Saylor's $15 Billion Bitcoin Bet: How ChatGPT Helped Unlock New Financing Channels

Michael Saylor, executive chairman of Strategy, revealed how ChatGPT helped his company unlock $15 billion in financing for its Bitcoin strategy. In an August 6 appearance on The Diary of a CEO podcast, Saylor explained that Strategy turned to AI after its existing financing channels became harder to scale.

The company had already pushed heavily into common-stock issuance and convertible bonds, but these instruments couldn't support the scale of capital needed for further Bitcoin purchases. Saylor said, 'We needed to invent a new type of security, a new type of credit instrument that we could use to borrow money to buy more Bitcoin.'

Strategy used AI to explore the design of preferred shares, which are securities whose terms can combine characteristics of debt and equity. This process led to the creation of STRK, a convertible preferred stock, as well as STRC, Strategy's variable-rate preferred stock.

Saylor said that Strategy raised about $2.5 billion in the initial offering of STRC and later sold another roughly $8 billion through subsequent issuance, taking the total raised through that instrument to about $10.5 billion. Combined with roughly $4 billion raised through other preferred securities, he put the total at about $15 billion.