Cole Bryant: Hey — okay, I want to start with a hypothetical, actually no, wait, it's not hypothetical at all. It's July 2026. You're an investor. You put real money into a fund run by a 22-year-old who was fired from OpenAI two years earlier. And the fund's entire pitch was essentially: 'I understand AI and you don't.'
Zara Reyes: You're describing Situational Awareness LP.
Cole Bryant: Leopold Aschenbrenner. Columbia valedictorian, enrolled at fifteen, former OpenAI Superalignment team — gets fired April 2024 over an alleged information leak. And the response to getting fired is: drop a 165-page essay in June called 'Situational Awareness,' argue that only a few hundred people in San Francisco actually understand AI's trajectory, and then — this is the move — name a hedge fund after the essay. Situational Awareness LP. Peak AUM: $45 billion.
Zara Reyes: The fund name is literally the essay title.
Cole Bryant: It's not even subtle! And Patrick and John Collison seeded it — the Stripe founders — so now there's real institutional gravity behind what is, if you squint at it, a guy monetizing his own firing as a brand origin story.
Zara Reyes: No but lowkey that's the cleanest personal brand play I've seen in this space. 'I got pushed out for knowing too much' is a better pitch than any track record he could have built in two more years at OpenAI.
Cole Bryant: Right? And it works — $45 billion works. Until, bro, it really doesn't.
Zara Reyes: The collapse is where I want to go — but how does Blackstone passing on this not kill the momentum earlier?
Cole Bryant: Dude, Blackstone passing is — wait, actually that's the exact thing I want to flip on you. Because the people who *did* say yes? Patrick and John Collison. Nat Friedman. Daniel Gross. That's not a random investor list. That's the same closed SF network the essay said was the only group that understood AI.
Zara Reyes: Right — but the part that doesn't fit is Blackstone. They're the world's largest hedge fund investor. No social obligation to the network. And they passed.
Cole Bryant: That's the tell, yeah.
Zara Reyes: Think about it like — okay, you have a friend who says they know which restaurants are about to blow up because they know every chef in the city. The edge isn't their palate. It's the rolodex. That's the whole pitch. And if you're *in* that chef network, you believe them. But if you're a Michelin inspector with no reason to trust the social graph? You want to see the food.
Cole Bryant: Blackstone wanted to see the food.
Zara Reyes: What was actually being sold was access to a network, not a replicable analytical edge. The Collisons aren't buying a model. They're buying proximity to the one guy engaged to Anthropic's chief of staff, Avital Balwit, who is literally in Dario Amodei's office every day.
Cole Bryant: No but — okay, I want to hedge the 'zero experience' frame too, because Bloomberg and Straits Times ran with 'no professional investing experience' and technically he was at FTX Future Fund. That's real allocation work, even if it's philanthropic.
Zara Reyes: It's philanthropic, though. And FTX imploded. So nobody's putting that on the résumé.
Cole Bryant: So the clean version is: the Collisons and Nat Friedman are buying a bet on their own network's thesis. Blackstone, with no skin in that social game, looks at it and goes — no. That's not hubris, that's a product that only works inside the room it was built in.
Zara Reyes: And so the product only working inside the room it was built in — that's exactly what breaks in July 2026, right? Because the room doesn't protect you from a semiconductor selloff.
Cole Bryant: That's — okay, this is where I want to give the take its partial win actually. Because the directional call on AI infrastructure? Probably correct. The thesis wasn't wrong. It was the leverage on top of a thesis that was always fragile to a macro event that nobody — not Leopold, not anyone in that SF network — had any edge on whatsoever.
Zara Reyes: The $35 billion loss.
Cole Bryant: Thirty-five billion. In July 2026. AI-related semiconductor stocks sell off hard — like, a macro repricing — and the fund gets caught holding leveraged positions. And then, dude, it gets worse. They have to do a distressed overnight fire sale of the pre-IPO Anthropic shares. Not a planned exit. A fire sale. David Mann, Mannsion Group, he gets the call — overnight — to buy the stake, and he goes public and says Aschenbrenner was, quote, 'forced to sell.'
Zara Reyes: 'Forced to sell' — David Mann said that publicly?
Cole Bryant: Publicly. The guy who bought the distressed stake told everyone the seller had no leverage in the negotiation. That's — I mean, that's the receipts.
Zara Reyes: No but picture the investor who wired $20 million into Situational Awareness LP in January 2026 on the '300 people understand this' pitch. It's a Sunday night in July, they get a margin call notification — not even market hours yet. The edge they paid for was supposed to be informational. A semiconductor macro swing doesn't care about your rolodex.
Cole Bryant: And — okay, I have to flag this because it's been bothering me — the peak AUM number. We keep saying $45 billion, but Yahoo Finance ran a figure closer to $20 billion and genuinely we cannot reconcile those two numbers. Which means the scale of the loss is also uncertain. The $35 billion loss figure itself depends on which starting point you use.
Zara Reyes: The uncertainty is the story though — and wait, the Anthropic IPO piece plus the Avital Balwit detail makes all of this structurally so much weirder, we're going to get there.
Cole Bryant: Okay but the Avital Balwit piece is the part that — wait, it actually reframes the IPO thing completely. Because she's chief of staff to Dario Amodei. His fiancée. While the fund is holding illiquid pre-IPO Anthropic shares. That's not a coincidence of relationships. That's the edge and the conflict of interest being the same person.
Zara Reyes: And the engagement happened during the collapse window.
Cole Bryant: Which is — I mean, what do you do with that timing?
Zara Reyes: Either he's completely detached from how it reads, or — and I think this is what actually happened — his credibility inside Anthropic was still intact even while the fund was burning. Because Dario Amodei's chief of staff doesn't get engaged to someone who's radioactive at the company.
Cole Bryant: No way. That's the tell?
Zara Reyes: That's the tell. But here's where the IPO is the actual trapdoor — Anthropic is valued at nearly a trillion dollars in pre-IPO contexts. The moment they file with the SEC, every piece of strategic information the fund was monetizing gets printed in a public document. The '300 people understand this' pitch dissolves. Not because he was wrong. Because the network can't stay closed once the 10-K exists.
Cole Bryant: So the thesis actually — wait, no — the thesis survives. The business model doesn't.
Zara Reyes: Exactly that. You can be right about AI's trajectory and still have built a fund whose only moat was information asymmetry. The IPO filing doesn't just affect the Anthropic position — it retroactively exposes what the whole pitch was built on. After that, Situational Awareness LP is competing on conventional investment skill. Which, lowkey, nobody actually stress-tested.
Cole Bryant: And that's the calibrated version. Not 'he was a fraud.' Not 'the thesis was wrong.' Just — he built a product that required the room to stay closed forever. And rooms don't stay closed.
Zara Reyes: My detail that I cannot let go: the fund is literally named Situational Awareness LP. After the essay. It's not a metaphor for what happened — the thought leadership and the financial product are the same object. When it blows up, the essay blows up with it.
Cole Bryant: Mine is David Mann going public. Like — bro bought the distressed Anthropic stake overnight and then told everyone the seller had zero leverage. That's not just receipts, that's a victory lap at someone else's margin call.
Zara Reyes: Okay but — actually, I want the last word on this — every SF AI insider whose pitch right now is 'I have situational awareness you don't'? Watch for the quiet rebrand. Because the second Anthropic's 10-K hits the SEC, that's not exclusive intelligence anymore. That's just called being a normal investor.
Cole Bryant: Yeah, 'personal brand as hedge fund' was always going to hit a wall eventually. I mean — maybe not a $35 billion wall, but. A wall.
Zara Reyes: To the rebrand. Already in progress, definitely not being announced.
