Strategy Inc. (NASDAQ:MSTR) co-founder Michael Saylor said OpenAI‘s ChatGPT helped Strategy design a novel preferred stock structure that ultimately enabled it to raise roughly $15 billion to purchase additional Bitcoin (CRYPTO: BTC).
How ChatGPT Helped Strategy Design a New Bitcoin Funding Vehicle
Speaking on The Diary of a CEO podcast on Thursday, Saylor said he turned to ChatGPT after Strategy had largely exhausted traditional fundraising options, including equity offerings and convertible bonds, as it sought additional capital to expand its Bitcoin holdings.
Saylor said the company needed to create an entirely new type of security that sat somewhere between common equity and debt.
He described using ChatGPT to explore different structures for a preferred stock, combining elements of financial engineering, securities law and digital assets.
“We went to the AI,” Saylor said. “I started exploring how do I design a preferred stock.”
The result was (NASDAQ:STRK), a convertible preferred stock that Saylor said was backed by the company’s Bitcoin strategy. He added that neither lawyers nor investment bankers had seen a similar structure before, often responding, “No one’s ever done it before.”
ChatGPT Made Me $15 Billion, Saylor Says
Saylor said ChatGPT helped the company refine the security’s design, including a variable monthly dividend mechanism intended to keep the instrument trading near its $100 par value.
He said the AI encouraged the team to pursue ideas that traditional advisers viewed as unconventional. “They never thought to do it,” Saylor said, referring to the financial industry.
When asked which AI model he used, Saylor replied, “ChatGPT, OpenAI.”
Saylor went on to say that the resulting financing vehicle became the year’s largest IPO at the time, raising about $2.5 billion before Strategy later sold billions more through additional offerings. Altogether, he said the company issued roughly $15 billion worth of credit instruments.
Strategy’s Q2 Earnings and Bitcoin Capital Raise
Last month, Strategy reported second-quarter revenue of $122.39 million, narrowly missing analysts’ consensus estimate of $122.91 million.
During the quarter ended June 30, the company raised approximately $8.41 billion in gross proceeds, followed by an additional $1.28 billion between July 1 and July 26, 2026.
Price Action: Strategy shares closed 1.55% lower at $96.85 on Thursday and edged 0.31% higher to $97.15 in Friday’s premarket trading, according to Benzinga Pro.
According to Benzinga Edge Stock Rankings, MSTR remains in a bearish trend across the short, medium and long term.
Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.
Photo courtesy: T. Schneider / Shutterstock
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