I sat down with Chamath Palihapitiya. He sold a company to Nvidia for $20 billion, woke up the next morning, saw $13 billion hit the account, and felt nothing. This is a guy who grew up in a home with alcoholism and abuse, immigrated to Canada with nothing, lost billions on SPACs, rebuilt, and now says the whole game is exactly that — a game. We got into the uncomfortable stuff: why pain is the single best predictor of entrepreneurial success, why investing is never a team sport and anyone who says otherwise is losing money, and why Bitcoin has a structural flaw that will permanently cap its ceiling. Chamath makes the case that Trump is the most effective political athlete America has ever seen, that some form of socialism is probably inevitable if we don't fix student debt and housing, and that his next obsession is building the machine that makes the machine — a software factory for the AI era.

00:00 Introduction

06:09 Chamath’s Painful Childhood & Hunger

11:16 What Actually Matters Beyond Success

17:06 Business as a Game, Not Life

22:04 The Machine That Makes Machines

29:11 Trump, Trade & America’s Political Reset

37:30 Investing Lessons: Conviction Over Consensus

43:12 Bitcoin’s Structural Flaws & Limitations

49:56 The Conceptual Stack for AI Investing

55:12 AI Hype, Valuations & Catastrophising

58:26 Socialism’s Inevitable Rise & Boundary Fixes

1:03:48 Building Sovereign Social Media from India

Pain, Power & The Game Nobody Wins | Chamath Palihapitiya x Nikhil Kamath | People by WTF

People by WTF

Lessons from drawdowns and SPAC losses

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