Be honest - when did you last go a full hour without checking your phone?

For me, the only reliable answer is when I'm running. You can't really scroll when you're out of breath and trying not to trip over your own feet. It's the closest thing I've found to actually switching off from work.

I've tried other things. I even bought one of those lockboxes - you put your phone in, set a timer, physically can't get to it. Lasted about an hour before I broke back in. The lockbox, it turns out, was never the problem. The discipline was.

Still working on that.

Today I'm getting into WeWork - the raise that had everything: a charismatic founder, billions in investor capital, a spectacular collapse and an ending nobody saw coming.

1/ Adam Neumann turned a desk rental business into a $47B valuation by convincing investors they were backing “the future of work”

2/ SoftBank threw $4.4B at WeWork after a 12-minute meeting. Investor FOMO, a powerful story and a charismatic founder will do that

3/ The IPO filing was so catastrophically bad - self-dealing, "community adjusted EBITDA" and private jets on company money - that investors pulled the plug and the board fired Neumann

4/ Neumann walked away with $1.7B, went straight to his next venture and raised $450M for a company with no product. The story, it turned out, was always the product

Let me ask you something. If someone walked into a room and told you they were going to "elevate the world's consciousness" - what would you do?

Most sane people would nod politely and edge toward the exit.

Investors gave Adam Neumann $22.2B.

That gap - between what sounds completely mad and what actually happened - is the most interesting thing about the WeWork story. And it starts, as most interesting stories do, with a person who you wouldn’t necessarily expect to succeed. 

Neumann grew up on a kibbutz in Israel - communal living, shared resources, collective over individual. He moved to New York in his mid-twenties with not much going for him.

A baby clothing business that went nowhere. A collapsible heel company that didn't take off. By most conventional measures, he was going nowhere fast.

Then in 2010, he co-founded WeWork with Miguel McKelvey. The concept was to take large commercial spaces, divide them up and rent them out to startups and freelancers who couldn't afford a traditional office. A real estate arbitrage play. IWG had been doing exactly that, profitably, across 3,000+ locations for years.

But Neumann didn't pitch it as a real estate business. He pitched it as a ✨movement✨. A reimagining of how human beings find meaning in their work. The official mission: to elevate the world's consciousness.

And once you've framed a desk rental business as a civilisation-defining movement, something strange happens to the people in the room. 

Questioning the unit economics starts to feel small. 

Asking about profitability starts to feel like missing the point entirely. 

Nobody wants to be the investor who looked at the future of human work and said no.

I know someone who passed on investing in what is now one of the biggest fintech businesses in the UK. That decision still haunts them. Nobody in venture capital wants to be that person. Nobody wants to watch everyone else make 300x while they sat it out because they were worried about the fundamentals.

Neumann understood that better than anyone. Get the right names on the cap table early. Make the story so big that saying no feels embarrassing. 

Let the FOMO do the rest.

In 2014, investors paid $355M for a $5B valuation. By 2017, SoftBank's Masayoshi Son committed $4.4B after a meeting that reportedly lasted twelve minutes. By 2019, WeWork had raised $22.2B and hit a peak valuation of $47B. For a company burning $2 for every $1 it made…

So, how on earth did he manage to secure that level of funding? Because - despite a catastrophically flawed operation - the story worked. And the story worked because nobody wanted to be left behind (back to that idea of FOMO).

It all came crashing down with the IPO filing - and what it revealed was wild.

Neumann had been charging WeWork $6M to use its own name - he'd bought the "We" trademark personally and sold it back to the company. He was leasing buildings he personally owned back to WeWork at above-market rates. Company money had gone toward private jets, a tequila business and a wave pool company. And his team had invented a completely new financial metric - "community adjusted EBITDA" - to make the numbers look better than they were.

Standard EBITDA is flexible enough. Creating your own version of it entirely is a different level.

Investors pulled the plug on the IPO. The board fired Neumann. The $47B valuation collapsed to nothing.

Neumann walked away with $1.7B.

Four years later, WeWork filed for bankruptcy with $18.6B in debt. By that point, Neumann had already raised $450M for his next venture - Flow, a residential real estate business with no product, no team and no track record beyond the one he'd just torched. He raised it anyway. 

Funnily enough, WeWork emerged from bankruptcy in June 2024, wiped out $4B in debt, cut its loss-making leases and installed a new CEO - John Santora, a real estate veteran with no interest in wave pools or tequila companies.

By early 2025, the business had posted six consecutive months of positive EBITDA. Revenue hit $2.2B in 2024. Around 600 locations still operating globally, 47 Fortune 100 companies using the spaces and a majority owner in Yardi Systems that actually understands property.

Turns out the co-working model was always viable. It just needed someone who treated it like a business rather than a spiritual movement.

The collapse was spectacular. The lessons are more useful than you'd think.

To recap: WeWork raised $22.2B. It also burned $2 for every $1 it made and eventually filed for bankruptcy with $18.6B in debt. 

Those two things happened simultaneously because raising capital and building a sustainable business are completely separate skills - and Neumann was extraordinarily good at one of them.

At its most basic level, a business is simple: can you acquire whatever you're selling for less than what you charge for it? If the answer is no, no amount of capital changes that. It just delays the conversation.

Neumann understood investor psychology better than most. Get the right names on the cap table early, make the story big enough that saying no feels embarrassing, and the FOMO does the rest. SoftBank committed $4.4B after a twelve-minute meeting. What is that, if not fear of missing out with a lot of zeros attached?

For founders, this cuts both ways. Understanding investor psychology is a legitimate part of raising capital. But building a business purely around manufactured FOMO - without the fundamentals to back it up - has a very specific shelf life.

WeWork's narrative was genuinely brilliant. Reframing a desk rental business as a cultural moment - craft beer on tap, community events, the idea that where you worked said something about who you were - was audacious. 

And look, I'll admit the whole "cultural movement" framing is a bit slippery. What does that even mean? Culture doesn't raise a valuation. What Neumann actually did was make renting a hot desk feel like a personality trait. And somehow, that was enough.

For a while, it worked spectacularly. The story got investors in the room and kept them coming back round after round.

But eventually, someone always asks to see the numbers. And when the numbers are burning $2 for every $1 you make, no story survives that conversation forever. Build the narrative - it matters. Just make sure the fundamentals are there to back it up when the room goes quiet.

The "community adjusted EBITDA" moment is one of the most ridiculous things ever submitted in a public financial filing. 

Investors aren’t daft. They've seen every version of financial engineering. The moment your numbers require a novel metric to look acceptable, you've already told them everything they need to know. 

Present your finances clearly and honestly - and if they don't look good yet, be straight about why and what you're doing about it.

Remember me telling you that Adam Neumann raised $450M for Flow with no product, no team and a track record? 

It was possible because his personal brand had grown so large that investors backed the person rather than the pitch. The self-dealing, the private jets, the wave pool business - all of it absorbed into the legend rather than used against him.

Elon Musk is a more current case study. Tesla's cars didn't change. The technology didn't change. But apparently spending your evenings doing Nazi salutes on a public stage is bad for electric vehicle sales. Global deliveries fell 13% in Q1 2025.

Two founders. Two personal brands. One used his to raise money from nothing. One used his to lose customers from everything. 

The lesson is the same: what you do personally and what happens to your business are not as separate as you might think.

This is the one that connects most directly to how I think about capital at FundOnion. WeWork had no structural protection - no hard assets, no owned property, just long-term leases and a narrative. When the narrative collapsed, there was nothing left to fall back on.

Good debt, structured correctly around real assets and real cash flow, gives you something that a story alone never can: staying power. The businesses that survive downturns, bad quarters and market shifts are almost always the ones that built something structural underneath the narrative - not the ones that raised the most money while things were good.

I’m envisioning him barefoot on a superyacht, contemplating how to elevate human consciousness over a glass of something expensive. 

A lot of people hate him for that. But if I’m honest, I think it's mostly jealousy. He walked away with $1.7B from a business that went bankrupt, then raised $450M for his next idea before the dust had settled.

If you've been building something profitable for years and nobody's throwing half a billion at you, that's going to sting.

He never really failed. Not personally. And that tells you more about how capital markets actually work than almost anything else.

If you're raising capital and want someone in your corner, I'm considerably easier to reach than Adam: [email protected]

Till next time,

James