Updates From the #1 AI Investor: Leopold's NVIDIA & Anthropic Strategy
June 17, 2026
AI Summary
5 min readLeopold's AI Portfolio Rotation: From Picks and Shovels to the Physical Buildout
The most revealing signal in AI investing right now might be that Nvidia—the world's most valuable company, with $13.7 billion in cash and gross margins that make other businesses weep—just raised $25 billion in a bond offering. The offering was four times oversubscribed, meaning $85 billion of capital wanted in. Nvidia's stated reason is financial bookkeeping: pay off and refinance some existing debt. But the timing is notable. In the last month and a half, Amazon, Google, and several other hyperscalers have also raised external debt financing. And Leopold Aschenbrenner, the 24-year-old former OpenAI researcher whose fund Situational Awareness has grown from $200 million to an estimated $20 billion in under two years, has $9 billion in put positions against Nvidia, ASML, and Oracle.
What the Nvidia Bond Raise Actually Means
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What you'll learn
- 1 (00:00) **Episode Setup: Leopold's $20B AUM & Nvidia Short** - Introduces Leopold Aschenbrenner, the 24-year-old AI investor, and his fund's explosive growth from $13B to over $20B, including his massive $9B short position on Nvidia.
- 2 (00:43) **The Trigger: Nvidia's $25B Debt Offering** - Nvidia just raised $25B in a bond offering, more than the planned $20B, which seems contradictory for a company with high margins and $13.7B in cash.
- 3 (03:32) **Unpacking the Bond Offering: Cheap Money or a Warning Sign?** - The debt is raised at near-government bond rates, effectively "free money." Nvidia's stated reason is financial bookkeeping and refinancing.
- 4 (06:07) **The Contradiction: Buybacks & Dividends vs. Borrowing** - On May 18th, Nvidia authorized $80B in buybacks and raised its dividend 25x. This contradicts a narrative of needing cash.
- 5 (07:56) **Leopold's Real Thesis: The Pick & Shovel Trade is Overcrowded** - Leopold isn't bearish on AI, but believes the infrastructure trade (Nvidia, ASML) is overcrowded, and money will rotate to the next bottlenecks.
- 6 (09:19) **The Wild Card: 20% of Leopold's Fund in Anthropic** - Uncovered by the Wall Street Journal, Leopold's fund holds a massive private stake in Anthropic, estimated at 20% of his portfolio.
- 7 (11:36) **Context: Leopold vs. Bill Ackman** - At 24, with no formal investing experience, Leopold's fund ($20B) has already reached the AUM of Bill Ackman's Pershing Square, built over 30 years.
+ Full timestamped outline available in the app
Show Notes
We discuss Leopold Aschenbrenner’s AI-focused portfolio, including his reported short on NVIDIA and large private investment in Anthropic.
We also cover NVIDIA’s bond offering and the idea that the AI infrastructure trade is shifting toward power, networking, and data-center buildout rather than just chips.
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TIMESTAMPS
0:00 Leopold’s AI Portfolio
1:24 NVIDIA Short Explained
3:43 Bond Deal Breakdown
7:35 Why He Rotated
9:19 Anthropic Surprise Stake
12:19 Next Infrastructure Wave
14:28 Picking the Winners
17:55 Optics and Fiber Edge
22:00 Bubble or Not?
23:25 Energy Is the Bet
24:47 Closing Thoughts
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RESOURCES
Josh: https://x.com/JoshKale
Ejaaz: https://x.com/cryptopunk7213
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