Billions in paper losses, and Michael Saylor is still not blinking. While critics have long called his all-in Bitcoin bet reckless, the executive chairman of Strategy just bought more anyway.
Strategy, the software-turned-Bitcoin-treasury company formerly known as MicroStrategy, purchased 1,031 Bitcoin between March 16 and 22 for approximately $76.6 million at an average price of $74,326 per coin. The buy pushed the firm’s total holdings to 762,099 BTC, acquired for $57.69 billion at an average cost of $75,694— still above Bitcoin’s current trading price, leaving the company with an unrealized loss of nearly $4 billion. Strategy’s stock rose 1.9% after the disclosure, with shares also gaining as much as 1.14% in pre-market trade.
Saylor has faced persistent criticism from Wall Street analysts and institutional investors who argue that concentrating corporate capital in a single volatile asset exposes shareholders to outsized risk. Skeptics have questioned whether the strategy serves the company or simply reflects one man’s ideological conviction. Yet markets, at least for now, keep rewarding the bet—Strategy shares are up roughly 5% this month despite sitting in the red on its Bitcoin position.
Underwater but Unbothered
Bitcoin traded near $70,000 at the time of the latest purchase, which is roughly $5,700 below Strategy’s average acquisition cost. That gap shows up directly on the balance sheet as a mark-to-market loss. Saylor’s answer has been the same every time: buy more.
Your completely free resource hub designed to boost your knowledge of cryptocurrencies
The broader market gave the stock a lift on Monday after President Donald Trump announced a five-day pause on threatened strikes against Iranian energy infrastructure following weekend talks, triggering a brief rally across equities and crypto. Bitcoin itself climbed nearly 2.5% in 24 hours, briefly crossing $70,000.
A $42 Billion Reload?
Strategy has no intention of slowing down. The company unveiled plans to raise up to $42 billion in fresh capital—split equally between new Class A common stock and perpetual preferred shares. At current prices, that capital could theoretically fund the purchase of around 595,000 additional Bitcoin, pushing total holdings well past Saylor’s stated target of one million coins.
Whether capital markets will absorb $42 billion in new securities from a stock trading 75% below its peak remains the central unanswered question.
