Bitcoin billionaire Michael Saylor, worth $4 billion according to Forbes calculations, has seen his wealth swing with the price of bitcoin since he pivoted his software company Strategy to a bitcoin accumulation vehicle in 2020.
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Strategy has bought almost 850,000 bitcoin worth just over $50 billion over the last six years, with many of its recent purchases funded by debt and equity sales.
Now, Saylor has credited artificial intelligence chatbots for helping him make $15 billion via the company’s controversial, bitcoin-backed preferred shares.
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Bitcoin billionaire Michael Saylor has claimed ChatGPT helped him create the financial products that made his company $15 billion.
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“I used AI to make $15 billion last year,” Saylor told The Diary Of A CEO podcast.
“You don’t want to learn how to do things the AI can do. What you want to do is learn how to ask the AI to do something that’s never been done before. If you want to create these incredible success things, you want to locate the magic opportunity.”
Strategy has seen its most controversial preferred stock, the 12% dividend-paying STRC, rebound in recent weeks back to near its intended $100 level after dropping to around $75 in late June.
Strategy’s Perpetual Strike Preferred Stock (STRK) and Perpetual Strife Preferred Stock (STRF) are preferred stock offerings launched in early 2025 to raise capital for bitcoin acquisitions. STRK offers an 8% dividend payable in cash or Strategy’s common stock stock and is convertible into common stock, while Strife is non-convertible and prioritizes stability for fixed-income investors.
However, Strategy has seen the value of its common stock plunge along with the bitcoin price over the last year, losing around 80% of its value.
The company has recently sold some bitcoin, which Saylor has said was both to “inoculate” the market to the possibility to Strategy selling bitcoin and to fund its debt and dividend commitments.
Alongside its $55 billion bitcoin stash, Strategy has also built up a $4 billion cash reserve, designed to give it two years of runway before it has to raise further funds.
“Terrifying confession or brilliant use of AI by Saylor,” asked technology investor and All In Podcast host Jason Calacanis, a regular Strategy critic, on X.
However, others have praised Saylor and Strategy for capitalizing on what they see as the implosion of the U.S. dollar, seen as buckling under the weight of spiralling U.S. debt.
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The bitcoin price has plunged from its peak, though many bitcoin backers remain very wealthy using AI tools like ChatGPT to bolster their fortunes.
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“History will show this as absolutely brilliant financial engineering in a major late stage U.S. debt cycle,” Bill Barhydt, the chief executive of bitcoin and crypto wealth platform Abra, replied to Calacanis.
“If you can borrow dollars and invest them in something that has a fixed float with fast adoption you should do it. [Saylor] legally can’t invest those dollars in securities since he’s not a ’40 Act company. That leaves bitcoin treasuries and gold. He’ll clearly make mistakes along the way but the strategy is brilliant.”
It’s not the first time Saylor has credited AI for helping him develop Strategy’s bitcoin-backed preferred securities, saying in May last year at his company’s developer conference that he used ChatGPT’s deep research mode to design the company’s convertible preferred stock products.