Michael Saylor said ChatGPT helped MicroStrategy design preferred stock structures that raised approximately $15 billion for Bitcoin acquisitions, according to remarks made on the Diary of a CEO podcast in early August.
Saylor, MicroStrategy's founder and executive chairman, used the AI tool to develop the financial instruments during a period when the company was executing its aggressive Bitcoin accumulation strategy. The preferred stock structures, referred to internally as STRK instruments, enabled MicroStrategy to access capital markets for its digital asset purchases without traditional equity dilution.
MicroStrategy has made Bitcoin acquisition a cornerstone of its corporate strategy since 2020. The company held approximately 207,000 Bitcoin as of mid-2024, making it one of the largest corporate holders of the asset. Its preferred stock offerings have been a key vehicle for raising capital to fund these purchases.
Saylor disclosed that large language models played a role in structuring corporate financial instruments during a wider discussion about how organizations should approach automation rather than resist it.
The $15 billion figure represents capital raised through these instruments over a specific period, not a single transaction. MicroStrategy completed multiple preferred stock offerings at different valuations between 2021 and 2024, each designed to capture market conditions while funding Bitcoin holdings.
Using AI to design financial structures is not uncommon among quantitative finance teams, but disclosure of the practice by a publicly traded company's chief executive remains relatively rare. MicroStrategy is regulated by the SEC and files quarterly reports detailing its capital raises and Bitcoin holdings.
MicroStrategy's financing approach secured $15 billion across multiple offerings, indicating that markets accepted the company's use of computational tools in designing them. If MicroStrategy discloses additional AI-assisted financial structures in future SEC filings, it could set a precedent for transparency about generative AI's role in corporate capital strategy.
