Invest Like the Best with Patrick O'Shaughnessy

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by Colossus | Investing & Business Podcasts

Conversations with the best investors and business leaders in the world. We explore their ideas, methods, and stories to help you better invest your time and money. Hear stock market and boardroom insights you can't find anywhere else. If you're a professional investor, CEO, entrepreneur, or business strategist, this is for you. Explore all our episodes and learn more at https://www.joincolossus.com

8 episodes summarized

Episodes

Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457]

Ben Horowitz - Backing America’s Future - [Invest Like the Best, EP.457]

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My guest today is Ben Horowitz, the co-founder of Andreessen Horowitz. Since its founding in 2009, a16z has grown into one of the most influential firms in venture capital, reshaping how technology companies are funded and how power and ideas move through Silicon Valley and around the world. This conversation focuses on sides of Ben’s story you don’t often hear. Ben reflects on the people who shaped him, including Nas, Andy Grove, and his father, and shares why he chose to personally fund new technology for the Las Vegas Police Department. We also talk about how he thinks about a16z’s responsibility in shaping the trajectory of America, the scale of his ambition for the firm, and what he sees as the biggest risk facing the country. Please enjoy this great and unique conversation with Ben Horowitz. 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.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at 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. ----- 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. 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 (00:02:43) Episode Intro: Ben Horowitz (00:03:27) The State of America Right Now (00:06:06) How Policy Could Destroy America (00:08:29) AI Changes the Laws of Company Building and Investing (00:11:40) Why AI Researchers are Paid $100M (00:13:16) Thoughts on Growing Inequality (00:18:07) Societal Challenges Due to AI (00:19:56) Ben’s Scope of Ambition for the Next 20 Years (00:22:48) Andy Grove’s Influence on Ben (00:27:44) Starting Andreessen Horowitz (00:32:53) Early Mistakes (00:36:17) What Capital Markets Are Missing (00:37:44) Why VC and Not PE (00:40:03) Tradeoffs with Scale (00:41:10) A Culture is Not a Set of Ideas, it’s a Set of Actions (00:43:05) Lessons from His Father (00:45:03) Exciting Use Cases of AI (00:46:46) Ben’s Friendship with Nas (00:50:05) Funding New Technology for the Las Vegas Police Department (00:54:07) The Kindest Thing

February 3, 202655:51
Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

Gokul Rajaram - Lessons from Investing in 700 Companies - [Invest Like the Best, EP.456]

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My guest today is ⁠Gokul Rajaram⁠. Gokul is one of the most prolific product builders 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. Please enjoy my conversation with Gokul Rajaram. 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.  ----- This episode is brought to you by ⁠Rogo⁠. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at ⁠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. ----- 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. 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 (00:00:53) 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

January 29, 20261:16:02
Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

Patrick O’Shaughnessy - Creating on Principle - [Invest Like the Best, EP.455]

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This week is a special episode. Only David Senra could get me to be on the other side of the mic. Because I don’t plan on being interviewed often, I wanted to share this conversation, which I so enjoyed, with our audience. It went in a very different direction than I expected. We barely talk about investing or interviewing. Instead, we talk about finding an organizing principle for life, undiscovered talent, and the idea that “the reward for good work is more work.” We also discuss the principles that guide how I think about building Invest Like the Best, Colossus, and Positive Sum. This conversation was originally recorded and released on David Senra, and I wanted to share on the Invest Like The Best feed as well. Please go follow what he’s doing, there’s no one like David. Enjoy! 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.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at 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. ----- 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. 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 (00:04:26) Intro (00:05:14) The Joy of Championing Undiscovered Talent (00:07:33) How One Tweet Changed David's Life (00:10:16) The Upanishads Passage That Shaped Patrick's Worldview (00:15:32) Growth Without Goals  (00:17:24) Why Media and Investing Are the Same Thing (00:33:05) The Search for True Understanding (00:35:36) The Daniel Ek Dinner That Launched David’s Podcast (00:39:02) Making Your Own Recipe From the Ingredients of Great Lives (00:43:46) The Privilege of a Lifetime Is Being Who You Are (00:52:06) Bruce Springsteen (00:57:23) Clean Fuel vs Dirty Fuel: The Source of Your Ambition (01:01:43) The Unfair Advantage of Podcasting (01:04:12) Relationships Run the World (01:11:10) The Origin Story of Invest Like the Best (01:12:45) Building Colossus: Why Start a Magazine in 2025 (01:18:42) People Are More Interested in People Than Anything Else (01:22:12) Hiring Through Output (01:26:23) Learn, Build, Share, Repeat (01:30:01) The Daisy Chain: How Reading Books Led to Everything (01:33:15) Red on the Color Wheel: Sam Hinkie's Observation (01:40:17) Finding Your Superpower and Becoming More Yourself (01:45:06) Repetition Doesn't Spoil the Prayer: Teaching as Leadership (01:48:11) Life's Work: A Lifelong Quest to Build Something for Others (01:52:00) The Ten Roles Game and What Matters Most (01:59:12) Husband, Father, Grandfather (02:01:52) The Kindest Thing

January 20, 20262:06:40
Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]

Tom Digan & Greg Stewart - Building the World’s Best Fitness App - [Invest Like the Best, EP.454]

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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.⁠⁠⁠⁠⁠⁠⁠⁠ ----- 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.  ----- This episode is brought to you by Rogo. Rogo is an AI-powered platform that automates accounts payable workflows, enabling finance teams to process invoices faster and with greater accuracy. Learn more at 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. ----- 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. 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  (00:04:26) 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

January 13, 20261:14:08
David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth - [Invest Like the Best, EP.450]

David George - Building a16z Growth, Investing Across the AI Stack, and Why Markets Misprice Growth - [Invest Like the Best, EP.450]

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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

December 2, 20251:06:01E450
Ari Emanuel - The Anti-AI Bet - [Invest Like the Best, EP.448]

Ari Emanuel - The Anti-AI Bet - [Invest Like the Best, EP.448]

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My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment, and media. He oversees TKO, which includes the UFC and WWE, serves as the Executive Chairman of WME Group, and recently founded MARI, a new company focused on global events and live experiences. At the center of this conversation is Ari's anti-AI bet: as AI makes digital content cheaper and everyday work more automated, he believes the value will increasingly concentrate in live and physical experiences. He explains how he’s building his portfolio around that belief, what defines a great live experience, and how he thinks about AI’s impact on content and IP. Ari is best known as a dealmaker, and he shares the principles behind his success – relentless follow-up, over-communication, velocity, and an obsession with making things happen – and how those things become the operating system he uses today. If you’re listening to this, I recommend watching the video of this interview. Ari’s energy is constant and visceral, and gives a different dimension to this episode. Please enjoy my conversation with Ari Emanuel.  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 (00:04:20) Meet Ari Emanuel (00:05:32) The UFC Story (00:10:03) Mindset, Relentlessness, and Emotional Endurance (00:13:52) AI’s Impact on Content and Distribution (00:18:44) Value, Taste, and the Future of Content (00:19:43) The Anti-AI Bet: Live Events and Experiences (00:22:39) Monetization, User Experience, and the Premium Economy (00:26:21) Building and Scaling Live Event Businesses (00:27:16) Boxing and the Business of Live Entertainment (00:28:45) Lessons from Dana White and Dealing with Dyslexia (00:31:32) Getting a Job at CAA and How to Be a Successful Agent (00:35:50) Ari’s Operating System (00:38:04) Lessons from Egon Durban (00:39:36) Betting on Himself and Elon (00:43:16) Who Wants to be Normal?! (00:44:23) The Art of Dealmaking (00:48:58) Money, Family, and Learning from Mistakes (00:52:45) The Future of Tech, Media and Content (00:57:32) Concerns and Excitement about the Future (01:00:16) Art (01:01:01) The Kindest Thing

November 19, 20251:01:24E448
Wolfgang Hammer - The Power of Story - [Invest Like the Best, EP.447]

Wolfgang Hammer - The Power of Story - [Invest Like the Best, EP.447]

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My guest today is my friend Wolfgang Hammer. Wolfgang is a successful film producer and executive who helped create House of Cards and ran several major studios, including Lionsgate, CBS Films and Miramax. He’s now building a new kind of film studio with support from Mitch Lasky and Marc Andreessen. Wolfgang also helps founders and CEOs use storytelling to better understand what they do, and why it matters. In many ways, this conversation is a manual for how to find that story and communicate it in a way that resonates. Wolfgang shares the questions and tools he gives leaders to help them do the same. Our conversation explores how stories work, what great ones have in common, and why understanding your own story can be transformative. We talk about the three layers every story must have — the external, the emotional, and the philosophical — and how they apply to building companies and leading people. So many CEOs — at both startups and massive Fortune 100 companies — have Wolfgang to thank for changing how they think and talk about their business, and I hope this episode gives you the tools to do the same. Please enjoy my conversation with the great Wolfgang Hammer. 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 (00:04:22) Meet Wolfgang Hammer (00:05:25) How to Tell Your Story (00:07:10) The Three Layers of Every Story (00:10:02) What a Good Story Unlocks (00:12:39) Applying Storytelling Principles to Business (00:17:24) Lessons From Filmmaking for CEOs (00:22:46) Everything is a Death Project (00:25:03) What Makes a Great Story (00:30:54) The Role of Status (00:31:48) Building a New Kind of Film Studio (00:35:20) The Version of Your Story so Big it Terrifies You (00:39:34) Grand Unified Theory (00:42:03) The Kindest Thing

November 11, 202541:32E447
Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]

Jesse Zhang - Building Decagon - [Invest Like the Best, EP.443]

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My guest today is Jesse Zhang. Jesse is the co-founder and CEO of Decagon, one of the fastest-growing AI customer service companies. Decagon provides a centralized AI engine to auto-resolve issues at any time, in every language, and across every channel. Jesse shares his systematic approach to finding product-market fit by asking potential customers exactly how much they'd pay for solutions. We explore why customer service and coding have emerged as the two clearest AI use cases for enterprises, and the key business and technical factors behind Decagon's momentum. We discuss the intense competitive dynamics of building in AI today, strategic decisions around building proprietary models, and deploying AI agents at enterprise scale. Please enjoy my conversation with Jesse Zhang. 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 (00:05:49) Building a Company in a Competitive Market (00:07:26) Personal Background and Competitive Upbringing (00:10:32) Challenges and Lessons from Previous Ventures (00:12:21) Ideation and Customer Discovery Process (00:19:31) Developing and Refining AI Customer Service Agents (00:32:26) Voice AI and Future Prospects (00:38:20) Utilizing Customer Interaction Data (00:39:59) Frameworks for Implementing AI in Business (00:41:48) Evaluating the ROI of Coding Agents (00:42:53) The Future of Company Agents (00:45:15) Brand Personality in AI Agents (00:47:48) Investor Interest in AI Companies (00:54:32) The Competitive Landscape of AI Talent (00:57:21) Building Proprietary AI Models (01:10:36) Customer Qualification and Engagement (01:17:27) The Kindest Thing

October 6, 20251:21:12E443