WeWork

SpaceX

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.

SpaceX

SpaceX makes money three ways. First, launch services — companies and governments pay SpaceX to put their satellites into orbit.

A Falcon 9 launch costs about $67 million, which undercut the competition by 75% when it debuted. Second, Starlink — SpaceX's own satellite internet constellation, which is now generating over $6 billion in annual revenue from 4+ million subscribers.

Third, government contracts — NASA pays SpaceX to ferry astronauts to the International Space Station and the DoD pays for national security launches.

The secret sauce is reusability. Before SpaceX, every rocket was used once and thrown into the ocean.

SpaceX figured out how to land the first stage booster back on Earth and fly it again. A single Falcon 9 booster has flown over 20 times.

That's like the difference between throwing away an airplane after every flight versus keeping it for decades.

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.

SpaceX

In 2001, Elon Musk had just sold PayPal to eBay for $1.5 billion and was sitting on roughly $180 million after taxes. Most people would buy an island.

Musk decided to buy rockets. His original idea was even weirder — he wanted to send a small greenhouse to Mars called "Mars Oasis" to reignite public interest in space exploration.

He flew to Russia three times to buy refurbished ICBMs. The Russians kept raising the price and at one point literally spat on him.

On the flight home from that last failed Russia trip, Musk opened a spreadsheet and started calculating the raw material costs of building a rocket from scratch. He realized the materials were only about 3% of the typical price of a rocket.

The rest was markup, inefficiency, and monopoly pricing by companies like Boeing and Lockheed Martin. He decided to build his own.

SpaceX was founded in June 2002 in a warehouse in El Segundo, California. Musk put in $100 million of his own money.

He hired Tom Mueller, a legendary rocket propulsion engineer who had been building rocket engines in his garage as a hobby. The first rocket, Falcon 1, was supposed to be the cheapest orbital rocket ever built.

It took six years and three spectacular explosions before it finally worked.

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.

SpaceX

SpaceX's growth strategy was simple: be cheaper than everyone, then be better than everyone, then be the only option.

They started by undercutting the launch market. The United Launch Alliance (Boeing + Lockheed Martin joint venture) was charging $300-400 million per launch.

SpaceX offered $67 million. Government agencies and commercial satellite companies started lining up.

Reusability was the real game-changer. Landing a rocket booster looked like science fiction when SpaceX first attempted it in 2013.

They failed over and over — spectacular ocean landings, explosions on drone ships, near-misses. But in December 2015, a Falcon 9 first stage landed back at Cape Canaveral.

It was the first time an orbital-class rocket had ever landed after a mission. Now they do it routinely — it's almost boring.

Starlink created a completely new revenue stream. Instead of just launching other people's satellites, SpaceX launched thousands of its own.

By 2024, Starlink had over 4 million subscribers and was generating billions in revenue. It turned SpaceX from a launch company into a telecom company.

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.

SpaceX

The early days nearly killed the company. SpaceX's first three Falcon 1 launches all failed.

The first one in 2006 crashed 25 seconds after liftoff due to a corroded fuel line nut. The second in 2007 reached space but the second stage shut down early.

The third in 2008 failed because the first and second stages collided during separation. Musk had enough money for one more attempt.

If flight four failed, SpaceX was dead.

Flight four worked. On September 28, 2008, Falcon 1 became the first privately developed liquid-fuel rocket to reach orbit.

Musk has said he was so stressed during that period he was throwing up regularly.

The financial pressure was existential. Musk was simultaneously funding Tesla, which was also on the brink of bankruptcy in 2008.

He had to split his last $40 million between the two companies. He borrowed money for rent.

But right at the end of 2008, NASA awarded SpaceX a $1.6 billion contract to resupply the International Space Station. That contract saved the company.

Starship development has been its own saga. The rocket has exploded multiple times during testing.

Each failure costs hundreds of millions. But SpaceX treats failures as data — they move faster by blowing things up and iterating than competitors do by being cautious.

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.

SpaceX

Falcon 9 is the workhorse — the most-launched rocket in the world. It carries satellites to orbit and astronauts to the ISS, and the first stage lands itself for reuse.

Falcon Heavy is three Falcon 9 boosters strapped together — the most powerful operational rocket in the world until Starship came along. Dragon is the spacecraft that carries astronauts and cargo to the ISS.

It's the only American vehicle currently flying humans to space. Starlink is the satellite internet service — over 6,000 satellites in orbit delivering broadband to 100+ countries.

Starship is the big one — the tallest and most powerful rocket ever built, designed to carry 100+ people to Mars. It's still in testing but has already completed a full flight.

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.

SpaceX

Founders Fund, Draper Fisher Jurvetson, Google, Fidelity Investments, Valor Equity Partners, Baillie Gifford, a]6z (Andreessen Horowitz), NASA (as customer/partner)