Michael Saylor says ChatGPT helped design the hybrid securities that raised roughly $15 billion for Strategy's Bitcoin purchases, a disclosure he made on The Diary of a CEO podcast. The AI-designed instruments, STRK and STRC, pushed the company's total holdings to 843,738 BTC as of late May 2026.
Michael Saylor turned to ChatGPT to solve a corporate finance problem, and the chatbot's answer ended up raising $15 billion for Strategy Inc., the company formerly known as MicroStrategy. Saylor disclosed the AI's role in designing the hybrid securities during an appearance on The Diary of a CEO podcast, describing how the company turned to ChatGPT after hitting practical ceilings with traditional financing methods.
From convertible bonds to AI-engineered securities
Strategy had funded its Bitcoin acquisitions mainly through convertible bonds for years. But the company ran into the natural limits of how much capital it could raise through conventional convertible debt, a wall that pushed Saylor's team to get creative.
Rather than hiring another investment bank to brainstorm, Saylor turned to ChatGPT. The AI helped design a new class of preferred stock that blends characteristics of both debt and equity, a hybrid structure that hadn't previously existed in quite that form.
The result was two instruments: 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 IPO of its kind at the time, and subsequent offerings pushed the total haul to around $15 billion.
AI as a starting point, not a replacement
The AI didn't replace the lawyers and bankers who normally spend weeks or months structuring such securities. Instead, it gave Saylor's team a blueprint they hadn't considered, and the instruments still went through standard regulatory and legal review before reaching the market.
$15 billion deployed into Bitcoin
Strategy has deployed the proceeds into Bitcoin at an aggressive pace, bringing its total holdings to 843,738 BTC as of late May 2026.
The variable dividend on STRC adjusts payouts to keep the instrument's price near par, a design meant to attract income-focused investors who might otherwise avoid a Bitcoin-linked security. That approach concentrates risk, though: Strategy's corporate identity now revolves around a single asset, and a prolonged Bitcoin downturn could pressure the company's ability to service its preferred stock obligations, regardless of how the instruments were designed.
Source: Crypto Briefing
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