Chaos Monkeys - Revised Edition: Obscene Fortune and Random Failure in Silicon Valley

I was drawn to this book after hearing that it was so controversial that it got the author fired from Apple. That situation seemed to be a case of wokeness gone amok. Apparently, the company had already vetted him and the contents of the book. However, a few weeks after he started, some other Apple employees became offended and he got the kibosh.

The book does complain plenty of things that can be offensive. However, the official line was that it was misogyny that got him fired. The portrayal of woman is generally what you would expect to hear from a frat boy. They are primarily an outlet for sexual urges. However, the book also describes powerful women. It seems more balanced than a simple misogynistic rant.

The main theme of the book is that "work" is everything in the Silicon Valley startup culture. Family and long term relationships are sacrificed at the the startup altar. However, just working hard does not guarantee success. There is a huge amount of luck and manipulation involved. 

In the story, he started out working on his doctorate at Berkeley. He then jumped at the chance of making huge amounts of money as a quant on Wall Street. He tired of that and went to work in Silicon Valley. He realized that his company was going nowhere, so he got together with a few friends to create a start up. They had moderate traction, but were looking for an exit. They got interest from both Twitter and Facebook. The company sold to Twitter. He went to Facebook. At pre-IPO Facebook, work was an all-encompassing affair that required long hours, relationship building and partying. He was on the ground as they were trying hard to monetize facebook. There were plenty of mistakes made, but luck ended up interceding. He managed to cash his options at the worst time and somehow ended up at Twitter.

On advertising, he has some interesting insights on privacy. People are concerned about companies knowing their "dirty little secrets". However, these tend to be of minimal value to advertisers. What the companies carry most about is the general persona that will spend money. There is still a long ways to go before internet advertising reaches its full potential.

For start-up cultures, he recognizes that there are people with a lot of money and little time, partnering with people with little money and a lot of time. If all goes well, everyone will get rich. However, often things don't go well. There are many start ups that burn through a lot of money and go nowhere. There are a few that do well.

The author mentions multiple times that the focus is on the overall big picture. He claims the "book persona" is different from his actual persona. Perhaps Apple could just not get that. Or perhaps they finally got cold feet after seeing all the bridges that the author did burn.