
Built to Lose
9 minHow the Billion-Dollar Dreams of WeWork Crashed and Burned
Introduction
Narrator: Imagine a three-day corporate summit in Los Angeles that feels more like a rock festival. Thousands of employees are flown in from around the world. The Red Hot Chili Peppers are the headline act. Celebrities like P. Diddy and Ashton Kutcher grace the stage. The charismatic founder, Adam Neumann, announces to a roaring crowd that the company has just secured a new investment, valuing it at an astronomical $47 billion. This was WeWork in January 2019—a company losing over $3,000 a minute, yet celebrated as the future of work. Less than nine months later, the valuation would collapse, the IPO would be abandoned, and its celebrated founder would be forced out in disgrace. How could a company reach such dizzying heights only to crash so spectacularly?
The book Built to Lose: How the Billion-Dollar Dreams of WeWork Crashed and Burned by Eliot Brown and Maureen Farrell provides the definitive inside account. It dissects the toxic mix of messianic ambition, Silicon Valley hype, and staggering financial recklessness that defined one of the most dramatic corporate implosions in modern history.
The Hustler's Blueprint
Key Insight 1
Narrator: Long before WeWork, Adam Neumann’s entrepreneurial spirit was defined by relentless hustle and a talent for selling a story. His journey began not with a grand vision to change the world, but with a simple, almost comical product: baby clothes with built-in knee pads. In 2006, after moving to New York from Israel with a dream of getting rich, Neumann launched a company called Krawlers. The slogan was, "Just because they don’t tell you, doesn’t mean they don’t hurt."
While the business logic was questionable—babies only crawl for a short period—Neumann’s charisma was not. He dropped out of college, borrowed money from his model sister and her wealthy boyfriend, and invested funds from his grandmother to get Krawlers off the ground. At trade shows, his salesmanship was undeniable, drawing in buyers with his energy and persuasive narrative. Krawlers never became a mass-market success, but it was a crucial training ground. It proved that Neumann’s greatest asset wasn't necessarily the product itself, but his extraordinary ability to sell an idea, a skill that would later convince the world’s most powerful investors to pour billions into a simple office rental company.
Selling a Feeling, Not Just an Office
Key Insight 2
Narrator: The true genesis of WeWork came after Neumann partnered with the quiet, architecturally-minded Miguel McKelvey. Their first venture, Green Desk, was a successful but conventional co-working space. Neumann, however, was restless. He sold his share and, with McKelvey, launched WeWork in 2010. This time, the vision was far grander. Influenced by his spiritually-minded wife, Rebekah, Neumann wasn't just renting desks; he was "manufacturing community." The mission was to "elevate the world’s consciousness" and help people "make a life, not just a living."
This narrative transformed a real estate company into a tech-like movement. Neumann pitched WeWork as a "physical social network," a tangible version of Facebook. This vision was magnetic to the venture capital world. In 2011, Michael Eisenberg, a partner at the prestigious firm Benchmark, received a call from Neumann. For two hours, Eisenberg was so captivated by Neumann’s fast-talking, visionary pitch that he had to plug his phone in to keep the call going. By the end, he was sold, telling Neumann, "Don’t take any investment from anyone else." Benchmark invested, valuing WeWork at over $100 million and giving Neumann the validation and capital he needed to start building his empire on the power of a feeling.
The SoftBank Effect: Pouring Gasoline on the Fire
Key Insight 3
Narrator: For years, WeWork grew rapidly, fueled by venture capital that bought into the "community" narrative. But the company’s trajectory shifted from fast to supersonic with the arrival of one man: Masayoshi Son, the enigmatic head of Japan’s SoftBank and its $100 billion Vision Fund. Son was known for making massive, gut-driven bets on founders he believed were crazy enough to change the world. In Neumann, he saw a kindred spirit.
Their first meeting in 2017 was legendary. Neumann was given just 12 minutes to tour the WeWork headquarters with Son. At the end, Son sketched out a deal on an iPad, offering a staggering $4.4 billion investment. He told Neumann that WeWork wasn't being ambitious enough and that he should be "10 times bigger." This injection of capital supercharged Neumann’s most reckless instincts. The mandate from his most important investor was no longer just to grow, but to dominate. WeWork went on a global expansion and spending spree, acquiring companies and signing leases at a breakneck pace. Son’s belief, and his capital, inflated the WeWork bubble to its peak, pushing the valuation to $47 billion and convincing Neumann that his vision was not just viable, but inevitable.
Cracks in the Foundation: A Business Built on Hype
Key Insight 4
Narrator: Behind the kombucha on tap and the glowing neon signs, WeWork’s business model was fundamentally flawed. The company was engaged in simple real estate arbitrage: signing long-term leases for office space and subletting it on short-term, flexible contracts. This created a massive mismatch between its long-term liabilities and its short-term, less reliable revenue. Despite this, Neumann insisted WeWork was a tech company and deserved a tech company’s valuation.
To support this narrative, the company invented its own financial metrics. The most notorious was "community-adjusted EBITDA," a profit metric that conveniently excluded core costs like marketing, administration, and design. It was a fantasy number designed to mask the company's colossal losses, which exceeded $1.6 billion in 2018 alone. At the same time, Neumann’s behavior grew more erratic and self-serving. He personally bought buildings and leased them back to WeWork, created a company to manage WeWork real estate, and even charged his own company nearly $6 million for the rights to use the word "We" after he rebranded it as The We Company. The foundation was built not on sound financials, but on hype, creative accounting, and the enrichment of its founder.
The Great Unraveling: From IPO to Pariah
Key Insight 5
Narrator: The fantasy came to an end in August 2019 when WeWork publicly filed its S-1 paperwork for its initial public offering. For the first time, the world could see the raw numbers and the bizarre corporate governance. The document was a bonfire of red flags. It detailed the staggering losses, the convoluted corporate structure, and Neumann’s immense power and conflicts of interest. The dedication page, "To the energy of We," was widely mocked. The public reaction was swift and brutal, summed up by one analyst as "WeWTF."
Investors balked, and the planned valuation plummeted from $47 billion to under $10 billion before the IPO was pulled entirely. With the company weeks from running out of cash, the board had no choice but to oust Neumann. In a final, galling twist, SoftBank orchestrated a bailout that handed Neumann a golden parachute worth over a billion dollars to walk away. Meanwhile, thousands of WeWork employees, whose stock options were now worthless, were laid off. The anger was palpable; that Halloween, white t-shirts with the "Made by We" logo became a popular costume, a symbol of the fallen founder. The man who promised to elevate the world’s consciousness had retreated into his vast fortune, leaving others to clean up the mess.
Conclusion
Narrator: The single most important takeaway from Built to Lose is a stark warning about the intoxicating danger of a charismatic narrative when it becomes detached from reality. WeWork was never a tech company; it was a real estate company wrapped in the language of a messianic movement. Its story reveals how the modern investment ecosystem, with its "cult of the founder" and oceans of available capital, can inflate a fundamentally flawed business into a global phenomenon, only to see it collapse under the weight of its own hubris.
The book’s epilogue quotes F. Scott Fitzgerald’s The Great Gatsby, describing people who "smashed up things and creatures and then retreated back into their money or their vast carelessness." This serves as a powerful final thought on the WeWork saga. It challenges us to ask: In a world that celebrates visionary founders and disruptive growth, where is the line between bold ambition and reckless destruction? And who is ultimately left to pay the price when the party is over?