Michael Saylor’s aggressive strategy for accumulating Bitcoin has raised questions about its sustainability in the face of potential market downturns. Prominent crypto analyst Willy Woo provides insights that offer some reassurance, but also flag longer-term risks.
Woo addressed rising concerns in the crypto community, asserting that Saylor’s company, referred to as Strategy, will not need to liquidate its Bitcoin holdings during the upcoming bear market. Notably, the critical liquidation threshold for Bitcoin is approximately $91,502, a figure that remains well below current market prices. Strategy currently holds 641,205 BTC, valued at around $64 billion.
A key factor in this resilience stems from the nature of Strategy’s debt, primarily composed of senior convertible bonds. These financial instruments grant the company essential flexibility, allowing it to settle debts via cash, common stock, or a blend of both. Specifically, Strategy faces a $1.01 billion maturity on September 15, 2027, and must maintain a stock price above $183.19 to avoid selling off any Bitcoin. Given that Strategy’s stock was trading at $245 despite Bitcoin’s drop below $100,000, this safety margin appears robust.
Woo further emphasized that forced liquidation would only occur under dire circumstances, stating, “Bitcoin would need to experience catastrophic performance.” He believes it would necessitate an “extremely prolonged bear market” for Strategy to consider such a move.
However, Woo also noted that a lack of significant growth in Bitcoin’s value could risk partial liquidations if the cryptocurrency fails to perform adequately by 2028. This caution contrasts sharply with more optimistic forecasts from industry leaders like Cathie Wood and Brian Armstrong, who predict Bitcoin could reach $1 million by 2030.
In light of his strategic moves, Saylor is not resting on his laurels. The company has recently filed for a public offering of euro-denominated shares, targeting European institutional investors. This initiative includes the issuance of 3.5 million shares priced at 100 euros each, with an annual dividend of 10%. Such geographic diversification showcases Saylor’s ambition to bolster the company’s standing.
However, Woo’s analysis unfolds during a turbulent period, with Strategy’s stock experiencing a nearly 6.7% drop in one day, marking its lowest point in seven months. Concurrently, Bitcoin has seen over a 10% decline in just a week, intensifying doubts about the durability of Saylor’s aggressive accumulation model.
Overall, while Strategy’s financial architecture appears well-equipped to withstand immediate market challenges, the long-term success of this strategy hinges on Bitcoin’s performance over successive market cycles. As Saylor’s reserves grow, so too do the stakes in his high-risk, high-reward bet.

