Michael Saylor (마이클 세일러), chairman of Strategy, said the company raised about $15 billion over the past year through a preferred stock product he designed with ChatGPT.

On Aug. 6, blockchain media outlet Cryptopolitan reported that Saylor said in an interview on the podcast "Diary of a CEO" that he used artificial intelligence to create a fundraising structure that did not previously exist.

Saylor said Strategy had used convertible bonds to secure funds to buy bitcoin, but that approach had effectively reached its limit. He said he then held long conversations with ChatGPT to examine whether a preferred stock structure was possible that would keep the market price around $100 by adjusting the monthly dividend rate. "ChatGPT concluded it was a legal and reasonable structure that no one had tried," he said, adding that in the early days bankers and lawyers also opposed it as having no precedent.

Based on the experience, Saylor said people should not try to work harder than robots, and stressed that AI should be used as a tool to create new things rather than something to compete with. He also said both bitcoin and AI are still in the early stages of adoption, and argued that combining the two technologies could create financial products that did not previously exist.

The $15 billion is not Saylor's personal profit but the amount of funds raised by Strategy. Forbes estimated Saylor's personal net worth at $3.3 billion.

Funding conditions are also coming under pressure as bitcoin and Strategy shares fall together. Bitcoin is down 26 percent so far in 2026, and Strategy shares have fallen about 38 percent from the start of the year. The stock traded around $98, about 76 percent below its 52-week high of $414.36.

Strategy recently moved to sell bitcoin for the third time. The company sold 1,638 bitcoin at an average of $63,957, securing about $104.7 million. The step was taken to fund preferred stock dividend payments, and the bitcoin sold so far totals 5,226 BTC, worth about $321 million.

The company also raised an additional $290.6 million through sales of common stock. It increased its cash-like reserves by $250 million to $4 billion. The aim is to cover annual preferred dividends and interest costs of about $1.76 billion for at least 12 months.

Strategy currently holds 842,138 BTC at an average purchase price of about $75,419. But as the bitcoin price has fallen below the average purchase price, large valuation losses have occurred on its holdings. Second-quarter results reflected an unrealised loss of $8.32 billion from bitcoin price declines and a dilutive loss of $24.45 per share.

Saylor, however, rejected criticism that the sales reversed his previous position that he would not sell bitcoin. On X, formerly Twitter, he said, "We have never had a policy of 'never selling.'"

Market attention is now focused on whether Strategy can continue to expand the fundraising structure it designed using AI. Another key variable going forward is whether it can reliably cover preferred dividends and interest costs even as bitcoin prices remain weak.