Leopold's Situational Awareness fund blows up, big tech earnings, Simile's $2B Series B

In this episode of Get the Check, the pod covers how Leopold's Situational Awareness fund lost $35B in a week, what big tech earnings say about the AI CapEx bet, and Simile's $200M Series B at a $2B valuation. They’re an AI startup that started as a PhD thesis about the Sims game.

They start with Leopold. Columbia valedictorian at 19, one of five people at the FTX Future Fund, fired from OpenAI's superalignment team, then raised $225M off a 165-page paper. He went long memory and neoclouds, short software…and most importantly was 4x levered. Citadel's research arm called a Fed rate hike, both sides of his book moved against him at once, and the Fed didn't even hike. Ken Griffin bought the wreckage in a one-time trade and the names ripped 20-30% the next day. Anika explains why 4x leverage turns a 25% drop into zero, and reads her dad's verdict, which is a lot harsher than the pod's.

Next, earnings. AWS growth reaccelerated to 37% and Amazon popped 10% on the back of Trainium, with 2027 capacity already booked out by Anthropic and OpenAI. Meta had the opposite quarter, free cash flow down 91%, stock down 20%, but its new ad models, GEM and Andromeda, lifted conversion 15% and price per ad 12% at the same time, which is huge.

Finally, the Get the Check segment: Simile, the user simulation startup founded by four Stanford PhDs out of Smallville, the project that dropped 25 LLMs into a Sims-style sandbox and watched them plan their own party. The user research market is $153B, but the pod's real question is whether Simile has a moat when Meta is the only company with a closed feedback loop. Priya gives Simile her check. Maya would take them over Aru, for reasons she admits are a little parasocial.

00:00 The Mac Mini situation03:10 The Situational Awareness blowup everyone's timeline is on03:39 Leopold was one of five people at the FTX Future Fund04:55 Why OpenAI fired him05:41 What the 165-page Situational Awareness paper argued08:09 How one Citadel research report took down the most hype hedge fund09:43 4x leverage wipes you out on a 25% drop12:17 Ken Griffin loves distressed assets13:46 Is Situational Awareness over?14:51 Would Leopold still get our check17:04 Maya thinks Citadel screwed retail on $GME on purpose22:03 AWS reaccelerates while Meta's cash flow drops 91%35:06 Simile raises at $2B five months after its Series A

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