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Invest Like the Best with Patrick O'Shaughnessy: Daily Summaries Delivered
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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.
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- Today56 min
Kareem Amin - Re-Enchanting the World - [Invest Like the Best, EP.478]
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: Welcome to Invest Like The Best Kareem Amin Clay's Origin Truth, Courage and Justice Adulation Risk, Courage & Self-Respect Jony Ive & Steve Jobs Role of Introspection Lack to Wholeness The Day Five Insight Running a Startup Unusually Learning from Magicians Music's Role in Your Life Making People Feel Something New Vision in Company Building Wealth & What It's Taught You All Problems Are Communication Problems Death Doula & Scaling The Kindest Thing
- 1 weeks ago1h 11m
Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]
My guest today is Alex Sacerdote, founder of Whale Rock Capital Management. Whale Rock is a technology focused investment firm that manages more than $17 billion across hedge fund, long only, and hybrid strategies. Over the past three years it has been one of the best performing hedge funds, compounding at roughly 44 percent a year. Alex invests through a single lens that he has refined over twenty years. He looks for technology S-curves, durable competitive advantages, and underappreciated earnings power. This conversation is a tour through how he applies that framework right now. We start with his highest conviction position, which is Anthropic, and use it to work through the entire AI stack from chips to models to applications. Please enjoy my conversation with Alex Sacerdote. 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: Welcome to Invest Like The Best Welcome to Invest Like The Best Alex Sacerdote Anthropic: Highest Conviction Position Investing in Private Markets at Scale S-Curves: The Full Framework When to Buy Tech Companies Identifying the Leader from the Pack Anthropic & OpenAI's Competitive Moats AI's Threat to Enterprise Software Network Effects in the Agent Era The Hardware Renaissance: Chips & Infrastructure Why So Few Investors Get This Right Key Risks to the AI Bull Case The Application Layer How AI Is Changing Research at WhaleRock The Role of Investor Networks & Idea Sharing Building a Multi-Product Firm WhaleRock as a Learning Machine The Kindest Thing
- 1 weeks ago1h 7m
Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]
My guest today is Dara Khosrowshahi, the CEO of Uber. Before Uber, Dara ran Expedia for thirteen years. We start with why he took this job in 2017, and a big part of that story is Daniel Ek, who told him that life is not about happiness, it is about impact. We talk about what the chaos felt like on day one, and how his family leaving Iran when he was nine shaped the way he handles pressure today. We spend most of our time on autonomous vehicles and Uber's role as the demand aggregator in a world of physical AI. Dara explains why Uber is a supply-led company, what it will take to win, and why he expects many winners in AVs rather than one. We also discuss Uber's $10 billion in free cash flow, the push toward a single app for everything, and what he has learned from Allen & Co, Barry Diller and Reed Hastings. 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: Welcome to Invest Like The Best Intro to Dara Khosrowshahi How Daniel Ek Convinced Dara to Take the Uber Job Bringing Order to Chaos Managing Stress as a Leader The Chip on His Shoulder Parenting Lessons Mandate for AI Adoption Uber's Role in Physical AI Winning the AV Demand Race Partnering vs. Competing with Waymo AV Success Unlocks New Markets Why Drones Haven't Arrived Yet Regional AV Rollout Differences Uber Eats International Winning Formula Key to Aggregating Supply Well Adding Hotels to Uber Platform Lessons in Marketing at Scale Apps vs. AI Agents in Seven Years What Dara Learned from Barry Diller What Dara Learned from Allen & Co Buybacks vs. Growth Investing Lessons from Reed Hastings The Kindest Thing
- 2 weeks ago1h 3m
Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]
My guest today is Dan Loeb, the founder and CEO of Third Point. Dan started Third Point in 1995 with a few million dollars, and today the firm manages over 24 billion across equities, corporate and structured credit, venture, and insurance. He is best known for his activist work at companies like Sotheby's, Sony, and Yahoo, and for the public letters he has written to boards over the years. What I find most interesting about Dan is how much his approach has evolved across thirty years. He came up as a credit and event-driven investor at Warburg Pincus and Jefferies, built Third Point, then layered in quality investing, thematic technology investing, and now a very large credit business that sits alongside the hedge fund. We cover how he thinks about the AI stack and the companies inside it he believes matter most, the difference between good and bad governance, what FTX taught him about due diligence, the Sony and Sotheby's stories, and the power of writing. Please enjoy my conversation with Dan Loeb. 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: Welcome to Invest Like The Best Dan Loeb Mental Models Information Overload Dan's Identity as an Investor The End of Classic Event-Driven Investing Evolving Strategy Over 30 Years Return Opportunities in Today's Market Sources of Alpha for Fundamental Investors Good vs. Bad Governance Writing as an Investing Tool The Sotheby's Story Activism Opportunities Today Third Point's Evolution to 60% Credit Dan as Sole Portfolio Manager Value Investor Perspective on Today's Market Investing Outside the US The Sony Activism Story Lessons from 30 Years of Investing Danaher and Operational Excellence Building the Insurance Liability Business The FTX Story Leading a Team Through Uncertainty Where Third Point Is Most Contrarian What Makes a Great Analyst Today The Next 10 Years The Kindest Thing
- 3 weeks ago46 min
Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]
My guest today is Darren Farber, and this is his second appearance on the show. Darren is a Managing Partner of Albion River, a defense-focused investment firm and he previously served as a special advisor to the Deputy Under Secretary of Defense. We recorded this conversation in the middle of the Iranian contingency, and we spent most of our time on what winning actually means in a theater like Iran. We discuss why magazine depth matters for the American industrial base, lessons from Ukraine, and what the rise of neo-prime defense companies will require from Congress. Please enjoy my second conversation with Darren Farber. 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: Welcome to Invest Like The Best Darren Farber Intro Defining What Winning Looks Like in Iran The Strait of Hormuz Eisenhower vs. Taylor: Two Military Doctrines Explained US Military Readiness vs. the Pentagon Era America's Magazine Depth China's Vulnerability Trading Freedom for Security Today's Industrial Base Lessons from the Ukraine War Impact of Iran Conflict on Taiwan Risk What Neo-Prime Defense Companies Need to Succeed Can We Win Without Full Regime Change in Iran? AI's Impact on Modern Warfare
- 3 weeks ago1h 16m
Gavin Baker - Watts and Wafers - [Invest Like the Best, EP.473]
My guest today is Gavin Baker, founding partner and CIO of Atreides Management, and this is our sixth conversation. The central theme is watts and wafers, the two physical constraints that in Gavin's view will dictate the next phase of AI. On power, he thinks the near-term shortage starts to ease in 2027 and 2028 as new sources of energy come online, and that orbital compute solves it in the long term. On wafers, he explains what is different this time from the dotcom bubble and why TSMC’s capacity decisions may be the single most important variable to watch. We also discuss Elon’s Terrafab, the disaggregation of GPUs, the role of new chip companies, and whether the economic value of AI will keep accruing to frontier models. 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: Welcome to Invest Like The Best Gavin Baker Intro Anthropic's Record ARR Growth Should OpenAI and Anthropic Raise at a Much Higher Valuation? How Elon Preserves Investor Trust Watts & Wafers Data Centers in Space Explained Orbital Compute’s Impact on Terrestrial Data Centers TSMC Supply Discipline & Bubble Risk Demand for Frontier Tokens & The Bitter Lesson Continual Learning & Memory New Chip Companies & Startups Prefill vs. Decode Disaggregation AI-Native Founders: Different & Hard Token Path & Application Layer How Gavin Uses AI in Atreides Signs of a Diversity Breakdown Google, Meta, Amazon, Microsoft Broader Knock-On Effects of AI
- May 13, 20261h 16m
Krishna Rao - Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence - [Invest Like the Best, EP.471]
My guest today is Krishna Rao, the CFO of Anthropic. The center of our conversation is how he navigates the decision around procuring and allocating compute, which he describes as the canvas on which everything else gets built. We talk about what he calls the cone of uncertainty, the three chip platforms Anthropic uses fungibly across Trainium, TPUs, and GPUs, and the daily meetings they run to allocate compute between model development, internal use, and serving customer demand. He explains why the returns to frontier intelligence keep getting higher, especially in enterprise, and how Anthropic thinks about the line between platform and application and why they choose to build their own products like Claude Code. Krishna has such a unique seat watching one of the fastest growing businesses in history, and he is generous in sharing what he has learned since joining the company two years ago. 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: Welcome to Invest Like The Best Episode Intro: Krishna Rao Compute as Anthropic's Lifeblood Three Fungible Chip Platforms The Cone of Uncertainty Competing Ways to Allocate Compute What Drives Compute Efficiency Why Frontier Returns Are So High How Claude Code Writes Its Own Code Will Talent Become Obsolete? How Scaling Laws Are Holding Exponential Thinking The Layer Cake of Compute How Anthropic Deploys New Compute Platform v. Application Layer Why Model Pricing Has Stayed Stable Measuring Return on Compute Working With Chip Providers How Anthropic's Finance Team Uses Claude The Jevons Paradox for Labor Anthropic's Fundraising & Growth Journey The Exponential Revenue Curve The Hardest Thing to Explain to Investors AI's Public Perception Problem Mythos Relationship With Government Inside Anthropic's Culture The Next Frontier: Virtual Collaborators How Leaders Scale With a Business The Biggest Risks to Continued Progress What Krishna is Excited About The Kindest Thing
- May 5, 20261h 15m
Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.470]
My guest today is Brian Chesky, the co-founder and CEO of Airbnb. Our conversation traces the path from his early training as an industrial designer at RISD through the pandemic moment that forced him into founder mode. He explains why he thinks AI founder mode will demand even more attention to the details and why founders are rarely good early CEOs. He walks through his eleven-star exercise, which is a way of imagining the most absurd version of a customer experience to achieve product market fit. We also talk about what changed for him when he stopped chasing adulation and started making things for the love of making them. 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: Welcome to Invest Like The Best Episode Intro: Brian Chesky Studying Industrial Design at RISD Why Founders Don't Make Good CEOs Founder Mode AI Founder Mode The End of Pure People Managers Consumer AI Project Hawaii Make the Problem as Small as Possible Becoming a Good CEO What Brian Learned From Hiroki Asai The Eleven-Star Experience AI and Creativity Making Things for the Love of It The Adulation Trap The Ham Sandwich Paradox Why Founder-Led Businesses Endure The Person as the Atomic Unit of Airbnb Disrupting Yourself With AI Lessons from Bodybuilding Hiring as the Most Important Job Are Founders Born or Made? The Motivation of an Artist The Kindest Thing
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About Invest Like the Best with Patrick O'Shaughnessy
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.
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