himself. Acquaintances describe him as smart and arro-
gant and almost entirely lacking in self-awareness. They say
hebelieveshimselftheepitomeofNewYorkCitystraight-
forwardness,whichdoesn’tnecessarilyplaywellinpassive-
aggressive California.
He’s also gotten away with some questionable behav-
ior.Ina discussionaboutwhethertoinvestinthestation-
arybikestartupPelotonInteractiveInc.in2017,according
totwopeoplewhowereinthemeeting,Housenbold
opinedthatitsexerciseequipmentappealedinpartto
menwhomasturbatedtoitsworkoutvideos.SoftBanksaid
Housenboldnevermadesucha comment,andtheVision
FundultimatelydidnotinvestinPeloton.Housenboldis
alsonotoriousforsparkinganinternalcompliancereview
thisAprilbysellingpersonalsharesinGuardantHealth,a
cancer-detectioncompanyinwhichSoftBankis thelargest
shareholder.Althoughhewasclearedofanywrongdoing
andthecomplianceprocesswasreconfiguredsotrad-
inginrestrictedcompaniesis nowescalatedforhuman
review,someVisionFundexecutiveswereshockedthat
Housenbolddidn’tfaceanyrepercussions.
Housenbold’sinvestmentsincludeseveralpromising
portfoliocompanies,includingstoragecompanyClutter
andColombiandeliverycompanyRappi,butatleasttwo
high-profilebetshavestruggled.Wag,whichhasfloun-
deredbecauseofa scarcityofpetownerswillingtostick
withthedogwalkingapp,shedCEOHilarySchneider
andboughtbackSoftBank’sstakeearlierthismonth.
HousenboldalsopushedTinaSharkey,co-founderof
onlineretailerBrandlessInc.,tobuilda warehouseand
distributionnetwork,thenforcedhertoresignandwith-
helda secondtrancheoffundingwhensalesdisappointed.
Theboardlaterdecidedit didn’tneedthefundingafter
thecompanymovedtoa newbusinessmodel.
At a portfolio meeting in October,Housenbold
defendedhisperformancebyarguinghe’dbeentry-
ingtobackfemaleCEOs.Thenheseemedtoblamethe
#MeToomovementforlimitinghisabilitytomaneuver,
bewilderingatleastoneattendee.A SoftBankspokesper-
sondeniedhemadesucha comment.
BrianWheeler,generalcounselatSoftBankInvestment
Advisers,says,“Theemployeesinvolvedcategorically
deniedtheseallegedeventsevertookplace”andthat
SoftBankhas“zerotoleranceforanyformofharassmentor
discrimination—itsimplyhasnoplaceinourorganization.”
Misra,forhispart,callsHousenbold“avaluedteam-
mateandoneofmytopperformers.”Morebroadlyhe
acknowledgesthecompanyhasmadesomebadbetsand
sufferedgrowingpains.Buthenotesthatintwoanda
halfyears,theVisionFundhasinvested$76.3billionin
capitalandhiredhundredsofinvestmentprofessionals
andsupportstaff.“Weareveryproudofwhatwehave
achieved,”hesays.“Didwemakemistakes?Yes.Andwe
continuetolearnfromthem.”I
f the company is, in fact, learning from its mistakes,
it will soon have a doctorate in WeWork. That fiasco
can’t be attributed to internal chaos or cultural issues
at SoftBank. It was all Son’s doing.
He was bewitched by Neumann, just as he’d once
been byAlibaba’sMa andYahoo’s Jerry Yang.He
ignoredhisadvisers,whoarguedthatrival office-
sharing companies were offering far better investment
terms, and instead followed his usual pattern, shower-
ing WeWork with money, demanding frantic growth,
and driving valuations higher. Son’s first investment was
in 2017, at a $20 billion valuation. Then, during a fund-
ingroundearlierthisyear,hepushedWeWork’svalue
ashighas$47billion,morethandoublingtheworth
ofamoney-losing company whose CEO bonded with
employees and prospective partners by drinking tequila
shots and smoking marijuana.
By the fall, when Wall Street roundly rejected
WeWork’s planned initial public offering, SoftBank
Group and the Vision Fund owned 29% of the company.
SoftBank was forced to buy a majority stake in it via a
lifeline of cash, equity, and debt refinancing and install
one of its own top executives, former Sprint Corp. CEO
Marcelo Claure, as executive chairman. “Masa picked
the wrong company,” says a person close to Son. “He
didn’t listen to the people who were pushing back. He
knows he made a mistake.”
Son has been uncharacteristically humble about
the disaster. “There was a problem with my own judg-
ment. That’s something I have to reflect on,” he said at
a recent press conference in Tokyo. An investor present
at a Vision Fund gathering in Pasadena, Calif., says Son
was careful to emphasize such phrases as “corporate gov-
ernance” and “a road map to cash flow” as he showed
abstract slides of rough seas alongside charts that vaguely
illustrated WeWork’s path to profitability. “Masa wasn’t
like this before,” the investor says.
For investors and analysts who cover SoftBank, a
public company listed on the Tokyo stock exchange,
the question is whether the hit Vision Fund took from
WeWork, combined with its other mistakes and operating
structure, have left it vulnerable. The one-third decline
in Uber Technologies Inc.’s value since its IPO in May, for
example, has observers worried about SoftBank’s large
stakes in ride-sharing competitors such as Didi Chuxing
in China, Grab Holdings in Southeast Asia, and Ola Cabs50