Michael Saylor has built a career on testing how far conviction can bend markets—part financier, part preacher. Now the Strategy Inc. chairman is betting that same belief on what may be his riskiest financing experiment yet.

Over the years, Saylor has urged followers to pour their savings into Bitcoin, mortgage their homes, even “sell a kidney.” To admirers, he’s a prophet with a balance sheet; to skeptics, a showman with an obsession. Either way, he’s turned a once-obscure software company into the world’s largest corporate holder of Bitcoin, playing the markets with a conviction most executives would never dare.

Now, Saylor is asking for a different kind of leap of faith: embracing an unorthodox financing instrument— perpetual preferred stock—to shift away from common stock sales and c

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