By Peter Eavis and Michael J. de la Merced

Anyone who has taken an Uber, sent a Slack message or enjoyed a free beer at a WeWork owes a little something to Masayoshi Son.
Through his Japanese conglomerate SoftBank and a $100 billion investment fund, Mr. Son plowed huge sums into these and other companies that aim to change how people work, travel and live. His investments enabled the young companies to throw caution to the wind and run up big losses as they expanded at a breakneck pace in recent years. Even in the start-up world, where idealism is abundant and losses are a badge of honor, Mr. Son’s approach and ambition stood out.
His early bet on the Chinese technology giant Alibaba earned a return of more than $100 billion and cemented his reputation as a farsighted investor. He has outlined a 300-year plan to make SoftBank a leader in artificial intelligence, robotics and other advanced technologies.
But this year, his grand designs collided with reality.
In what may turn out to be a reckoning for Mr. Son, Wall Street has started running from companies backed by SoftBank and its Vision Fund. The chief executive ofWeWork stepped down this week after a botched
initial public offering. Uber’s stock has fallen nearly 30 percent from
its I.P.O. price in May. And shares in Slack, which provides a workplace
messaging service, have tumbled more than 40 percent from their first
day of trading in June.
Through his Japanese conglomerate SoftBank and a $100 billion investment fund, Mr. Son plowed huge sums into these and other companies that aim to change how people work, travel and live. His investments enabled the young companies to throw caution to the wind and run up big losses as they expanded at a breakneck pace in recent years. Even in the start-up world, where idealism is abundant and losses are a badge of honor, Mr. Son’s approach and ambition stood out.
His early bet on the Chinese technology giant Alibaba earned a return of more than $100 billion and cemented his reputation as a farsighted investor. He has outlined a 300-year plan to make SoftBank a leader in artificial intelligence, robotics and other advanced technologies.
But this year, his grand designs collided with reality.
In what may turn out to be a reckoning for Mr. Son, Wall Street has started running from companies backed by SoftBank and its Vision Fund. The chief executive of
SoftBank’s critics
said its investments have poisoned the ecosystem for young companies by
encouraging founders to take excessive risks with little regard for
building businesses that can last through the ups and downs of the
economy. They are hoping the WeWork debacle will force investors to be
more skeptical about fast growing companies. Even Mr. Son has
acknowledged that the businesses his company invests in need to become
financially sustainable more quickly.
“I’m hoping this is the tipping point that brings more sanity into the capital markets,” said Len Sherman, a former senior partner at Accenture who is now an adjunct professor at Columbia Business School.
“I’m hoping this is the tipping point that brings more sanity into the capital markets,” said Len Sherman, a former senior partner at Accenture who is now an adjunct professor at Columbia Business School.

SoftBank
and the Vision Fund now face the prospect of harsh write-downs on some
of their investments. WeWork and its advisers considered selling shares
in its public offering at a valuation as low as $15 billion, well below
the $47 billion valuation at which SoftBank last invested in the company
in January. If the stock market does value WeWork at $15 billion,
SoftBank could be forced to take a $2 billion loss on its investment in
the office-space business, according to analysts at Bernstein.
The prospect of such sizable losses has cast a cloud over SoftBank and raised doubts about Mr. Son’s investment style. And that, in turn, could undermine his effort to raise an estimated $108 billion for a second Vision Fund. SoftBank said in July that it expected Apple, Microsoft and other companiesto contribute to
the new fund, but the most important investors in the first fund — Saudi
Arabia and Abu Dhabi — have yet to commit to it. ( Apple declined to
comment on the fund, and a Microsoft spokesman said the company’s
participation had not changed since the July announcement.)
The prospect of such sizable losses has cast a cloud over SoftBank and raised doubts about Mr. Son’s investment style. And that, in turn, could undermine his effort to raise an estimated $108 billion for a second Vision Fund. SoftBank said in July that it expected Apple, Microsoft and other companies
A spokeswoman for SoftBank declined to comment.
Speaking to executives of companies backed by the Vision Fund last week at the Langham Hotel in Pasadena, Calif., Mr. Son said they needed to be able to bring in enough revenue to more than cover expenses within a few years of going public, according to a person who attended the event but was not authorized to discuss it.
Simply increasing sales is not sufficient, Mr. Son said in what people in the audience understood as an implicit reference toWeWork .
Mr. Son, 62, built his business empire on huge bets and an unshakable belief in his own convictions. One frequently told story about him is that he once threatened to set himself on fire in the offices of a Japanese telecom regulator unless policymakers gave him what he wanted. He was one of the first corporate moguls to visit President-elect Donald J. Trump in 2016, promising to invest $50 billion and create 50,000 jobs in the United States.( The pledge was based on investments that SoftBank had already planned to make.)
Born to a family of Korean descent, he grew up in Japan and studied computer science at the University of California, Berkeley, where he made his first foray into business — creating an electronic translator that he sold to Sharp.
Speaking to executives of companies backed by the Vision Fund last week at the Langham Hotel in Pasadena, Calif., Mr. Son said they needed to be able to bring in enough revenue to more than cover expenses within a few years of going public, according to a person who attended the event but was not authorized to discuss it.
Simply increasing sales is not sufficient, Mr. Son said in what people in the audience understood as an implicit reference to
Mr. Son, 62, built his business empire on huge bets and an unshakable belief in his own convictions. One frequently told story about him is that he once threatened to set himself on fire in the offices of a Japanese telecom regulator unless policymakers gave him what he wanted. He was one of the first corporate moguls to visit President-elect Donald J. Trump in 2016, promising to invest $50 billion and create 50,000 jobs in the United States.
Born to a family of Korean descent, he grew up in Japan and studied computer science at the University of California, Berkeley, where he made his first foray into business — creating an electronic translator that he sold to Sharp.
Image
He
started a computer parts shop in Tokyo called SoftBank in 1981 and
built it into a technology and telecommunications conglomerate. His
wealth swelled during the dot-com boom, withered in the early 2000s and
slowly recovered as SoftBank became one of Japan’s biggest cellphone
companies.
In 2000, Mr. Son put $20 million into Alibaba, a stake that is now worth nearly $119 billion even after SoftBank sold off some of its shares three years ago. That windfall also helped pump up Mr. Son’s personal net worth to an estimated $20 billion.
In 2000, Mr. Son put $20 million into Alibaba, a stake that is now worth nearly $119 billion even after SoftBank sold off some of its shares three years ago. That windfall also helped pump up Mr. Son’s personal net worth to an estimated $20 billion.
Mr. Son has sought to duplicate his Alibaba investment again and again.
“You cannot think small,” he told analysts in May 2017. With the prospect of what he called a “gold rush” in the tech industry, now was the time to “open up our mind, open up our heart and think big.”
The Vision Fund has hit some home runs. The fund earned a roughly $1.5 billion return on its 2017 investment in Flipkart, an Indian e-commerce company, when Walmart acquired that business last year. Despite missteps likeWeWork , the fund might need only a few bets that pay off big to make up
for losses elsewhere, said Tom Nicholas, a professor at Harvard Business
School.
“That said, when you invest at high valuations — as SoftBank is prone to doing — it puts a lot of pressure on the fund to generate truly outsized returns from the successful portfolio investments,” Mr. Nicholas said in an email.
Several of Mr. Son’s investments have been disappointments, including one of SoftBank’s biggest forays into the United States: the 2013 acquisition of a controlling stake in Sprint, the struggling wireless company.
“You cannot think small,” he told analysts in May 2017. With the prospect of what he called a “gold rush” in the tech industry, now was the time to “open up our mind, open up our heart and think big.”
The Vision Fund has hit some home runs. The fund earned a roughly $1.5 billion return on its 2017 investment in Flipkart, an Indian e-commerce company, when Walmart acquired that business last year. Despite missteps like
“That said, when you invest at high valuations — as SoftBank is prone to doing — it puts a lot of pressure on the fund to generate truly outsized returns from the successful portfolio investments,” Mr. Nicholas said in an email.
Several of Mr. Son’s investments have been disappointments, including one of SoftBank’s biggest forays into the United States: the 2013 acquisition of a controlling stake in Sprint, the struggling wireless company.
Image
Mr. Son paid $21.6 billion
and took on billions more in debt to buy the company. But he predicted
that SoftBank would help Sprint overtake its bigger rivals, Verizon and
AT&T, in part by upgrading the company’s network to deliver the
better services and faster speeds.
Yet that promise remains just that. Excluding accounting changes that lifted Sprint’s earnings, the company’s bottom line has stayed roughly flat under SoftBank, said Craig Moffett, a research analyst at MoffettNathanson. Sprint has not only fallen further behind its bigger rivals, but also lost ground to T-Mobile, a smaller competitor.
Yet that promise remains just that. Excluding accounting changes that lifted Sprint’s earnings, the company’s bottom line has stayed roughly flat under SoftBank, said Craig Moffett, a research analyst at MoffettNathanson. Sprint has not only fallen further behind its bigger rivals, but also lost ground to T-Mobile, a smaller competitor.
“It’s been a terrible investment,” Mr. Moffett said.
Mr. Son tried several times to combine Sprint with T-Mobile. Only last year did SoftBank finally strike a deal by agreeing to sell Sprint to T-Mobile, a deal that 18 attorneys general are seeking to block.
That deal is crucial to Sprint’s survival, Mr. Moffett said. “There’s a very solid argument that Sprint’s equity is worthless if the merger doesn’t go through,” he said.
Several of SoftBank’s more recent investments have also struggled.
Analysts say one of the biggest problems for the company is that its enormous investments instart-ups have pushed up valuations for young companies
to levels that no other investors are willing to pay.
WeWork is a
prime example. Mr. Son first agreed to invest in that company after a
2016 meeting with its founder and chief executive, Adam Neumann, that
lasted less than an hour. In January this year, the last time SoftBank
invested in the office-space company, the two sides agreed to value the
company’s shares at $47 billion, up from the $20 billion they said the business was worth in 2017.
Another major flaw with SoftBank’s approach, critics say, is that it imposes few constraints onfounders of the companies it invests in. Corporate
governance experts were aghast when they learned of some of the
conflicts of interests at WeWork that Mr. Son and SoftBank tolerated.
For example, the company rented space in buildings partly owned by Mr.
Neumann. ( The stakes were later assumed by a WeWork affiliate.)
Mr. Son’s chosenstart-ups may also lack discipline because he lavished
hundreds of millions or billions of dollars on them before they had even
figured out what customers really wanted and how to turn a profit, said
Bill Aulet, a professor at the Massachusetts Institute of Technology’s
Sloan School of Management. “Hungry dogs hunt best,” he said.
Mr. Son tried several times to combine Sprint with T-Mobile. Only last year did SoftBank finally strike a deal by agreeing to sell Sprint to T-Mobile, a deal that 18 attorneys general are seeking to block.
That deal is crucial to Sprint’s survival, Mr. Moffett said. “There’s a very solid argument that Sprint’s equity is worthless if the merger doesn’t go through,” he said.
Several of SoftBank’s more recent investments have also struggled.
Analysts say one of the biggest problems for the company is that its enormous investments in
Another major flaw with SoftBank’s approach, critics say, is that it imposes few constraints on
Mr. Son’s chosen
Erin Griffith contributed reporting.
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