Key Highlights
- Michael Saylor said ChatGPT helped Strategy develop new financing structures for Bitcoin purchases.
- According to Saylor, the company raised about $15 billion through preferred stock and other capital markets offerings.
- Strategy currently holds 842,138 BTC, making it the world’s largest corporate Bitcoin holder.
Strategy Executive Chairman Michael Saylor said artificial intelligence played a role in helping the company raise billions of dollars.
Speaking on The Diary of a CEO podcast with Steven Bartlett on Thursday, Saylor said he used ChatGPT while developing financing structures that he said assisted the company in raising approximately $15 billion. “I used AI to make $15 billion in a way that no one would ever conceive that you could make $15 billion,” Saylor said. “This is a true story.”
According to data from BitcoinTreasuries, Strategy, formerly MicroStrategy, currently holds 842,138 Bitcoin, making it the world’s largest corporate holder of the cryptocurrency.
Strategy needed a new way to raise capital
According to Saylor, the company had already relied extensively on equity offerings and convertible bonds to finance its Bitcoin purchases. He said Strategy eventually became one of the world’s largest issuers of convertible bonds, making it increasingly difficult to continue raising capital through the same approach. “It wasn’t scalable,” he said.
Saylor said the company needed an entirely new financing instrument to continue funding its Bitcoin strategy, prompting discussions about structures that had not previously existed in public markets.
How ChatGPT helped explore new financing structures
Saylor said ChatGPT became part of the brainstorming process while Strategy explored whether it could create a new type of preferred stock that combined characteristics of debt and equity. That effort eventually led to the launch of STRK, which Saylor described as the first Bitcoin-backed convertible preferred stock.
Saylor said lawyers and investment bankers initially rejected the concept because no comparable product existed. He said Strategy nevertheless moved forward, combining financial engineering, securities law, legal analysis and digital asset expertise to build the product.
He also said the company later developed a variable-dividend preferred stock designed to trade close to $100 by adjusting its dividend rate periodically. Discussing the process, Saylor said ChatGPT indicated the structure could work with the appropriate design.
“Is it illegal? No. Why has no one ever done it? No one ever had a reason to do it,” he added.
Strategy raised about $15 billion
According to Saylor, the initial STRK offering raised approximately $2.5 billion, which he described as one of the year’s largest public offerings. He said Strategy later expanded the program through a shelf registration that generated another $8 billion, while additional financing instruments contributed roughly $4 billion, bringing total proceeds to around $15 billion.
During the interview, host Steven Bartlett summarized the story by saying, “ChatGPT made you $15 billion.”
Strategy’s fundraising activity has been disclosed through public filings. However, the extent of ChatGPT’s contribution to designing the securities has not been independently verified and is based solely on Saylor’s description of the process.
Strategy continues financing Bitcoin amid recent pressure
Saylor’s comments come as Strategy continues to rely on new financing to expand its Bitcoin holdings while navigating increasing financial pressure.
Last week, the company reported an $8.22 billion second-quarter loss, largely driven by a non-cash Bitcoin markdown, and authorized the potential sale of up to $5 billion in Bitcoin to help fund obligations tied to its preferred stock offerings.
Earlier this week, blockchain data also showed Strategy moving 1,030 BTC worth about $102 million, though the company did not say whether the transfers were related to a sale or internal treasury management.
Despite those developments, Saylor said Strategy has raised roughly $65 billion in total capital, with most of the proceeds used to acquire Bitcoin.
Saylor sees AI as a tool for new ideas
Saylor said artificial intelligence is most valuable when applied to problems that have not previously been solved rather than simply automating existing work. He said, “Don’t try to outwork the robots.”
He added, “What you want to do is ask the AI to do something that’s never been done before.” According to Saylor, many users underestimate AI by asking it to improve existing workflows instead of exploring entirely new approaches.
Strategy’s Bitcoin bet continues
Saylor also outlined the scale of Strategy’s balance sheet, saying the company currently carries roughly $6.5 billion in convertible debt alongside approximately $15 billion in preferred stock, supported by around $58 billion in assets.
Addressing criticism over Strategy’s earlier Bitcoin sale, Saylor said the company sold a portion of its holdings near $59,000 per BTC to demonstrate it could liquidate Bitcoin without destabilizing either the market or its own balance sheet. According to him, the move was intended to prove the sustainability of Strategy’s financing model rather than signal any shift in its long-term Bitcoin strategy.
While Strategy’s fundraising history and Bitcoin purchases are documented in public filings, Saylor’s description of ChatGPT’s role in developing the financing structures reflects his own account and has not been independently verified.
Also Read: Strategy’s $4B Cash Reserve Buildup Renews Focus on STRC Preferred Stock
