Michael Saylor: ChatGPT Helped Strategy Raise $15B for Bitcoin

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Michael Saylor said ChatGPT helped Strategy design a new preferred stock structure to support Bitcoin purchases.
Strategy reportedly issued about $15 billion in credit instruments through the financing approach.
The structure included STRK convertible preferred stock and a variable monthly dividend mechanism.
Saylor said Strategy turned to ChatGPT after relying heavily on equity offerings and convertible bonds.
Strategy raised about $8.41 billion during the second quarter and another $1.28 billion through July 26.

Strategy co-founder Michael Saylor said ChatGPT helped the company design a new preferred stock structure that supported about $15 billion in financing for Bitcoin purchases.

Speaking on The Diary of a CEO podcast, Saylor said Strategy turned to OpenAI’s ChatGPT after traditional funding routes became harder to use. The company had already relied on equity sales and convertible bonds to fund its growing Bitcoin purchases.

Strategy Used AI to Design Preferred Stock

Saylor said Strategy needed a security that could sit between common shares and debt. He used ChatGPT to test different preferred stock structures and review ideas linked to finance, securities law, and digital assets.

The process led to STRK, a convertible preferred stock tied to Strategy’s Bitcoin plan. Saylor said lawyers and investment bankers had not seen a similar structure before the company introduced it to investors.

ChatGPT Helped Refine Dividend Structure

Saylor said ChatGPT also helped shape a variable monthly dividend system. The company designed the mechanism to help keep the security trading close to its $100 par value over time.

He added that AI pushed the team to consider options that traditional advisers had not proposed. When asked which model he used, Saylor identified OpenAI’s ChatGPT during the podcast interview.

Financing Reached About $15 Billion

Saylor said the financing vehicle raised about $2.5 billion during its initial offering. Strategy later completed more offerings and issued about $15 billion in credit instruments in total.

During the quarter ended June 30, Strategy raised about $8.41 billion in gross proceeds. The company then raised another $1.28 billion between July 1 and July 26, 2026.

The company continues using preferred securities to support its Bitcoin purchases.

Strategy Revenue Misses Estimates

Strategy reported second-quarter revenue of $122.39 million last month. That figure came slightly below the analyst consensus estimate of $122.91 million.

Strategy shares closed Thursday at $96.85, down 1.55%. The stock then rose 0.31% to $97.15 in Friday premarket trading as investors reviewed the company’s funding activity and Bitcoin strategy.

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