Michael Saylor Used ChatGPT to Help Design $15 Billion in Securities for Bitcoin Buys

Strategy raised roughly $15 billion through a new class of hybrid securities designed with help from ChatGPT, using the proceeds to grow its bitcoin holdings to 843,738 BTC.

From Convertible Bonds to AI-Assisted Design

Saylor revealed the AI’s role in a recent appearance on The Diary of a CEO podcast, explaining that Strategy had relied heavily on convertible bonds to fund its bitcoin purchases for years but eventually hit practical limits on how much it could raise that way. Instead of turning to another investment bank, Saylor said he asked ChatGPT to help design a new type of preferred stock combining features of both debt and equity.

Two New Instruments Emerge

The result was STRK, a convertible preferred stock, and STRC, which includes a variable monthly dividend built to keep its price stable near par value. One offering alone raised about $2.5 billion, which Saylor called the largest IPO of its kind at the time, with later offerings pushing the total to around $15 billion.

AI as a Starting Point, Not a Replacement

Saylor described the process as using ChatGPT to generate an initial structural blueprint, which his legal and finance teams then refined before bringing it to market through standard regulatory review. The core combination of convertibility features, dividend mechanics, and pricing structure originated from the AI model itself.