Michael Saylor Bets on a $100 Billion Bitcoin ‘Credit’ Dream

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 ...