The Rise and Fall of WeWork – A Billion-Dollar Rollercoaster Ride for Entrepreneurs

Dear Readers

Buckle up because today, we’re diving deep into one of the wildest business stories of our time—WeWork. If you’ve ever dreamed of building a billion-dollar company (and hopefully not crashing it like a bad soap opera), this is one case study you need to know.

WeWork is a story about big dreams, bigger egos, and an epic downfall. It’s got everything: a charismatic founder, a business model that looked like magic, investors throwing money like confetti, and, of course, a crash so dramatic it could’ve been scripted for Netflix.

So, let’s break it down—how WeWork started, how it made money (or didn’t), what went wrong, and the lessons every entrepreneur should take away from it.

Chapter 1: The Birth of a “Revolutionary” Idea (Or Was It?)

In 2010, Adam Neumann and Miguel McKelvey founded WeWork. Their pitch?

They weren’t just renting office space—they were changing the way people worked.

WeWork provided cool, shared office spaces where freelancers, startups, and even big companies could rent desks or private offices. It wasn’t just about space; it was about community, networking, free beer, and good vibes.

Adam Neumann, a tall, long-haired, larger-than-life entrepreneur, sold this idea like a rockstar. He convinced people that WeWork was not just a real estate company—it was a tech startup. Investors ate it up. And so began WeWork’s meteoric rise.

Chapter 2: How Did WeWork Make Money?

On paper, WeWork’s business model was simple:

1. Lease office buildings on long-term contracts (sometimes for decades).

2. Slice them up into smaller spaces.

3. Rent those spaces out to freelancers, startups, and companies on short-term contracts.

4. Profit!

Sounds smart, right? In theory, yes. But in reality, it had some big, ugly flaws (we’ll get to those soon).

But for a while, WeWork looked unstoppable. By 2019, it had:

• 500+ locations in 29 countries

• Over 500,000 members

• A jaw-dropping $47 billion valuation

Everything looked perfect… until it wasn’t.

Chapter 3: The Warning Signs (a.k.a. “Uh-oh, this is bad”)

Despite the hype, cracks started to show:

• WeWork wasn’t making a profit. Like, at all. It lost $2 billion in 2018 alone.

• Spending was out of control. Adam Neumann treated WeWork’s money like his personal piggy bank—buying private jets, throwing lavish parties, and even trademarking the word “We” (then selling it to his own company for $5.9 million—yep, you read that right).

• The business model was risky. WeWork was locked into long-term leases but relied on short-term tenants. If a recession hit and people stopped renting offices, WeWork would still owe billions in rent.

• It wasn’t really a tech company. Investors started realizing—wait, this is just a real estate business, not a groundbreaking tech unicorn. And that changed everything.

Chapter 4: The IPO Disaster – The Moment Everything Fell Apart

In 2019, WeWork decided to go public. Their IPO filing was a disaster.

Investors actually read the numbers and saw the truth:

• WeWork was bleeding money.

• Adam Neumann had way too much control.

• The company was full of red flags.

WeWork’s $47 billion valuation? Poof! Gone. Within weeks, it collapsed to $8 billion.

The IPO was scrapped. Neumann was forced out with a $1.7 billion golden parachute (because apparently, failing spectacularly still pays well).

SoftBank, WeWork’s biggest investor, had to step in to save the company from total collapse.

Chapter 5: Where Is WeWork Now?

Fast forward to today—WeWork isn’t dead, but it’s far from its glory days.

• The company filed for bankruptcy in 2023.

• It’s trying to restructure and stay alive, but it’s a shadow of its former self.

• The dream of being a $100 billion company? Gone.

WeWork still operates some locations, but the hype is long over.

Factors which lead to failure of WeWork

1. The Economics Never Actually Worked WeWork was losing money FASTER as they grew. In 2018, they lost $1.9 billion on $1.8 billion in revenue. You don’t need an MBA to know that’s… problematic. Their basic model (lease long-term, rent short-term) is incredibly vulnerable to economic downturns. When times get tough, their customers can leave instantly, but WeWork is still on the hook for billions in lease obligations.

2. The IPO Filing Revelations When WeWork filed to go public, their S-1 document was a treasure trove of red flags: . Bizarre corporate governance structures • Neumann had borrowed hundreds of millions against his WeWork shares •

3. Neumann had personally purchased buildings and leased them back to WeWork. The company had paid Neumann nearly $6 million for the trademark “We” (yes, the WORD “we”) • Neumann’s wife had the power to select his successor if he became incapacitated Investors read this and collectively said: “Yeah… that’s gonna be a no from me, dawg.”

4. The Culture Problems Former employees described a workplace full of: Wild parties • Mandatory tequila shots • Capricious decision-making • A culture where loyalty to Adam trumped actual business sense • Strange rules and sudden strategy shifts

5. The Masayoshi Son Factor SoftBank CEO Masayoshi Son reportedly decided to invest billions after a 12-MINUTE car ride with Neumann. Son allegedly told Neumann to make WeWork “crazier” and encouraged its rapid, unprofitable expansion.

6. The Reality Distortion Field Collapsed Once people started questioning if WeWork was actually a revolutionary company or just an office subletting business with good marketing, the entire house of cards began to wobble. As one Wall Street analyst put it: “They were dressing up a traditional business in trendy clothes and calling it innovation.”

7. COVID-19: The Final Blow Just as WeWork was attempting to rebuild post-IPO disaster, a global pandemic made shared workspaces about as appealing as… well, shared anything in 2020.

Chapter 6: Lessons for Entrepreneurs

So, what can you learn from WeWork’s rise and fall?

1. Hype is not a business model.

   • Sure, WeWork had great branding, but at the end of the day, numbers don’t lie. If your business doesn’t make money, it’s not sustainable—no matter how cool it looks.

2. Be real about what you are.

   • WeWork tried to convince everyone it was a tech company, but it was actually a real estate business. Investors aren’t stupid—they figured it out. Be honest about your industry and what you’re offering.

3. Don’t burn money like it’s unlimited.

   • Neumann’s reckless spending helped sink WeWork. If you’re running a startup, treat investor money like your own. Every dollar counts.

4. Leadership matters.

   • WeWork’s toxic culture, lack of financial discipline, and chaotic leadership all led to its downfall. A great idea needs great execution.

5. Long-term costs can kill you.

   • WeWork got stuck in long leases while renting out short-term spaces. Always match your costs with your revenue model—or you’ll be in trouble.

6. Unit Economics Matter… A LOT

   • No amount of free kombucha can compensate for a business model that loses more money with each new customer. Make sure your basic unit economics work before scaling.

Could WeWork Have Been Saved?

With my perfect 20/20 hindsight glasses on, here’s what might have saved WeWork:

1. Slower Growth: Expand based on profitability, not available capital

2. Asset-Light Model: Partner with building owners rather than taking on massive lease liabilities

3. Focus on Enterprise Clients: They were actually making progress with larger, more stable corporate clients before the implosion

4. Proper Governance: A strong board that could rein in Neumann’s excesses

5. Honest Identity: Embrace being a real estate company with tech elements, not pretending to be something else entirely