It's spooky season. Halloween is nigh. I've started pulling out the decorations and old costumes — and I fell into a rabbit hole this week that was scarier than anything in my costume box: the story of WeWork, Adam Neumann, and how $47 billion evaporates.
It started, as these things always do, with a podcast. I was listening to Diary of a CEO with Steven Bartlett, and the guest was Adam Neumann — "the real story behind WeWork, a $4 billion cab ride, and surviving a $460 million debt." And my first thought was: WeWork? That sounds very familiar. Where have I heard that before?
Then it hit me. I remembered this business being in the news — the overhauled buildings, the communal workspaces, the whole thing. And that was the beginning of the rabbit hole. By the end of the week I'd listened to several other podcasts and a stack of YouTube documentaries on the subject. Here's the story, in my own words.
The Kid Who Wanted to Be a Billionaire
Adam Neumann moved here from Tel Aviv, Israel, with one goal. As I put it in the episode:
"He wanted to be a billionaire, and the only way to do that is through the American dream. Be a founder and build a multi-billion dollar business."
Before WeWork, there were the small businesses that went nowhere — including, and I love this detail, a baby clothes line called Crawlers (spelled with a K) that started because a friend joked about getting a crawling baby some knee pads. Adam thought it was a brilliant idea. He actually made a little profit. But baby knee pads were never going to make him a billionaire, so he stepped away.
The real story starts at a party, where he met Miguel McKelvey. To save money on rent for the baby-clothes office, Adam started subletting a corner of his space — and noticed how easy it was to rent a desk. He pitched their building's landlord on dividing a vacant property into small semi-communal workspaces. That same afternoon he pitched the concept to McKelvey, who designed the name GreenDesk, the logo, and a basic website overnight. And that was the seed of everything.
The Masa Meeting: Where the Ego Took Over
The pivotal moment — and Neumann himself says this — was the meeting with Masayoshi Son, leader of the SoftBank Vision Fund. They scheduled 90 minutes in the morning. Masa showed up, and in the telling of it, this was the moment the ego took over. It marked the beginning of the end of discipline.
What followed was one of the wildest funding runs in startup history. SoftBank poured billions in. The valuation climbed to $47 billion. WeWork expanded into China with $500 million from SoftBank in July 2017 alone. The company was opening locations at a staggering pace, and the mission — "elevate the world's consciousness," communal workspaces, a world where people make a life and not just a living — got louder as the fundamentals got shakier.
Then came the IPO attempt, the public scrutiny, the leaked numbers, and the whole thing unraveled in weeks. In October 2019, Neumann received close to $1.7 billion from SoftBank to resign. Let that sink in: $1.7 billion to walk away.
The Part Nobody Talks About: It Sort Of Worked
Here's what surprised me most in the research. Today, WeWork operates roughly 600 locations across more than 30 countries and 100 cities. It's a profitable business now — a steep drop from the $47 billion valuation, sure, but the underlying idea wasn't crazy. Communal workspaces, and people are actually using them.
And Neumann? He's partnered with legendary venture firm A16Z on Flow, a residential real estate company designed to solve the modern loneliness epidemic — which got a $2 billion valuation before they even opened any doors. The man fails upward like nobody I've ever seen.
What I Actually Took Away
I closed the episode with Neumann's own five lessons, and honestly they're worth more than the whole $47 billion saga:
"Choose your life partner, friends, and business partners for the worst day in your life, not for the best."
"Control doesn't come from power. It comes from influence, and influence needs to be earned every single day from the beginning."
"We all have a destiny and a journey. Get to know yourself so you can start living yours."
Strip away the private jets and the tequila and the messianic mission statements, and there's something real underneath: a mission-driven kid from Tel Aviv who believed in creating a world where people make a life, not just a living — and who let the money convince him the mission needed to be infinite. The ego didn't just take over the company. It took over the story.
Oh — and in old business this week: the Rick Rubin clip about AI went mildly viral on my socials and collected several angry comments. My take, then and now: the creativity is in the prompt. Whatever AI generates is just the storyboard. You still have to make the movie.
Thanks for listening. See you next week.
Show notes
- Main topic: The WeWork story — Adam Neumann, the SoftBank billions, and the $47 billion collapse
- Spark: Steven Bartlett's Diary of a CEO interview with Adam Neumann ("a $4 billion cab ride, and surviving a $460 million debt")
- Research rabbit hole: multiple podcasts plus YouTube documentaries, including coverage of the Masa Son / SoftBank Vision Fund meeting
- Key figures: Adam Neumann (co-founder), Miguel McKelvey (co-founder), Masayoshi Son (SoftBank), Rebecca Neumann
- Key numbers: $47B peak valuation → ~$1.7B SoftBank payout for Neumann's resignation (Oct 2019) → ~600 locations across 30+ countries today, now profitable
- Neumann now: Flow, a residential real estate company backed by A16Z, valued at $2B pre-launch
- Old business: Rick Rubin on Diary of a CEO — "the creativity is in the prompt" (AI as tool, not replacement)
- Closing: Neumann's five lessons — choose partners for your worst day; control comes from influence, earned daily; know yourself and start living your journey