Michael Saylor, executive chairman of Strategy — the firm formerly known as MicroStrategy — told the Diary of a CEO podcast that a preferred-stock product he designed with the assistance of ChatGPT enabled his company to raise approximately $15 billion over the past year.

Saylor's message to entrepreneurs was direct: stop competing with machines and start directing them. "Don't try to outwork the robots," he said. "What you want to do is ask the AI to do something that's never been done before."

ChatGPT and the Creation of STRK

During the interview with host Steven Bartlett, the 61-year-old executive framed artificial intelligence as a collaborative partner rather than a competitive threat. He noted that both Bitcoin and AI remain in early stages of adoption, and suggested that companies combining the two technologies could develop entirely new categories of financial products. Strategy, which began converting its treasury into Bitcoin in August 2020 and has since accumulated the largest corporate holdings of any publicly listed company, has been closely watched as a test case for corporate adoption of digital assets.

Saylor explained that Strategy had previously relied on convertible bonds to fund its Bitcoin acquisitions but eventually reached the practical limits of that approach. He then spent hours going back and forth with ChatGPT, testing whether a monthly preferred stock that remained stable near $100 was feasible. According to Saylor, the AI informed him that no such instrument had ever been created, but confirmed it was both legal and reasonable.

Bankers and lawyers initially pushed back, as nothing comparable had ever been brought to market. The resulting product, known as STRK, was designed to bridge debt and equity while continuing to finance additional Bitcoin purchases. ChatGPT also helped structure STRC as a Bitcoin-backed convertible preferred stock and suggested mechanisms for adjusting the dividend rate on a monthly basis, which helps maintain the market price near its $100 par value. If the model proves durable, it could offer other Bitcoin-holding firms a template for issuing yield-bearing instruments backed by digital assets without liquidating their positions.

The $15 billion figure refers to total capital raised by the company, not Saylor's personal earnings. Forbes estimates his personal net worth at $3.3 billion.

Microsoft CEO Satya Nadella has similarly described AI as a "co-pilot," using the term at the World Economic Forum in Davos in 2023. Billionaire investor Mark Cuban has also argued that entrepreneurs leveraging AI could generate outsized wealth.

Strategy's Bitcoin Sales and Financial Position

Bitcoin has declined 26% in 2026, while Strategy shares have fallen approximately 38% year to date. The stock is trading near $98, down roughly 76% from its 52-week high of $414.36.

Strategy has sold Bitcoin for the third time, recently offloading 1,638 Bitcoins for approximately $104.7 million at an average price of $63,957 each, as reported by Cryptopolitan. In total, the company has sold approximately 5,226 BTC for roughly $321 million to cover preferred dividend payments.

The firm also raised $290.6 million through the sale of common shares and added $250 million to its cash reserve, bringing the total to $4 billion. This reserve is designed to cover at least 12 months of preferred dividend and interest obligations, which amount to approximately $1.76 billion annually.

Strategy still holds 842,138 Bitcoins at an average cost of about $75,419 per coin. With Bitcoin trading below that acquisition cost, the company is carrying a multibillion-dollar unrealized loss. Second-quarter results reflected an $8.32 billion unrealized loss tied to declining Bitcoin prices and a diluted loss of $24.45 per share. The gap between the current Bitcoin price and Strategy's average acquisition cost has drawn attention to whether the company's preferred dividend obligations — fixed in dollar terms — can be sustained if the cryptocurrency remains below cost basis for an extended period.

Saylor has pushed back against suggestions that he abandoned his long-standing Bitcoin stance. As quoted by Cryptopolitan, he wrote on X: "We have never had a 'never sell' policy."

During the dot-com era, MicroStrategy's surging stock price made Saylor a billionaire. The company later restated its financial results and disclosed that 1999 revenue had been overstated. The stock lost 62% of its value in a single day, and Saylor subsequently settled SEC charges by paying $8 million without admitting wrongdoing.