Michael Saylor Hit by Market Revolt as His Bitcoin Premium Sinks

Michael Saylor’s once-celebrated Bitcoin experiment is mired in a market backlash, raising questions about the sustainability of the corporate-treasury model he pioneered.

Shares of Strategy Inc., formerly MicroStrategy, have fallen 15% this month, erasing much of the premium the firm long enjoyed over its Bitcoin holdings. The company, long a bellwether for crypto sentiment, is now drawing fresh skepticism.

At the center of the concern is the firm’s financing tactics. Strategy’s new preferred stock — billed as its main vehicle for future Bitcoin purchases — has drawn tepid demand. A recent sale raised just $47 million, well short ...