Invest Like the Best
Hosted by Patrick O'Shaughnessy
Conversations with the best investors and business leaders.
73 episodes processed
Episodes
Walter Russell Mead discusses the historical pattern that has allowed the US, Britain, and the Dutch to repeatedly defeat centralized continental rivals. He outlines his five-point playbook for global dominance and analyzes how Trump turned fame into political power. The conversation also covers the four schools of American foreign policy, the rise of tech Hamiltonians, how drone warfare is reshaping military power, and why deterrence is eroding in the Middle East.
Sarah Guo, founder of Conviction, shares her thesis that AI will be an open ecosystem, not dominated by a few giants. She explains why early-stage AI investing requires conviction without historical data, the talent race where top researchers question their purpose, and why home robots are closer than most realize.
Neil Movva, founder of Sail, joins Invest Like the Best to chart the future of AI inference. Sail is a 'token factory' built for a world dominated by long-running autonomous agents, where cost per token matters far more than real-time latency. The conversation tours the full stack of intelligence — chips, software, and power — exploring Movva's 'scavenger strategy' for buying overlooked compute and energy, why the premium frontier labs charge for being months ahead may collapse, and his contrarian bet against NVIDIA's dominance as the market shifts from training to persistent, cost-sensitive inference workloads.
Ben Thompson, founder of Stratechery, joins Patrick O'Shaughnessy to dissect the competitive dynamics of the AI boom. The conversation maps the entire big tech landscape—from OpenAI and Nvidia to Apple, Microsoft, Google, and Amazon—examining the race with China, the coming capital constraints that dwarf compute as a bottleneck, and the structural lessons of past infrastructure buildouts like 1870s railroads and container shipping. Thompson applies his Aggregation Theory lens to the AI era, explores why consumer AI might need an advertising model, and breaks down which big tech companies are best positioned for the next phase.
Eric Vishria, General Partner at Benchmark, joins Patrick O'Shaughnessy to discuss his decade of experience investing in software and hardware. The conversation centers on what the history of AWS reveals about the current AI platform shift, what he has learned from his investments in companies like Fireworks, Sierra, and Cerebras, and how the bar for success has risen for both founders and investors. Eric draws from his deep knowledge of cloud infrastructure to make sense of AI's transformative potential.
Gavin Baker, founding partner and CIO of Atreides Management, returns for his seventh conversation on Invest Like the Best. He discusses the disconnect between public market AI stock performance and the continued AI investment on the ground in Silicon Valley, as well as dynamics in GPU pricing, memory supply, and the strategic importance of SpaceX's orbital compute ambitions. The conversation was recorded at Benchmark's famous table.
Sam Altman, CEO of OpenAI, discusses the company's trajectory from ChatGPT through Codex to hardware and the new Jalapeno chip. The conversation covers early decisions to buy compute at unprecedented scale, plans to build a gigawatt of capacity weekly, competitive dynamics with Kimi and distillation attacks, and implications of raising children in a world of abundant AI intelligence. A wide-ranging exploration of how OpenAI is approaching infrastructure, competition, and the future of AI abundance.
Matthew Smith, founder and CIO of Chronometer Partners, presents a contrarian thesis: starting in 2028, AI data centers and LNG exports will demand more natural gas than the US can produce and deliver, potentially exhausting working storage by 2030 and creating unbounded upside risk to prices. The episode explores the structural forces behind this bottleneck, why US exports can't simply be halted, winners and losers across energy sectors, and the only viable long-term solution.
John Kim, one of the world's most prolific fundraisers, walks through the mechanics of raising billions of dollars. Kim served as chief client officer at General Catalyst and is now chairman and president of corporate development at Lila Sciences. The conversation covers the psychology of persuasion, the difference between belief and trust, and the specific laws and frameworks that move large pools of capital.
Jeremy Giffon returns to discuss lessons learned from hundreds of conversations with founders and capital providers in private markets over the last 18 months. The conversation explores what these patterns reveal about founder and investor dynamics, the emergence of 'poster class' dynamics in venture, the hidden intellectual history shaping Silicon Valley, and practical implications for navigating modern private markets.
Gavin Uberti and Rob Wachen, founders of Etched, discuss building a startup AI chip company that succeeded against long odds. They taped out a working chip on their first attempt and secured over a billion dollars in customer demand. The conversation covers their technical architecture, the decision to build an entire rack system for inference, and a hiring strategy that blended industry legends with elite young talent. They also explain why they believe inference will become one of the world's largest markets.
Vlad Barbalat, Chief Investment Officer of Liberty Mutual Investments, discusses how the mutual insurance structure creates a distinctive capital allocation platform with $120 billion in assets. The conversation explores Liberty's investment philosophy, criteria for new deals and partners, and Barbalat's personal journey from Soviet Moldova to building one of finance's most unique allocator seats in America.
Kareem Amin, co-founder and CEO of Clay (a $4B+ software company), discusses his unusual framework for running a company centered on three core values: truth, justice, and courage. The conversation explores how these abstract principles translate into concrete business decisions, what he learned about risk and ambition from a ten-day silent meditation retreat, and the philosophy behind Clay's approach to helping companies find and reach their best customers at scale.
Alex Sacerdote, founder of Whale Rock Capital Management, discusses his framework for investing through technology cycles. Over 20 years, he's refined a single investment lens focused on technology S-curves, durable competitive advantages, and underappreciated earnings power. The conversation works through the entire AI stack—from chips to models to applications—using his highest conviction position in Anthropic as a case study. Whale Rock has compounded at roughly 44% annually over the past three years.
Dara Khosrowshahi, CEO of Uber, discusses his journey from running Expedia for thirteen years to taking the helm at Uber in 2017—a decision shaped by Daniel Ek's insight that life is about impact, not happiness. He reflects on navigating the chaos of his first days at Uber and how his family's escape from Iran when he was nine influences his approach to pressure. The conversation centers on autonomous vehicles, Uber's role as a demand aggregator in the physical AI era, and why Uber is fundamentally a supply-led company positioned to win in a multi-winner AV landscape. Khosrowshahi also explores Uber's $10 billion in free cash flow, the vision of a super-app ecosystem, and lessons learned from mentors including Barry Diller and Reed Hastings.
Dan Loeb, founder and CEO of Third Point, reflects on 30 years of investing evolution—from credit and event-driven strategies to quality, thematic technology, and a major credit business. He discusses activist investing at companies like Sotheby's, Sony, and Yahoo, his approach to AI stack investing, the importance of governance, lessons from FTX's collapse, and the power of clear written communication with boards.
Darren Farber, Managing Partner of Albion River and former special advisor to the Deputy Under Secretary of Defense, returns to discuss what winning means in a theater like Iran. The conversation covers magazine depth as a foundation for American industrial capacity, lessons from Ukraine's defense needs, and what the rise of neo-prime defense contractors will require from Congress and the defense establishment.
Gavin Baker returns for his sixth conversation, focusing on the two physical constraints shaping the future of AI: energy supply (watts) and semiconductor fabrication capacity (wafers). He argues that near-term power shortages will ease by 2028, with orbital compute as a longer-term solution, and that TSMC's capacity decisions are the key variable for the industry. The discussion also covers Elon Musk's Terrafab, the disaggregation of GPUs, the rise of new chip companies, and the open question of where AI's economic value will accrue.
Krishna Rao, CFO of Anthropic, joins Invest Like the Best to discuss how he navigates compute procurement and allocation using a 'cone of uncertainty' framework, leveraging three chip platforms fungibly across Trainium, TPUs, and GPUs. He explains the daily meetings that allocate compute among model development, internal research, and customer demand, and why Anthropic believes the returns to building frontier intelligence are still increasing. The conversation also covers the blurry line between platform and application and why Anthropic builds its own products like Claude Code. Throughout, Rao shares insights from two years at one of the fastest-growing businesses in history.
Brian Chesky, co-founder and CEO of Airbnb, joins Invest Like the Best to discuss his journey from industrial design student at RISD to navigating the pandemic's existential threat to the company. He explains the philosophy of 'founder mode'—the hands-on, detail-obsessed approach that became necessary during the crisis—and predicts that AI will intensify this need. Chesky shares his 'eleven-star' design exercise for uncovering product-market fit, and reflects on how his creative drive shifted from seeking adulation to the intrinsic joy of making.
Paul Tudor Jones, founder of Tudor Investment Corporation and legendary macro trader, discusses five decades of market lessons including his approach to risk management, the psychology of identifying rare high-conviction opportunities, his views on current market bubbles and AI risk, and why he still wakes at night to monitor global markets. The conversation spans trading discipline, the difference between trading and investing, and the ideas both financial and philosophical that have shaped his life.
Dylan Patel, founder of SemiAnalysis, discusses the explosive demand for frontier AI models and the supply constraints limiting their scaling. He explains why frontier models command nearly unbounded willingness to pay, how his firm's AI spending has grown from tens of thousands to $7M in a year, and the critical bottlenecks in memory, logic, and fab equipment that will determine how fast AI infrastructure can scale. The conversation also covers perception challenges facing leading AI labs.
My guest today is Alex Karnal. Alex is the co-founder and managing partner of Braidwell, a life sciences investment firm he built after spending 15 years at Deerfield Management. The frame we use throughout the episode is the health stack.
Scott Nolan spent 12 years at Founders Fund looking for the most important problems that no one else was funding. Then he found a problem so critical, and so ignored, that he couldn't find a company to back. So he started one. General Matter is rebuilding US uranium enrichment.
My guest today is Alan Waxman, co-founder and CEO of Sixth Street, a $130B global investment firm. Private credit is one of the most discussed topics in markets right now, and there is a lot to make sense of. The current discourse is almost entirely focused on symptoms.
My guest today is Sergey Levine, a professor at UC Berkeley and co-founder of Physical Intelligence. The company is building robotic foundation models designed to control any embodied system to do any task in any environment.
My guest today is Mitchell Green. Mitchell Green is the co-founder and managing partner of Lead Edge Capital, a growth equity firm that has spent 15 years building one of the most disciplined investment machines in the business.
William Hockey is the co-founder of Plaid and the founder and CEO of Column, a software company that owns a bank and powers Ramp, Wise, Bilt, Mercury, and others. He funded Column by borrowing against his Plaid shares and has never raised outside capital.
My guest today is Shyam Sankar, the CTO of Palantir Technologies. In this conversation, we explore the ideas that shape how Shyam thinks about technology, talent, and national power.
My guest today is John Arnold. John is probably the most famous energy trader of all time and certainly the most successful. One of the things John talks about is cultivating the best seat in your industry – the seat with the best perspective, the most information, the best systems..
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.
This is my second conversation with Josh Kushner, founder and managing partner of Thrive Capital. I recorded this conversation in October after publishing the Colossus cover story about him and Thrive. Given the overwhelming response, we created some breathing room before releasing it.
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.
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.
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.
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.
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.
My guest today is Reed Hastings, the co-founder and former longtime CEO of Netflix. Netflix is an example of two ideas that everyone talks about, but are extremely hard to do in practice. The first is finding a simple idea and taking it extraordinarily seriously.
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.
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.
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.
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.
My guest today is David George. David is a General Partner at Andreessen Horowitz, where he leads the firm’s growth investing business.
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. Palmer Luckey is a relentless builder and original thinker.
My guest today is Martín Escobari. Martín is Co-President and Head of Global Growth Equity at General Atlantic.
My guest today is Ari Emanuel. Ari runs one of the most influential portfolios in global sports, entertainment, and media.
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.
My guest today is Luca Ferrari. Luca is the co-founder and CEO of Bending Spoons, which he describes as 25 percent private equity and 75 percent technology company. Founded in 2013, Bending Spoons fully acquires and operates digital companies like Evernote, Meetup, Vimeo, and most recently AOL.
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.
Today I am replaying my conversation with Ken Langone. Ken is a legendary American businessman best known for his co-founding of Home Depot. He is also a former director of the New York Stock Exchange and a passionate philanthropist.
My guest today is Karim Atiyeh. Karim is the co-founder and CTO of Ramp, the fastest-growing finance automation platform in history, reaching over $1 billion in revenue in just over five years.
My guest today is Dan Wang. Dan is a technology analyst and author who spent six years living in China studying its manufacturing ecosystem and tech development, best known for his new book Breakneck. Dan offers the most nuanced framework I've encountered for understanding US-China competition.
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.
My guest today is Dylan Patel. Dylan is the founder and CEO of SemiAnalysis.
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. This Business Breakdowns on Rolex is a long-time stand out.
My guest today is Barry Diller. Barry is the former CEO of Paramount Pictures, Fox Broadcasting, and the founder of IAC.
Jim O'Shaughnessy joins his son Patrick to discuss the intersection of investing, creativity, and technology. They explore how AI will change investing, why creativity is the ultimate competitive advantage, and what father-son business partnerships teach about trust.
Howard Marks discusses his 'Sea Change' memo with Patrick O'Shaughnessy: the shift from 40 years of declining interest rates (which made everything go up) to a new era of higher rates that will separate skilled investors from lucky ones.
Shopify CEO Tobi Lutke discusses building a $100B+ company while maintaining a programmer's mindset. He argues that most companies are over-managed and under-engineered — and that the best CEOs should be able to do the actual work of the business, not just manage people who do.
Morgan Housel discusses the relationship between risk, luck, and narrative with Patrick O'Shaughnessy. His key insight: we attribute success to skill and failure to bad luck, but the reverse is often equally true.
Chris Mayer argues that patience is the single most undervalued edge in investing. In a world of 5.5-month holding periods, the investor willing to hold for 10-20 years has an almost unfair advantage.
Stripe co-founder John Collison discusses building internet payment infrastructure with Patrick O'Shaughnessy. He argues that Stripe's advantage isn't technology — it's the willingness to solve unsexy, complex problems (compliance, fraud, international payments) that no one else wants to touch.
Naval Ravikant discusses specific knowledge with Patrick O'Shaughnessy: the unique combination of skills, interests, and experiences that can't be taught or replicated. He argues that the highest-earning individuals are paid for specific knowledge, not general skills.
Founders podcast host David Senra joins Patrick O'Shaughnessy to discuss the patterns he's identified across 300+ founder biographies. They connect founder patterns to investing patterns, finding that the traits of great founders mirror the traits of great investors.
Hamilton Helmer, author of 7 Powers, discusses his framework for understanding competitive advantage with Patrick O'Shaughnessy. He argues that durable businesses possess at least one of seven 'powers' (scale economies, network effects, switching costs, etc.) — and businesses without power are destined for commodity competition.
Tyler Cowen discusses his book Talent with Patrick O'Shaughnessy, arguing that talent identification is the most underappreciated skill in business and investing. He shares unconventional interview questions and explains why credentials are a weak signal of ability.
Annie Duke discusses the application of her book Quit to investing with Patrick O'Shaughnessy. She argues that the sunk cost fallacy, escalation of commitment, and identity attachment keep investors in losing positions far longer than rational analysis would suggest.
Lux Capital founder Josh Wolfe discusses investing at the frontier of science with Patrick O'Shaughnessy. He argues that the biggest investment returns come from backing the inevitable — technologies that are so clearly needed that the only question is timing, not whether.
Reed Hastings reflects on building Netflix from DVD-by-mail to the global streaming giant. He discusses the culture of radical candor, the decision to invest in original content, and why most companies fail to make the leaps Netflix made.
Charlie Munger, in one of his final interviews before his death, shares decades of wisdom on business success, mental models, and the ingredients of long-term competitive advantage, in conversation with Stripe co-founder John Collison.
The Collison brothers discuss Stripe's evolution, their approach to building infrastructure, why they focus on increasing the GDP of the internet, and the importance of speed and taste in building products.
Morgan Housel discusses his book Same as Ever, which argues that the most important truths about human behavior never change. While technology and culture evolve, the psychology of greed, fear, risk, and storytelling remains constant across centuries.
Josh Kushner discusses the investment philosophy behind Thrive Capital, why concentration beats diversification in venture, and how he identifies founders with the conviction to build transformational companies.