Saylor’s Bitcoin Machine Is Misfiring on Every Cylinder (1)

Michael Saylor built Strategy Inc. around a straightforward idea: raise money to buy Bitcoin, then never sell it. Over time, that simple bet has turned far more complicated.

After years of raising money to buy more Bitcoin, Strategy now has three investor groups to satisfy: Bitcoin investors, equity traders seeking leveraged exposure to the token, and preferred shareholders collecting cash dividends. That arrangement worked when Bitcoin was rising and investors were eager to finance ever-larger purchases.

Now all three are under pressure. The token is trading near a four-month low after the latest selloff, while Strategy’s stock has fallen about ...