Saylor’s New $4.2 Billion Bitcoin Plan Aims to Reassure Skeptics
(Bloomberg) — Michael Saylor isn’t backing down. The Strategy co-founder is preparing to sell $4.2 billion more in preferred stock to fuel his latest Bitcoin bet — while throwing a lifeline to investors worried he’s diluting them into oblivion.
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The plan, unveiled with second-quarter earnings on Thursday, is Saylor’s latest answer to the big question hanging over his stock: how long can he keep using a lofty premium to fund ever-larger Bitcoin buys?
To reassure shareholders, Strategy pledged it won’t issue new common shares at less than 2.5 times its net asset value, except to cover debt interest or preferred dividends. At the same time, Saylor will keep tapping the market “opportunistically” when the premium is high, turning equity sales into fresh Bitcoin buys.
The move does two things at once: it locks in a floor aimed at reassuring any skeptical shareholders and arms the company with a larger war chest to keep buying Bitcoin. It’s a double play that pits Saylor directly against hedge fund managers like Jim Chanos, who have been betting the company’s premium will collapse.
“That would put common shareholders who are concerned about potential dilution at ease,” said Brian Dobson, managing director for Disruptive Technology Equity Research at the brokerage firm Clear Street. “The market is reacting positively to Strategy’s equity products. The demand is there as evidenced by their substantial capital raises.”
It’s the latest in a string of financial maneuvers that have transformed a once-obscure software firm into a leveraged Bitcoin proxy.
The dual move showcases Saylor’s mastery of capital markets during these bullish digital-asset times: using a self-imposed floor to placate critics, while simultaneously arming the company with fresh ammunition to keep buying Bitcoin.
The company – which is known formally as MicroStrategy Inc. — has already raised more than $10 billion this year through stock and structured offerings, feeding a balance sheet now holding $74 billion in Bitcoin. Its stock has surged 3,300% since Saylor’s first crypto purchase, outpacing Bitcoin itself and forcing hedge funds into a high-stakes battle over whether his premium-fueled strategy can last.
Since Strategy’s first Bitcoin 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.