For all of Elon Musk’s eccentricities—smoking a spliff with Joe Rogan, tweeting about a boner-killing Bill Gates—it is his financial quirks and contradictions that are most predictive of his Twitter endgame. The world’s richest man is famously illiquid, undiversified, and was largely uninterested, until last month, in operationalizing his assets in nonindustrial domains, such as Gates has done in philanthropy, or frenemy Peter Thiel in politics, or Steve Ballmer in sports. And yet even more than those other billionaires, the definitive feature of Elon’s extraordinary wealth creation has been a preternatural tolerance for risk, honed over the years by his messianic certitude, titanic successes, and near-failures.