Fortune has raised concerns that the premium investors are paying for Strategy’s stock — roughly 31% above its estimated net asset value — could come under threat amid rising debt and preferred stock obligations. The analysis points to a precarious capital structure where fixed liabilities have ballooned to approximately $21.8 billion, amplifying the impact of any Bitcoin price decline on common shareholders.
According to Fortune’s calculations, Strategy holds about 844,000 Bitcoin worth around $51.1 billion at a price of $60,500 per coin. Combined with its software business valued at $1.5 billion and $1 billion in cash, total assets reach about $53.6 billion. After subtracting $6.2 billion in convertible debt and $15.5 billion in preferred stock, common shareholders are left with roughly $31.8 billion — yet the market capitalization stands near $41.6 billion, creating a 31% premium.
The preferred stock financing strategy is central to the concerns. Since early 2025, Strategy’s combined debt and preferred stock obligations have surged from $6.9 billion to $21.8 billion, driven largely by preferred stock issuances to fund Bitcoin purchases. If Bitcoin falls to $50,000, Fortune estimates the net asset value could drop to around $23 billion, with fixed liabilities magnifying the hit to common equity.
Another risk highlighted is dilution. Since 2020, Strategy’s outstanding share count has increased from 98 million to 353 million. Meanwhile, questions around dividend funding persist. Strategy recently shifted its STRC preferred stock dividends from monthly to semi-monthly payments — now on the 15th and last day of each month — which management says aims to stabilize price and boost liquidity.
Strategy also increased its cash reserve by $100 million to $1 billion and resumed Bitcoin purchases, acquiring 1,550 BTC worth approximately $101.3 million between June 1 and June 7, bringing total holdings to 845,256 BTC. However, earlier sales of 32 Bitcoin for $2.5 million in late May, the first sale since December 2022, raised eyebrows. JPMorgan viewed the sale as symbolic but cautioned that future dividend commitments could strain reserves.
Annual preferred stock dividend obligations now total about $1.5 billion, and Fortune warns that continued reliance on new preferred stock issuances to pay dividends could add further pressure. Not all analysts agree; BTCTOP CEO Jiang Zhuoer argued that leverage remains manageable even if Bitcoin drops to $30,000, and suggested Strategy could use low-cost holdings to meet obligations while still raising capital for accumulation.