Michael Saylor’s strategy is now underwater in Bitcoin. Is the outlet open?


Michael Saylor, the advocate of Bitcoin (BTCUSD) and Executive Chairman of Strategy (MSTR) (formerly known as MicroStrategy), started his aggressive accumulation strategy in 2020 when BTC was around $11,000. Undeterred by volatility, he ramped up buying through bull and bear markets, piling up holdings even as the cryptocurrency soared to a high above $126,000 last October.

Today, Strategy holds 712,647 Bitcoins with an average purchase price of $76,037. But overnight, Bitcoin fell below $75,000 amid a broader crypto selloff, marking the first time the company’s huge treasury has been underwater with unrealized losses exceeding $900 million. That reversal erases recent gains and raises alarms about Saylor’s leveraged bet. How far does it have to go before the strategy runs into real financial trouble?

www.barchart.com
www.barchart.com

Strategy is a provider of business analytics and AI-powered business intelligence software, enabling organizations to make data-driven decisions using cloud-native platforms. Headquartered in Tysons Corner, Virginia and listed on the Nasdaq under MSTR, it has become the world’s largest Bitcoin treasury company, holding BTC as a primary reserve asset to protect against inflation and drive shareholder value. This dual identity combines traditional software operations with cryptocurrency exposure.

In 2026, MSTR shares are down 4% year-to-date (YTD), underperforming the S&P 500 ($SPX) by 1.7% over the same period. Over the past year, however, MSTR has plummeted 56%, in stark contrast to the S&P 500’s 15% rise, reflecting the overflow of Bitcoin volatility.

Valuation metrics show a mixed picture: the trailing P/E ratio stands at 6.7, well below the software industry average of 28, indicating potential undervaluation based on earnings, especially if BTC rebounds boost profits. The forward P/E is even lower at 2, suggesting weak expected growth. However, the price-to-sales ratio of 89.4 is extraordinarily high compared to the industry’s typical 5-10, driven by MSTR’s market price as a Bitcoin proxy rather than software revenue alone, compared to its historical average P/S of around 100 during the height of BTC enthusiasm. Overall, MSTR looks overvalued even for risk-tolerant investors betting on a crypto recovery, let alone more conservative investors.



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