Michael Saylor admits Strategy shareholders ‘would suffer’ if Bitcoin were to ‘fall 90% and stay there for 4 or 5 years’
- May 15, 2025
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Strategy’s executive chairman and crypto evangelist Michael Saylor revealed in a Financial Times video if Bitcoin were to fall 90% and stay down for roughly half a decade, the company would be stable, but equity holders would be wiped out because Strategy is heavily leveraged through convertible debt and bond offerings.
Business-software firm Strategy—formerly known as MicroStrategy—is the world’s largest corporate Bitcoiner. By converting its stock sales and convertible bond issuance into cryptocurrency, the company now owns 568,840 BTC worth nearly $59 billion .
Saylor’s investment strategy consists of placing all his chips onto crypto.
“We think bitcoin is the highest form of property, the apex property in the world, and it’s the best investment asset,” Saylor told Yahoo . “So the endgame is to acquire more bitcoin. Whoever gets the most bitcoin wins. There is no other endgame.”
Rather than focusing on organic growth from its business software, former Bank of America head of equity capital markets Craig Coben told the Financial Times the company’s focus is on “new recruits” and “new money.”
In an effort to raise capital to buy more Bitcoin, the company launched a new preferred stock offering in January, which pays a dividend and includes a liquidation preference at $100 per share, meaning investors would be paid that amount of the company is ever liquidated. The investment vehicle raised $580 million, according to the FT .
Additionally, in March, the company launched another offering, the perpetual strife preferred stock, again, to raise money to buy Bitcoin. This offering “will be payable solely in cash,” according to a release .
While Strategy explores every avenue to invest more money into Bitcoin, Coben said the moves “raises questions about the sustainability of what they are doing,” especially if Bitcoin craters.
As of March 31, Strategy held $60.3 million in cash, just a fraction of the $43.5 billion it held in Bitcoin, according to its form 10-Q . If the company was “forced to sell” its bitcoin “at a significant loss” in order to meet working capital requirements, a practice Saylor firmly opposes , “our business and financial condition could be negatively impacted.”