Cars (00:50:16) Carvana's Financing and Customer Service (00:51:43) Economies of Scale and Trust (00:54:40) Challenges and Management Insights (01:04:07) Operational Issues and Market Challenges (01:23:56) Questioning Carvana's Sales Strategy (01:24:17) The Role of Word of Mouth in Carvana's Growth (01:25:28) Identifying Early Adopters (01:26:00) The Impact of Market Conditions on Carvana (01:27:10) Carvana's Operational Challenges (01:28:10) Cutting Costs and Organizational Efficiency (01:32:19) The Apollo Deal and Debt Restructuring (01:39:21) The Psychological Toll of Investment (01:50:16) Future Investment Strategies and AI (01:54:48)The US Market and Investment Opportunities (01:59:51) The Kindest Thing Anyone Has Ever Done For Cliff

Welcome to this classic episode. Classics are my favorite episodes from the past 10 years, published once a month. These are N of 1 conversations with N of 1 people. There aren't many people like Cyan Banister [https://x.com/cyantist]. Her 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. For the full show notes, transcript, and links to mentioned content, check out the episode page here. [https://joincolossus.com/episodes/62018848/banister-investing-for-a-higher-purpose] ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes [https://www.joincolossus.com/episodes].  Past guests include Tobi Lutke [https://joincolossus.com/episodes/64592621/lutke-building-a-modern-business?tab=transcript], Kevin Systrom [https://joincolossus.com/episodes/60313963/krieger-how-to-build-a-great-product?tab=transcript], Mike Krieger [https://joincolossus.com/episodes/60313963/krieger-how-to-build-a-great-product?tab=transcript], John Collison [https://joincolossus.com/episodes/34646260/collison-growing-the-internet-economy?tab=transcript], Kat Cole [https://joincolossus.com/episodes/15230717/cole-how-to-operate-lessons-in-brand-distribution-and-leadership?tab=transcript], Marc Andreessen [https://joincolossus.com/episodes/58516750/andreessen-making-the-future?tab=blocks], Matthew Ball [https://joincolossus.com/episodes/69430337/ball-the-future-of-media-movies-the-metaverse-and-more?tab=transcript], Bill Gurley [https://joincolossus.com/episodes/12224182/gurley-all-things-business-and-investing?tab=transcript], Anu Hariharan [https://joincolossus.com/episodes/99792081/hariharan-lessons-in-growth-investing?tab=transcript], Ben Thompson [https://joincolossus.com/episodes/91241527/thompson-platforms-ecosystems-and-aggregators?tab=transcript], 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 [https://www.joincolossus.com/newsletter]. Follow us on Twitter: @patrick_oshag [https://twitter.com/patrick_oshag] | @JoinColossus [https://twitter.com/JoinColossus] Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com [https://thepodcastconsultant.com/]). Show Notes: [00:00:00] Welcome to Invest Like the Best [00:04:06] Contrarian Thinking in Investing [00:05:30] Joining Founders Fund and Learning from Peter Thiel [00:11:15] Investing in Companies that Change Lives [00:14:00] The Importance of Overcoming Adversity for Founders [00:16:02] Personal Journey and Choosing Hope [00:20:56] Embracing Curiosity and Wonder in the Face of Adversity [00:21:20] Reconnecting with Our Inner Child [00:24:46] The Interruption and Resumption of the Conversation [00:27:20] The Power of Intuition in Business Decisions [00:32:28] The Story Behind the Investment in Uber [00:38:46] Conclusion: Following the White Rabbit of Curiosity [00:39:08] Investing in Uber: The Beginning [00:41:50] The Impact of Success: Personal Wealth and Privacy [00:50:22] The Intersection of Spirituality and Investing [00:59:34] The Bill Murray Experience: A Lesson in Presence [01:09:54] The Violin Kid: A Tale of Curiosity and Generosity [01:12:43] The Evolution of Investing: A Personal Journey [01:16:34] The Philosophy of Giving: The Universe's Return [01:17:36] The Spirit of a Venture Firm: Founders Fund [01:23:09] The Power of Integral Family Systems [01:28:41] The Trillion Dollar Question: Disrupting Hollywood [01:36:05] The Future of Artistry: AI and Creativity [01:41:39] The Power of Kindness

My guest today is Matt Huang [https://www.paradigm.xyz/team/matt-huang], co-founder of Paradigm, a leading crypto investment firm with over $12 billion in assets under management. Before launching Paradigm in 2018 with Coinbase co-founder Fred Ehrsam, Matt was a partner at Sequoia Capital, where he led many of the firm's crypto investments. It’s widely reported that Michael Moritz called Matt “the only regrettable loss in Sequoia’s history.” In our conversation, Matt shares his framework for navigating the often illegible frontier of crypto, how his early investment in ByteDance (now worth 10,000x his initial capital) shaped his approach to identifying exceptional founders, and why he believes so deeply in crypto’s long-term potential. His firm, Paradigm, not only invests in many of the leading companies in the industry, it also builds open-source tools used by most of crypto. Matt has a rare blend of IQ and EQ that allows him to understand technical complexity, bring together unique talents, and ride out crypto’s notorious volatility. Whether you're crypto-curious or crypto-skeptical, I think you'll find his perspective valuable. Please enjoy my great conversation with Matt Huang. Matt Huang's Profile [https://joincolossus.com/article/paradigm-shifts-matt-huang/] in Colossus Review. For the full show notes, transcript, and links to mentioned content, check out the episode page here. [https://joincolossus.com/episode/investing-at-the-frontier/] ----- This episode is brought to you by Ramp [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest]. Ramp’s mission is to help companies manage their spend in a way that reduces expenses and frees up time for teams to work on more valuable projects. Go to Ramp.com/invest [https://ramp.com/250-signup-bonus?utm_source=podcast&utm_medium=paid-podcast&utm_campaign=podcast-colossus-250&utm_content=invest] to sign up for free and get a $250 welcome bonus. – This episode is brought to you by Ridgeline [https://www.ridgelineapps.com/]. Ridgeline has built a complete, real-time, modern operating system for investment managers. It handles trading, portfolio management, compliance, customer reporting, and much more through an all-in-one real-time cloud platform. Head to ridgelineapps.com [https://www.ridgelineapps.com/] to learn more about the platform. –  This episode is brought to you by AlphaSense [https://www.alpha-sense.com/invest/]. AlphaSense has completely transformed the research process with cutting-edge AI technology and a vast collection of top-tier, reliable business content. Invest Like the Best listeners can get a free trial now at Alpha-Sense.com/Invest [https://www.alpha-sense.com/invest/] and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com [https://thepodcastconsultant.com/]). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:15) Matt Huang's College Years and Early Career (00:12:27) The Failed Startup and Lessons Learned (00:16:51) Matt's Pivotal Trip to China and ByteDance Investment (00:25:58) Sequoia's Culture of High Standards (00:32:51) Discovering Bitcoin and Crypto (00:39:33) Founding Paradigm (00:45:40) Building a Unique Investment Team (00:48:03) Challenges and Volatility in Crypto (00:53:10) The Relationship Between Legibility and Investing (00:58:40) Crypto as a New Financial System (01:05:19) The Importance of Stablecoins (01:09:54) AI and Crypto: The Next Frontier (01:16:19) Personal Motivations and Important Crypto Use Cases (01:29:23) The State of Regulation in Crypto (01:32:27) The Kindest Thing Anyone Has Ever Done for Matt