Michael Saylor’s Bitcoin Bet Faces Short-Term Setback Amid Market Volatility

Michael Saylor’s company, Strategy (formerly MicroStrategy), is facing major unrealized losses despite its long-term Bitcoin gains. Recent data reveals a nearly $1 billion loss from its latest Bitcoin purchases, highlighting the risks of its aggressive accumulation strategy.

Strategy employs dollar-cost averaging (DCA) to buy Bitcoin at various price points, even during market dips. While this approach has delivered a 37.71% overall gain, its recent purchases at $95,000 to $106,000 per BTC are now deep in the red, as Bitcoin struggles to reclaim the $92,000-$94,000 range.

A major blow came on Jan. 27, 2025, when Strategy purchased $1.11 billion worth of BTC at an average price of $105,596 per coin—now down over 16%. This underscores the danger of buying aggressively during local market peaks.

Despite the short-term losses, Strategy remains committed to Bitcoin. The firm has essentially transformed into a Bitcoin ETF, attracting investors looking for BTC exposure through traditional markets. Its resilience in holding through market downturns has reinforced its reputation as a steadfast Bitcoin supporter.

However, its strategy carries significant risk. Frequent Bitcoin purchases at varying price points expose Strategy to high volatility, leading to steep short-term declines that could shake investor confidence. The timing risk of aggressive buying in uncertain market conditions is also a concern.

If Bitcoin fails to reclaim $100,000, Strategy may need to reassess its approach. While long-term bullish sentiment remains, short-term market setbacks highlight the risks of accumulating BTC without clear signs of recovery.