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In the high-flying world of AI investing, sometimes you get the bull, and sometimes you get the horns. After a long ride on the bull, Gen Z hedge-funder Leopold Aschenbrenner found out last week how quickly things can shift, even for a whiz kid once called the "Nostradamus of AI."
It's a story that was instantly etched into Wall Street lore: A 24-year-old former valedictorian and OpenAI employee pens a 165-page AI opus called "Situational Awareness" and is immediately lauded as a visionary genius. He starts a hedge fund named after the paper and its assets under management swell at breakneck speed, from a few hundred million dollars to $45 billion in less than two years. Returns are bountiful. At one point in 2026, the fund is up 1,000% after fees since inception.
Then the wheels fall off — and quickly. Aschenbrenner goes from market oracle to cautionary tale in near-record time. Citadel steps in to scoop up most of his public book. The market rallies in response. He watches as the very stocks he championed surge without him.
After such a wild week, there's really only one question: How could this happen? Aschenbrenner actually made some textbook mistakes that everyday investors can learn from.
1. He went wild with leverage and overall risk-taking
Situational Awareness' public-equity book was essentially designed to be heavily exposed to market fluctuations. The fund's approach was to borrow money to grow positions, while also hedging by shorting stocks it saw as AI laggards.
It's a great approach — as long as AI stocks are going up. But when the trade hit a recent rough spot, Aschenbrenner, as my colleague Ali Barr described it, got his "face ripped off." Then, once blood was in the water, rivals started betting against top holdings. As losses mounted, banks started issuing margin calls.
You get the idea. The fund's issues kept compounding — which is what happens when you lever yourself to the gills.
2. He had too many eggs in too few baskets
We're really hitting all the traditional portfolio-management rule violations. Aschenbrenner went against the cardinal rule of not being overconcentrated in too few positions. This tends to happen when an investor is utterly convinced they're right — which leads to a third truth:
3. Markets can stay irrational longer than you can stay solvent
It's entirely possible Aschenbrenner's overall investment thesis was right. After all, his original research paper predicted many ongoing trends. But he ran into an unfortunate reality of high-conviction investing: you can be right and still lose.
Ali Barr put it best: the market doesn't care how smart you are.
But don't cry for Aschenbrenner
Despite reportedly shopping his private book in the week leading up to the meltdown, Aschenbrenner hung onto those assets. He's still invested in Anthropic, and the company was last valued at nearly $1 trillion.
(Side note: Aschenbrenner got married this past weekend to — drum roll please — the chief of staff for Anthropic's CEO.)
Citadel and other tech investors are doing just fine too
I'll conclude with a chart. The one below shows the eye-watering rally in AI-linked stocks, particularly chipmakers, in the two days after Citadel stepped in to buy most of Aschenbrenner's stocks.
The rally shows that investors view Aschenbrenner's fund implosion as user error, not a systemic market issue. He's out of the mix after flying too close to the sun, but the AI trade rolls on.
