How Michael Saylor’s preferred stock gamble could trigger a death spiral for Strategy

By late last week, the sudden drop in Bitcoin’s price was crushing shares of Strategy, controlled by the signature crypto currency’s most famous champion and beneficiary, Michael Saylor. What’s gone mainly unnoticed: Strategy’s still selling at a big premium to the underlying value of its assets, almost entirely parked in Bitcoin, less the multiple-billions it effectively owes to borrowers and holders of its preferred stock. That extra lift appears to be a vestige of Saylor’s past sorcery in getting his stock’s value racing far faster than the price of Bitcoin, a dynamic that enabled him to keep raising the tokens investors “owned” per share in a kind of magical “accretion” game. But that wizardry disappeared months ago as the scenario flipped and Strategy shares tumbled at a pace multiple times the retreat for the coins that are practically its sole holding. Hence, it’s something of a mystery that investors are still paying way more for Strategy shares than what it would reap by selling all of its assets, and paying off its liabilities and preferred shares. Put simply, if the Saylor boost disappears, Strategy’s stock would fall way below where it sits today. It’s the Michael Saylor math problem that practically no one’s talking about. Strategy holds 844,000 Bitcoin, worth $51.1 billion at today’s quote of $60,500. Strategy also operates a software franchise that was its prime business before Saylor started buying crypto in Q3 of 2020. In 2025, it garnered just $477 million in revenue and lost roughly $40 million. Its sales are stuck at the levels of late 2010s. So it’s more than fair to give software the same value it enjoyed then, around $1.5 billion. In addition, Strategy’s disclosed that it harbors around $1 billion in cash, actually a dangerously low amount, but still a plus on the balance sheet. All told, Strategy’s salable and liquid assets total approx