Masayoshi Son’s radar clearly isn’t what it used to be.

Back in 2000, the SoftBank founder did more than help create China’s most important startup. The $20 million he handed Jack Ma also made Son’s reputation as venture capital guru—the “Warren Buffett of Japan,” as he was dubbed. When Ma took Alibaba public in 2014, Son’s stake had swelled to $50 billion.

This reputation is now taking a big hit as WeWork essentially implodes before our very eyes.

Twelve months ago, Son couldn’t heap enough praise at the office-rental startup Adam Neumann cofounded. Son claimed that WeWork is the “next Alibaba” as he raised his stake. By January, Son’s $100 billion Vision Fund had piled nearly $11 billion into WeWork, which his team valued at $47 billion.

Recent days haven’t been kind to Son’s bet. Raging questions about its business model–and plunging valuations—forced WeWork to shelve a hotly anticipated initial public offering. Now, the company’s directors are reportedly looking to shunt CEO Neumann aside, not unlike how Uber sidelined Travis Kalanick.

All this leaves Son with some difficult explaining to do as he cobbles together a second $100 billion VC fund.

Son’s initial fund is essentially a leap of faith on his gambling skills. His big win on Ma’s Alibaba led him to another headline-making success on Singapore’s GrabTaxi. The $250 million he handed to cofounder Anthony Tan baffled many at the time. Now, Grab is the dominant ride-sharing power in Southeast Asia. WeWork, though, is a notable stumble—one that calls into question Son’s entire strategy.

How the “Sage of Tokyo” missed that WeWork is essentially a leveraged property investor whose fortunes are tied to real estate market zigs and zags is anyone’s guess. The glitzy office designs and free-flowing coffee and beer make it easy to forget WeWork’s similarities to McDonald’s. Just as the burger giant’s real business is scoring good land deals for franchisers, WeWork is largely concerned with winning prime locations. Not very “new economy,” is it?


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