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SoftBank’s Masa Son still trusts his gut and isn’t done splashing billions on ‘crazy’ entrepreneurs

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Just a few weeks ago Masayoshi Son was smarting from having to bail out one of his big investments. Now he’s reminding his critics of another time he threw billions of dollars at a “crazy” entrepreneur that turned out very differently.

The SoftBank CEO appeared on a panel alongside Alibaba founder Jack Ma on Friday, where he underlined his belief in an investment style that is driven by “guts” and instinct. The talk comes just weeks after SoftBank rescued WeWork after a botched attempt to take the company public by founder Adam Neumann.

Speaking at the Tokyo Forum at the University of Tokyo, the two billionaire entrepreneurs recounted how Son famously invested $20 million in Ma’s company after meeting him for just 10 minutes.

Among all the entrepreneurs he met during a visit to China in 2000, Ma was the only one who didn’t ask for money and who didn’t have a business plan, Son recalled. But he had a “fighter’s spirit” and was passionate about how the internet was going to change China.

“Jack was the only one with the eyes sparkling and [he] caught my heart,” said Son.

Son said he then had to work to convince Ma to take his money, first offering $50 million, which Ma thought was too much, before eventually settling on $20 million for a 32% stake in Alibaba.

SoftBank has since sold some Alibaba shares, and its stake of roughly 26% in China’s e-commerce giant is now worth nearly $135 billion.

Son passed on other Chinese startup founders he met on that trip because “their passion, their true belief, is not in their heart,” he said.

Asked how he could tell, Son simply said: “I can feel.”

Son’s emotional investing style has come under scrutiny in recent months.

Son and SoftBank pumped millions of dollars into WeWork, only to see it scrap a highly anticipated public offering after investors questioned the office sharing startup’s sky-high valuation and management practices under Neumann.

SoftBank ended up bailing WeWork out with a $9.5 billion rescue plan that valued the company at $8 billion, far lower than its peak of $47 billion.

Other companies in Son’s $100 billion Vision Fund portfolio have also been struggling of late. Shares in Uber and Slack are both down some 40% from their June highs.

The declines led SoftBank to report an operating loss of nearly $9 billion for the July to September quarter.

But Ma gave Son a ringing endorsement on Friday, praising his vision of a future driven by technology.

“He probably has the biggest guts in the world on doing investment. Very few people in the world have that courage,” Ma said.

“Too much guts, sometimes I lose a lot of money,” Son interrupted. The exchange drew laughs from the audience.

Son’s remarks, and his appearance next to his most famous bet, suggest he’s not about to change his investment style. He said he wants SoftBank to last long after he is gone, and the only way to ensure that is to back hundreds of companies, technologies and the “most shining new entrepreneurs of that age.”

Son said that he knew Ma was a multi-billion dollar prospect after just a few minutes because “I could smell him.”

“We are both a little crazy,” Son said.

“Yea, people say we’re crazy but we’re not that stupid, right? We can be crazy, we shouldn’t be stupid,” Ma responded.

Ma is riding high on the blockbuster secondary listing of Alibaba shares in Hong Kong last month. The listing raised nearly $13 billion in the world’s second largest share offering this year after Saudi Aramco’s record IPO and ahead of Uber’s market debut back in June.

Article Topic Follows: Biz/Tech

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