Invest Like the Best with Patrick O'Shaughnessy

Today, I am replaying my conversation with Nick Kokonas, one of my favorites from the show. 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. In this conversation, Nick shares his experience of bringing a business mindset to the restaurant industry. 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 the right way. I felt like this conversation could have gone on for hours and I hope you enjoy it. 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). Timestamps: (00:00) Welcome to Invest Like The Best (03:58) Intro to Nick Kokonas (4:36) – Why it’s so important to own something (6:09) – Make decisions that have outcomes (8:34) – His interest in the restaurant business (10:28) – Why restaurants are so tough (13:39) – How their business mindset changed their running of the restaurant (16:09) – Words they would avoid in the restaurant (17:53) – Asking the right questions in the restaurant business (22:14) – Importance in taking the right risks (23:36) – Coming up with innovative strategies for ticketing, selling meals ahead of time, and dynamic pricing (31:42) – Can dynamic pricing be extended to other businesses (32:54) – Origin of Tock (37:51) – Early days of Tock and identifying the right customers/challenges (43:07) – Importance of the first customer (45:56) – The typical restaurant business model (50:57) – Lessons from Tock and the importance of knowing what you’re selling (55:21) – Lessons from publishing (57:18) – Other aspects of business that people know but do nothing about (1:01:53) – Their response to Covid and lessons learned (1:09:17) – The real impact to the food delivery companies (1:10:58) – How businesses communicate their end processes to their customers (1:15:41) – The Kindest Thing

Ric Elias - The Art of Living Well - [Invest Like The Best, CLASSICS] 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. Ric Elias is the CEO and co-founder of Red Ventures, which has a portfolio of fast-growing digital businesses like Lonely Planet, The Points Guy, Bankrate, and large investments in a variety of other businesses across industries. He began the business in 2000 and has grown it to now a global company with thousands of employees. Ric walks us through the early struggles that have led to what is now a flourishing investing platform, but mostly this episode is a masterclass on cultural values and philosophies that transcend mere financial gain. We discuss the difference between living good and well, the power of forgiveness, and compounding more than just your capital. Ric’s story is one of resilience, humility, and grace. His story about being in the front row of the plane that Captain Sully landed in the Hudson is singular and very moving. Please enjoy my conversation with Ric Elias. 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 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 ----- Editing and post-production work for this episode was provided by The Podcast Consultant (https://thepodcastconsultant.com). Timestamps: (00:00:00) Welcome to Invest Like the Best (00:02:00) Meet Ric Elias (00:02:49) Chasing the Big Dream (00:05:38) Understanding Red Ventures: Origin and Evolution (00:10:25) Operational Success and Company Culture (00:25:30) Reflections on Money and Personal Well-being (00:28:49) The Difference between Good and Well (00:32:55) The Hudson River Plane Crash Experience (00:42:37) Reconnecting with Puerto Rico and Reviving the Basketball Team (00:45:07) Underdogs to Champions (00:48:09) How to Build Trust and Culture (00:52:29) Reflections on Leadership (00:56:12) The Role of Confidence and Courage (00:59:38) The Value of Family and Friendships (01:01:57) The Pursuit of Purpose Over Profit (01:06:52) Recruitment and Company Culture (01:10:07) Reflecting on Success (01:14:33) The Importance of Pace and Speed (01:16:23) Other Business Philosophies (01:23:17) The Kindest Thing

My guest today is Henry Ellenbogen, founder and Managing Partner of Durable Capital Partners. Henry built his reputation at T. Rowe Price, where he led the New Horizons Fund and turned it into one of the best-performing small-cap growth portfolios in the country. In 2019, he left to start Durable. His philosophy is grounded in a simple belief that great investing is about understanding people and change. Henry has spent his career studying the rare 1% of companies that drive nearly all long-term returns . Durable’s edge comes from being able to tell the difference between a company that is failing and one that is transforming. Henry often talks about “Act II” teams – founders who take the lessons from their first company and apply them to a new frontier. Durable itself is his Act II. In our latest Colossus profile, Managing Editor Dom Cooke traces Henry’s story and specifically how he became one of the most influential investors of the 21st century, having learned from founders like Jeff Bezos and John Malone in the early part of his career. I always hear the same thing from founders who’ve met Henry: “he understood my business faster than anyone”. The thing that sticks with me from our conversation and Dom’s profile is just how much he loves 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 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 (00:04:00) Meet Henry Ellenbogen (00:05:29) Origin of Henry’s Investment Philosophy (00:08:12) Identifying the 1% of Great Companies (00:12:53) Patterns of Successful Compounders (00:20:34) Act Two Entrepreneurs and Teams (00:25:43) Building Durable Capital: Henry’s Act Two (00:30:11) Dollar Cost Averaging Up Strategy (00:35:02) Market Structure and Agency Problems (00:38:26) Impact of Quant Funds and Short-Term Capital (00:42:21) AI as Transformative Change (00:45:30) How Affirm Uses AI (00:48:23) Amazon’s Cost Curve Advantage (00:51:48) Leadership Through Change (00:56:54) Robotics and Physical Kaizen (01:01:29) Favorite Types of Competitive Advantages (01:05:25) Investment Memo Structure (01:09:21) 2022 CEO Tour on Market Transition (01:19:18) Hiring and Developing Talent (01:24:09) Making Colleagues Better (01:27:56) Being Intellectually Honest in Investing (01:29:11) Lessons from Success (01:33:04) Case for Going Public (01:36:32) Netflix Transition Example (01:41:29) Two Types of Greatness (01:45:42) The Kindest Thing

My guest this week is Gavin Baker. Gavin is the managing partner and CIO of Atreides Management, and he has been on the show many times before.  I will never forget when I first met Gavin in 2017. I find his interest in markets, his curiosity about the world to be as infectious as any investor that I've ever come across. He's encyclopedic on what is going on in the world of technology today, and I've had the good fortune to host him every year or two on this podcast. Gavin began covering Nvidia as an investor more than two decades ago, giving him a rare perspective on how the company – and the entire semiconductor ecosystem – has evolved. A lot has changed since our last conversation a year ago, making this the perfect time to revisit the topic. In this conversation, we talk about everything that interests Gavin – Nvidia’s GPUs, Google’s TPUs, the changing AI landscape, the math and business models around AI companies and everything in between. We also discussed the idea of data centers in space, which he communicates with his usual passion and logic. In closing, at the end of this conversation, because I've asked him my traditional closing question before, I asked him a different question, which led to a discussion of his entire investing origin story that I had never heard before. Because Gavin is one of the most passionate thinkers and investors that I know, these conversations are always amongst my most favorite. I hope you enjoy this latest in the series of discussions with Gavin Baker. 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 (00:04:00) Meet Gavin Baker (00:06:00) Understanding Gemini 3  (00:09:05) Scaling Laws for Pre-Training (00:12:12) Google v. Nvidia (00:14:53) Google as  Lowest Cost Producer of Tokens (00:25:18)  AI Can Automate Anything that can be Verified (00:30:23) The AI Bear Case: Edge AI (00:33:43) Going from Intelligence to Usefulness (00:36:34) AI Adoption in Fortune 500 Companies (00:41:40) Frontier Models and Industry Dynamics (00:48:05) China’s Mistake and Blackwell’s Geopolitical Leverage (00:50:11) OpenAI’s Code Red (00:52:50) Data Centers in Space (00:58:00) Cycles in AI (01:01:14) Power as a Bottleneck (01:03:51) AI Native Entrepreneurs (01:05:41) Semiconductor VC (01:09:26) The Mistake the SaaS Industry is Making (01:14:53) Series of Bubbles (01:16:31) Whatever AI Needs, It Gets (01:17:53) Investing is the Search for Truth (01:18:37) Gavin’s Investing Origin Story

My guest today is David George. David is a General Partner at Andreessen Horowitz, where he leads the firm’s growth investing business. His team has backed many of the defining companies of this era – including Databricks, Figma, Stripe, SpaceX, Anduril, and OpenAI – and is now investing behind a new generation of AI startups like Cursor, Harvey, and Abridge. This conversation is a detailed look at how David built and runs the a16z growth practice. He shares how he recruits and builds his team a “Yankees-level” culture, how his team makes investment decisions without traditional committees, and how they work with founders years before investing to win the most competitive deals. Much of our conversation centers on AI and how his team is investing across the stack, from foundational models to applications. David draws parallels to past platform shifts – from SaaS to mobile – and explains why he believes this period will produce some of the largest companies ever built. David also outlines the models that guide his approach – why markets often misprice consistent growth, what makes “pull” businesses so powerful, and why most great tech markets end up winner-take-all. David reflects on what he’s learned from studying exceptional founders and why he’s drawn to a particular type, the “technical terminator.” Please enjoy my conversation with David George. 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 (00:04:00) Meet David George (00:03:04) Understanding the Impact of AI on Consumers and Enterprises (00:05:56) Monetizing AI: What is AI’s Business Model (00:11:04) Investing in Robotics and American Dynamism (00:13:31) Lessons from Investing in Waymo (00:15:55) Investment Philosophy and Strategy (00:17:15) Investing in Technical Terminators (00:20:18) Market Leaders Capture All of the Value Creation (00:24:56) The Maturation of VC and Competitive Landscape (00:28:18) What a16z Does to Win Deals (00:33:06) David’s Daily Routine: Meetings Structure and Blocking Time to Think (00:36:34) Why David Invests: Curiosity and Competition (00:40:12) The Unique Culture at Andreessen Horowitz (00:42:46) The Perfect Conditions for Growth Investing (00:47:04) Push v. Pull Businesses (00:49:19) The Three Metrics a16z Uses to Evaluate AI Companies (00:52:15) Unique Products and Unique Distribution (00:54:55) Tradeoffs of the a16z Firm Structure (00:59:04) a16z’s Semi-Algorithmic Approach to Selling (01:00:54) Three Ways Startups can Beat Incumbents in AI (01:03:44) The Kindest Thing