Invest Like the Best with Patrick O'Shaughnessy

Invest Like the Best with Patrick O'Shaughnessy

Colossus | Investing & Business Podcasts

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Episode (200)

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11
William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy

William Hockey - Building the Operating System for the Dollar and Silicon Valley Heresy

Mar 17, 2026

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...

12
Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]

Shyam Sankar - Celebrating Heretics - [Invest Like the Best, EP.462]

Mar 10, 2026

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. We discuss the o...

13
John Arnold - China, Energy Markets and Fixing America's Systems

John Arnold - China, Energy Markets and Fixing America's Systems

Mar 04, 2026

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 ind...

14
Dan Sundheim - The Art of Public and Private Market Investing

Dan Sundheim - The Art of Public and Private Market Investing

Feb 24, 2026

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. He manages...

15
Josh Kushner - Concentration and Conviction

Josh Kushner - Concentration and Conviction

Feb 18, 2026

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 Thriv...

16
Alex Behring and Daniel Schwartz - Inside 3G Capital

Alex Behring and Daniel Schwartz - Inside 3G Capital

Feb 10, 2026

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...

17
Ben Horowitz - Backing America’s Future

Ben Horowitz - Backing America’s Future

Feb 03, 2026

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 co...

18
Gokul Rajaram - Lessons from Investing in 700 Companies

Gokul Rajaram - Lessons from Investing in 700 Companies

Jan 29, 2026

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. He has built the core ad and prod...

19
Patrick O’Shaughnessy - Creating on Principle

Patrick O’Shaughnessy - Creating on Principle

Jan 20, 2026

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 enjoy...

20
Tom Digan & Greg Stewart - Building the World’s Best Fitness App

Tom Digan & Greg Stewart - Building the World’s Best Fitness App

Jan 13, 2026

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 ...

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