Michael Saylor says ChatGPT played a role in designing the preferred stock financing model that helped Strategy raise about $15bn to support its Bitcoin-focused balance sheet.
Strategy’s executive chairman described using the artificial intelligence chatbot to examine and develop financing structures linked to the company’s Bitcoin strategy. He discussed the process in an interview with The Diary of a CEO, according to a 6 August report by Fortune.
“AI helped me create $15 billion,” Saylor said.
The money was not generated directly by ChatGPT. The figure refers to capital raised through Strategy’s preferred stock products and related financing arrangements. ChatGPT helped Saylor explore the structure, while investors, underwriters and Strategy executives were responsible for executing the offerings.
Strategy has developed a range of Bitcoin-backed preferred securities, including STRC, STRK, STRF and STRD. Each product offers investors a different mix of dividends, volatility and exposure to the company’s balance sheet, which is heavily weighted towards Bitcoin.
Saylor said artificial intelligence was changing the way individuals and companies could create value. He argued that people should concentrate on asking more effective questions and use machines to develop ideas that might otherwise demand greater amounts of time or specialist expertise.
“Don’t try to outwork the robots,” he said.
The comments present AI as a way to strengthen human decision-making rather than simply remove repetitive tasks. Saylor suggested future entrepreneurs could gain an advantage by combining human judgement and creativity with the speed and analytical capacity of AI systems.
The episode is also an example of generative AI being used in corporate finance in the United States. However, proposals produced with ChatGPT would still need to undergo legal, accounting and regulatory checks before a publicly traded company could use them in securities offerings.
Strategy’s preferred shares have differing dividend commitments and risk profiles. Their performance remains tied to the company’s ability to manage its capital structure and its substantial Bitcoin holdings.
Bitcoin holdings under review
Saylor’s remarks come as Strategy has shown greater flexibility in managing its Bitcoin position.
A Securities and Exchange Commission filing dated 3 August said the company had sold 1,638 BTC for about $104.73m between 27 July and 2 August. Strategy used $52.4m of the proceeds to finance preferred stock dividend payments and $52.3m to buy back STRC shares.
The transaction reduced Strategy’s reported holdings to 842,138 BTC as of 2 August. The company said it had spent $63.51bn in total acquiring the Bitcoin, representing an average purchase price of $75,419 per coin.
On 5 August, blockchain-tracking service Lookonchain identified a further transfer of 1,030 BTC, valued at approximately $66.14m, from wallets it linked to Strategy. Strategy had not confirmed that the movement represented another sale, and no subsequent SEC filing had reduced the company’s reported holdings when the article was prepared.
Strategy is also expanding its employee benefits as it develops its wider corporate operations. On 5 August, the company joined the Invest America Business Pledge and committed to contributing $250 a year to Trump Accounts for eligible children of its US employees.
Children born on or after 1 January 2025 will also receive a one-off $1,000 contribution from Strategy, matching the initial deposit made by the US government.
The next challenge for the company will be determining whether its preferred stock model can continue to attract investors while financing dividend payments and preserving its Bitcoin holdings. Saylor’s account illustrates how ChatGPT influenced the model’s design, but its long-term success will depend on demand in the capital markets, the price of Bitcoin and Strategy’s execution.
