He Saw the Future, yet Lost $35 Billion: The Untold Story of Leopold Aschenbrenner

August 2026. A 24-year-old gets married by the sea in California. His hedge fund had been worth about $45 billion. In the last few weeks, it fell to about $10 billion, and his phone won't stop ringing. His name is Leopold Aschenbrenner. He wrote a famous essay about seeing the future of AI before everyone else. So how does a guy who saw the future not see THIS coming? In this episode, Pip explains leverage, margin calls, hedging and the Kelly criterion with a tower of blocks, an umbrella stall, a coin-flip game and a very patient man feeding pigeons. No finance degree needed. ⏱️ Chapters 0:00 The Wedding Week 1:03 The Kid Who Skipped Ahead 2:28 Two Jobs, Two Explosions 4:39 The 165-Page Crystal Ball 5:59 Leo Starts a Fund 8:05 All In 11:02 The Umbrella and the Sunglasses 12:07 Pip's Coin-Flip Game 15:29 July 17:35 The Night Sale 20:02 What Happened Next 21:02 Three Rules from Pip 📚 Sources Leopold Aschenbrenner, "Situational Awareness: The Decade Ahead" (June 2024) Dwarkesh Patel podcast interview with Leopold Aschenbrenner (June 2024) Reporting by Bloomberg, CNBC, The Wall Street Journal, Reuters, the Financial Times and The New York Times (July–September 2026) Yahoo Finance; The Motley Fool; Tae Kim; Cracking the Vault ColdFusion, "How to lose $35 Billion Dollars Betting on AI"; Patrick Boyle, "We Need To Talk About Leopold" Reports differ on some numbers (for example how much of the $45 billion was borrowed, and the exact size of the Citadel sale); we used the figures most outlets agree on. Some details are simplified to make the story easy to follow. The characters are cartoon stand-ins; their voices are not the real people's voices. This video is for education and entertainment only and is not financial advice. 🎵 Music "Lightless Dawn", "Fluffing a Duck", "Sneaky Snitch", "Hidden Agenda", "Floating Cities", "Life of Riley", "Scheming Weasel (slower version)", "Local Forecast - Elevator", "Monkeys Spinning Monkeys", "Carefree", "Pixel Peeker Polka - faster", "Merry Go", "Easy Lemon", "The Descent", "Volatile Reaction", "Covert Affair", "Long Note Four", "Heartwarming", "Majestic Hills" Kevin MacLeod (incompetech.com) Licensed under Creative Commons: By Attribution 4.0 License http://creativecommons.org/licenses/b... #LeopoldAschenbrenner #SituationalAwareness #ExplainedLikeImFive