Billion Dollar Loser

The Epic Rise and Spectacular Fall of Adam Neumann and WeWork


By Reeves Wiedeman

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A Wall Street Journal Business Bestseller: This "vivid" inside story of WeWork and its CEO tells the remarkable saga of one of the most audacious, and improbable, rises and falls in American business history (Ken Auletta).

Christened a potential savior of Silicon Valley's startup culture, Adam Neumann was set to take WeWork, his office share company disrupting the commercial real estate market, public, cash out on the company's forty-seven billion dollar valuation, and break the string of major startups unable to deliver to shareholders. But as employees knew, and investors soon found out, WeWork's capital was built on promises that the company was more than a real estate purveyor, that in fact it was a transformational technology company.

Veteran journalist Reeves Weideman dives deep into WeWork and it CEO's astronomical rise, from the marijuana and tequila-filled board rooms to cult-like company summer camps and consciousness-raising with Anthony Kiedis. Billion Dollar Loser is a character-driven business narrative that captures, through the fascinating psyche of a billionaire founder and his wife and co-founder, the slippery state of global capitalism. 

A Wall Street Journal Business Bestseller 

“Vivid, carefully reported drama that readers will gulp down as if it were a fast-paced novel” (Ken Auletta) 


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      “Either Adam will end up in jail, or he’ll become a millionaire.”

—Adam Neumann’s high school driving instructor


ON THE MORNING of April 12, 2019, Adam Neumann welcomed me into his office for one of the final interviews he would give as the cofounder and CEO of WeWork. Visitors to Adam’s office over the years, as WeWork moved from one headquarters to another, were often struck by the fact that as his company got better at squeezing workers into ever-smaller spaces, Neumann’s personal office kept getting bigger and bigger. He no longer had the punching bag, the gong, or the bar that occupied his previous suite, but this version had a private bathroom with a sauna and a cold-plunge tub. As we sat down at a round table so large it wouldn’t fit inside many of the glass-walled cubicles for which WeWork had become known, Neumann apologized for the fact that his time was limited. “It’s hard in a short time to get to know someone,” he told me. “And to authentically describe truth.”

Neumann had been running late, as he often was, which gave me time to survey the main floor of WeWork’s headquarters, a workday playland at the top of a six-story building in New York City. It was late morning, and a barista was serving a second helping of caffeine to WeWork employees and their smiling visitors—refugees from stale offices elsewhere in the city. A large foyer was filled with couches and low-slung lounge chairs upholstered in bright primary colors, foosball and bumper-pool tables, and three flat-top arcade machines where pairs of employees were taking meetings.

Beneath a kitchen canopy draped with hanging plants, several water coolers were stuffed with a rotating orchard of fruit—watermelon, pineapple, cantaloupe—and a dozen taps serving beer, cider, cold brew, seltzer, Merlot, Pinot Grigio, and kombuchas, plural. A placard helpfully explained to the company’s fresh-faced workforce, where thirty-year-olds felt like senior citizens, that tilting your glass while dispensing a beer would lead to a smoother pour. The kitchen was flanked on one side by a series of restaurant-style booths, for casual meetings, and on the other by several long tables with no assigned seats. Each position had a sensor allowing any WeWorker to digitally mark that territory as his or hers for the day.

This was a version of the offices WeWork operated in more than four hundred locations around the world. People seemed to be getting work done, but it was hard to tell. The whole floor was crowded and noisy. The speaker system loudly played Lenny Kravitz’s “Fly Away.” A sign advertised a happy hour celebrating the final season of Game of Thrones.

When Neumann appeared, he strode into the room from the back of the sixth floor past the long tables where a few dozen of his employees worked on laptops. At six feet five inches, he towered over the trio of businessmen he was escorting to the exit, along with everyone else in the room. Neumann had come to induce fear in many of the WeWork executives who worked most closely with him, and caution among those wary of his ambition. But to many others—the employees inspired by his motivational speeches, the landlords who happily fed his insatiable appetite for real estate, the investors eager to latch themselves onto the next rocket ship—Neumann had become a millennial prophet for a new way of working and living, brushing back his flowing dark hair as he dispensed koans and made bombastic proclamations that somehow came true.

WeWork’s core business was simple. It leased space, cut it up, and rented out each slice with an upcharge for hip design, flexibility, and regular happy hours. Other companies had risen, and in many cases fallen, by offering more or less the same service, which amounted to a straightforward arbitrage: lease long, rent short, and collect the margin. What separated Neumann’s company was not only the impressive amount of physical space it occupied, with locations across thirty countries and counting, but also the grandeur of Neumann’s vision for what the company would become. He had long resisted the obvious—that WeWork was a real estate leasing company—insisting that it was anything but: it was a tech start-up, a social network, a “community company,” an organization bent on reshaping society. “We are here in order to change the world,” Neumann once said. “Nothing less than that interests me.”

*  *  *

IN THE NINE YEARS since WeWork’s founding, practically every New York landlord, investor, and industry titan could tell a personal story about Neumann punctuating a business meeting with tequila shots. When we met, Neumann was wearing sneakers, black jeans, and a gray T-shirt—a study in nonchalance—and asked one of his assistants for hot water with lemon and ginger. He was still five months from the swift and sudden events that would find him walking the streets of New York barefoot, trying to maintain control of his company in the middle of the most humiliating attempt at a public offering in American business history, followed by his ouster with what appeared to be a billion-dollar exit package that fell apart once the world became a place where the last thing anyone wanted was high-density office space.

If Neumann sensed that the seeds of his demise had already been planted and were beginning to sprout, he showed no fear. “Our trajectory looks like Amazon’s,” Neumann told me, with a Magic 8 Ball resting behind him on his desk. “Except our market is larger and our growth is faster.”

The boast was one Neumann had repeated many times, but he had a way of delivering canned lines with an enthusiasm that made each one feel handcrafted for its recipient. By 2019, every hyperambitious start-up founder—was there now any other kind?—presented his or her business as having the makings of a world-changing global behemoth. But it took a special kind of hubris to claim you would one day stare down Jeff Bezos in the rearview mirror. “Think of the stage that we’re in as the books for Amazon,” he said. “They used books to enter into the Everything Store. We used the work mission to enter into a larger category.” What category was that? “The larger category of life.” WeWork had just announced a new location in Johannesburg, putting the company on its sixth continent. “We’re not going to Africa because we think that’s a huge growth opportunity,” Neumann told me. He described the decision to open in South Africa as a duty, given what he says he knew about “how we affect the GDP, how we affect employment.”

Claiming an ability to bend entire economies to his will was a bold declaration for an entrepreneur just shy of his fortieth birthday. But Neumann had reason to feel confident. WeWork had become the largest office tenant in New York City, and second in London only to Her Majesty’s Government. The company had tapped into a desire, especially strong among young workers, for an in-office experience more fulfilling than the one their parents’ cubicles offered. The company’s revenue had more or less doubled every year for a decade, and Neumann had raised more than $11 billion of investment capital. The vast majority came from Masayoshi Son, the founder of SoftBank, a Japanese technology conglomerate, and one of the few executives in the world whose ambition exceeded Neumann’s. Son had first invested in WeWork in 2017, partly through the Vision Fund, a $100 billion venture capital bazooka funded primarily by the Saudi Arabian government. He spent the final years of the 2010s investing previously unimaginable amounts of venture capital in an attempt to reshape a range of industries around the globe: $7.7 billion for Uber, $300 million for a dog-walking app, $375 million for pizza-making robots. Son had judged WeWork, and in particular Neumann, as uniquely capable of disrupting the roughly $200 trillion global real estate market. In January 2019, a few months before I sat down with Neumann, SoftBank had invested again, boosting WeWork’s theoretical value to $47 billion and making it the second most valuable private start-up in America. WeWork bought Lord & Taylor’s flagship Manhattan department store with plans to make it the company’s next headquarters—a metaphor for the economic shifts of the 2010s: an old-world institution gobbled up by a fresh-faced newcomer fueled by Middle Eastern oil money, a sheen of technological disruption, and an impulse toward empire.

In his office, Neumann pulled out the pitch deck that he and his WeWork cofounder, Miguel McKelvey, had made in 2009, before WeWork opened its first space. The document imagined a variety of We-branded business lines: WeBank, WeSail, and so on. “This is clarity,” Neumann said of his early vision. A few months before we spoke, WeWork had rebranded as the We Company, with three separate business lines—WeWork, WeLive, and WeGrow—under the banner of a new mission statement: “To elevate the world’s consciousness.” I told Neumann that when I shared the slogan with others, their first reaction was often to ask, What does that even mean? “That’s a good thing,” he said. “If they say, ‘What does that mean?’ it’s a conversation topic. We’re already there!” He said that each branch of the company aimed to make the world a better place—while making plenty of money in the process. WeWork’s mission was to help people “make a life and not just a living.” He believed that WeLive, which rented out microapartments with large communal spaces, could mitigate increases in loneliness and suicide so that “no one ever feels alone.” WeGrow, the newest venture, was an elementary school run by his wife, Rebekah, with an annual tuition of up to $42,000 and a goal of “unleashing every person’s superpower.”

I asked Neumann what his superpower was. “Change,” he said. “It’s the best superpower to have.” He said that this ability gave him “access to all superpowers,” and asked if I had seen the TV show Heroes, which aired its final season on NBC in 2010, just as WeWork was launching. The show featured a cast of ordinary people who found themselves suddenly endowed with various powers: telepathy, precognition, the ability to fly. Neumann self-identified with one character in particular. “There was one that was very strong,” he said. “He had the ability to have all superpowers.” The show in fact had two characters with this particular gift. Sylar, a serial killer, takes on the powers of people he murders. Peter Petrelli, the show’s protagonist, absorbs the powers of those around him, becoming so strong at one point that the energy building inside him nearly blows up New York City.

*  *  *

“WHAT’S YOUR INTENTION when you came here today?” Neumann asked me toward the end of our interview. “Are you looking for good? Bad?” I had spent the latter half of the 2010s as a staff writer at New York magazine, exploring the increasingly warped start-up economy. I wrote about a rap lyrics website aspiring to “annotate the internet”; about Vice, a punk magazine looking to become “the new CNN”; and about Uber, the ride-sharing company that insisted it was much more than that. I visited Uber’s headquarters in the spring of 2017, just as Travis Kalanick was being chastened for recklessness in the rabid pursuit of global domination. It felt as if most start-ups could think of no other worthy goal, and now an office-management company in New York City was deploying the same bravado as the new class of world-altering tech companies emerging from Silicon Valley.

WeWork seemed to capture both the early hope of the 2010s and the fractures forming as it came to a close. The company promised community to post-recession millennials entering the workforce with Obama-era ideals—Yes, we can. Neumann himself had been a college dropout, an immigrant on the verge of being forced to leave the country, and a failed entrepreneur. Yet through a mix of grit, luck, charm, ruthlessness, impeccable timing, and chutzpah, he had become, on paper, one of the world’s wealthiest people—a bipartisan American hero. He mixed spirituality and business more intimately than any other entrepreneur, at a time when the line separating the two became especially blurry, and the world was embracing a new generation of messianic start-up founders who emerged in the wake of Steve Jobs’s death, in 2011. “The past ten years was the decade of ‘I,’” Neumann said then, passing the torch to himself. “This decade is the decade of ‘We.’”

As the Obama era faded, Neumann watched his friend Jared Kushner, whom he met as a boyish New York landlord, follow his father-in-law to the White House. Hyperbole, autocratic leadership, and a disconnect from reality were suddenly assets on the path to power. Neumann attached himself and his company to the fire hose of cheap capital that washed over entrepreneurs willing to take giant risks, enabling new fortunes to be made on little more than ambition and an insistence that your company was harnessing the power of technology—no need to say exactly which one—to disrupt a new industry. Elizabeth Holmes, another once-lauded start-up founder, was revealed to be a fraudster who promised something her company, Theranos, couldn’t deliver. Spreadsheets were out; megalomania was in.

For all of WeWork’s success, its employees had followed the Theranos story with a growing sense of unease as cracks began to appear in WeWork’s ever-optimistic narrative. SoftBank’s investment was gargantuan by any measure, but Masayoshi Son, Neumann’s chief advocate and business mentor, had backed out of an even larger deal at the end of 2018, as the blistering economy of the previous decade showed signs of quavering. Neumann’s company spent so much money expanding around the world in 2018 that it lost nearly $2 billion, and even his employees didn’t know exactly what it meant to say that they were now trying to elevate the world’s consciousness. Neumann had been racing against time for the past decade, riding the longest economic expansion in American history while telling anyone who questioned his risky growth strategy that he wasn’t playing by traditional business rules: he had launched WeWork on the heels of the Great Recession, and his goal was to become the kind of institution deemed Too Big to Fail before the next one arrived.

Now, in the decade’s final turn, he was racing to the finish line. WeWork was running out of money. Neumann had tapped out the world of private capital and racked up hundreds of millions of dollars in debt. He was preparing to take WeWork public: the only viable path to continue its growth, as well as an opportunity to cash in on what he and others at WeWork had built. Neumann had played the post-recession economy to perfection. The challenge, as his company’s stock market debut loomed, was whether he could get out in time.

“Before you ask, let’s set an intention,” Neumann told me in his office, when I started to pose a final question. “Ask a question that has an opportunity to give something to your readers that could make them grow. And maybe take a second to think.” I paused and thought about something that had been bothering me. As WeWork snatched up real estate and expanded into various categories of life, the community Neumann was building seemed to be an insular one that excluded rather than embraced the rest of the world. He liked to call WeWork a “physical social network,” in homage to the tech companies he hoped to emulate, but those companies had begun the decade as paragons of a new era only to reveal themselves to be doing as much harm as good. I asked Neumann if he worried that he was building a dystopian WeWorld separate from everything around it, benefiting a few, like him, to the detriment of everyone else. “It’s a good question, so you did very well under pressure,” Neumann said. He believed that his company was positioned to bring about positive change. “Instead of thinking of it as a WeWorld, let’s just think of Powered by We,” he said. “Think of it as what we call internally a WeOS. An operating system that makes work better, living better.” He wanted to share a new company ethos that he said would define the year ahead: “We are captivated by the limitless potential of We.”

Neumann got up to walk me to the door. “I saw you change as we were talking, just so you know,” he said, standing over me. “You took in what I said about the fact that you could set an intention. It doesn’t mean you’re not going to find things that are problematic.” He said that if I had any other questions as I spent more time looking into his company, he would happily talk with me again. “We’re getting to know each other, and I hope we have a long relationship,” Neumann said. “I’m planning to be here for some time.”

Chapter One

Capitalist Kibbutz

WHEN ADAM NEUMANN was a teenager and still living with his mother and sister in Israel, he started taking lessons from a driving instructor. The Neumanns had bounced around for much of Adam’s childhood—he lived in thirteen different places before he got to New York, at age twenty-two—and like any teenager longing for some sense of control over his fate, a car offered as much ownership as one could hope for. His mother, Avivit, spent some time teaching Adam the basics on quiet desert roads just east of the Gaza Strip. But toward the end of high school, Adam enrolled in classes with Arie Eigenfeld, who taught driver’s ed in Kfar Saba, a town just north of Tel Aviv where the Neumanns had settled.

Eigenfeld didn’t need long to recognize that Adam stood out among his peers. He had transferred to the school in eleventh grade, and his classmates remember him as being shy on the first day but never again after that. He wore his hair long, made casual conversation with teachers, and dated older students. More than twenty years later, one of his classmates can still remember Adam walking down the hallway past a group of girls who turned their heads in unison to follow his trail. Arie Eigenfeld liked Adam, too, but worried that he might be too charming for his own good. After watching Adam, with his hands at the wheel of a fast-moving vehicle, Eigenfeld declared at the time that he saw only two paths for Neumann. “Either Adam will end up in jail,” Eigenfeld said, “or he’ll become a millionaire.”

Adam was not born with his high school confidence. He was the child of two doctors, Avivit and Doron Neumann, who met in medical school at Ben-Gurion University. Avivit became an oncologist, while Doron went into ophthalmology. They married in 1978, and a year later, when Avivit was twenty-two, she gave birth to Adam in the desert city of Beersheba. Adam found his hometown so unremarkable that, years later, when WeWork employees suggested the company open one of its offices there, he objected. Beersheba, Adam said, was “a dump.”

Adam endured what he often described as a difficult upbringing. (His great-grandfather emigrated from Poland to Israel in 1934 but failed to persuade his ten brothers and sisters to join him before it was too late.) The Neumanns moved from one small desert town to another, then to the suburbs of Tel Aviv, a nomadic life that forced Adam to break into strange communities as the new kid again and again. He was an indifferent student, and no one noticed that he was dyslexic until second grade, when his grandmother took him to lunch and realized he couldn’t read the menu. He had become skilled at fooling his teachers and coaxing others to do what he needed. His parents, meanwhile, were distracted by struggles in their marriage, and Adam had a strained relationship with both of them. Avivit often brought Adam and his younger sister, Adi, to the cancer ward where she worked. “He always saw people suffering,” Avivit later told an Israeli publication. “I didn’t conceal suffering from them.” The long hours at the hospital could be exhausting, and one night after work, Avivit was reading the tale of Snow White as a bedtime story to her daughter when she blurted out, “Snow White had growth in her liver and went to hospice.”

Two weeks before their tenth wedding anniversary, Avivit and Doron got divorced. Adam later described this as the hardest moment of his life. He grew bitter toward his mother as she dragged Adam and Adi to more new homes. Soon after the divorce, the three Neumanns moved to Indianapolis, where Avivit finished her medical residency. Adam struggled to adapt again, this time to a new country where he didn’t speak the language—the American government chopped off the last n from the family surname—at an already difficult juncture. “He fell apart,” Avivit said of her son.

In Indianapolis, Avivit took Adam to see a child psychiatrist, who handed him a glittery wand. Adam had been asking his mother when she would reconcile with Doron. “Wave it around your parents three times, and they’ll get back together,” the doctor said. Adam told him that he didn’t believe in magic. If that was the case, the psychiatrist said, why was he still clinging to a fantasy? “We went for eight sessions, and I got a brand-new kid—no drugs required,” Avivit said later. But the Neumanns were unhappy in Indianapolis, living on Avivit’s meager salary. Adam started working a newspaper route and insisted on giving half his earnings to his mother, to cover his share of the rent.

After two years in Indiana, the Neumanns moved back to Israel in 1990, settling in a small town called Nir Am, a mile from the Gaza Strip, in a rocky desert lined with date palms and pomegranate trees. Nir Am is a kibbutz, one of the utopian communities that had sprung up in Israel over the preceding decades, initially defining themselves through a mixture of socialism and Zionism as part of an effort to build self-sustaining communities across the country. Kibbutzniks share both child-rearing duties and professional responsibilities, working different jobs for the same salary.

Even in a more egalitarian setting, Adam struggled to make friends. Most kids on the kibbutz had lived there since birth, and Adam was bullied when he first arrived. One early attempt at fitting in was foiled when he invited several kids to watch a movie on the Neumanns’ VCR only to arrive home and find that his mother had taken the device to the hospital to entertain one of her cancer patients.

Adam would eventually look back fondly at his time on the kibbutz. He made friends and grew into the kind of teenager residents recall wearing his hair in a ponytail and breaking into the kibbutz swimming pool to go skinny dipping. But he would also claim to recognize something rotten at the core of Nir Am’s utopian idealism. There were crops to till, citrus groves to pick, and dairy cows to milk, but the primary industry was a silverware factory. Adam observed that one man worked grueling sixteen-hour days running the factory that kept the kibbutz afloat while another man only had to spend half as much time taking care of the kibbutz garden. “I knew that they both made the same amount of money,” Adam said later. “And it never made sense.” Having lived a disjointed life, marked by divorce, displacement, and a perpetual sense of feeling left out, he had finally discovered a community that filled some of those gaps only to find it lacking. The Neumanns spent just a few years at Nir Am, but when Adam began building WeWork, he said that he had learned some foundational lessons from his time there. WeWork would be “a capitalist kibbutz,” he said. “On the one hand, community. On the other hand, you eat what you kill.”

*  *  *

AFTER HIGH SCHOOL, Adam surprised his classmates by enrolling in the Israeli Naval Academy, an officer training program that typically requires at least six years of military service rather than the usual three. Adam’s fellow cadets remember him as a talented sailor who seemed to treat officer school as a game, bucking protocol to do whatever he wanted. One of them recalled Adam being reprimanded after giving an unauthorized TV interview with his sister, who had won a national modeling competition that made her famous and turned Adam into a mini-celebrity by proxy. “Every system should have an Adam,” one of Neumann’s fellow officers said. “It makes life more interesting.”

Adam graduated officer school and served on a missile boat stationed in Haifa, but he left before his full term of service was up. He later described his navy career in varying terms depending on his audience, telling early WeWork employees he was a flunky who applied for submarine duty despite his height, while boasting to a friend, over drinks at a chic bar in the West Village, that he had been in command of a warship in the Persian Gulf.

Among the virtues of moving to New York: you can tell your story however you want. Adi had moved to the city to pursue modeling and called every now and then to implore Adam to join her. He arrived in Manhattan shortly after 9/11, with little idea what he wanted to do. Adi had already built a successful career as a model, appearing on the cover of Russian Vogue and Elle Spain. She rented a fifteenth-floor apartment at the top of a building in Tribeca, ten blocks north of Ground Zero, and let her older brother move in rent-free. Adam’s grandmother covered his tuition at Baruch College, in Manhattan, where he enrolled as a twenty-two-year-old freshman.


  • The New York Times Bestseller- Editor's Choice/Staff Picks from the Book Review
  • Billion Dollar Loser would be absorbing enough if it were just one man’s grandiosity, but Wiedeman has a larger argument to make about what Neumann represents.”—Jennifer Szalai, New York Times
  • “Startling and mordantly funny . . . Wiedeman approaches his subject with a wealth of documentation and a deadpan incredulity at the absurdity of Neumann’s actions and ambitions.” —New Yorker
  • “Wiedeman’s finest feat of reporting and double portraiture is his evocation of Neumann’s relationship with his financial savior (for a time) Masayoshi Son. . . to delve any further into their relationship would be to give away the plot of “Billion Dollar Loser,” which, like the most engrossing nonfiction stories, has a plot indeed, one that only reality could contrive.” —New York Times Book Review, Editors Choice
  • "A frisky dissection of how a rickety real-estate leasing company tricked the world into seeing it as an immensely valuable, society-shifting tech unicorn....Wiedeman arranges the absurd details of their high lives in the C-suite into a pointillist portrait of wild hubris. "—Wired
  • "When life transcends art, tell it straight. That’s what Reeves Wiedeman, a New York contributing editor since 2016, has done with Billion Dollar Loser, the propulsive tale of WeWork’s, and Neumann’s, rise and fall."—The Atlantic
  • “A rollicking Hyperloop of a ride.”San Francisco Chronicle
  • Billion Dollar Loser, a new book by journalist Reeves Wiedeman, assembles a definitive chronology of a company doomed not by one bad business strategy—or even Neumann’s outsize ego—but by the rot of a postrecession economy that nurtured a certain flavor of investor-class mania. Particularly after the 2020 Covid pandemic and a new economic recession, WeWork’s nightmarish if relatively short-lived reign hints at what one future nihilistic phase of capitalism could look like if market-fueled economic inequality is allowed to continue to grow unchecked.”—New Republic
  • "Wild and well-researched"—Fortune
  • "An impressively reported and fast-moving tale of Neumann and WeWork's co-working house of cards...Wiedeman does a wonderful job uncovering the strange, surreal details that reveal what it was like to be in Neumann's orbit."—Pitchbook

On Sale
Jul 6, 2021
Page Count
304 pages
Back Bay Books

Reeves Wiedeman

About the Author

Reeves Wiedeman is a contributing editor at New York magazine, and has written for the New Yorker, the New York Times Magazine, Rolling Stone, Harper's, and other publications. 

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