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SoftBank’s Masayoshi Son is No. 6 on the Recode 100.

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SoftBank’s Masayoshi Son is about to make either himself or you look like a fool

Son is No. 6 on the Recode 100.

Masayoshi Son is one of the few people in Silicon Valley who is able to satisfy two utterly contradictory stereotypes at the same time — and still maintain the ability to destroy your deal.

To snickering venture capitalists, the 5’5” SoftBank chief executive is the definition of hubris, an egotistical investor who will chase any deal, pay any price, rush any diligence and ignore any warning, all so he can acquire the tiniest sliver of the sexiest companies in the world and drain himself clean of his $100 billion technology fund.

To worshipping CEOs, the man known simply as “Masa” is a visionary without peer, a charismatic daredevil who is one of the few tech investors willing to actually sacrifice his own billions, his own reputation and his own labor — whatever it takes — to gain access to a once-in-a-lifetime generation of companies that will enrich his investors and himself.

Love him or hate him, Son has reshaped Silicon Valley finance in 2017.

Son has, without a doubt, emerged as the most controversial and powerful tech investor of the year — not so much because of the companies he pursues but the extraordinary lengths he is willing to go to land them. After raising billions from foreign governments like Saudi Arabia, the United Arab Emirates and his own Japanese conglomerate, SoftBank, Son this year deployed the $100 billion in dramatic fashion.

There was the $4.4 billion he put into WeWork, making it far less likely that public markets would see the office-rental company anytime soon. There was the $1.1 billion round into biopharmaceutical company Roivant, which is employing Son’s favorite technology, artificial intelligence. And there is, of course, the deal that requires no introduction: Son’s hairy, ceaseless and at times sensational attempt to acquire an ownership position in Uber, the world’s most valuable startup.

The Uber deal has exposed Son at his most fundamental: Privately, he has negotiated the $10 billion deal with Uber’s existing investors with trademark hardball — offering low-ball pricing, gag orders and an ever-shifting coalition of alliances in order to better position himself in the deal of the year. Publicly, he has promised the world the Uber deal isn’t that important — he could walk away at any moment, he insists as he flashes a grin, and invest in Lyft instead.

Make no mistake, even with Son’s good humor and talk of an AI-enabled future, the man poses an existential threat to current venture capitalists who see themselves as the top dogs — and perhaps to the entire entrepreneurial system in Silicon Valley.

He has stoked worry on Sand Hill Road that they can be priced out of every deal of consequence due to the size of his fund. He has stoked worry on Wall Street — already suffering from a sluggish IPO market — now that companies have even more private runway thanks to his fundraising mega-rounds. And he has stoked worry among aspiring entrepreneurs, who now wonder, only somewhat unreasonably, about whether their new startup ideas should be tailored to an area of interest that Son has publicly identified.

Some early-stage venture capitalists selfishly acknowledge that while Son is a destabilizing force in Silicon Valley, he is a force for good if he can buy out their shares in secondary transactions — offering them and their own investors an early exit. Son is happy to oblige.

But there is no reason to rule out that, at some point, Son will move downstream to eat the lunch of seed and venture funds and compete for deals. Soon they too could be cursing the name of the wealthiest man in Japan.

SoftBank seems to be, for now, reveling in this intimidation factor. Rumors of different stripes have swirled around Silicon Valley that teeter perfectly between plausible and apocryphal: The time Son supposedly quintupled the valuation offered by a blue-chip venture fund (dubious); the time Son overruled his diligence team that advised him against a deal that he couldn’t let go (believable); or the times Son fantastically spoke of a larger second fund even though he was just beginning to spend from the first (confirmed).

It’s that last point that should shake Silicon Valley to its core: Son’s first fund has already made him a man without equal. What will his second, third or fourth do?

This article originally appeared on

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