When Bitcoin prices turned against Michael Saylor, he quietly pivoted to risky financial gambit at Strategy

Fortune

by Shawn Tully

February 20, 2026

AI-Generated Deep Dive Summary

Michael Saylor, CEO of Strategy (formerly MicroStrategy), has shifted his approach after Bitcoin prices fell, turning to issuing preferred stock as a risky financial strategy. This move aims to offset losses from Bitcoin investments but has raised concerns due to significant share dilution. Once focused on buying Bitcoin using equity issuance, Strategy's model relied on rising share prices to increase Bitcoin holdings per share. However, this strategy failed when Bitcoin prices dropped, leading Saylor to issue preferred stock—a more complex and potentially riskier approach—while continuing to sell shares at inflated prices. Strategy's share dilution rate, increasing from 76 million in 2020 to 314 million by early 2025, far exceeds peers like Wayfair and Twilio. This dilution has caused a sharp decline in Bitcoin per share (BPS) value, reducing shareholder returns despite Saylor's emphasis on growing BPS. The shift highlights the dangers of aggressive financial strategies when market conditions change. Investors are wary of such tactics due to their impact on long-term value and trust, making this strategy a critical issue for businesses

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Originally published on Fortune on 2/20/2026