Masa's Last Laugh?

Between the WeWork debacle and the coronavirus, the markets have deemed his $100 billion Vision Fund largely worthless. But the world’s most important investor over the past three years, SoftBank’s Masayoshi Son, has other assets, a track record—and a plan

- ALEX KONRAD

With a flurry of slammed black SUV doors, SoftBank Founder Masayoshi Son and his entourage duck into the hush-hush private space within America’s top seafood restaurant, Le Bernardin, the Japanese billionaire easy to mark by the metallic-gray Uniqlo down jacket he wears over his suit.

The man known simply as Masa has gathered around twenty of the world’s largest asset managers in Midtown Manhattan on this day in early March. He hands over a colorful tote bag he’s using instead of a briefcase and assumes the empty chair at the dead center of one side of a large three-sided table. The day before, he’d spoken to a larger group of investors, but he’s billing this morning as an exclusive “Pre-IPO Summit,” and he’s drawn a multitrillion-dollar audience, including BlackRock’s Larry Fink, who sits next to him.

“Despite people’s view that SoftBank might be struggling, we continue to grow,” Son tells them. “Don’t think about the past.”

Easier said than done. SoftBank’s $100 billion Vision Fund is surely the most-scrutinized in the world, and for good reason. Over the past three years, Masa has made a dizzying number of huge, bold bets—88, to be precise—at huge, bold valuations. Things haven’t gone exactly as planned. First, there was Uber, which the Vision Fund backed late, leaving it hundreds of millions underwater. And then WeWork, into which SoftBank has pumped more than $10 billion since 2017, and which cratered since it withdrew its much-maligned IPO plan following the sloppy exit of its self-centered, self-dealing founder, Adam Neumann. A “tough time,” Masa concedes to the group. The previous day, he had given a longer explanation to