How ChatGPT shaped STRK
Saylor said he turned to the AI to help structure the preferred stock, which is convertible into common shares. The variable dividend rate version, he argued, is a first in history. By early 2025, Strategy held roughly $30 billion in Bitcoin, making the company the largest corporate holder of the cryptocurrency.
The instrument's design matters because it's a way for Strategy to raise capital without diluting common shareholders. With the preferred stock, investors get a dividend that can adjust, and they have the option to convert into equity. Saylor's use of ChatGPT to build the structure is a notable example of AI entering the boardroom.
The $15 billion raise and a liquidity test
STRK raised over $15 billion, and Strategy has become the world's largest issuer of convertible bonds, maxing out that market. To show the company could sell Bitcoin without tanking the price, Saylor sold some near $59,000. The move eased concerns about the growing preferred stock load, he said. Strategy's break-even point, according to Saylor, sits at about 3.2%.
That sale was a signal: Strategy can move large amounts of Bitcoin without spooking the market. For a company whose balance
