Invest Like the Best with Patrick O'Shaughnessy

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. Explore all our episodes and learn more at https://www.colossus.com

Episodes

Walter Russell Mead - How America Keeps Winning - [Invest Like the Best, EP.490]

September 8, 2026 • 78 mins
My guest today is Walter Russell Mead. Walter is a columnist at the Wall Street Journal and the author of Special Providence and God and Gold, two of the best books written on American power.  He has spent decades studying how the United States came to dominate the world, and our conversation is about whether it can keep doing so.  Walter lays out the five step playbook that carried the Dutch, then the British, then Ame...
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Sarah Guo - Funding the Frontier - [Invest Like the Best, EP.489]

September 1, 2026 • 59 mins
My guest today is Sarah Guo, founder and managing partner of Conviction, the venture firm she built to back AI-native companies from their earliest days.  Sarah has become one of the most sought-after early-stage investors in AI, often the first check into the companies defining the frontier.  In this conversation, we go inside that frontier: what the small group of people actually building AI believe right now, why som...
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Neil Movva - Making AI 10x Cheaper - [Invest Like the Best, EP.488]

August 25, 2026 • 78 mins
My guest today is Neil Movva, founder of Sail. Sail is building what Neil calls a token factory, an inference company designed for a specific kind of future, one where AI agents run in the background for hours or days at a time rather than answering a human in real time.  In that world, latency matters less and cost matters more, and Neil has built the whole company around driving the cost of a token as low as it can possibly...
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Ben Thompson on Big Tech, China, and the AI Boom Running Out of Money - [Invest Like the Best, EP.487]

August 18, 2026 • 76 mins
My guest today is Ben Thompson, the founder and author of Stratechery. Ben is one of my favorite business thinkers and I love talking to him about everything happening in markets and technology.  We go through every important company, including OpenAI, Nvidia, Intel, Apple, Microsoft, Google, and Amazon. We also discuss why he thinks it would be dangerous for the United States to win the AI race outright, what container shipp...
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Eric Vishria - A Decade of Lessons Investing in Software & Hardware - [Invest Like the Best, EP.486]

August 11, 2026 • 65 mins
My guest today is Eric Vishria, a General Partner at Benchmark.  Eric has spent his career in software and cloud, and few people know the history of these markets as well as he does. What makes him special is his ability to use that history to make sense of today.  We discuss what the rise of AWS teaches us about AI, what he has learned from investing in Fireworks, Sierra, and Cerebras, and how the criteria for winning ...
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Gavin Baker - AI Market Jitters - [Invest Like the Best, EP.485]

August 4, 2026 • 65 mins
My guest today is Gavin Baker, founding partner and CIO of Atreides Management. This is our seventh conversation, and just two months after Gavin's last appearance. It's about the gap between what the market is doing and what companies are seeing. It's been a tough month or so for public AI names, but there's no sign of a slowdown on the ground in Silicon Valley. We discuss the latest moves, contracted vs. spot GPU prices, the ga...
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Sam Altman - How to Make an Abundant Future - [Invest Like the Best, EP.484]

July 28, 2026 • 53 mins
My guest today is Sam Altman, CEO of OpenAI. It's a conversation spanning the history, present, and future of OpenAI, from the origin of ChatGPT through Codex, hardware, and their new Jalapeno chip. We discuss the early decision to buy compute at a scale nobody thought was rational, and the plan to build a gigawatt of new capacity every week.  We talk about Kimi and distillation, the Hugging Face incident and what it means ...
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Matthew Smith — Natural Gas: The Next Bottleneck - [Invest Like the Best, EP.483]

July 21, 2026 • 56 mins
My guest today is Matthew Smith. Matthew is the founder and CIO of Chronometer Partners, which invests in energy, industrials, materials, power and utilities, and related infrastructure. For the last 18 months he and his team have modeled nearly every natural gas well, pipeline, and processing asset in the United States. He's reached a conclusion most of the market doesn't share.  Starting in 2028, AI data centers and LNG ex...
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John Kim - How to Raise a Few Billion Dollars - [Invest Like the Best, EP.482]

July 14, 2026 • 50 mins
Today my guest is John Kim. John is one of the world's top and most prolific fundraisers.  He was chief client officer at General Catalyst, where he helped raise many of the firm's flagship funds. He is now chairman and president of corporate development at Lila Sciences, a company building scientific superintelligence, where he has helped raise several hundred million dollars.  He is also the author of The Tao of Fundr...
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Jeremy Giffon - The Billion Dollar PDF - [Invest Like the Best, EP.481]

July 7, 2026 • 75 mins
My guest today is Jeremy Giffon.  Jeremy has been on the show before as one of our most popular guests, and this conversation is every bit as enjoyable as the first. Over the last 18 months, Jeremy has had hundreds of conversations with founders and with the capital behind their companies. I don't know many investors with such a high rep count in the most interesting corners of private markets, so I asked him what he has learned....
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Etched - Building AI Hardware to Make Inference Faster and Cheaper - [Invest Like the Best, EP.480]

June 30, 2026 • 87 mins
My guests today are Gavin Uberti and Rob Wachen, the founders of Etched.  A few years ago, when they set out to build a better AI chip than the largest companies in the world, almost everyone I called told me it could not be done. They have since done it, taping out a working chip on their first attempt and becoming the first hardware company founded after ChatGPT to do so. They already have more than a billion dollars of cu...
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Vlad Barbalat - Investing $120 Billion in Permanent Capital - [Invest Like the Best, EP.479]

June 23, 2026 • 69 mins
My guest today is Vlad Barbalat, the Chief Investment Officer of Liberty Mutual Investments, the $120 billion investment platform that sits within one of the largest insurance companies in the world.  Vlad grew up in Soviet Moldova, came to America in 1990, and built a career that eventually led him to one of the most distinctive capital allocator seats anywhere in finance.  Today we talk about how the mutual insurance ...
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Kareem Amin - The Unusual Approach to Company Building - [Invest Like the Best, EP.478]

June 16, 2026 • 56 mins
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 &m...
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Alex Sacerdote - How to Invest Through Technology Cycles - [Invest Like the Best, EP.477]

June 9, 2026 • 70 mins
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 techn...
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Dara Khosrowshahi - Uber's Bet on AVs, AI, and Building a Super-App - [Invest Like the Best, EP.476]

June 3, 2026 • 67 mins
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 o...
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Dan Loeb - Lessons from 30 Years of Investing - [Invest Like the Best, EP.475]

May 28, 2026 • 63 mins
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 interesti...
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Darren Farber on Iran, China, and the Rise of Neoprimes - [Invest Like the Best, EP.474]

May 26, 2026 • 46 mins
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 dep...
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Gavin Baker - Watts and Wafers - [Invest Like the Best, EP.473]

May 20, 2026 • 76 mins
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 wha...
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Krishna Rao - Anthropic's CFO on Compute, Scaling to $30B ARR, and the Returns to Frontier Intelligence - [Invest Like the Best, EP.472]

May 13, 2026 • 76 mins
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 devel...
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Brian Chesky - AI Founder Mode - [Invest Like the Best, EP.471]

May 5, 2026 • 75 mins
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 th...
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