Strategy founder Michael Saylor says the company turned to artificial intelligence to help design the financing instruments that raised roughly $15 billion for its Bitcoin accumulation strategy, an unusual admission from a company known for pioneering corporate Bitcoin treasury strategy well before AI tools were part of the conversation. Saylor made the disclosure during an August 6 appearance on The Diary Of A CEO podcast, saying he had "used AI to make $15 billion."
According to Saylor's account, Strategy had funded its Bitcoin purchases primarily through convertible bonds for years but eventually ran into the practical limits of how much capital it could raise through that structure alone. Rather than bringing in another investment bank to workshop alternatives, Saylor said he turned to ChatGPT to help design new instruments.
Two new instruments, one old goal
The result was two new securities: STRK, a convertible preferred stock, and STRC, which carries a variable monthly dividend engineered to keep its market price stable near par value. One of these instruments alone raised approximately $2.5 billion, which Saylor described as the largest offering of its kind at the time, with subsequent offerings stacking on top of that initial raise to push the total haul to around $15 billion. All of it, by Saylor's account, was funneled into further Bitcoin purchases.
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The scale of Strategy's Bitcoin bet
The AI-assisted capital raise is just the latest chapter in Strategy's aggressive accumulation strategy, which has made it the largest corporate holder of Bitcoin by a wide margin. The company's total holdings reached roughly 843,738 BTC as of late May 2026, a stockpile built almost entirely through the kind of creative capital markets financing Saylor has become known for since Strategy first adopted Bitcoin as a treasury reserve asset. That accumulation runs alongside a broader wave of institutional Bitcoin demand playing out through spot ETFs, though Strategy's approach of buying and holding directly on its own balance sheet remains structurally different from ETF-based exposure.
Why the AI framing matters
Whether or not ChatGPT genuinely originated the structural ideas behind STRK and STRC, Saylor's framing of the raise as AI-assisted fits his broader public messaging about productivity tools and unconventional capital strategy. It also underscores how normalized AI-assisted financial engineering has become at even the largest, most scrutinized corporate treasuries — a claim that would have seemed implausible for a multi-billion-dollar capital raise just a few years earlier.
