Best Non-Fiction Books to Read: Billion Dollar Loser (Reeves Wiedeman)

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Billion Dollar Loser is in a very specific type of genre of books I enjoy reading, which I would define as investigative journalism. It is similar to other books I have recommended such as Billion Dollar Whale, Bad Blood, Kochland, etc.

Billion Dollar Loser is about WeWork and its founder, Adam Neumann. WeWork is famous around the world not only for its buildings, but because of its reputation as a tech unicorn. WeWork was one of many companies that received insane amounts of funding from Masayoshi Son and his Vision Fund, although the investment proved to be unsuccessful.

Like many other investigative journalism books, Billion Dollar Loser is a frustrating book to read. It is frustrating to read because it shows how dumb, manipulative people can raise billions of dollars in funding (which they can then funnel towards themselves) based solely off their charisma and charm. While Adam Neumann is a personable guy, he is not a good businessman, nor is he a particularly gifted individual (he just knows how to talk and charm other rich men). This is essentially what led him to getting funding rounds for WeWork, even when the business model of WeWork was nothing special.

The book also goes into detail about Neumann’s wife, Rebekah Neumann, who also happens to be a first cousin of Gwyneth Paltrow. Reading about Rebekah is even more painful than reading about Adam because she starts to gain control and influence over the company simply for being Adam’s wife (and affecting the lives of thousands of WeWork employees in the process). Although she was totally unqualified for her positions, Adam put her in positions of power where she was in charge of billions of dollars.

While the book is not the most objective source of information, it is clear that there were many faults with both the Neumann’s and WeWork. The book makes you feel happy when WeWork begins to fail, yet ultimately Adam Neumann still walked away with a ton of money (way more than he deserved). Overall, reading Billion Dollar Loser is frustrating, but it forces readers like myself to learn from Adam’s mistakes and become better business people than him.

Billion Dollar Loser Recommendation Rating: 4

This post has now been updated to reflect a new ratings system that I have implemented, which is scored as follows:

1: Something worth checking out if you have time

2: Something that is a hit for some people, but not a must for everyone

3: Something worth prioritizing if interested

4: Something worth making time to check out

5: An absolute home run, worth going out of your way for


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