Invest Like the Best with Patrick O'Shaughnessy

My guest today is Kareem Amin, co-founder and CEO of Clay. Clay has become one of the fastest-growing software companies of the last few years, valued at over four billion dollars. It helps companies find their best customers and reach them at scale. But this conversation is about a lot more than Clay. Kareem is one of the most original thinkers I know. We talk about the statues he keeps at the center of how he runs Clay — truth, justice, and courage — and what those words demand of him in practice. We talk about risk, ambition, and what he learned about both on a ten-day silent meditation retreat. I've had a lot of conversations with Kareem over the years. This is one I'll remember. Please enjoy this unique conversation with Kareem Amin. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠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. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Invest Like the Best listeners get a special offer of $1,000 off Vanta when you go to ⁠vanta.com/invest⁠. ----- WorkOS⁠ is the infrastructure B2B and AI-native companies use to sell to enterprise. It covers everything enterprise security requires: SSO, SCIM, RBAC, Audit Logs, AI governance, and more. Trusted by 2,000+ fast-growing companies, including OpenAI, Anthropic, Cursor, and Vercel. ----- Rogo is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠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. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgelineapps.com⁠. ----- 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 (00:02:29) Kareem Amin (00:03:07) Clay's Origin (00:10:50) Truth, Courage and Justice (00:16:09) Adulation (00:18:28) Risk, Courage & Self-Respect (00:21:14) Jony Ive & Steve Jobs (00:21:42) Role of Introspection (00:23:08) Lack to Wholeness (00:27:27) The Day Five Insight (00:29:57) Running a Startup Unusually (00:34:41) Learning from Magicians (00:36:27) Music's Role in Your Life (00:39:38) Making People Feel Something New (00:41:20) Vision in Company Building (00:44:29) Wealth & What It's Taught You (00:47:40) All Problems Are Communication Problems (00:52:14) Death Doula & Scaling (00:55:06) The Kindest Thing

My guest today is Dan Sundheim. Dan is the founder and CIO of D1 Capital Partners. He thinks about markets and businesses constantly, and has built a career entirely around that obsession. He manages over $30B across both public and private markets, with investments in SpaceX, OpenAI and Anthropic, and a public portfolio of names you may never have heard of. Dan shares the story of the short case he wrote on Orthodontic Centers of America and posted on Value Investors Club, which crashed the stock, and helped him land his first job. He shares why he backed Anthropic at a moment when many people told him it was the Lyft to OpenAI’s Uber, what reading Dario Amodei’s essays reminded him of Jeff Bezos, and how he thinks about LLM business models through the lens of Netflix and Spotify. We spend time on the extraordinarily stressful moment in early 2021 when GameStop hit the firm, and what Dan believes is the single biggest tail risk facing the global economy right now. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠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. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠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. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- 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 (00:02:43) Intro: Dan Sundheim (00:03:58) The State of Public & Private Investing (00:07:32) Investing in OpenAI and Anthropic (00:10:22) LLMs Business Model (00:14:13) How LLMs are like Netflix and Spotify (00:17:08) Focus v. Scope (00:22:43) The Bear Case for Hyperscalers (00:26:36) The Software Sell-Off (00:31:08) If Scaling Laws Stopped (00:32:18) Advice to a 12-Year-Old Investor (00:33:54) GameStop: D1’s Darkest Hour (00:37:14) The Pivotal Dinner with LPs (00:40:56) Staying Calm and Confident (00:42:08) Economic Optimism vs. Societal Uncertainty (00:44:26) Investing on SpaceX and Rivian (00:48:09) Why Dan Loves Shorting (00:48:51) Sources of Inefficiency in Today’s Markets (00:51:45) The Importance of Loyalty (00:53:11) Dan’s Group Chat for Founders (00:55:39) What Motivates Dan (00:57:28) Posting on Value Investors Club (01:01:46) What Dan Learned at Viking (01:04:22) The Beauty of Art (01:06:49) Under-appreciated Parts of the Global Economy (01:08:00) The US-China-Taiwan Collision Course (01:12:10) Good Leaders vs. Good Businesses (01:13:15) The Kindest Thing

My guests today are Alex Behring and Daniel Schwartz, Co-Managing Partners of 3G Capital. 3G has built one of the most distinctive firms in investing around a simple idea: there are only a handful of truly great businesses and even fewer great CEOs. Their model is to raise capital with the intention of making just one investment per fund, commit meaningful amounts of their own money alongside their partners, and focus all of their time and best people on that single opportunity. Their approach has produced a series of iconic deals, including Burger King, Tim Hortons, Hunter Douglas, and Skechers. They have also become known for developing talent early, giving young leaders real responsibility and ownership, and holding an unusually high bar. I highly recommend you read our in-depth profile on them and 3G Capital. They gave our managing editor Dom Cooke unprecedented access and the outcome is an excellent profile about the fifty year history of 3G and how the model began with Jorge Paulo Lemann in Brazil. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠. ----- Become a Colossus member to get our quarterly print magazine and private audio experience, including exclusive profiles and early access to select episodes. Subscribe at ⁠colossus.com/subscribe⁠. ----- ⁠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. ----- Trusted by thousands of businesses, ⁠Vanta⁠ continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit⁠⁠ ⁠WorkOS.com⁠⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠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. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- 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 (00:02:43) Episode Intro: Daniel Schwartz & Alex Behring (00:04:03) The “One Investment Per Fund” Model (00:08:22) Great Businesses Own the Relationship With Their Customers (00:11:23) The Unique Structure of 3G Capital (00:13:36) How a Transaction Takes Shape (00:17:04) Why Hunter Douglas Was Appealing (00:21:34) The Advantages of Staying Small (00:23:58) Alex’s Railroad Story (00:26:36) Ownership is Key (00:30:26) Centralize the What, Decentralize the How (00:31:55) The “Burger King is Run by Children” Story (00:34:21) Negotiating with Tim Hortons (00:40:39) Never Compromise on Quality (00:42:01) Talent Over Tenure (00:50:26) 3G’s Operating System (00:57:14) When a Brand is Bigger than the Business (01:00:17) Why Burger King Was Undervalued (01:03:15) The Beauty of the Franchise Model (01:06:24) Kraft Heinz: A Case Study in Concentration Risk (01:09:07) Skechers: Great Product Meets Great Distribution (01:16:07) Finding Forever Businesses (01:17:52) Zero-Based Budgeting & When It Works (01:21:10) The Current State of Capital Markets (01:25:23) Misconceptions About 3G (01:32:01) The Power of Patience (01:33:39) The Kindest Thing

My guest today is ⁠Gokul Rajaram⁠, Founding Partner at Marathon Management. Gokul is one of the most prolific product builders and investors of the last twenty years. He has built the core ad and product businesses at Google, Facebook, Square, and DoorDash, working at each company during its most formative scaling periods. Alongside his operating career, Gokul has invested in more than 700 companies, giving him an unusually broad view into how products are built and scaled. This conversation is about how product building is changing with AI. We discuss the one thing Gokul believes is truly future-proof in AI, why companies like Zendesk and Slack are more exposed than Salesforce or NetSuite, and the only sources of defensibility. We also talk about everything Gokul has learned from helping build the most important ads businesses, including the only three ways an ad business can make money, how those constraints shape product decisions, and what consumer behavior change threatens every major platform. Gokul shares lessons from working closely with Larry and Sergey, Mark Zuckerberg, Jack Dorsey, and Tony Xu. 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 ⁠⁠Vanta⁠. Trusted by thousands of businesses, Vanta continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit ⁠vanta.com/invest⁠. -----⁠ Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- 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. Visit⁠ ⁠WorkOS.com⁠⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠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. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- 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 (00:00:53) Meet Gokul Rajaram (00:02:05) How Product Development is Changing with AI (00:07:32) Philosophy of Product Management (00:10:19) What is Future-Proof in AI Era (00:11:25) Building AI Applications Today (00:15:03) Systems of Record vs Agent Companies (00:16:58) Which Legacy Software Companies Are Most Exposed (00:22:15) Stickiness in the AI Era (00:24:10) Learning from Larry Page and Sergey Brin (00:28:15) Learning from Mark Zuckerberg (00:31:31) Learning from Jack Dorsey (00:35:40) The Art of Great Product Design (00:36:49) Weekly CEO Communication (00:40:27) Three Ways to Succeed in Advertising (00:44:27) What Should Scare Major Ad Platforms (00:48:24) North Star Metrics (00:50:09) Self-Serve Products (00:54:50) Careers in the AI Era (00:59:03) Stay Long Enough to Have Impact (01:00:10) Founder Authenticity and Superpowers (01:02:21) Navigating the Idea Maze (01:03:42) Role of Boards (01:06:31) Excellence in Customer Acquisition (01:09:11) The Kindest Thing

My guests today are Tom Digan and Greg Stewart. Tom is the co-founder of Ladder, and Greg is its CEO. Ladder was my first angel investment. What followed over the next seven years is one of the most unlikely and dramatic business stories I’ve been a part of. Today, Ladder is the number one grossing fitness app in the App Store, approaching $100M in ARR with more than 300,000 paying members. But the path from near death to dominance involved debt collectors, leadership changes, and a full reset during the pandemic. Tom and Greg built Ladder by being relentlessly empirical about their customers, ruthless about prioritization, raising money wherever they could, and doing whatever it took when most founders would have quit. We cover the messy early years when survival meant negotiating creditors, how they found PMF by reading thousands of app store reviews, and how they built a TikTok growth engine with no performance marketing experience. They share their long-term vision for becoming the category winner for health and fitness and the impact of AI and GLP-1s on their business. This is a conversation about how hard it really is to build something valuable, told by two people who lived through all of it. For the full show notes, transcript, and links to mentioned content, check out the episode page ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠here⁠⁠⁠⁠⁠⁠⁠⁠.⁠⁠⁠⁠⁠⁠⁠⁠ ----- ⁠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. ----- ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Vanta is trusted by thousands of businesses and continuously monitors your security posture and streamlines audits so you can win enterprise deals and build customer trust without the traditional overhead. Visit vanta.com/invest. ----- ⁠Rogo⁠ is the AI platform for finance. They're building agents for Wall Street that are trained to understand how bankers and investors actually do work: from diligence and modeling, to turning analysis into deliverables. To learn more, visit rogo.ai/invest. ----- ⁠WorkOS⁠ is a developer platform that enables SaaS companies to quickly add enterprise features to their applications. Visit ⁠WorkOS.com⁠ to transform your application into an enterprise-ready solution in minutes, not months. ----- ⁠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. Visit⁠ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ridgeline.ai⁠. ----- 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 (00:04:26) Episode Intro (00:05:45) Ladder: The #1 Fitness App (00:09:28) The Messy, Early Years (00:14:47) Sponsors (00:16:20) The Darkest Point (00:18:17) Why Greg Joined Ladder (00:19:45) The Turning Point: Ladder 2.0 (00:21:57) The Key to Negotiating with Creditors (00:23:16) Fundraising Challenges and Strategies (00:25:50) Developing Ladder Teams (00:31:31) Listen to Your Customers (00:32:57) Launching Nutrition (00:38:53) Sponsors (00:39:31) Don’t Listen to Investors on Product Feedback (00:40:18) The Cave Process (00:43:13) Crossing the Chasm (00:43:53) How to Crack TikTok (00:51:10) The Content Frontier (00:52:07) Controlled Bets at Scale (00:54:19) Why you should Build a B2C Company (00:57:37) The Impact of AI and GLP-1s (01:02:32) Sponsors (01:02:53) Staying Focused on the Core Product (01:05:00) Building the System of Record for Health and Fitness (01:09:45) What It’s Like Talking to Investors Now (01:12:32) The Kindest Thing