Review: Chaos Monkeys

Posted in Reading, Startups

I picked up Chaos Monkeys curious about how it would portray the same Silicon Valley that I’ve been a part of for over a dozen years. In particular, one of the characters in the narrative—Gokul Rajaram—had led my product organization at Square for a while.

At least some parts of the story met my expectations.

Chaos Monkeys is an autobiographical story of someone who came to the Bay Area looking for their chance to break out in the world of startups. From that standpoint, I shouldn’t be too surprised at the author comes off as a smart aleck with a side of annoying “finance bro”: his favorite narrative technique consists of using impressive historical quotes and analogies to describe business and sexual conquests. The caricatures he draws for tertiary characters and his often cynical dismissals of their motivations end up distracting.

It’s a little too much Wolf of Wall Street for me to take his retelling completely literally. I get that sex and drama sells, but for me those embellishments were more a distraction than a draw. If anything, I appreciated that the author took the time to try to explain some of the inside baseball of startups, things like South Park startup alcove or how acqhires work or even some of the technical underpinnings of online ad marketplaces. Having made similar (and only partial) explanations of how startups work to family and friends, it’s not easy to simplify what has evolved into a complex, somewhat detached ecosystem.

As to the content itself, many reviews point out that the book is split into two halves: the author’s more exciting initial foray into the startup scene, and the eventual somewhat boring employment at Facebook on their nascent ads business. To me, though, the latter half at Facebook is probably much more reminiscent of the vast majority of careers within Silicon Valley. That is, we work on (sometimes interesting) technical and business problems, and run into people politics from time-to-time. It’s not all that different from most other office work, except that the technicalities of software systems may take a couple more pages to lay out.

Understandably, it’s difficult to dress up mundane office work, as hard as the author tries. It’s also much less exciting to recount events and personalities from a lower vantage point; he had to continually guess and invent motivations of larger players within Facebook to connect to major, well-publicized events. The fiction isn’t as outrageous as something like Hatching Twitter, but there’s a reason most stories feature protagonists at the top, imbued with the opportunity and authority to make changes.

Chaos Monkeys isn’t my type of book. Silicon Valley has its dark and dirty side1, but I much prefer the style of investigative journalism, where multiple sources can be corroborated to give weight to outlandish claims2. When it’s done from the perspective of a single flawed individual, much of it comes across as petty, and the rest end up being questionable in accuracy and motivation.


  1. Though much of it is hidden from the rank-and-file employees anyway.

  2. That doesn’t mean that journalists don’t have an agenda or that they can be completely neutral. But it does provide additional perspective.