Michael Saylor Amps Up Bitcoin War Chest With $2.8 Billion Sale

Michael Saylor’s one-of-a-kind capital markets machine just got bigger.

As crypto prices continue to boom, Saylor’s Bitcoin holding company, Strategy launched a new kind of preferred stock, and then promptly upsized the deal from $500 million to $2.8 billion, according to a person familiar with the transaction who asked not to be identified. 

The security that priced on Thursday, which the company is calling Stretch, promises buyers a hefty 9% annual payout, with no end date attached — unusual in the arcane world of preferred stock offerings. 

The deal offered the latest demonstration of Saylor’s Wall Street wizardry as he continues his years-long effort to transform a middling software firm, which used to be known as MicroStrategy, into a financial juggernaut obsessed with one goal: raising as much money as possible to acquire as many Bitcoin as possible. Some 600,000 coins, or around $70 billion worth at last count. 

“This is not the first financial engineering initiative by Strategy,” said Campbell Harvey, a professor at Duke University. “In any situation where your company is worth far more than fundamental value, you raise money.”

Since Strategy’s first purchase in 2020, Saylor has sold equity, issued various types of debt and layered stacks of preferred shares on top. In the process, he has encouraged a fleet of imitators and spurred a new industry of public companies following a so-called treasury strategy dedicated to buying and holding cryptocurrencies. 

Many of the previous financial instruments that have fueled Strategy’s rise have ended up being more popular than expected, but even against that backdrop the demand for Stretch was notable. The company’s common shares rose 0.5% on Wednesday, and are up 43% for the year.  

In Strategy’s complicated and unusual capital structure, the new shares sit above the company’s common stock and its other preferred shares — which carry names like “Strike” and “Stride” — but remain subordinate to its convertible bonds and a preferred stock known as “Strife.” 

Unlike those earlier offerings, Stretch allows Strategy to tweak the dividend. Each month, the firm will set a new payout rate aimed at keeping the share price near $100, raising or lowering the level as needed. It’s part pricing model, part trust exercise, and a clear reminder that Strategy creates its own rules.

That flexibility may appeal to Saylor’s large fan base of retail investors, but it also adds a fresh layer of uncertainty to an already complex capital structure. And there are signs that Saylor’s tactics may be hitting up against somewhat diminishing returns. The value of the company, relative to the Bitcoin it owns, has gone down.  

In its latest offering, Strategy offered the Stretch shares at a discount to win over investors. The shares, which are set to carry an initial dividend of 9%, are being sold for $90 each, the bottom of a marketed range and a discount to their face value of $100, according to the person familiar with the deal.

But the outsized demand for the deal provides the latest sign of both Saylor’s avid following and the continued speculative fervor running through the markets. 

Morgan Stanley, Barclays Plc, Moelis & Co. and TD Securities worked on the deal, Bloomberg previously reported. 

Read more on IPOs: For the latest news on equity capital markets activity in the US, Canada and Latin America, follow the channel or visit NI BFWECMUS. To subscribe to ECM Watch, Bloomberg’s daily roundup of news from around the region, click here. 

(Adds commentary in fifth paragraph.)

© 2025 Bloomberg L.P.