Michael Saylor, executive chairman of Strategy (formerly MicroStrategy), revealed that the AI chatbot ChatGPT played a key role in designing a preferred stock financing model that helped the company raise approximately $15 billion over the past year. Speaking on the Diary of a CEO podcast, Saylor described how he spent hours iterating with ChatGPT to explore a monthly preferred stock that could stay stable near $100 while bridging debt and equity. The resulting products—STRC, STRK, STRF, and STRD—were used to fund additional Bitcoin purchases and manage the company’s capital structure.
“AI helped me create $15 billion,” Saylor said, though the figure represents total capital raised through these instruments and related market activity, not direct profit. Despite initial pushback from bankers and lawyers, ChatGPT confirmed the structure was legal and reasonable, and it suggested ways to adjust dividend rates monthly to keep the market price close to the $100 par value.
The revelation comes as Strategy has recently shown more flexibility with its Bitcoin holdings. A Securities and Exchange Commission filing showed that between July 27 and August 2, the company sold 1,638 BTC for roughly $104.73 million to cover preferred stock dividends and repurchase STRC shares. As of August 2, Strategy held 842,138 BTC at an average cost of $75,419 per Bitcoin—leaving the company with a multibillion-dollar unrealized loss as Bitcoin prices trade below that level.
Saylor's broader message to entrepreneurs is to "harness the robots" rather than try to outwork them, framing AI as a tool that expands human decision-making. While ChatGPT helped design the financing model, the long-term performance of these preferred stocks will depend on market demand, Bitcoin’s price, and the company’s execution.
