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Michael Saylor's Bitcoin Strategy Results in $3 Billion Unrealized Loss

Discover how Michael Saylor's aggressive Bitcoin accumulation strategy has led to significant losses, highlighting the risks of market timing and DCA during peak prices.
Published on 2025-03-31

Michael Saylor's Bitcoin Losses Hit $3 Billion

Michael Saylor, the executive chairman of MicroStrategy and a prominent Bitcoin backer, is facing mounting pressure as his aggressive Bitcoin acquisition strategy results in substantial losses. Recent data reveals that Saylor’s purchases over the past four months have incurred an unrealized loss of $3 billion, marking one of the most challenging periods in his Bitcoin investment history.

Key Details of the Losses

  • Purchase Timeline: MicroStrategy accumulated billions of dollars in Bitcoin between November 2024 and March 2025, with purchase prices ranging from $84,000 to over $106,000 per BTC.
  • Notable Transactions: On February 24, MicroStrategy bought 820,356 BTC at an average price of $97,514, currently down by nearly $318 million. Another significant purchase of 22,048 BTC for $1.92 billion at $86,969 per BTC was made recently.
  • Largest Loss: The most significant loss stems from the January 27 purchase of 810,107 BTC at $105,596 each, now reflecting a 24% drawdown and an unrealized loss of $269 million.

Market Timing and Implications

Saylor’s most active buying period coincided with Bitcoin’s local peak in early 2025, followed by a market correction. This mismatch has left MicroStrategy vulnerable, despite Saylor’s long-term bullish thesis. The total loss exceeds $3 billion, underscoring the risks of aggressive dollar-cost averaging (DCA) during periods of peak bullish sentiment.

Outlook for MicroStrategy

The positions remain deeply in the red, with recovery contingent on a significant Bitcoin price rebound. The DCA trendline remains below recent purchase levels, highlighting the strain on MicroStrategy’s balance sheet. If Bitcoin fails to rebound above the $90,000-$100,000 range, Saylor’s conviction and the company’s financial health may face further challenges.

This situation serves as a cautionary tale about the dangers of aggressive DCA during market peaks, even for long-term investors.

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