MicroStrategy, recently rebranded as Strategy, has released a Bitcoin investment guide that emphasizes downside risks, warning investors that Bitcoin has experienced a 93.1% crash in its trading history. Executive Chairman Michael Saylor shared the document, which dedicates substantial focus to potential losses, custody failures, and position sizing concerns.
Historical Losses and Interim Volatility
The 93.1% decline cited in the guide represents Bitcoin's deepest historical drop, which occurred at the 2011 low. The guide also notes a worst one-year return of minus 83.6%. According to MicroStrategy, the document's emphasis is on investor survival rather than price direction, highlighting that long-term Bitcoin conviction does not protect investors during sharp interim downturns.
The guide cautions that "an investor can be correct that Bitcoin appreciates and still lose money through leverage, option decay, an unfavorable capital structure, corporate risks, counterparty failure, excessive fees or forced liquidation."
Saylor's Personal Experience with Market Crashes
The warning carries particular weight given Saylor's history. On March 20, 2000, MicroStrategy restated three years of revenue, causing the stock to fall 62% in a single day from a peak of $333. The SEC subsequently charged Saylor with fraud; he paid $8.28 million in disgorgement and a $350,000 penalty without admitting wrongdoing.
Company's Substantial Bitcoin Holdings
Strategy holds 845,050 BTC as of September 7 at an average cost of $75,412. With Bitcoin near $77,106, the company's position is barely 2% above water and 38.8% below its October 2025 record. Recent purchases, including 4,603 BTC bought on August 31 at an average of $80,318, are already underwater.
Conflicting Interests
The Bitcoin guide functions simultaneously as a product menu, listing investment options in Strategy's common stock and preferred stock of its BTC treasury company. While Strategy discloses this conflict, noting plainly that it profits from higher Bitcoin prices, the juxtaposition creates tension: Saylor advises investors to size for a 93% decline while his own company is positioned for appreciation.
