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Key Takeaways
- Saylor said ChatGPT helped design STRK and a variable-rate preferred stock, together raising roughly $15 billion after Strategy exhausted its convertible-bond capacity
- Saylor defended a sale of more than 1,600 Bitcoin near $59,000, framing it as proof the company could sell without disrupting the market or its dividend obligations
- Saylor projects Bitcoin near $12 million by 2046 on a 30%-then-20% annual growth path, a target that remains contested amid Strategy’s stock struggling to close above $150
Strategy Executive Chairman Michael Saylor said he used OpenAI’s ChatGPT to help design a Bitcoin-backed preferred stock that raised more than $15 billion for the company, an instrument he described as unprecedented in structure. Saylor made the comments in an interview with Steven Bartlett on the Diary of a CEO podcast, where he also defended a recent Bitcoin sale and reiterated a two-decade price target for the token.
Bitcoin traded near $64,500 at the time of the interview.
AI-Assisted Design Produced a New Class of Preferred Stock
By early 2025, Strategy held about $30 billion in Bitcoin and had become the largest issuer of convertible bonds in the world, effectively maxing out that funding channel. Saylor said the company turned to ChatGPT to help design a new financing instrument once that route was exhausted.
The result was STRK, a convertible preferred stock, followed by a version carrying a variable monthly dividend rate. Saylor said the variable-rate structure had never been created before in the history of preferred stock issuance. The two instruments combined raised roughly $15 billion, with about $10.5 billion from one offering and close to $4 billion more from the other, according to Saylor’s account.
Saylor Defends Bitcoin Sale as a Response to Short-Seller Pressure
Saylor addressed criticism tied to Strategy’s Bitcoin holdings, which stood near 4% of total supply and had drawn arguments from short sellers that the company could never sell without crashing either Bitcoin’s price or its own stock. That argument, Saylor said, threatened confidence in the dividend payments backing Strategy’s preferred stock instruments.
He said the company sold Bitcoin near $59,000 to demonstrate it could do so without disrupting the market, and that the price rose in the aftermath. Strategy confirmed a sale of more than 1,600 Bitcoin over one week, even as Saylor maintained he has personally never sold a token himself.
Saylor put the company’s Bitcoin sale break-even point at about 3.2% of holdings, saying,
“If you want people to believe […] you have to do the thing.”
The sale also addressed concerns some analysts had raised about whether Strategy’s growing preferred stock obligations were straining the mechanism the company uses to fund additional Bitcoin purchases.
Saylor’s Math Implies Bitcoin Near $12 Million by 2046
Saylor reiterated his long-term Bitcoin price outlook during the interview, projecting roughly 30% annual appreciation for the next 20 years before growth slows to about 20% a year. Compounded over that period starting from Bitcoin’s current price, that trajectory would put the token near $12 million by 2046, based on Saylor’s stated growth assumptions.
Saylor framed the prediction as part of a broader argument that entrepreneurs should stop competing with tasks artificial intelligence can already perform and instead use the technology to pursue questions that have not yet been asked.
Skeptics Point to Strategy’s Stock Performance and Alternative Bitcoin Theories
Saylor’s price target has drawn skepticism from other market participants. Strategy’s own stock has repeatedly failed to close above $150 this year, a gap some analysts point to as evidence that public equity markets have not fully embraced the bull case Saylor has built around Bitcoin’s long-term appreciation.
Macro trader Arthur Hayes has offered a different explanation for any eventual move toward seven-figure Bitcoin prices. He ties that scenario to a broader credit bust driven by artificial intelligence spending rather than continued corporate accumulation of the kind Strategy has pursued.
The differing explanations reflect that Bitcoin’s path to Saylor’s target remains unconfirmed and contested among analysts, even as Strategy continues to expand its holdings.
