Invest Like the Best with Patrick O'Shaughnessy

Today we are replaying my conversation with 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. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. ----- 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: (00:00:00) Welcome to Invest Like the Best (00:03:07) The Role of Early Career Energy in the System (00:07:47) The Importance of Being Thematic and Process-Driven (00:08:25) The Journey of Building a Business (00:09:50) The Perfect Shore Capital Deal (00:15:44) Building Competitive Advantage through Volume (00:19:02) The Role of Board Members in Investment Success (00:25:10) Choosing Industrial Subsectors Over Software (00:29:37) Identifying Industry Leaders (00:34:15) The Process of Identifying Potential Investments (00:37:35) The Impact of Business Consolidation on Reputation (00:46:33) Exploring the Concept of Unfair Advantages (00:51:03) Building Platforms, Not Buying Them (00:52:16) The Power of Operations and Knowledge Sharing (00:57:36) The Excitement of Sports Franchise Ownership (01:09:48) The Kindest Thing Anyone Has Ever Done For Justin

My guest today is Joe Liemandt. Joe is the Principal at Alpha School and the founder of Triliogy Software and ESW Capital. He became the youngest member of the Forbes 400 in the 1990s before vanishing from public view for two decades—only to emerge with a $1 billion bet that he can make kids learn 10x faster using AI. Joe has built an AI tutoring system so effective that students at his Alpha School literally beg not to take summer breaks, achieving 2x learning outcomes in just 2 hours with standardized test results that compete with the best of them. We dive deep into why this could be the most valuable product he's ever built, his contrarian thesis that traditional SaaS is facing AI-driven obsolescence, and how his experience buying 100+ software companies prepared him for this moonshot in a trillion-dollar market that hasn't innovated in 200 years. For investors, this is a masterclass in deploying patient capital to rebuild broken systems from first principles, with insights on everything from regulatory moats to the intersection of AI and human psychology. As your excited skeptic, I push hard on the technology readiness, parental adoption hurdles, and whether this audacious vision can actually scale to a billion kids. Additionally, in a Colossus Profile released last week, our editor-in-chief Jeremy Stern reported, for the first time, Joe as the product guy behind Alpha School in a can’t miss piece of writing. And now please enjoy my conversation with Joe Liemandt. Joe Liemandt’s Colossus Profile by Jeremy Stern. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:08) The Alpha School Revolution (00:12:47) Personalized Learning with AI (00:35:51) Motivating Students: The Key to Success (00:42:06) Life Skills Workshops: Real-World Learning (00:44:48) Scaling Personalized Learning (00:47:47) High Standards and Student Motivation (00:52:33) The Role of Guides and Coaches (00:58:22) Feedback Loops and AI in Education (01:17:52) Filling Knowledge Gaps in Education (01:20:15) Changing Perceptions of Academic Ability (01:28:20) Challenges in Public School Systems (01:31:16) Entrepreneurship in Education (01:41:56) Gamified Learning and Technology (01:55:05) Efficiency Gains in Software Systems (01:59:48) Transition to a Private Life (02:01:21) Trilogy (02:10:39) Lessons from Mentors (02:17:25) Pushing Limits and Finding Passion (02:24:22) The Future of Education (02:27:12) The Kindest Thing

My guest today is Mark Bertolini. Mark is the former CEO of Aetna and the current CEO of Oscar Health. He shares one of the most extraordinary leadership stories I've encountered—surviving a catastrophic skiing accident that left him in chronic pain for 18 years while simultaneously leading one of healthcare's most successful corporate turnarounds. His personal experience navigating his son's life-threatening cancer battle and his own medical challenges fundamentally changed his approach to healthcare, leading to innovations in employee welfare that Wall Street initially questioned but ultimately celebrated. During his tenure at Aetna, Mark generated 652% total shareholder return by implementing revolutionary employee policies and is now applying these lessons at Oscar Health to disrupt the $4 trillion healthcare industry with a technology-first approach. We discuss the power of servant leadership, employer-sponsored insurance vs individual choice-based plans, and the horizons of healthcare. Please enjoy this incredible conversation with Mark Bertolini. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:52) Mark's Ski Accident and Recovery (00:07:54) Early Life and Career Beginnings (00:12:51) Leadership Philosophy and Career Highlights (00:19:03) Healthcare System Insights and Innovations (00:25:31) Oscar Health: Current State and Future Vision (00:42:06) Personal Stories and Eastern Belief System (00:51:57) Discovering the Healing Power of Yoga (00:57:21) Transforming Employee Benefits and Wages (01:02:41) Personal Journey Through Chronic Pain (01:08:10) Reflections on Business Success and Leadership (01:15:54) Joining Bridgewater and Transitioning Leadership (01:22:47) Leading Oscar Health and Future Goals (01:34:12) Enduring Hardships and Finding Purpose (01:32:34) The Kindest Thing Anyone Has Ever Done For Mark

My guest today is Peter Lacaillade. Peter is the Chief Investment Officer for Private Investments at SCS Financial and has built one of the most respected private equity allocation platforms in wealth management, overseeing $50 billion for ultra-high-net-worth families and earning the same access as top-tier endowments. He shares how SCS's pooled vehicle structure enables them to compete with institutional giants for the best funds, avoiding the adverse selection that plagues most wealth platforms. Peter shares his investment philosophy across lower middle market buyouts, emerging independent sponsors, and early bets on category-defining managers like Thrive Capital and Shore Capital. We discuss what separates exceptional private equity managers, the evolution of the industry toward AI-powered strategies, and private markets going mainstream. Please enjoy this conversation with Peter Lacaillade. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:31) Advantages of Private Equity Over Public Markets (00:08:59) Talent Acquisition and Growth at SCS (00:10:28) SCS's Wealth Management Strategy (00:19:51) Challenges and Risks in Private Equity (00:26:06) The Future of Wealth Management (00:12:42) Trends in Private Equity (00:20:14) Challenges and Risks in Private Equity1 (00:22:58) Building Successful Private Equity Partnerships (00:26:06) The State of the Wealth Management Industry (00:35:07) Lower Middle Market Buyouts and Independent Sponsors (00:49:38) Introduction to Long Lake and Its Innovative Approach (00:50:21) AI-Powered Tools for Homeowners Associations (00:52:46) Permanent Capital Vehicles vs. Drawdown Funds (00:54:26) The Rise of Holding Companies (00:57:03) Emerging Trends in Venture Capital 01:05:44) The Role of Endowments and Liquidity Solutions (01:10:40) Jake and Frank's Partnership (01:13:57) The Kindest Thing Anyone Has Ever Done For Peter

My guest today is Andrew Milgram. Andrew is the founder of Marblegate Asset Management, an alternative investment firm that invests in credit opportunities and special situations. He joins me to discuss his unique approach to distressed investing in the middle market, revealing how middle market EBITDA has declined 20-25% since 2019, creating what he calls the "K-shaped economy." His investment stories are legendary, particularly his $600+ million bet on NYC taxi medallions, which we go into in great detail. We discuss Marblegate’s approach to negotiation, sourcing deals directly from hundreds of regional banks, and understanding the human element in distressed situations. Please enjoy this conversation with Andrew Milgram. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:04:58) Understanding the K-Shaped Economy (00:07:08) Middle Market Challenges and Data Insights (00:16:56) Distressed Investing Explained (00:25:06) The Taxi Medallion Investment Story (00:46:46) Navigating New York's Taxi Medallion System (00:47:17) Building Relationships with Regulators and Unions (00:50:22) Taking the Taxi Operation Public (00:51:26) The Future of Autonomous Vehicles and Medallions (00:54:30) Investment Strategies and Risk Management (00:58:41) Negotiation Principles and Human Drama (01:11:55) Personal Reflections and Formative Experiences (01:17:22) The State of the American Economy (01:23:29) Insights on Private Credit and Equity Markets (01:30:39) Future of Asset Management (01:33:16) The Kindest Thing Anyone Has Done For Andrew

My guest today is Ramtin Naimi. Ramtin is the founder of Abstract Ventures, one of the most talked-about seed funds in Silicon Valley. What makes Ramtin's story so compelling isn't just his firm's remarkable track record—including early investments in Rippling, Solana, and dozens of unicorns—but also the unconventional path he took to get there. From running a hedge fund straight out of high school to filing for bankruptcy at 24, then bootstrapping his way to building a $2 billion AUM venture firm using AngelList and relentless hustle. Our conversation begins in an unexpected place—the art world—where Ramtin has become a sophisticated collector, learning from mentors like Michael Ovitz about market dynamics that surprisingly mirror venture capital. We dive deep into how the art world actually works, and Ramtin explains how these lessons about "masterpieces" apply directly to identifying power-law companies in venture. We go deep on his approach to early-stage investing and how he built Abstract as a co-investment vehicle alongside firms like Sequoia, Benchmark, and Andreessen Horowitz. We explore his portfolio construction model, his philosophy on dilution-sensitive founders, and why he takes upwards of 30 pitch meetings per week to build his "frame of reference." We discuss why Abstract has the highest graduation rate from seed to Series A among all seed funds, and how this competitive advantage compounds over time. This is his first time telling his story, and we discuss the power of pattern recognition, relentless work ethic, and the unique opportunities available to those willing to start from scratch in Silicon Valley. Please enjoy this great conversation with Ramtin Naimi. Colossus Review Profile: Ramtin Naimi For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠here⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠⁠. 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 and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. ----- 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 (00:05:40) Learning from Mentors and Starting to Collect (00:08:50) Parallels Between Art and Venture Capital (00:12:57) Challenges in Art Collecting (00:20:45) The Role of Status in the Art World (00:25:00) Who Makes the Most Money in the Art World? (00:28:19) Abstract Ventures: Early Stage Investing (00:42:34) Starting a Venture Capital Firm from Scratch (00:43:12) Overcoming Bankruptcy and Early Struggles (00:50:34) Evaluating Technical Capabilities and Momentum (01:02:53) Competing for Deals and Building Relationships (01:15:25) The Role of Brand in Venture Capital (01:22:39) Early Life and Entrepreneurial Beginnings (01:28:40) Starting a Hedge Fund and Learning Hard Lessons (01:31:26) Transition to Venture Capital (01:37:19) Building Abstract and Family Life (01:52:03) The Kindest Thing Anyone Has Done For Ramtin

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. Brad Jacob's simple principle of "think big, move fast" is one I think about often. 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 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 is a true force of nature, and I hope you enjoy his episode. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠⁠⁠WorkOS⁠⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠⁠WorkOS.com⁠⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- 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 (00:00:00) Welcome to Invest Like the Best (00:02:11) 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 guest today is Zach Dell. Zach is the co-founder and CEO of Base Power Company. Base is a modern power company building a reliable and affordable home energy service powered by distributed batteries. We explore one of the most underappreciated machines in our world: the electrical grid. Zach walks us through the complex world of electricity infrastructure and explains why the 100-year-old grid is woefully unprepared for the explosion in demand coming from AI, electric vehicles, and industrial electrification. Base's approach involves creating a distributed network of home batteries that provide backup power to customers while serving as grid resources, elegantly solving infrastructure bottlenecks that plague traditional utility-scale projects. We discuss energy as the fundamental enabler of human progress, scaling distributed energy assets, and the vertical integration strategy driving Base's unit economics. Please enjoy my conversation with Zach Dell. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠here⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Arcana⁠⁠⁠. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit⁠⁠ ⁠arcana.io⁠⁠⁠ to request a demo and learn more. ----- Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠⁠⁠⁠⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠⁠⁠⁠⁠⁠⁠). Show Notes: (00:00:00) Introduction and Show Overview (00:05:06) Understanding the Electrical Grid (00:09:10) The History and Evolution of the Grid (00:09:51) Regulation and Deregulation in the Energy Sector (00:18:25) The Importance of Energy in Human Progress (00:28:41) Base's Innovative Energy Solutions (00:38:25) Economic and Operational Insights of Base (00:44:31) Understanding Electricity Market Variability (00:45:01) The Boom and Bust of Battery Economics (00:48:43) Battery Technology and Chemistry (00:50:56) Global Battery Manufacturing Landscape (00:54:06) Capital Markets and Financing Strategies (00:59:56) Vision for the Future of Energy Technology (01:02:30) Personal Journey and Entrepreneurial Insights (01:09:48) Lessons from Influential Leaders (01:16:52) The Kindest Thing Anyone Has Done For Zach

My guest today is Alan Waxman. Alan is the co-founder and CEO of Sixth Street, one of the most unique investment firms with a "go anywhere, do anything" mandate across asset classes, geographies, and time horizons, and over $110 billion in AUM. He describes his journey from CIO of Goldman Sachs’ Special Situations Group and the frameworks he brought with him to lay the foundation for Sixth Street. Alan details their famous investments like Spotify and Airbnb during challenging periods, their innovative sports partnerships with Real Madrid and FC Barcelona, and their $30 billion "TAO" vehicle that allows them to write billion-dollar checks while keeping individual fund sizes matched to opportunities. We discuss hiring people without egos, enabling a truly multi-strategy approach, and Sixth Street’s "face the tiger" philosophy. Please enjoy this great conversation with Alan Waxman. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠⁠here⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠⁠. 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 and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. ----- 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 (00:04:57) Introducing Alan Waxman and Sixth Street (00:05:58) The Formative Goldman Sachs Years (00:10:21) Unitizing Risk and Return (00:14:23) Facing the Tiger: Sixth Street's Culture and Values (00:34:51) Spotify and Airbnb: Case Studies in Investment (00:39:20) Ambitious Investment Strategies (00:40:40) Strategic Partnerships in Sports (00:41:23) Navigating COVID with Airbnb (00:43:36) Risk and Return Analysis (00:46:56) Investing in Sports and Live Entertainment (00:52:23) Developing Investment Themes (00:55:29) Balancing Leadership and Investment (00:57:30) The Importance of Culture (01:10:33) Future Self and Long-Term Vision (01:15:09) The Kindest Thing Anyone Has Ever Done For Alan

My guest today is Caryn Seidman-Becker. Caryn is the Chairman and CEO of Clear. She bought the company out of bankruptcy for $6 million in 2010 and built it into the identity platform millions use in airports and stadiums today. Her Wall Street background investing in Apple, Amazon, and Priceline taught her to recognize when products become platforms, which shaped her vision for Clear as the "definitive secure identity platform" far beyond travel. Caryn shares the gritty early days of literally hunting down hardware in airport storage facilities and rebuilding the entire business from scratch. She embodies an incredible "bias for action." We discuss turning around a business, scaling a platform, and why she believes your face will soon be your key to everything. Please enjoy my conversation with Caryn Seidman-Becker. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠Arcana⁠⁠. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit⁠ ⁠arcana.io⁠⁠ to request a demo and learn more. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. ----- 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 (00:05:43) The Vision for CLEAR (00:09:08) From Wall Street to CLEAR (00:13:42) The Origins of CLEAR (00:14:23) The Bankruptcy and Rebirth of Clear (00:34:41) Building the Business Model (00:47:46) The Future of Airport Innovation (00:48:33) Investing Insights and Strategies (00:52:17) The Importance of Free Cash Flow (00:55:26) Biometrics and Privacy Concerns (00:59:40) Expanding Clear's Vision (01:04:13) Personal Mission and Genetic Screening (01:12:28) Leadership and Company Culture (01:14:23) Future of Technology and Identity (01:25:38) The Kindest Thing Anyone’s Ever Done For Caryn

My guest today is Jens Grede. Jens is the co-founder and CEO of Skims, the shapewear and clothing brand he co-founded with his wife Emma Grede and Kim Kardashian. Our conversation left my head spinning. Jens has this remarkable ability to be both creative and commercial. He puts brilliant frameworks into plain terms and knows consumer like the back of his hand. Jens explains how pop culture is the only remaining hack to the consumer economy in our fragmented media landscape and describes today’s cultural shift as "clamoring for comfort" in uncertain times. We discuss individual voices trumping institutions, moving at the speed of culture rather than corporate planning cycles, and why big brands will increasingly win. Please enjoy this fascinating discussion with Jens Grede. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠. 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 and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. ----- 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 (00:05:18) The Power of Pop Culture in Business (00:09:28) The Role of Individuals vs. Institutions (00:11:27) Cultural Shifts: From Hip Hop to Country (00:18:36) The Resurgence of Fallen Brands (00:24:33) The SKIMS Origin Story (00:33:42) Building a Strong Product and Brand (00:36:14) The Partnership with Kim Kardashian (00:49:18) Effective Content Creation in Popular Culture (00:50:55) Decision Making in Real-Time (00:51:35) Leveraging Popular Culture for Brand Success (00:57:28) The Role of Networks and Individual Voices (01:14:38) The Future of Status and Digital Influence (01:16:20) Investing Insights and Long-Term Views (01:20:39) Scaling SKIMS and Future Plans (01:23:52) Reflections on Entrepreneurship and Personal Growth (01:29:49) The Kindest Thing Anyone Has Ever Done For Jens

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. Charlie Songhurst is a brilliant strategist, accomplished executive, and prolific angel investor. This episode is one of my all-time favorite conversations, not just on the podcast, but period. Please enjoy this timeless discussion with Charlie Songhurst. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠here⁠. ----- This episode is brought to you by ⁠⁠WorkOS⁠⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠⁠WorkOS.com⁠⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- 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 (00:00:00) Welcome to Invest Like the Best (00:01:25) Stack ranking the vices of power, money, and fame (00:02:41) Memorable response to the stack ranking question (00:03:13) Best scenario to explore this stack ranking concept (00:03:55) Other ways to rank founders (00:04:44) Quick look at this career (00:05:16) Time at Microsoft (00:06:03) Features he looks for in startups (00:10:55) Managing the declining curve of productivity (00:14:55) Why founders are often unique people (00:14:57) ⁠Jeff Gramm Podcast Episode⁠ (00:15:04) ⁠ Aliens, Jedi & Cults⁠ (00:09:43) How early entrepreneurs need to make recruitment a serious part of their work (00:23:06) How successful founders win the best candidates (00:25:27) The East Coast vs. West Coast investment strategies (00:30:40) When it’s time to bring in quantitative factors into early stage investing (00:34:36) The markers that pop up in companies that hit (00:37:22) Boring but successful investments (00:39:28) Investor aesthetics (00:41:29) Characteristics of investors that he believes are important to success (00:42:57) Impacts of Covid and some of the permanent changes that have happened as a result (00:47:49) Investing opportunities in the local community (00:49:13) His take on cryptocurrencies (00:53:47) Most misvalued asset in the world (00:55:16) Investing opportunities in Europe (00:57:34) Make up of his 483 investments (00:57:58) ⁠Matt Clifford Podcast Episode⁠ (00:59:17) Curation as a skill (01:01:54) Timing and startup success (01:05:11) Kindest thing anyone has done for him

My guests today are Alex Pall and Drew Taggart, who you might know as The Chainsmokers. We explore their fascinating evolution from scrappy DJs to global superstars to serious venture capitalists with their fund Mantis. Drew and Alex share how the same high-touch, relationship-driven approach that built their music empire now defines their investment philosophy. Their framework for backing founders mirrors their artistic process: they invest in obsessive individuals who will pursue their vision regardless of external validation, much like how they've remained authentic to their sound despite industry pressures. We discuss parallels between creative iteration in music and venture investing, particularly around managing failure, maintaining intentionality in an age of abundance, and the importance of taste as a differentiating factor. Please enjoy this fascinating discussion with The Chainsmokers, Alex Pall and Drew Taggart. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠⁠⁠ ⁠Arcana⁠. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit ⁠arcana.io⁠ to request a demo and learn more. ----- 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 (00:06:16) The Creative Process Behind Songwriting (00:07:33) Exploring the Emotional Depths of Music (00:11:50) Navigating the Music Industry and AI (00:17:45) The Importance of World Building in Music (00:21:27) Finding Your Creative Itch (00:35:04) The Chainsmokers' Journey and Work Ethic (00:40:37) The Business Side of the Chainsmokers (00:45:43) Venturing into Tech and Investments (00:51:39) The Evolution of Mantis (00:53:11) Overcoming Celebrity Investor Stereotypes (00:55:20) Supporting Founders Like Record Labels (00:57:26) The Art of Collaboration (01:04:02) The Grind to Success (01:13:49) Investing Insights and Evolution (01:26:39) The Kindest Thing Anyone Has Ever Done for Drew and Alex

My guest today is Jay Hoag. Jay is the co-founder of Technology Crossover Ventures, known as TCV, which pioneered the growth investing category and has backed legendary companies like Netflix, Spotify, and Expedia over three decades. Jay explains how macro factors like regulation have become unexpectedly central to technology investing. He offers his contrarian take on today's market, arguing that consumer internet represents significant opportunity while most investors chase SaaS and AI deals. We discuss investing in new technology versus commercialization, TCV’s evolution from cold-calling to AI-powered sourcing of 11 million companies, and their three-person unanimous investment committee structure. Please enjoy my conversation with Jay Hoag. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠ ⁠⁠⁠⁠here.⁠⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠⁠ Ramp⁠⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠ AlphaSense⁠⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:18) Market Conditions and Investment Opportunities (00:06:57) Consumer Internet Businesses and AI (00:09:04) Technology Commercialization Challenges (00:11:30) Public vs. Private Market Dynamics (00:15:32) Growth Investing and Competitive Dynamics (00:22:34) History and Resilience of TCV (00:26:32) Understanding the Firm's Investment Lifecycle (00:27:06) Evolution of Sourcing Strategies (00:28:33) The Role of Data Intelligence in Sourcing (00:29:41) Internal Investment Process at TCV (00:34:31) Challenges and Strategies in Long-term Investments (00:41:15) Reflections on the Investment World (00:43:48) Personal Insights and Final Thoughts

My guest today is Dinakar Singh. Dinakar is the founder and CEO of Axon, the family office successor to TPG-Axon, which was a successful global long-short hedge fund. We wanted to share his story on Father’s Day to honor the person and the dad that Dinakar is. He shares one of the most extraordinary stories at the intersection of finance and medicine I've ever encountered. This conversation explores the highest-stakes investment themes—timing, concentrated conviction, exceptional team building, and deploying resources toward outcomes that matter most. I will let him tell you his story. Please enjoy my conversation with Dinakar Singh. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠ here.⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠ Ramp⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠ Ridgeline⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠ AlphaSense⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:06:17) The Diagnosis and Initial Reactions (00:07:29) Understanding SMA and the Scientific Challenge (00:09:15) The Drive to Fund Research and Find a Cure (00:14:10) Building a Virtual Company for Drug Development (00:19:02) Breakthroughs and the First Approved Drugs (00:24:16) Personal Reflections and the Impact of the Journey (00:40:25) Challenges in the Biotech Industry and Future Hopes (00:46:43) The Kindest Thing Anyone Has Ever Done For Dinakar

My guest today is Bill Gurley. Bill was the general partner at Benchmark Capital. He joins me for his sixth time on Invest Like the Best with his most comprehensive market analysis yet, examining the realities reshaping venture capital. Bill tackles the uncomfortable math underlying today's venture returns, with companies staying private for far longer. He also walks through why no one—from GPs to LPs to founders—has proper incentives to mark assets accurately, creating a system-wide coordination problem. And, we dig into the investment implications of AI as a platform shift, ranging from evaluating AI revenue quality to international competitive dynamics. Bill offers crucial perspective on playing the game both as it exists today and as it may evolve. Please enjoy my conversation with Bill Gurley. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠⁠ here.⁠⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠⁠ Ramp⁠⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠⁠⁠ Arcana. Arcana is the world’s most advanced portfolio intelligence platform, trusted by institutional investors managing trillions in AUM — including market neutral, long-short, long-only, and capital allocators. Arcana enables portfolio managers, risk teams, analysts, and CIOs to drill into exposures and idio, construct optimal portfolios, and decompose performance at incredible granularity. Visit arcana.io to request a demo and learn more. ----- 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 (00:05:23) State of the Union: Venture Capital Edition (00:07:58) The Rise of Mega VC Funds (00:09:38) Zombie Unicorns: The Overvalued Giants (00:17:29) The IPO and M&A Market Stalemate (00:24:08) The AI Wave and Its Impact (00:26:03) Private Markets and LP Liquidity Issues (00:29:57) The Future of Capital Markets (00:37:49) Advice for Founders in a Changing Landscape (00:39:27) The High-Stakes Game of Capital Battles (00:41:35) AI: The New General Purpose Technology (00:42:57) Challenges and Opportunities in AI Revenue Models (00:44:37) The Role of Founders in the AI Revolution (00:46:44) The Impact of Time and Liquidity on Venture Capital (00:50:35) Navigating the Future of Venture Capital (00:58:45) International Dynamics in the AI Race (01:13:58) Advice for Founders in the AI Era

Today, we are dropping a special episode in the Invest Like the Best Feed. 50X is back, a fan favorite series from Will Thorndike and the team at Compounding Labs. Will's book, "The Outsiders," is one of the best business and investing books that you'll find. You'll hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.Season two features Asurion. Colossus is excited to partner with Will as he sits down with the management and investors behind this legendary investment. We kick off this special drop with a short interview that I did with Will on everything he learned studying this business, followed by the full three-part series. Learn more and dive into our research at ⁠50xpodcast.com⁠ —- This episode is brought to you by⁠⁠ Ramp⁠⁠. 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 to sign up for free and get a $250 welcome bonus. — This episode is brought to you by ⁠Oberle⁠. Oberle is a specialty insurance brokerage providing insurance services to search funds, independent sponsors, family offices, and private equity firms. Oberle supports its clients with a comprehensive insurance due diligence covering a wide range of items, including commercial insurance, Employee Benefits, key person life insurance, and reps and warranty coverage. Additionally, Oberle has a thriving personal lines practice, designed for entrepreneurs seeking a higher-level service and expertise when it comes to insuring one’s home, vehicles, and valuables. If you’re interested in connecting with the Oberle team: ⁠https://oberle-risk.com/50x⁠ — This episode is brought to you by ⁠System Six⁠, a searcher-owned outsourced bookkeeping and accounting services firm that has been a great partner to us at Compounding Labs. With the right modern tools and a strong team, System Six will eliminate headache for you and give you time back so you can focus on growing your business. Whether you're a CEO or CFO stuck in the weeds, or an investor trying to support your CEOs and portfolio companies, reach out to hello@systemsix.comand mention the podcast for your first month of ongoing bookkeeping free. —- 50X is a property of Colossus, LLC. For more episodes of 50X, visit⁠⁠⁠ joincolossus.com/episodes⁠⁠⁠. Editing and post-production work for this episode was provided by The Podcast Consultant (⁠⁠⁠https://thepodcastconsultant.com⁠⁠⁠). Follow us on Twitter: @50Xpodcast | @joincolossus Show Notes (00:00:00) Welcome to 50X (00:04:52) Patrick interviews Will Thorndike (00:18:16) The Early Days (‘95-‘01) with Kevin Taweel (01:24:44) The Flywheel Era (‘01-‘07) with Kevin Taweel (02:24:32) Retracing the Path to 100 times 50x with Irv Grousbeck

My guest today is John Zito. John is the Co-President of Apollo Global Management. He shares how they've quietly built one of the most important financial institutions of our time, originating over $250 billion annually. John's thesis on the convergence of private and public markets - and Apollo's positioning to capture 100% of client portfolios rather than just alternatives allocations - offers a fascinating glimpse into where institutional investing is heading. We discuss the cultural and strategic elements that drive John, Apollo’s merger with Athene, the idea of artistry at scale, and the evolution of capital markets. Please enjoy my conversation with John Zito. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠⁠ here.⁠⁠⁠ ----- This episode is brought to you by⁠⁠⁠ Ramp⁠⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠⁠⁠ Ridgeline⁠⁠⁠⁠. 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 to learn more about the platform. – This episode is brought to you by⁠⁠⁠ AlphaSense⁠⁠⁠. 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 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). Show Notes: (00:00:00) Welcome to Invest Like the Best (00:05:55) The Rise of Apollo and Credit Markets (00:08:05) Innovations in Asset Management (00:11:42) The Role of the US in Global Capital Markets (00:15:26) The Future of Asset Management and Investment Strategies (00:21:03) The Impact of Interest Rates on Investment (00:25:27) Apollo's Business Model and Growth (00:25:17) The Changing Landscape of Private Markets (00:46:03) Apollo's Culture and Vision (00:47:54) The Importance of Company Culture (00:52:52) The Future of Private and Public Markets (00:57:50) Building a Great Origination Platform (01:02:03) Exciting Deals and Personal Stories (01:14:47) The Role of AI and Future Opportunities (01:22:16) Maintaining Company Culture Amidst Change (01:24:06) The Kindest Thing Anyone Has Ever Done For John

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. In the midst of her transition to OpenAI, we are spotlighting the force that is Fidji Simo. She is the former CEO of Instacart and 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. For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by ⁠WorkOS⁠. WorkOS is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. With a single API, developers can implement essential enterprise capabilities that typically require months of engineering work. By handling the complex infrastructure of enterprise features, WorkOS allows developers to focus on their core product while meeting the security and compliance requirements of Fortune 500 companies. Visit ⁠WorkOS.com⁠ to Transform your application into an enterprise-ready solution in minutes, not months. ----- 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 (00:00:00) Welcome to Invest Like the Best (00:03:51) 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 (00:46:58) The possibility of becoming the major software platform for most retailers (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 (01:11:10) The future of AI personalities and customizing your shopping experience (01:12:35) The kindest thing anyone has ever done for her

My guest today is Graham Weaver. My guest today is Graham Weaver. Graham is the founder of Alpine Investors, a large private equity firm targeting an interesting market inefficiency. Alpine focuses on the thousands of $20 million revenue businesses whose baby boomer owners want to retire, but lack succession plans. Alpine buys companies and installs 28-year-old military veterans and top MBA graduates as CEOs, leveraging 25 years of intellectual property on how young executives can successfully run established businesses. Alpine's CEO-in-training program is now the most applied-to job at Harvard, Stanford, and Kellogg business schools. We discuss the past, present and future of their unique approach. Please enjoy my conversation with Graham Weaver. For the full show notes, transcript, and links to mentioned content, check out the episode page⁠⁠ here.⁠⁠ ----- This episode is brought to you by⁠⁠ Ramp⁠⁠. 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 to sign up for free and get a $250 welcome bonus. – This episode is brought to you by⁠⁠ AlphaSense⁠⁠. 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 and experience firsthand how AlphaSense and Tegus help you make smarter decisions faster. – This episode is brought to you by⁠⁠ Ridgeline⁠⁠. 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 to learn more about the platform. ----- 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 (00:05:13) The Journey to Private Equity (00:06:59) Early Influences and Personal Growth (00:09:54) The Power of Wrestling and Rowing (00:11:45) Choosing Your Path and Making Decisions (00:14:48) College Goals and Rowing Success (00:18:05) Lessons from Early Business Ventures (00:26:24) Founding Alpine and Early Challenges (00:34:46) Core Beliefs and Talent Development (00:39:07) Fun Board Meetings and Team Dynamics (00:40:42) Platform Building 101 (00:44:08) Talent and Training Programs (00:49:12) Employee and Customer Engagement (00:52:27) Financial Outcomes and Asymmetric Returns (00:55:52) Incentivizing Young CEOs (01:00:26) The Role of Emotional Intelligence (01:02:45) The Alpine CEO in Training Program (01:03:40) Teaching at Stanford and Influential Mentors (01:07:58) Helping Students Find Their Passion (01:10:22) Visualizing Your Future Self (01:11:19) Scalability of Coaching (01:12:15) Personal Growth Through Teaching (01:16:16) The Role of Executive Coaching (01:24:45) Lessons from a Bad Deal (01:31:50) Daily Routines and Success (01:36:13) The Future of Private Equity (01:35:24) Unleashing Heroes at Alpine (01:38:09) The Journey of Building Alpine (01:41:31) The Kindest Thing Anyone Has Ever Done For Graham