Musings on Markets: The Situational Awareness Blow-up: The Collateral Damage from Investing Conviction!

Monday, August 10, 2026

The Situational Awareness Blow-up: The Collateral Damage from Investing Conviction!

Earlier this year, I was asked what I thought about Leopold Aschenbrenner and I admitted that I knew little about him other than what I had read about him, more in social media, than in the press - that he was a 25-year-old wunderkind who had started at OpenAI but had left to start a hedge fund. That hedge fund, built entirely around a bet that AI would pay off big time and near term, buying companies in the AI orbit and selling short on the businesses (especially software) that AI would disrupt, had been able to raise billions of dollars from well-heeled and presumably sophisticated investors, and had posted eye-popping returns, up almost 450% through late June. Success of that magnitude needs no nitpicking, but it is worth remembering that there is nothing that markets enjoy more than cutting inflated egos and reputations down to size. In this case, the fall from grace was precipitous, and over the course of four weeks, the fund's public equity holdings lost more than two thirds of its value, but was also forced to liquidate, with Citadel buying almost all of its public equity holdings.<br>The reads on the swift rise and fall of Leo have been fascinating, a Rorschach test of investing priors. For older investors, the lesson was that you can be blessed with intelligence, but that wisdom required experience, which, at least in their saying, conveniently comes with age. For value investors, many of whom chafed at Leo being hailed as the next Buffett, there was vindication that there will never be another Buffett. For AI skeptics, who have long been on the lookout for catalysts that will break AI fever, there was at least a brief moment of hope that this was the catalyst. There is some truth and some overreach in each of these responses, and I don't plan to rehash them. Instead, I would like to use this story to talk about investing conviction , words used mostly in a favorable way, when people talk about success in markets. I am not as convinced that investing conviction is a net plus, but to get to that conclusion, I think we need to look at what it is, where it comes from and what it leads investors to do.<br>The Story of Situational Awareness<br>The Situational Awareness story is inextricably tied to the story of Leopold (Leo) Aschenbrenner. The short version of his life story is that he was born in Germany in 2001, and enrolled at Columbia University when he was 15. After graduating with a degree in economics in 2021, doing research briefly at Oxford University and working at Sam Bankman-Fried's FTX fund, Leo joined OpenAI as part of the team working on AI safety. He was fired in 2024 for leaking data on the firm, though his motivations for doing so are murky and he contests the allegation, and he published a long (167 page) paper titled "Situational Awareness: The Decade Ahead", which was not only widely circulated, but also became the blueprint for the fund that he created.

The Situational Awareness fund, founded in July 2024, and initially funded by tech luminaries, quickly took off as its bets on AI chips and infrastructure and against AI-damaged sectors paid off. Its early success allowed it to attract more money, with Jane Street being one of the more prominent names involved., and with the additional capital in play, it expanded its presence. While most of the companies that made the fund's list were publicly traded, it also had a stake that Leo had acquired in Anthropic, still a private business. The numbers posted by the fund made investors notice, as can be seen by its rise From August 7, 2025, to June 23, 2026, its highest mark day:

Source: Portfolios Lab<br>Measuring returns from August 7, 2025, Situational Awareness was up about 367% through June 19, 2026 and its returns since founding are even more stratospheric. Even at its peak, there were three caveats that any investor with experience in the market would (or should) have brought up. First, in market time, where decades of over performance are needed to separate luck than skill, a fund that has been successful for a little more than two years qualifies more as a shooting star than as a beacon of light. Second, to deliver returns of this magnitude, you not only have to be right in your guesses, but those guesses must be super-charged by adding substantial leverage to your strategy, either explicitly (by borrowing) or implicitly (by using options). Third, the fund followed the classic 2% (of funds under management) and 20 (% of specified upside) fee structure, an abomination that not only creates an almost insurmountable handicap, in the long term, for investors in the fund, but also encourages reckless risk taking on the part of management.<br>If the rise of the fund was breathtaking, its fall was even more so, and you can see the...