Billion Dollar Loser by Reeves Wiedeman

4/5 stars

A few months ago, I worked with a career coach based in the City of London, with an office in a Spaces, a WeWork-style coworking building owned by British office giant Regus. I had worked in a lot of offices that attempted to imitate the WeWork style, but it was the first time I was actually inside one of these fabled halls of freelancing and start-ups. This was in the brief blip before the second Covid wave when Boris Johnson was encouraging us to all go back to the office, but no one seemed to be there. It was eerie to see such a huge space so deserted–as I waited to meet the coach, the only other soul I saw was a janitor mopping the parquet floors. The coffeeshop’s lights were dimmed and there were still posters on the walls for events in March and April that had almost certainly been cancelled.

On the walk back to the Tube I passed no less than three WeWork propers and a handful of knockoffs, all dark and empty. I was reminded of my old office in New York, where just the short walk from Penn Station to my cubicle was a game of “is it a WeWork or a Pret?” WeWork thought they were changing the world–they bought the flagship of Lord & Taylor that had been open since 1914–but instead the world left them in the dust. So what exactly happened?

Billion Dollar Loser traces the history of WeWork and its charistmatic founder and ex-CEO, Adam Neumann. Raised on a kibbutz in Israel, he became enamoured with the American dream when he left the Israeli Navy and enrolled at Baruch College. His first foray into business was baby clothes with kneepads (yes, really) until he and a friend launched a WeWork prototype called GreenDesk in Brooklyn in the late 2000s. With the Great Recession in full swing, companies were downsizing and more and more career creatives were launching freelance businesses. Adam caught this wave at the right time, building what he sometimes called a “capitalist kibbutz”–and then, through a combination of hubris and high-profile investors he mostly met through his involvement in Kabbalah, it all came crashing down.

Wiedeman’s writing is snappy and well-paced, following WeWork through its early years to its heyday, culminating in a debauched private festival in a field in Kent. Sometimes the descriptions of the work culture can cut a little close to the bone–in the same way that watching The Office can make you cringe if you’ve spent time in a dysfunctional workplace. Adam was ambitious and was eager to divert investor attention away from the core product to new ventures, including a “co-living” apartment complex and a school run by his wife who had zero education experience. Brushes with conflict, from labour disputes with cleaners to employee outrage over government contracts with Saudi Arabia after the Khashoggi murder, appear to slide right off of him.

Much of Billion Dollar Loser focuses on the company’s disastrous IPO launch–there is a lot of Wall-Street-y, finance language in these sections, which was a little dense for my liking, but there was always another wild Adam story around the corner that kept me pulled in. Just the stories of him and his wife trying to design the IPO documents and getting told by the SEC to stop sending in font edits felt ripped from a Secession script. Honestly, I could’ve read about 500 more pages of this, plus watched a 10-part documentary series and then some. I can’t get enough of crazy work stories! If you’ve enjoyed everything-goes-wrong books like Bad Blood by John Carreyrou, you’ll love Billion Dollar Loser. Although WeWork wasn’t quite doomed in the same way Theranos was, there’s no better way to understand 2020 than to read about the foile a deux that can consume startups–at the very least, it will make you grateful to still be working from home. is a great, easy way to buy your books–each purchase supports indie bookstores across the UK. If you’re gift shopping, why not consider a e-gift card?

And no matter where you are in the world, Blackwell’s is a great independent option with international shipping and competitive prices.

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