How decision-making by Masayoshi Son, who estimated WeWork would be worth $10T by 2028 and wanted Adam Neumann to be “crazier”, led to WeWork's implosion
This Wall Street Journal reconstruction lands mid-saga. Two years earlier, Masayoshi Son had already called his WeWork bet a mistake and a "harsh lesson" after SoftBank posted its first quarterly loss in 14 years; reporting on Adam Neumann had traced the rot from his pre-IPO $700M-plus cash-out through the governance chaos detailed in a profile of his chaotic management style. What the 2021 piece adds is the decision-making layer: Son's $10-trillion-by-2028 valuation estimate and his push for Neumann to be "crazier" — conviction overriding internal objection.
Read forward from the archive, the piece reads as an autopsy of how that conviction operated — and the endpoint was confirmed when WeWork filed for bankruptcy in 2023, closing out a saga that cost SoftBank more than $11.5B.
First-order effects
SoftBank absorbs the direct damage — over $11.5B lost on WeWork by the time of the 2023 bankruptcy filing — with Son personally owning the call after overriding lieutenants' objections to keep funding Neumann.
Vision Fund portfolio companies face the fallout of Son's post-mortem discipline: he said in 2020 he expected roughly 15 of them to go bankrupt as he reined in the fund's model.
Second-order effects
SoftBank's investment strategy gets rebuilt around the lesson: Son publicly remakes the firm and pivots its strategy toward AI, replacing founder-indulgence bets with a new thesis.
Governance scrutiny tightens around founder-controlled startups seeking mega-rounds — the WeWork arc becomes the reference case investors and boards cite when resisting charismatic-founder valuations.
Third-order effects
If the pattern holds, the era of sovereign-scale cheques written on a single executive's conviction gives way to thesis-driven deployment — visible in Son channeling capital into concentrated AI bets like OpenAI and data-center infrastructure rather than sprawling founder portfolios.
Founder-governance norms harden structurally: cash-out-before-IPO behavior and unchecked dual-class control become pricing and diligence factors across late-stage venture markets.
The trend: SoftBank is converting the WeWork failure into the founding rationale for its AI-first reinvention — trading conviction-led mega-bets on founders for concentrated infrastructure bets, with the same single-decision-maker risk now repriced rather than removed.
-WeWork's Adam Neumann once asked Masa Son for $70 B -Masa sent him a motivational picture of Yoda -Masa planned for WeWork to be worth $10 Trillion by 2028 -Adam's strategy: a triangle of trillions Please read our book excerpt for THE CULT OF WE (!) https://www.wsj.com/...
Masa and Adam Neumann sketched out plans to build WeWork into a $10 trillion company. Read our story for more details on how their relationship led to the rise and fall of WeWork https://www.wsj.com/...
“As Mr. Son pushed Mr. Neumann for more, and as the two charted out the future, their plans tested the boundaries of the world's financial system.” https://www.wsj.com/...
Also, we have Adam Neumann's *ACTUAL SLIDE PRESENTATIONS* to Masa https://www.wsj.com/... Here's one calling for a chill $182 B in annual revenue from a business WeWork hadn't developed yet https://twitter.com/...
“After he met U.S. Sen. Chuck Schumer in the Capitol, he turned to his staff. ‘No more mayors,’ he said. ‘Only senators from now on.’” https://twitter.com/...
One of many cringy moments in this story: “Following a dinner with Walter Isaacson, WeWork founder Adam Neumann gathered staff around to read a complimentary email from the author. He told his employees he wanted Isaacson to write a biography about him.” https://www.wsj.com/...
I am reading @eliotwb's book on WeWork and it is a rollicking ride through startup insanity. Here is the first excerpt out this AM: https://www.wsj.com/... And BUY it: https://www.amazon.com/...
How billions fly around: Here is the Yoda picture SoftBank CEO Masa Son sent to Adam. ‘10k 10k 10k’ refers to WeWork's 10,000 targets for salespeople, RE people and buildings. They had hundreds at the time https://twitter.com/...
On the topic of messianic visions... after Adam Neumann met Chuck Schumer in the capitol, he reveled in the status of the big name. He turned to his aides and said: “No more mayors,” he said. “Only senators from now on.”
Here is Masa's handwriting on a chart of WeWork projecting a cool $101 B in revenue in 2023. Masa extends the hockey stick chart to 2028 Total planned valuation: “$10 T” (T = Trillion) https://twitter.com/...
That time Adam Neumann requested, and this is not a typo, $70 billion from Masa Son. 🤑 Guys, this @eliotwb @maureenmfarrell book is gonna be 🔥 https://www.wsj.com/...
Frame this, mint it as an NFT, whatever: the defining image of late-2010s venture capital has been located. “Chicken First!!” by Masa Son (2018). https://www.wsj.com/... https://twitter.com/...
Adam Neumann and Masayoshi Son: Inside the WeWork partnership that didn't work. (interesting anecdotes about didi & uber, and lyft. also, hard to see masa as not being partly culpable.) https://www.wsj.com/...