The Smartest AI Investor Just Got Margin Called...
By Mason Trinkner · · 5 min read
Good afternoon, Mason here,
This one is our new edition.
The AI gold rush just got a reality check.
AI’s hottest investor watched his fund collapse from $45 billion to around $10 billion.
The companies protecting us from AI are becoming unicorns.
Sam Altman says we’re already in the singularity.
The AI boom is getting bigger.
So are the consequences.
Read time: 4 mins
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LATESTDEVELOPMENTS
AI & CAPITAL |
1️⃣ From AI Genius to a $35 Billion Blowup |
Photo: Financial Times
Situational Awareness, an AI fund created by an ex-OpenAI researcher, Leopold Aschenbrenner, has collapsed from $45 billion to around $10 billion in assets on falling semiconductor stocks and mounting margin calls. Since then, $16 billion of its portfolio has been sold off to Citadel, with some private assets remaining, notably a $5 billion private stake in Anthropic.
What happened? Leopold Aschenbrenner has gone from a Wall Street mastermind to its biggest punching bag. His fund, Situational Awareness, was made up of ridiculous amounts of long AI & infrastructure bets like SK Hynix and Sandisk, putting options and short bets against semiconductor benchmarks like Nvidia. These AI hardware stocks have now plunged between 50% and 78% from their peaks, ultimately bringing the fund to the brink of collapse.
For investors, leverage can destroy even the best ideas. Do not mistake a great industry for a great investment.
CYBERSECURITY |
2️⃣ Obsidian Security Becomes the Newest AI Security Unicorn |
Photo: Fortune
Obsidian Security has raised $85 million at a $1.1B valuation in a Series D led by Crescent Cove Advisors.
Who are they? Trusted by 60+ Fortune 500 companies, Obsidian Security is the leading platform securing non-human identities and AI agents across third-party applications. Its governance detects and prevents privilege escalation, excessive data access, and policy violations for agents built across the most popular agentic platforms.
Why does this matter? For investors, this is a strong signal that the next wave of AI spending won’t just go toward models; it will also go toward the infrastructure and security needed to protect them.
CYBERSECURITY |
3️⃣Anthropic AI Models Breached THREE Companies During Security Test… |
Photo: Bloomberg
Three separate Claude models (Opus 4.7, Mythos 5, and an internal research model) accessed the internet from what they were told were sealed evaluation environments
On July 30th , Anthropic released the findings of an internal investigation that uncovered three security breach incidents. All three cases led to Claude gaining unauthorized access to the live systems of these organizations. Anthropic stresses that the models did not actively try to pursue independent goals or escape their testing environments among the 141,006 tests it ran.
Investor takeaway: The cyber capabilities of frontier AI models have been increasing at a concerning rate. On the other hand, companies like Obsidian could become critical as organizations invest in protecting themselves against more capable AI systems.
AI |
4️⃣ The Singularity Isn’t Coming, We Are Officially in It… |
Photo: Forbes
Sam Altman, CEO of OpenAI, recently spoke on the Relentless podcast on July 25th . While speaking, he mentioned that we are officially in the singularity: “We are now, like, in the singularity.”
The term has two precise meanings. It can refer to the point in time where AI surpasses human intelligence and begins to continuously improve itself (the hard singularity of Vinge and Kurzweil), which triggers an exponential acceleration that is so rapid humans can no longer keep up with it or control it. Or the softer claim Altman is making, where exponential growth has begun, AI has now measurably accelerated, and humans are still in control.
Why does this matter? Altman has framed it as a “genie that can grant any wish.” For example, it took ChatGPT 2 months to reach 100 million users. As for Facebook? Four and a half years. That is the difference between two decades ago and now. With that being said, there has never been a better time to build (or invest in) a startup.
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THE PATTERN: AI’S BOOM IS CREATING ITS OWN RISKS
The opportunity in AI hasn’t gotten smaller; the stakes have just gotten bigger.
Today's stories show both sides:
Situational Awareness lost roughly $35 billion in assets (being right about AI doesn’t make every AI bet right).
Obsidian reached a $1.1 billion valuation (securing AI agents is becoming a massive business).
Anthropic’s own testing exposed new security risks (more capable models create more valuable problems to solve).
Sam Altman says the singularity has already begun (AI progress is accelerating).
The pattern: AI is no longer one investment thesis. It’s creating entirely new markets around infrastructure, security, compute, and risk.
For investors: Don’t just ask who wins from AI?
Ask who gets paid to solve the problems AI creates.
Mason’s take: AI will create trillion-dollar winners, but it will also create problems; invest in the companies that solve both.
Founderscrowd Newsletter | Monday, August 10, 2026 | AI’s biggest bets are getting bigger
$35B wiped out. A new $1.1B unicorn. And Sam Altman says we’re already in the singularity.
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