Michael Saylor says he turned to ChatGPT to help design a novel class of preferred stock that ultimately raised roughly $15 billion for Strategy over the past year, after the company's long-running strategy of issuing convertible bonds to fund Bitcoin purchases reached its practical limit.
Speaking on the Diary of a CEO podcast, Saylor described spending hours going back and forth with the model, testing whether a monthly preferred stock that could hold a stable price near $100 was even possible. According to Saylor, the AI told him no one had structured an instrument quite like it before, but that it was legal and workable, and it suggested adjusting the dividend rate every month as a way to keep the market price anchored close to that $100 par value.
Bridging Debt and Equity to Keep Buying Bitcoin
The resulting instruments, including the STRC and STRK preferred shares, were built to bridge the gap between debt and equity financing while continuing to fund Strategy's Bitcoin accumulation. Saylor's traditional financing muscle, dollar-denominated convertible bonds, had grown difficult to scale further without diluting shareholders or straining the balance sheet, making a new structure with its own dividend mechanics an appealing alternative for continuing to buy Bitcoin without leaning entirely on new share issuance.
Saylor also disclosed the scale of Strategy's current balance sheet: roughly $6.5 billion in convertible debt alongside about $15 billion in preferred stock, all supported by an estimated $58 billion in total assets, primarily the company's Bitcoin holdings.
Related: Wintermute Registers as US Broker-Dealer, Targets Wall Street
The Instrument Is Being Tested by a Rough Year
The timing of Saylor's comments is notable given how the strategy has performed lately. Bitcoin is down 26% and Strategy shares are down 38% so far in 2026, and the company has reportedly had to sell Bitcoin to keep funding dividend payments on the very preferred stock ChatGPT helped design. That combination puts real pressure on an instrument built around maintaining a stable $100 price, since a sustained Bitcoin drawdown squeezes the same balance sheet that backs the dividend.
Even so, Saylor's framing treats the AI collaboration as a genuine institutional-finance breakthrough rather than a novelty, part of a broader pattern of crypto-native firms pushing into increasingly sophisticated, Wall Street-style financial engineering as the industry matures beyond simple spot trading and custody.
