Masa Madness

By the end of the decade, Masa had developed a reputation for audacious bets.

Massive amounts of venture capital, much of it flowing directly from Masa and the Vision Fund, were flooding into everything from scooters to food delivery to all-you-can-watch movies.

Masa was enamored by Adam, but others at SoftBank and the Vision Fund were less convinced.

it was hard to imagine an investor—even one as flush as Masa—who would be willing to weather losses on that scale.

WeWork also presented a unique opportunity for the Vision Fund. It would be impossible to invest $100 billion in five years by funding a flock of nimble sparrows; Masa needed to find albatrosses that could use his cash to overcome barriers to entry in industries where the theoretical returns

SoftBank was not a democracy. Masa liked to say that while his team might perform months of diligence on a company, “my first insight in the first few minutes is sometimes more meaningful.”

anyone, the market crashed. SoftBank’s stock sank more than 90 percent by year’s end, and Masa himself lost $70 billion—more wealth than any single investor had ever lost.