Billion Dollar Loser

You’d be forgiven for wondering, while reading Billion Dollar Loser, whether it’s a book about a company or a cult. By the end, I concluded it might have been both, at least as far as Adam Neumann himself was concerned. The book charts the extraordinary rise and fall of WeWork, but more specifically, of Neumann.

One thing you can’t fault him for is self-belief. Several times while listening to this (mostly during runs), I found myself laughing and muttering aloud, “This guy was absolutely nuts.” The sheer audacity of some of his decisions and statements makes for both fascinating and, at times, absurd reading.

There’s no denying there are remarkable elements of WeWork’s ascent, not least the pace of it and I suspect the collapse might have come sooner had Neumann not crossed paths with Masayoshi Son, the CEO of SoftBank. (I’ll cover Son separately in a Gambling Man review) Both men share a deep sense of conviction, self-belief and ambition. Unfortunately, as much as these traits can create brilliance, they can also lead to blind spots the magnitude of which can easily be your downfall.

The book is thoroughly entertaining throughout. I haven’t yet watched WeCrashed, the miniseries based on the same story, but I can imagine it captures the same sense of chaos and charisma that defined Neumann’s reign. Ultimately, Billion Dollar Loser serves as a cautionary tale of unchecked ambition and someone who like Icarus flew too close to the sun, ignored every warning, and inevitably crashed back down.

I’d worked from WeWork offices before and remember how quickly they became the go-to workspace with beer on tap and trendy interiors. What I hadn’t realised, until reading this, was the madness behind the scenes. The speed, scale, and recklessness that fuelled their rise needs to be read to be believed!

It’s worth a read, less as a business manual and more as a study in excess, ego, and what not to emulate in entrepreneurial leadership.

Who’s it for?

Anyone curious about how WeWork imploded after its meteoric rise will enjoy this. If you liked Bad Blood (the story of Theranos and Elizabeth Holmes), you’ll likely find similar intrigue here. It also makes for ideal holiday reading as its relatively light, entertaining, and full of lessons, even if many of them come from what went wrong rather than what went right.