Strategy's Saylor says ChatGPT helped raise $15 billion for Bitcoin

Strategy raised about $15 billion over the past year using a preferred stock product that Executive Chairman Michael Saylor said he designed with ChatGPT.

"ChatGPT concluded it was a legal and reasonable structure that no one had tried," Saylor said on The Diary of a CEO podcast, published Aug. 6. He said bankers and lawyers initially opposed the structure because no comparable product existed.

The initial STRK offering raised about $2.5 billion, a shelf registration generated another $8 billion, and additional instruments contributed roughly $4 billion, according to Saylor. Strategy holds 842,138 BTC at an average purchase price of $75,419, making it the largest corporate holder of the cryptocurrency, per BitcoinTreasuries data.

The model faces a test as Bitcoin trades near $64,272, down 26 percent in 2026, leaving Strategy's holdings with a multibillion-dollar unrealized loss and forcing the company to sell Bitcoin to cover $1.76 billion in annual preferred dividends and interest.

A Security Designed to Trade Near $100

Saylor said Strategy had relied on convertible bonds to fund Bitcoin purchases, but that approach had reached its limit after the company became one of the world's largest issuers of the securities. He said he held extended conversations with ChatGPT to examine whether a preferred stock structure could keep the market price near $100 by adjusting the monthly dividend rate.

The result was STRK, a Bitcoin-backed convertible preferred stock with a variable dividend, which Saylor described as the first product of its kind. He said the company later developed a variable-dividend preferred stock designed to trade close to $100 by adjusting its dividend rate periodically.

"Don't try to outwork the robots," Saylor said, urging workers to use AI to create products that have never existed rather than compete with automation on routine tasks. He said both Bitcoin and AI remain in early adoption stages, and combining the two could produce financial instruments not previously seen in public markets.

Funding Pressure Builds as Bitcoin Falls

Strategy has sold Bitcoin three times this year to fund obligations tied to its preferred stock. The company sold 1,638 BTC at an average of $63,957, securing about $104.7 million, with $52.4 million used for preferred dividends and $52.3 million to repurchase STRC shares, according to an Aug. 3 SEC filing. Total Bitcoin sold stands at 5,226 BTC, worth about $321 million.

The company also raised $290.6 million through common stock sales and increased cash-like reserves by $250 million to $4 billion, aiming to cover annual preferred dividends and interest costs for at least 12 months. Strategy's second-quarter results reflected an $8.32 billion unrealized loss from Bitcoin price declines and a diluted loss of $24.45 per share.

Strategy shares traded near $98, down about 38 percent from the start of the year and roughly 76 percent below the 52-week high of $414.36. The company carries about $6.5 billion in convertible debt alongside roughly $15 billion in preferred stock, supported by about $58 billion in assets, Saylor said.

Saylor rejected criticism that the sales reversed his earlier stance on holding Bitcoin. "We have never had a policy of 'never selling,'" he said on X. The extent of ChatGPT's contribution to designing the securities has not been independently verified and is based solely on Saylor's account.

The next test is whether Strategy can keep attracting investors to its preferred stock while Bitcoin prices remain weak and the company covers $1.76 billion in annual dividend and interest obligations. Saylor said Strategy has raised roughly $65 billion in total capital, with most proceeds used to acquire Bitcoin.

This article is for informational purposes only and does not constitute investment advice.