A recent analysis has raised alarms over Strategy’s financial approach, particularly concerning its heavy reliance on perpetual preferred equity as a mechanism for capital management. Analysts caution that while the company currently enjoys a cash runway of 30 months, it faces the looming threat of running out of cash if it fails to sell equity to cover approximately $876 million in planned annual dividends.
The company’s first significant financial hurdle appears to be a $1.01 billion “put” option in September 2027, which could force cash repayment if the stock price does not meet investor expectations. This situation could create a negative cycle wherein declining stock prices diminish the company’s ability to raise capital, further intensifying the downward pressure on the stock.
In a recent announcement, Strategy revealed that its perpetual preferred equity has now surpassed its convertible debt, with a permanent capital standing at $8.36 billion compared to $8.21 billion in dated debt. Experts point out that while this marks a significant milestone for protecting the company’s substantial Bitcoin holdings, it may introduce new risks that could work against its long-term viability. The move essentially replaces the ticking clock of debt deadlines with ongoing dividend obligations, thereby creating a financial structure that could trigger a forced sale of Bitcoin if things go awry.
Perpetual preferred equity allows companies to raise funds without a maturity date, meaning that the capital does not need to be repaid. Instead, investors receive fixed dividends indefinitely. For Strategy, this translates to a steady cash outflow while eliminating the risk of having to repay principal. According to reports, the firm currently maintains about $2.25 billion in cash reserves, though it faces an annual dividend obligation estimated at $876 million.
Yet, even with its existing cash reserves, analysts note that the revenue of approximately $463.5 million still leaves a considerable funding gap that must be covered externally. Derek Lim, the head of research at a crypto market-making firm, indicated that if the equity markets experience a downturn, Strategy could find itself in grave danger.
Initially, the company began acquiring Bitcoin in August 2020 using its cash reserves, later opting for a mix of convertible debt and equity issuance. This shift aligns with CEO Michael Saylor’s belief in a long-term “holder forever” strategy for Bitcoin, eschewing the risks associated with forced sell-offs to settle debt obligations. However, upcoming maturities between 2027 and 2032 pose brewing challenges, particularly as investors can exercise their put options if the stock price materializes unfavorably.
Some market predictions on Myriad suggest a 25% chance of Strategy needing to liquidate some of its Bitcoin holdings by year-end. Analysts have highlighted that while Saylor’s growth strategy assumes a climate of favorable market conditions, it presents multiple potential failure points.
For instance, a protracted bearish market could severely undermine Strategy’s stock premium, which would make raising new capital prohibitively dilutive. Furthermore, the requirement for ongoing cash payments on preferred dividends poses another risk. A failure to meet these could signal distress to the market, leading to further declines.
Moreover, the high correlation between Strategy’s stock and Bitcoin’s price movements amplifies both potential losses and gains. Recent declines in Bitcoin’s value have had a significant negative impact on Strategy, highlighting the interconnectedness of the two. The company’s current valuation under $90,000—a nearly 30% drop from previous highs— could foster an exodus among investors.
In terms of Market-to-Net Asset Value (mNAV), a critical metric that gauges the company’s stock performance against its crypto holdings, many users on prediction markets anticipate a decline to 0.85 times its value—a worrying trend indicating potential struggles ahead.
The convergence of these risk factors creates a precarious situation for Strategy, where a single stressor could precipitate a broader crisis. Analysts have noted that the most probable adverse outcome would not be a dramatic collapse but rather a slow deterioration of performance relative to Bitcoin over the years, evolving into a cautionary tale in corporate treasury practices.
In summary, Strategy is navigating a tightrope, balancing the complexities of perpetual equity against the inherent volatility of Bitcoin. The company’s experiment could either establish a solid corporate framework for Bitcoin investment or lead to a significant liquidity crisis that reverberates through the crypto markets, challenging the robustness of its asset strategy.

