Masayoshi Son is man of extremes.

His $20 million bet on Alibaba Group Holding became the most successful of all time when it swelled to more than $70 billion after a decade. He also lost $70 billion of his net worth in the dotcom crash, but then managed to raise one of the biggest investment funds of all time — the $100 billion Vision Fund — in 2017. The 67-year-old has been on a roller coaster that would put most mortals in therapy for life.

He is unapologetically dramatic, once threatening to set himself on fire if he wasn’t granted a telecom license in Japan and shoots from the hip in business deals. He says he backed Alibaba because of founder Jack Ma’s "strong eyes, shining eyes,” and he convinced the crown prince of Saudi Arabia to put $45 billion into his Vision Fund in a single, 45-minute conversation, by offering him "a Masa gift, a trillion-dollar gift,” according to Son’s 2017 interview with Bloomberg’s David Rubinstein.