Welcome back to the Deep Dive. Today we are looking
at a story that, frankly, feels like it was written
by a screenwriter. Oh, absolutely. You know,
a screenwriter who was told to come up with the
most implausible business thriller possible.
And then the producer came back and said, yeah,
that's good. Dial it up another 20 percent. Right.
Make it crazier. It's a story about a man who
explicitly stated, and this is an exaggeration,
he wanted to be the world's first trillionaire.
Not billionaire. Crillionaire. Which is a number
so large the human brain, you know, it has trouble
actually visualizing it. Exactly. And he didn't
stop there. He mused about living forever. And
this is my personal favorite. He genuinely had
aspirations to become president of the world.
A position that, and I feel compelled to point
out. Does not exist. There is no job opening
for that. Details, details. But look, the reason
we are obsessing over this story isn't just because
the ambitions were so wild. It's the the gap
between those ambitions and what actually happened.
A chasm. It's a chasm. Yeah. We are tracing a
trajectory that goes from claiming to elevate
the world's consciousness to a reality involving.
Well, a marijuana stuffed cereal box on a private
jet and one of the most spectacular high velocity
corporate implosions in the history of capitalism.
We are, of course, talking about the saga of
Adam Neumann and WeWork, but I think it is crucial
to set the stage for why we're doing this deep
dive today, February 6th, 2026. Yes. Because
if you just watch the news back in 2019 or even
2023, you might think this story just ended.
You know, with the crash. Right. If you haven't
been glued to the business pages lately, you
probably assume WeWork is dead, buried, and maybe
turned into a spirit Halloween store somewhere.
Right. But it's not. Maybe close. Far from it.
The company has actually emerged from bankruptcy.
It has new owners. And believe it or not, it's
actually profitable. But the twist, the real
reason we are here, is that Adam Neumann didn't
just fade away into the sunset with his billions.
No. He is back. He has a new company called Flow,
and he is effectively competing with the monster
he created. It is the ultimate business soap
opera. So today we have a stack of sources here.
Biographies, court filings from the bankruptcy,
the infamous S -1 document that started the fire,
and of course, media coverage of his new ventures
right up to this year, 2026. Our mission today
is to unpack the unicorn. the fall and the surprising
flow into a second act. It is at its core a case
study in charisma, total governance failure,
and the, well, the commodification of community.
That's the perfect word for it. Okay, so let's
unpack this. We have to start with the man himself,
who is Adam Neumann, because you don't just wake
up one day and decide you want to be president
of Earth without some interesting backstory.
Not at all. And to understand WeWork, you cannot
just look at the real estate market in New York.
You have to go back. You have to look at Israel
in the 1980s and 90s. Okay. Neumann was born
in Beersheba in 1979. His childhood was defined
by severe instability. His parents divorced when
he was seven, and he was constantly moving. By
the time he was 22, he had lived in 13 different...
homes. 13 homes by age 22. That is, I mean, that's
chaotic. It creates a specific psychology, right?
When you are always the new kid, you have to
be You have to learn to charm people and charm
them quickly because you don't have the luxury
of long -term relationship building. You need
to be magnetic immediately. Immediately. You
have to walk into a room and own it. But the
most critical piece of the puzzle, the thing
that appears in almost every analysis of his
philosophy, is the time he spent living on a
kibbutz as a teenager. Okay. For the listeners
who might only know the word from, I don't know,
crossword puzzles, can we define what a kibbutz
actually is? Sure. So historically, a kibbutz
is a collective community in Israel. It started
with agriculture. It's based on socialist communal
principles. So everyone works together. Everyone
works together. You eat in a communal dining
hall. Children often sleep in communal houses.
Income is shared. It is the ultimate expression
of we over I. It's the socialist utopia in theory.
In theory, yes. But for Neumann, it was this
incredibly formative emotional experience. He
later explicitly stated that he wanted to replicate
that feeling of togetherness he felt there because
he thought it was completely lacking in the West,
specifically in the U .S. Okay, but this is where
my brain starts to hurt. Go on. He takes this
socialist communal living model and he hypercapitalizes
it. He decides to package that feeling of belonging
and sell it for a premium per square foot. That
is the central irony that drove the entire business.
That's the whole thing right there. WeWork was
essentially selling a non -capitalist feeling.
Friendship, belonging, community using a hypercapitalist
structure. It's brilliant. It is. He identified
a loneliness epidemic in the emerging freelance
economy and realized people would pay extra just
to feel like they were part of a tribe. He was
selling a cure for loneliness. Which is a powerful
product. But before he was this guru of community,
he was just a guy trying to make a buck in New
York. He served in the Israeli Navy first, right?
Yes, he was a junior officer, a captain in the
Navy. He brings that up a lot to establish his
leadership bona fides. But he also struggled
immensely with severe dyslexia. He couldn't really
read or write until third grade. I want to pause
on that for a second. Dyslexia often forces people
to develop other skills, doesn't it? If you can't
rely on reading the manual, you have to rely
on people, on your charm. Precisely. Many, many
successful entrepreneurs are dyslexic. It often
forces you to become an excellent oral communicator
or storyteller. You learn to delegate the details
because the details are literally difficult for
you to process. You become the vision guy out
of necessity. So he lands in NYC. He attends
Baruch College. Drops out, by the way, though
he did, to his credit, go back and finish his
degree in 2017. After he was already a multi
-billionaire. Yeah. Right. And he starts trying
to launch businesses. And this is where we find
my favorite early venture of his. Crawlers. Ah,
yes. The crawlers. I did a double take when I
saw this in the notes. This was his big idea
before Office Space. Baby clothes. It was. Baby
clothes with built -in knee pads. Because babies
are injuring their knees. Is that a thing? That
was the premise. He was absolutely convinced
that babies were suffering from knee trauma while
crawling around. Has a single baby in human history
ever complained about knee trauma? They're practically
made of rubber. That is exactly the point. He
was solving a problem that didn't exist. The
tagline was something like, just because they
don't tell you doesn't mean they don't hurt.
It's classic Newman logic, even back then. Create
a narrative of a hidden problem and then sell
the only solution. And he also... Tried to sell
women's shoes with collapsible heels. Yes. High
heels that could retract and turn into flats.
Again, not a terrible idea in theory, but the
engineering was a disaster. He was just throwing
ideas at the wall, desperate to hit it big. But
the pivot happened in 2008. The financial crisis.
The financial crisis. And he met Miguel McKelvey
through a mutual friend. And Miguel is the other
half of this equation. He's often described as
the quiet architect to Adam's loud salesman.
Exactly. Miguel was trained as an architect.
He was the one who could actually visualize how
to carve up a physical space, how to make it
feel cool. They were in the same building and
Adam noticed all these empty floors. And his
mind just starts racing. Starts racing. He goes
to the landlord and pitches this idea. They start
a company called Green Desk in Brooklyn. This
was the precursor to WeWork. Right. It's 2008.
The financial world is collapsing. Lehman Brothers
is gone. People are getting laid off left and
right. And suddenly there is a flood of freelancers.
People who used to have an office now have a
laptop in a coffee shop. And Neumann and McKelvey
see this. They start Green Desk as an eco -friendly
co -working space. Which is funny because eco
-friendly in 2008 usually just meant we reuse
some wood and the lights are CFLs. Pretty much.
But it worked, right? It was profitable. It worked.
It was profitable almost immediately. But the
landlords they were working with, they wanted
them to just stick to Green Desk, maybe open
another one in Brooklyn. Adam and Miguel wanted
to build a global brand. So in a move that kind
of foreshadows everything, they sold their stake
in Green Desk back to their landlord. For just
a few hundred thousand dollars. And they used
that cash to fund the big idea, WeWork. Which
launched in 2010 in Soho, Manhattan. Now, usually
when you start a business, especially in a recession,
you scrape by, you count every penny. But Noman
had this ability to convince people to bet big
on him immediately. It's his superpower. Their
first major investor, a real estate guy named
Joel Schreiber, put in $15 million for a 33 %
stake. I want to emphasize how insane that is.
$15 million. For a third of a company that barely
existed, run by a guy whose previous hit was
Kneepad Pants for Babies, it valued the company
at roughly $45 million right out of the gate.
How? How do you convince someone to do that?
What is in that pitch? It's the conviction. Absolute,
unwavering, almost religious conviction. Neumann
doesn't pitch, he preaches. He made investors
feel like the train was leaving the station,
and if they didn't get on right now, they would
miss the next Apple or Google. And to be fair,
in those early days, the product actually worked.
It was cool. It was. The early WeWorks were genuinely
great. They had free beer on tap, glass walls,
nice lighting, a sense of energy. It was way
better than a Starbucks or your kitchen table.
And then they get a huge piece of validation
in 2011. PepsiCo. Yes. PepsiCo placed a few employees
in a WeWork location. That feels like a major
turning point. It was a massive validation. It
proved that this wasn't just for, you know, a
couple of guys in hoodies building an app. Big,
boring Fortune 500 corporations wanted a piece
of this energy. And those Pepsi employees acted
as scouts, right? Rubbing shoulders with startups,
seeing what was new. Exactly. It gave WeWork
credibility to go to landlords and say, see,
we attract the big guys, not just risky freelancers.
Give us your whole building. So you have the
proof of concept. The engine is running. Now
we get to the part where they don't just add
fuel to the engine. They pour rocket fuel into
it. A whole tanker truck of it. From 2014 to
2019, this company goes super. We're talking
about a valuation jumping from $5 billion to
$47 billion. And you cannot talk about this era,
this explosion of capital, without introducing
the other main character of this tragedy, Masayoshi
Son. Masa, the CEO of SoftBank. The man with
the $100 billion Vision Fund. You have to understand
Masa's psychology to understand WeWork's rise.
He was a guy who invested early in Alibaba and
made a fortune. He believes in the singularity,
in AI, in companies that grow faster than physics
should allow. He's a gambler on a global scale.
There is that famous story about their first
meeting. Adam gets 12 minutes in the back of
a car, right? It was supposed to be a short car
ride. Adam gives him the tour of the WeWork headquarters.
At the end of it, Masa invites him into his car,
pulls out an iPad, and sketches a deal right
there on the spot. For how much? For $4 .4 billion.
After a 12 -minute tour. But the most important
part, the part that changed everything, is what
Masa said to him. He looked at Adam and told
him that WeWork wasn't thinking big enough. He
said, and I'm quoting here, In a fight, the crazy
guy always wins. You were not crazy enough. Imagine
telling Adam Neumann. a man who wants to be president
of the world, that he isn't crazy enough. It's
like telling a pyromaniac that the fire is a
little too small. It was pure validation for
every single one of his wildest impulses. Completely.
SoftBank ended up pouring over $10 billion into
WeWork over time. This created a specific economic
distortion field around the company. It's called
blitzscaling. OK, what's that? The idea, popularized
in Silicon Valley, is that you prioritize speed
over efficiency. You intentionally lose money
on every customer, but you grow so fast that
you wipe out all competitors and own the entire
market. Then, theoretically, once you have a
monopoly, you raise prices and finally make a
profit. But to do that, you have to burn cash
at an unbelievable rate. An unbelievable rate.
In 2018 alone, WeWork lost over $2 billion. That's
almost $6 million a day. They were lighting money
on fire to open locations in London, Tokyo, Rio,
everywhere. They were trying to be on every street
corner like Starbucks. And as the money poured
in, the cult of we started to get really, really
weird. Yeah. It stopped being about desks. It
started to be about encompassing every second
of your existence. Total mission creep. They
launched We Live, which was their communal apartment
concept. They had Rise by We, which was a gym
and spa. And my personal favorite, We Grow. The
school. A private elementary school inside the
headquarters for children age three to grade
four. And it was run by Rebecca Neumann, Adam's
wife. Rebecca is a crucial figure here, too.
Gwyneth Paltrow's cousin, deeply spiritual, into
Kabbalah, and she brought this very new age language
into the boardroom. The mission of WeWork officially
changed from renting desks to elevating the world's
consciousness. Which is hard to measure on a
quarterly earnings call. Impossible. And they
started buying things that made absolutely no
sense. They bought a majority stake in a wave
pool company called Wave Garden. Why? Why does
a landlord need a wave pool company? The official
justification was that surfing is a community
activity. But in reality, it was because Adam
liked to surf. That's pretty much it. They bought
Meetup, the social gathering platform. They bought
a coding academy called the Flatiron School.
They were desperately trying to prove to the
world that they were a tech company, like Amazon
or Google, not a boring real estate company.
That's the grift, isn't it? Convincing the world
you're a tech platform when you're actually just
subleasing office space. That was the entire
game. Tech companies get 20x revenue valuations.
Real estate companies, if they're lucky, get
2x. The whole $47 billion number was based on
pretending they were tech. And with this expansion
came this incredible, almost paternalistic level
of control. In 2018, Newman banned all employees
from expensing meals with pork, poultry, or red
meat. For what reason? He said it was for the
environment. And sure, meat has a high carbon
footprint. But think about the dynamic. You are
the CEO and you are telling your accountants
and your sales reps what they're allowed to eat
for lunch if they want to get reimbursed. It's
a level of personal control that really crosses
the line into cult -like behavior. Meanwhile,
the culture inside the company wasn't exactly
a monastery. Far, far from it. The sources we
looked at describe a frat boy culture on steroids.
We are talking about mandatory tequila shots
during job interviews. Not at all. He would walk
around with a bottle of Don Julio 1942, and if
he offered you a shot and you didn't take it,
that was a bad sign. And then there were the
mandatory summer camp festivals. Why was that?
Thousands of employees were flown from all over
the world to fields in the UK or upstate New
York for three days of partying, music, and free
-flowing alcohol. It sounds fun if you're 22,
but I'm guessing it was an absolute nightmare
for the HR department. A total nightmare. In
October 2018, a former director of culture filed
a lawsuit alleging she was sexually assaulted
at company events. She described a culture where
alcohol was just everywhere, completely unchecked.
There were multiple suits regarding gender pay
gaps, age discrimination. It was a chaotic, high
testosterone environment masked by this soft,
new agey language of love and community. So you
have this chaotic, high spending. Party -fueled
rocket ship. It's early 2019. The valuation is
at its peak, $47 billion. They are arguably the
hottest startup in the world. And they decide,
let's take this thing public. They file for an
IPO. And that is the moment the music stopped.
Cold. August 2019. The release of the S -1 filing.
For our listeners, the S -1 is the big document
a company files with the SEC to list on the stock
market. It's supposed to be a boring technical
brochure saying, here are our financials, here
are our risks, please buy our stock. Instead,
this document read like the diary of a madman.
Let's open it up. First of all, the dedication.
You mentioned it earlier. Most S -1s are dedicated
to, you know, our shareholders or our amazing
team. This one was dedicated to the energy of
we. And the first sentence of the document was,
we dedicate this to the energy of we greater
than any one of us, but inside each of us. That
is not something a Goldman Sachs banker wants
to read. No, they want to see numbers. And when
they finally got to the numbers, it was even
worse. But the real horror show was the corporate
governance section. This is where investors actually
started screaming. Let's break down the governance
nightmares, because this is where the scam accusations
really started to fly. Let's start with the big
one. The trademark issue. It's almost comical.
So the company decided to rebrand from WeWork
to the We Company to reflect its expansion into
living and schools and wave pools. Okay, rebranding.
Standard corporate stuff. Except Adam Neiman
personally owned the trademark for the word We
through a private holding company. He had bought
it before the rebrand. And then the We Company
paid him $5 .9 million to license the rights
to use that word. Hold on. Let me get this straight
for the listener. He was the CEO. He decided
to change the company name to a word that he
personally owned. And then he made the company
pay him nearly $6 million for the privilege of
using the name that he chose. You've got it.
It was peak audacity. It signaled to everyone
on Wall Street that he viewed the company as
his personal piggy bank. He was just extracting
cash from the investors right in front of their
faces. Did he get away with it? No. The public
outcry was so intense that he eventually returned
the money. But the fact that he thought he could
get away with it in the first place, it terrified
them. And it wasn't just the name. There were
the buildings, too. Right. The related party
transactions. This was another huge red flag.
Newman personally bought commercial buildings,
often using lines of credit secured by his WeWork
stock. And then he would lease those buildings
back to WeWork. So he was the landlord and the
tenant. He was on both sides of the deal. If
WeWork paid really high rent on a building, WeWork,
the company, lost money. But Adam Newman, the
landlord, made a fortune personally. It's conflict
of interest 101. Unbelievable. What else is in
there? The stock structure. This is the key to
his power. We mentioned governance. Neumann had
set it up so that his shares gave him 20 votes
for every one vote a normal shareholder would
get after the IPO. 20 to 1. 20 to 1. It meant
that even if he sold off half his financial stake,
he could never be fired. He had total dictatorial
control over the company forever. He couldn't
be removed by the board. And there was a clause
in there about his wife, right? Yes. The succession
clause. The S -1 stipulated that if Adam died,
his wife Rebecca would be on the committee to
choose his successor. Like a monarchy. Passing
control through the family. Exactly like a monarchy.
And public market investors, we're talking pension
funds, mutual funds, the people who manage your
401k, they looked at this structure and said,
absolutely not. We are not investing in a dictatorship.
And while the entire financial world is reading
this S -1 and freaking out, a story breaks in
the Wall Street Journal that just perfectly,
perfectly encapsulates the madness. The cereal
box incident. This is the anecdote that I think
really turned the tide of public opinion. It
painted him not as a brilliant, eccentric visionary,
but as an unstable liability. Completely. Set
the scene for us. Okay, so it's the summer of
2018. Newman and his friends charter a Gulfstream
G650, a top -of -the -line $60 million private
jet, to fly from the U .S. to Israel. The best
plane money can buy. On the flight over, they
are smoking so much marijuana that the smoke
is thick in the cabin. According to the reporting,
the flight crew had to put on their oxygen masks
because they were worried they'd fail a drug
test from inhaling the secondhand smoke. That's,
I mean, that's just dangerous. Forget everything
else. It's insane. So they land in Israel. Adam
and his entourage get off and go to their party.
But the flight crew stays behind to clean the
plane for the return trip. And what do they find
stuffed in a compartment? A cereal box. A cereal
box. And it's not full of Cheerios. It's stuffed
full of a large amount of weed. Just left there
in the cabin. Now, this is an international flight.
This crosses the line from partying into international
drug traffic. That's a felony, a serious one.
Exactly. So the owner of the jet gets a frantic
call from the pilot. The owner realizes that
if this plane tries to leave Israel and get searched
by customs, the plane could be seized. The pilot's
arrested. So he orders the plane to return to
the U .S. immediately empty. So Adam is stranded
in Israel. Yes. The CEO of a supposed $47 billion
company is stranded because he left his drugs
in a cereal box on a rented jet. It just showed
a complete lack of discipline, a total lack of
judgment. It showed he thought the rules simply
didn't apply to him. And when you combine the
shocking financials, the insane governance issues
and this kind of reckless personal behavior,
the IPO just completely collapsed. The valuation
crash from $47 billion to, oh, the bankers tried
to salvage it at maybe $20 billion and people
were whispering $10 billion. But in the end,
the IPO was pulled entirely. They ran out of
cash. And in September 2019, the board led by
SoftBank, who had the most to lose, finally decides
we have to cut the head off the snake. They move
to oust him. But, and this is the part that still
drives people crazy, because of those super voting
shares we talked about, they couldn't just fire
him. They had to buy him out. The golden parachute.
This wasn't a golden parachute. This was a platinum,
diamond -encrusted parachute. To get him to leave
and give up his voting control, SoftBank put
together an exit package initially valued at
nearly $1 .7 billion. 1 .7. Billion dollars for
essentially breaking the company. It included
SoftBank buying about a billion dollars of his
shares, refinancing his massive personal debts,
and get this, $185 million consulting fee. They
paid him $185 million to consult on how to run
a company into the ground. Did they ever actually
call him for advice? I highly, highly doubt it.
That was just a bribe. is the price to get him
to walk away quietly and give up the keys. Now,
that deal was renegotiated later. There were
lawsuits, and the final number he got was lower.
But he still walked away with hundreds of millions
in cash. He failed, and he became a billionaire
because of it. An unbelievable outcome. So Neumann
is out. He's rich. He's in his mansion. But WeWork,
the company, the thousands of employees, the
landlords, they are still there. And we move
into what I'd call part four, the wilderness
years. 2020 starts. SoftBank takes control. They
bring in a new CEO, Sandeep Mithrani. He's a
veteran real estate executive. He's the anti
-atom. Serious, boring, focused on the balance
sheet. His only job is to stop the bleeding.
And then, just as he's trying to perform surgery,
the universe decides to play a cruel joke. COVID
-19 hits. It's the worst possible timing. Think
about it. WeWork's entire business model is based
on density, packing people into small glass offices,
sharing kitchens, sharing air, sharing everything.
And suddenly the governments of the world say,
stay six feet apart, work from home. It was an
extinction level event for their business model.
The offices emptied out. I remember walking past
WeWorks in 2020 and 2021. They were just ghost
towns, lights off. They immediately stopped the
free beer. They started closing locations. They
laid off thousands and thousands of people. But
they had a massive fundamental problem being
into their books. The leases. They had signed
15 -year leases on hundreds of buildings back
when rents were at their peak. But their customers,
the tenants, were on flexible month -to -month
contracts. That is the fundamental flaw of the
model, the asset liability mismatch. You owe
the landlord for 15 years, but your customer
only owes you for the next 30 days. Exactly.
When all the customers canceled their memberships,
WeWork was still on the hook for billions in
rent. They were bleeding cash at an apocalyptic
rate. But surprisingly, they managed to go public
anyway in 2021. How? I mean, who would buy this
stock in the middle of a pandemic when nobody
was in an office? They used a SPAC. A special
purpose acquisition company. We saw a lot of
these during the pandemic bubble. Can you explain
the mechanics briefly for our listeners? Sure.
Think of a SPAC as a backdoor IPO. A group of
investors lists a blank check company on the
stock market. It has no business, just a big
pile of cash. Then that public shell company
goes and merges with a private company. In this
case, WeWork. It's a faster, easier way to go
public with less scrutiny than a traditional
IPO. So WeWork merged with a SPAC called BOEX.
Yes. And it valued WeWork at $9 billion. Which
is a long, long way down from $47 billion. But
it's still $9 billion. It is. And more importantly,
it gave them access to a fresh injection of cash
from the SPAC. They desperately needed that money
just to survive the pandemic. But even that wasn't
enough. The debt load was just too heavy. The
old expensive leases from the Adam era were like
an anchor dragging the ship to the bottom of
the ocean. And so we get to the inevitable conclusion
of this first act. November 2023. WeWork files
for Chapter 11 bankruptcy. Now, bankruptcy sounds
like death to most people, like going out of
business. But Chapter 11 is different, right?
It's a tool. Correct. Chapter 11 is reorganization,
not liquidation. It's a court supervised process
where you get to pause your debts and crucially
renegotiate your contracts. For WeWork, it was
a strategic weapon. It allowed them to go to
all their landlords across the world and say,
look, we are legally rejecting this lease. You
can take the keys back and have an empty building
or you can cut our rent by 50 percent. It was
a way to purge all the toxic overpriced leases
from the Adam Neumann era. Exactly. They shed
billions in future rent obligations. SoftBank
had to write down almost their entire investment.
Masayoshi's son admitted on an earnings call
that he lost billions and that his judgment was
flawed. The unicorn was, for all intents and
purposes, officially dead. Was it? Because here
we are. It's February 2026. And WeWork is still
here. My local WeWork is open. It is. And this
brings us to the part of the story that often
gets ignored. The resurrection. WeWork emerged
from bankruptcy in May 2024. Who owns it now?
It's not SoftBank anymore, is it? A company called
Yardi Systems is now the majority owner. I've
never heard of them. And that's probably a good
thing. They are a massive, profitable, and frankly
boring back -end software company for the real
estate industry. They provide the software that
landlords use to manage their buildings and track
rent. They took a 60 % stake. SoftBank is still
there with about a 20 % stake, but they're not
in charge. And how are they doing this new, boring
WeWork? Surprisingly well. Because they used
the bankruptcy process to cut all the bad locations,
they closed about 160 unprofitable spots. They
are now running a much leaner ship. By the fourth
quarter of 2024, the company actually hit break
-even EBITDA. EBITDA. Earnings Before Interest,
Taxes, Depreciation, and Amortization. Basically,
their day to day operating profit. Right. And
by the first quarter of 2025, they were actually
EBIT deposit. The core business model, flexible
office space actually works. People want it.
The demand is there, especially in a hybrid work
world. It was just the insane execution, the
crushing debt and the hubris of the first iteration
that broke it. So under disciplined. Boring management.
It's a totally viable business. A totally viable
business. But we have to talk about the plot
twist that happened during the bankruptcy. This
is the moment where I actually laughed out loud
when I read the news reports from 2024. An attempted
buyback. February 2024. Adam Neumann, the man
who brewed the company, the man they paid over
a billion dollars to leave. Yeah. He tried to
buy it back. He did. While the company was at
its most vulnerable, in bankruptcy court, he
swooped in with a bid of over $500 million to
regain control of WeWork. The audacity. It's
just, it's breathtaking. I broke it, you paid
me to leave, now it's on sale for pennies on
the dollar because I broke it so I'll just buy
it back cheap. It is stunning, Chutzpah. He was
backed by a big hedge fund, Third Point. He argued
that the current management didn't understand
the magic of the brand. He wanted to bring the
vibe back. And what did the company and its creditors
say? They essentially ghosted him. Publicly,
they said they'd review all offers, but privately,
the reports say they viewed him as radioactive.
They did not want him anywhere near the controls
again. They eventually went with the much safer
Yardie deal instead. Probably a wise bet. But
Adam Neumann is not the type of person to just
sit on a beach and count his money. He didn't
get WeWork back, so he decided to build something
else. And that brings us to his second act. Enter
Flo. Okay, let's look at Flo. This is his current
venture in 2026. What is it? Initially, the pivot
was to residential real estate. If WeWork was
community for work, Flo was supposed to be community
for living. So WeBut at 2 .0. Pretty much, but
on a much bigger scale. He started going on a
buying spree, buying thousands of apartment units
in Miami, Fort Lauderdale, Atlanta, Nashville.
The idea is the same. Renting an apartment sucks.
It's a lonely transactional experience. The landlords
are unresponsive. Flo wants to create a branded
living experience. What does that mean in practice?
It means there's an app, there are community
events, neighbors actually know each other. It's
the WeWork plea book applied to where you sleep.
And crucially, he got funding. Massive funding.
This is the part that shocked the entire tech
and venture capital world. In 2022, Andreessen
Horowitz, also known as A16s, one of the most
prestigious VC firms in the world, wrote their
largest single check ever to a single founder.
Not much. They invested roughly $350 million,
and it valued flow at over $1 billion before
it had even opened its doors to a single tenant,
before it had a product. Okay, stop. After the
S -1, after the cereal box, after the bankruptcy,
after the $10 billion write -down by SoftBank,
how does Marc Andreessen, a guy who literally
invented the modern web browser, look at Adam
Neumann and say, here's $350 million? It speaks
to a very powerful theory in venture capital
called founder mode. Andreessen wrote a whole
blog post justifying the investment. He argued
that Adam is a singular visionary. He said that
Adam fundamentally redefined the commercial office
space. And sure, he made mistakes, but he has
the energy and the vision to do it again for
the home. They're betting that the crazy is a
feature, not a bug. That's exactly it. They're
betting he's learned his lesson about governance.
Or more cynically, they're betting that he'll
just make them a ton of money before he crashes
the plane again. That is the billion -dollar
question. But Flo didn't stick to just apartments,
did it? No. In late 2024, the rivalry reignited.
Neumann announced that Flo would launch a direct
rival to WeWork, offering flexible office space
within their residential buildings. So he is
competing head to head with the company he founded,
using the money he made from leaving it, backed
by new investors who think he can do it all again.
Precisely. And he's doing it with that signature
eccentric flair. In 2024, he also bought a magazine
called Whalebone, a cool little surf and culture
magazine based out in Montauk, and he renamed
it Flo Trip. Flow Trip. Flow Trip. It's a marketing
vehicle for the brand. It's full of beautifully
shot articles about wellness, community, travel,
and surfing. It's the we vibe all over again,
just with a new logo. So here we are in early
2026. Let's recap. Adam Neumann is back on the
billionaire list. Forbes estimates his net worth
at around $2 .2 billion. His company, Flow, is
operating thousands of apartments and now office
spaces in places like Florida and even Saudi
Arabia. And at the same time, WeWork is operating
separately, it's profitable, and it's run by
a boring software company. It's like a split
reality. It raises a really difficult question
about our economic system, doesn't it? Was Adam
Neumann a visionary who was just right too early?
Or was he a brilliant salesman who sold dollar
bills for 50 cents? I think the answer might
be both. He clearly, clearly identified a real
hunger for community in modern life. He saw that
the way we work was changing before almost anyone
else did. He forced the entire state real estate
industry to modernize. He did. If you walk into
a boring office building today and there is a
lounge with nice coffee and a couch, that is
because Adam Neumann's influence forced them
to compete. He set a new standard. But he also
proved that community is incredibly hard to scale.
You can't mass produce a genuine feeling of belonging
like you can mass produce iPhones. At some point,
it becomes fake. And he proved, maybe more than
anyone else, that in the modern economy, failing
big is actually much safer than failing small.
That is the so what for our listener. If you
borrow $50 ,000 from a bank to start a bakery
and you fail, the bank takes your house, you're
ruined. But if you burn through $10 billion of
venture capital, you get a golden parachute,
you keep your mansions, and Andresen Horowitz
gives you another $350 million to try again.
It's the fail -up phenomenon. It suggests that
confidence, the pure, unadulterated ability to
tell a compelling story. might be the single
most valuable asset in the 21st century economy.
Maybe more valuable than actual competence. In
the short term. Absolutely. The market rewards
great storytellers. It rewards people who can
create a reality distortion field and suspend
disbelief. Adam Neumann is arguably the greatest
salesman of his generation. The fact that the
first WeWork collapsed doesn't change the fact
that he sold the dream effectively enough to
become a billionaire. So as we wrap up this deep
dive, we leave you with this image. WeWork survived.
It shed its charismatic, reckless founder and
became a healthy, normal business. It grew up.
But Adam, Adam refused to grow up. He just found
a new playground. And a new, even bigger allowance.
Exactly. And it forces us to ask, does failure
actually matter anymore if you feel big enough?
Or is catastrophic failure just a stepping stone
for the 0 .01 %? A provocative thought to end
on. Something to mull over on your commute. And
hey, if you happen to be listening to this in
a co -working space right now, do me a favor.
go to the kitchen, check the cereal boxes. Just
to be safe. Just to be safe. You never know.
Please check the show notes for all our sources,
including that wild S1 filing and the breakdown
of the flow deal. Thanks for listening to The
Deep Dive. We'll see you next time.