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Michael Siler: ChatGPT helped him raise $15 billion in Bitcoin strategy

2026-08-07 18:15:57
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TLDR

Contents

TLDR

Strategy uses AI to design preferred stocks

ChatGPT helps optimize dividend structure

Financing scale reaches approximately US$15 billion

Strategy revenue fell short of expectations

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Michael Saylor said ChatGPT helped Strategy design a new preferred stock structure to support its purchase of Bitcoin.

Strategy reportedly issued approximately US$15 billion in credit instruments through this financing method.

The structure includes STRK convertible preferred shares and a variable monthly dividend mechanism.

Saylor said Strategy turned to ChatGPT after relying heavily on equity issuance and convertible bonds.

Strategy raised approximately $8.41 billion in the second quarter and raised another $1.28 billion before July 26.

Strategy co-founder Michael Saylor said ChatGPT helped the company design a new preferred stock structure that provided approximately $15 billion in funding for the purchase of Bitcoin.

On the "The Diary of a CEO" podcast, Saylor said Strategy turned to OpenAI's ChatGPT after traditional financing channels became difficult to use. The company has previously relied on equity sales and convertible bonds to fund its growing Bitcoin purchases.

Strategy uses AI to design preferred stocks

Saylor said Strategy needed a security somewhere between common equity and debt. He uses ChatGPT to test different preferred stock structures and review ideas related to finance, securities law and digital assets.

This process ultimately led to the birth of STRK, a convertible preferred stock linked to the Strategy Bitcoin program. Saylor said lawyers and investment bankers had never seen similar precedents before the company introduced the structure to investors.

ChatGPT helps optimize dividend structure

Saylor said ChatGPT also helped shape a variable monthly dividend system. The company designed the mechanism to help keep the security's price near its $100 face value over time.

He added that artificial intelligence prompted teams to consider options that traditional consultants had not proposed. When asked which model was used, Saylor confirmed in a podcast interview that it was OpenAI's ChatGPT.

The financing volume reached approximately US$15 billion

Saylor said the financing tool raised approximately US$2.5 billion on its initial offering. Strategy subsequently completed additional issues, issuing a total of approximately $15 billion in credit instruments.

During the quarter ended June 30, Strategy raised approximately $8.41 billion in total earnings. Subsequently, between July 1 and July 26, 2026, the company raised another US$1.28 billion.

The company continues to use preferred securities to support its purchase of Bitcoin.

Strategy revenue fell short of expectations

Strategy last month reported second-quarter revenue of $122.39 million. The figure was slightly lower than analysts 'consensus forecast of $122.91 million.

Strategy shares closed at $96.85 on Thursday, down 1.55%. Subsequently, as investors reviewed the company's financing activities and Bitcoin strategies, the stock rose 0.31% to $97.15 in pre-market trading on Friday.

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