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The mystery of Masayoshi Son, SoftBank’s great disrupter

He has won and lost fortunes with his bets on technology. So is the investor a visionary — or a gambler who got lucky?

Late one afternoon in October 2023, as the sun slipped down over Tokyo Bay, Masayoshi Son was sitting in his private office at SoftBank headquarters, at the head of a wooden table almost as long as Vladimir Putin’s in the Kremlin. A diminutive, balding figure dressed casually in a jacket and slacks, Son was recounting to me the low point of his career, a year earlier, when he announced he was disappearing from public view.

“What a shitty life!” he exclaimed, with a trace of self-pity. “You know on my Zoom call, I see my face often on the video screen and I hate looking at my face. What an ugly face. I’m just getting old . . . What have I achieved? . . . I have done nothing that I can be proud of.”

At face value, it was an astonishing admission. Son, then 66, ranked among the world’s most renowned investors. He invested in ecommerce giants Yahoo and Alibaba before they became household names. At the height of the dotcom bubble in early 2000, he was briefly the richest man in the world. When it burst, he lost 97 per cent of his fortune, around $70bn. 

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