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The most famous crypto investors are betting on a $100 billion dream to buy Bitcoin

Michael Saylor, the most famous investor in buying and stacking Bitcoin, has built his career on testing the limits of certainty in the markets. Today, the chairman of Strategy Inc. puts his faith in a financial adventure that may be the riskiest in his history.

Over the years, Saylor has encouraged his followers to pump their savings into Bitcoin, and mortgage their homes, to buy more. Skeptics see him as just a crazed promoter. In either case, he has managed to transform an obscure software company into the world's largest institutional holder of Bitcoin, with a determination that few other executives dare to match.

Now, Saylor is asking for a new leap of faith: adopting an unconventional financial instrument — Perpetual Preferred Stock — to move away from selling common stock and convertible bonds, the instruments that helped him build a 'Bitcoin arsenal' worth $75 billion. Ironically, these securities never mature, and some can defer dividend payments, making them flexible for the issuer but concerning for investors.