ChatGPT helped shape Strategy’s financing plan
Strategy Executive Chairman Michael Saylor said he used ChatGPT to explore and develop a preferred stock financing model tied to the company’s Bitcoin strategy, according to an Aug. 6 Fortune article. He discussed the process during an interview with The Diary of a CEO, saying the AI chatbot helped him examine financing structures that Strategy later used to raise billions of dollars from investors.
“AI helped me create $15 billion,” Saylor said.
The figure refers to capital raised through Strategy’s preferred stock products and related financing, not revenue generated directly by ChatGPT. The AI tool helped Saylor work through the structure, while investors, underwriters and company executives carried out the offerings.
Preferred stock products
Strategy has built a group of Bitcoin-backed preferred securities, including STRC, STRK, STRF and STRD. The products give investors different combinations of dividends, volatility and exposure to the company’s Bitcoin-heavy balance sheet.
Saylor urges workers to ‘harness the robots’
Saylor said AI is changing how individuals and companies create value. In his view, workers should focus on asking better questions and using machines to pursue ideas that would otherwise require more time or expertise.
“Don’t try to outwork the robots,” he said.
His comments frame AI as a tool that can expand human decision-making rather than merely replace repetitive work. Saylor argued that future entrepreneurs would gain an advantage by combining human judgment and creativity with the speed of AI systems.
The claim also provides a practical example of generative AI being used in U.S. corporate finance. However, ChatGPT-generated proposals still require legal, accounting, and regulatory review before a publicly traded company can use them to sell securities. Strategy’s preferred shares carry different dividend obligations and risk profiles, and their performance remains closely connected to the company’s ability to manage its capital structure and its large Bitcoin position.
Strategy adjusts its Bitcoin treasury policy
Saylor’s comments come as Strategy has shown greater flexibility in managing its Bitcoin holdings.
An Aug. 3 Securities and Exchange Commission filing showed that the company sold 1,638 BTC for approximately $104.73 million between July 27 and Aug. 2. Strategy used $52.4 million to fund preferred stock dividends and $52.3 million to repurchase STRC shares.
- The sale reduced Strategy’s holdings to 842,138 BTC as of Aug. 2.
- The company reported an aggregate purchase cost of $63.51 billion and an average acquisition price of $75,419 per Bitcoin.
On Aug. 5, Lookonchain identified another transfer of 1,030 BTC, worth roughly $66.14 million, from wallets it associated with Strategy. Strategy had not confirmed that the transfer represented another sale, and no later SEC filing had reduced its reported holdings when this article was prepared.
Strategy expands beyond Bitcoin financing
New employee benefits initiative
Strategy is also adding employee benefits as it develops its broader corporate operations. On Aug. 5, the company joined the Invest America Business Pledge and committed to support eligible children of its U.S. employees. Eligible children born on or after Jan. 1, 2025, will receive a one-time $1,000 company contribution matching the U.S. government’s initial deposit.
The next test for Strategy will be whether its preferred stock model can continue attracting investors while supporting dividend payments and protecting its Bitcoin holdings. Saylor’s account of using ChatGPT shows how AI influenced the model’s design, but its long-term performance will depend on capital-market demand, Bitcoin prices and Strategy’s execution.
