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
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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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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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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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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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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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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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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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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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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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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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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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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April 28, 2026 • 66 mins
My guest today is Paul Tudor Jones. Paul is the founder of Tudor Investment Corporation and one of the greatest macro traders of all time, known for calling and profiting from the 1987 crash and compounding capital at extraordinary rates over more than four decades.
Paul is also one of the most entertaining and interesting people I have ever met. He is full of stories and hard-earned lessons from a lifetime in markets that feels l...
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This is my second conversation with Dylan Patel. Dylan is the founder and CEO of SemiAnalysis, where he tracks the semiconductor supply chain and AI infrastructure buildout.
This conversation is about the supply and demand of tokens. On demand, Dylan describes something completely explosive. He explains why the frontier model is the only model anyone wants, and willingness to pay for it is nearly unbounded. His own firm has gone f...
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April 21, 2026 • 92 mins
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. Alex talks about how most of the diseases that will claim most of our lives are already addressable with medicines that exist today. We work through the five layers of what a defensive health s...
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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. The United States was the world leader in enrichment through the 1980s and then stopped entirely. Today roughly a quarter of US enriched uranium comes from...
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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. Alan Waxman has spent the time diagnosing the root cause.
Alan thinks about the financial system the way a historian would, studying the incentives, guardrails, a...
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March 31, 2026 • 66 mins
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.
Sergey argues that solving robotics at full generality is the right path, and that building systems that learn across many robots, environments, and tasks may be the more scalable approach than building narro...
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March 24, 2026 • 54 mins
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.
Unlike most firms chasing power law outcomes, Lead Edge is designed to deliver consistent returns by talking to thousands of companies a year, applying a rigorous eight-point criteria to filter down ...
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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.
William talks about what owning 100% of his company allows him to do that other venture-backed founder cannot and the personal risk he took to do so. He shares how Silicon ...
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