WeWork

Stripe

WeWork

WeWork's model was fundamentally a real estate arbitrage play dressed up as a tech company. They signed long-term leases on buildings (often 10-15 years), spent millions renovating them, then rented desks and offices to members on month-to-month or annual contracts.

The spread between what they paid landlords and what members paid was supposed to be the profit.

The problem was the mismatch. Long-term obligations on the lease side, short-term flexibility on the revenue side.

In good times, buildings are full and the spread is healthy. In bad times — say, a global pandemic that empties offices — you're locked into paying rent on empty buildings while members cancel month-to-month.

Neumann tried to juice margins with ancillary services: WeWork Labs for startups, Powered by We for enterprise buildouts, and WeWork's own internal ventures. The company also launched WeLive (apartment living) and WeGrow (a private elementary school run by Neumann's wife).

These distractions drained cash without generating meaningful revenue.

Stripe

Stripe charges a flat 2.9% + $0.30 per transaction. That's it.

No setup fees, no monthly fees, no hidden charges. The simplicity is the product.

When a customer pays on a website using Stripe, Stripe handles everything — fraud detection, currency conversion, bank transfers, tax calculation, compliance. The merchant just sees money arrive in their account.

On top of the core payments, Stripe has built an entire financial infrastructure stack. Billing for subscriptions, Connect for marketplace payments, Atlas for incorporating a company, Issuing for creating virtual cards, Treasury for banking-as-a-service, and Radar for fraud prevention.

They're basically building the financial plumbing for the entire internet.

WeWork

Adam Neumann was a 6'5" Israeli former naval officer with a talent for fundraising that bordered on hypnosis. Miguel McKelvey was an architect from Oregon with hippie parents who raised him in a commune.

Together in 2010, they launched WeWork from a single building in SoHo, New York — though they actually started with a predecessor called Green Desk in 2008, which was a sustainable coworking space in Brooklyn that they sold to their landlord.

The original concept was dead simple: lease entire floors of commercial buildings at bulk rates, renovate them with trendy design — exposed brick, beer on tap, inspirational quotes on the walls — then sublease individual desks and offices at a premium. The "community" angle was the differentiator.

WeWork wasn't just selling desks. It was selling belonging, networking, the feeling of being a startup founder even if you were a freelance graphic designer working alone.

The timing was perfect. After the 2008 recession, commercial real estate was cheap and available.

The gig economy was exploding. Millennials were entering the workforce with different expectations about work environments.

And startups that couldn't afford traditional office leases needed flexible space. WeWork grew from 1 location to 5 within two years, and the waitlists were long.

Stripe

Patrick Collison was 19. His brother John was 17.

They had already built and sold a company — Auctomatic, an eBay auction tool — for $5 million while still teenagers in Limerick, Ireland. Patrick went to MIT, John went to Harvard, and they both dropped out because they had a better idea.

The idea was embarrassingly obvious in hindsight. In 2010, accepting payments on the internet was a nightmare.

You had to get a merchant account, negotiate with a payment processor, deal with a gateway provider, handle PCI compliance, and write thousands of lines of code. It took weeks or months.

The Collisons thought it should take five minutes.

They built a simple API — seven lines of code — that let any developer start accepting credit card payments immediately. No merchant account.

No paperwork. No phone calls with banks.

Just paste seven lines of code and you're in business. They originally called it /dev/payments, then changed it to Stripe in 2011.

Peter Thiel and Elon Musk — the PayPal mafia — were among the first investors. Sequoia and Andreessen Horowitz piled in soon after.

The Collisons had built exactly what every developer on Earth had been wishing for.

WeWork

WeWork grew through sheer aggression funded by seemingly unlimited capital. They would enter a city, sign leases on multiple buildings simultaneously, renovate at premium cost, and absorb losses until locations filled.

The playbook was Uber-style: spend aggressively, dominate the market, worry about profitability later.

The "community" brand was powerful marketing. WeWork events, networking mixers, and the overall vibe attracted a loyal member base that became free ambassadors.

Instagram photos of beautiful WeWork interiors drove organic demand.

Enterprise was the real growth engine. By 2019, over 40% of members were from companies with 500+ employees.

Microsoft, Amazon, and Salesforce all had teams in WeWork. Enterprise clients signed longer contracts and were more predictable than freelancers, but WeWork still spent far more acquiring and building out space than it earned from these relationships.

Stripe

Stripe grew almost entirely through developer love. They didn't hire a sales team for years.

They didn't run ads. They just built the best developer documentation anyone had ever seen and let word of mouth do the rest.

The developer-first strategy was deliberate. The Collisons realized that in a startup, the developer usually decides which payment provider to use.

If you make the developer happy, you win the company. Stripe's API documentation became legendary — clear, beautiful, with working code examples in every language.

They also grew by growing with their customers. Early Stripe customers included tiny startups that later became giants — Lyft, DoorDash, Instacart, Shopify.

As those companies scaled to billions in revenue, Stripe's processing volume scaled with them. Stripe didn't need to acquire new customers because its existing ones kept getting bigger.

The international expansion was methodical. Instead of launching everywhere at once like Uber, Stripe carefully added country after country, making sure each one worked perfectly with local payment methods, currencies, and regulations.

By 2024 they were processing payments in 195 countries.

WeWork

Where to begin? The S-1 filing in August 2019 was a masterclass in red flags.

It revealed that WeWork lost $1.9 billion in 2018 on $1.8 billion in revenue — spending more than a dollar for every dollar earned. Neumann had taken $700 million off the table through stock sales and loans before the IPO.

He owned the "We" trademark personally and charged the company $5.9 million to license it. He had family members on payroll.

He flew on a private jet funded by the company.

The planned $47 billion IPO was pulled in September 2019 after investors revolted. The valuation was slashed.

Neumann was forced out and given a $1.7 billion exit package — for nearly destroying the company. SoftBank took control, cut thousands of jobs, and spent years trying to restructure.

WeWork finally went public via SPAC in 2021 at a $9 billion valuation.

Then COVID hit the commercial real estate market like a meteor. Remote work became permanent for many companies.

WeWork's occupancy plummeted. They filed for Chapter 11 bankruptcy in November 2023, listing $18.7 billion in debt.

The cautionary tale was complete.

Stripe

Valuation whiplash. In 2021, Stripe hit a peak valuation of $95 billion during the fintech boom.

By 2023, they had to mark it down to $50 billion during the tech correction — a 47% drop that made headlines everywhere. Employees who had been paper millionaires suddenly weren't.

The valuation has since recovered to $91 billion after a secondary share sale in 2025, but those two years were rough for morale.

Competition is relentless. Adyen, the Dutch payments company, has been eating into Stripe's enterprise market.

Square (now Block) competes on the small business side. PayPal is everywhere.

New fintech players pop up constantly. The payments business has razor-thin margins and everyone is fighting for the same 2.9%.

Going public is the elephant in the room. Stripe has been expected to IPO for years.

Investors, employees, and the media keep asking when. The Collisons have consistently said they're in no rush, but with $8.7 billion raised and thousands of employees holding stock options, the pressure to provide liquidity is enormous.

As of 2025, they've opted for secondary sales instead of a public offering.

WeWork

WeWork All Access — a membership that gives access to any WeWork location worldwide, targeting remote workers and traveling professionals. Dedicated Desks — assigned workstations in shared open-plan spaces for individuals and freelancers.

Private Offices — enclosed offices for teams, the bread-and-butter product generating most revenue. WeWork Workplace — enterprise software for managing hybrid work, office scheduling, and space utilization analytics.

On Demand — pay-by-the-day access to meeting rooms and workspace without a monthly commitment.

Stripe

Stripe Payments is the core — accept credit cards, debit cards, Apple Pay, Google Pay, and 135+ payment methods in 195 countries. Stripe Connect lets marketplaces and platforms pay out to sellers (Shopify, Lyft, DoorDash all use it).

Stripe Billing handles subscription and recurring billing. Stripe Atlas lets you incorporate a US company from anywhere in the world — fill out a form, get a Delaware C-corp, bank account, and tax ID in days.

Stripe Radar uses machine learning to block fraud in real time. Stripe Treasury lets platforms offer banking services to their customers.

Stripe Tax automatically calculates and collects sales tax in every jurisdiction.

WeWork

SoftBank Vision Fund was the largest and most consequential investor, pouring over $10 billion into WeWork across multiple rounds. Masayoshi Son reportedly agreed to invest after a 12-minute meeting with Neumann.

Benchmark was an early investor. JPMorgan Chase provided debt financing.

T. Rowe Price, Fidelity, and Goldman Sachs participated in later rounds.

The company raised more money than most companies ever generate in revenue.

Stripe

Peter Thiel, Elon Musk, Sequoia Capital, Andreessen Horowitz, General Catalyst, Founders Fund, Tiger Global, GV (Google Ventures), Goldman Sachs, Baillie Gifford