Does Leopold Have Situational Awareness?

Does Leopold Have Situational Awareness?

August 11, 2026 · 40 min · Season 6 · Episode 32

About this episode

The episode discusses the downfall of Leopold Aschenbrenner's hedge fund and the implications of leverage and risk management in trading.

Last week, 24-year-old Leopold Aschenbrenner — former FTX staffer, ex-OpenAI researcher, and author of the viral 165-page essay "Situational Awareness" — managed to lose roughly two-thirds of his $45 billion hedge fund in a matter of weeks. The margin calls arrived during his wedding weekend.In this video I break down how a trader with no professional experience raised billions from Silicon Valley, why his AI "hedge" wasn't a hedge at all, and how leverage plus a concentrated bet on artificial intelligence stocks turned a great-looking expected return into a catastrophic outcome. Along the way we look at the cultural gap between Silicon Valley and Wall Street, why Ken Griffin's Citadel ended up buying the collapsing portfolio in an overnight fire sale, and the maths of volatility drag — the reason a high expected return can still drag an investor's typical outcome straight into the ground.It's a story about leverage, risk management, expected versus median returns, and what happens when you go "full Kelly." Featuring reporting from the Wall Street Journal, The New York Times, Bloomberg, and the Financial Times, plus Victor Haghani's lessons from The…

People in this episode

Host: Patrick Boyle

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Mentioned in this episode

Organizations: FTX, OpenAI, Citadel, Wall Street Journal, The New York Times, Bloomberg, Financial Times

Books & works: Situational Awareness

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