Book Review: Chaos Monkeys

Reading Time: 3 minutes

Antonio Garcia Martinez
Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley
ISBN: 978-0-06-245820-9

Imagine a story featuring some of the best, most talented people in America, along with some of the worst. What if some of the characters in that story fit both descriptions? And, what if those people were responsible for the technology in your everyday life? This isn’t fiction – it’s the sad reality of Silicon Valley in the 21st century.

Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley is a peak behind the Silicon Valley curtain – a fascinating look at the state and culture of some of the biggest tech companies in the world roughly a decade ago. Rogue actors, fierce competition, and both helpful and harmful gatekeepers come and go during the story, mostly true to detail but semi-fictionalized in places to protect the innocent. It’s an unsurprising read today, given the behavior of Big Tech in the last few years. However, it’s a great reminder of some of the toxic attitudes and behaviors that local entrepreneurial ecosystem builders like myself have worked to remove or discourage.

The main thing that stuck with me while reading this book was the level of disorganization the author noted at a number of companies – teams of people who seemingly kept failing upward due to the names and the money protecting them. This level of institutional rot can’t happen without seemingly endless buckets of money being thrown at problems. You see this problem in large, legacy companies as well, where the success of the past can usually overcome the incompetence of the present. It made me wonder if these same tech companies were still as disorganized today, even after their IPOs and scrutiny over the last few years. Perhaps another individual will step forward and update all of us in a few years.

The saga of the lawsuit reminded me both about the importance of balanced gatekeeping in an entrepreneurial ecosystem, and some of the toxic traits of founders that can both propel a startup to greatness, but can also be the downfall of that same organization. I dislike most forms of gatekeeping in entrepreneurial ecosystems – it can lead to the retention of toxicity while keeping out people who could contribute amazing ideas and energy. However, if it’s used for good, as it was in this case through the author’s connection to Y Combinator, the little guy stands a chance and the ecosystem benefits. Gatekeeping is a powerful tool, and should be used with a light touch.

The author did have his own flaws, which he was happy to admit. I was glad he took responsibility for some of his actions, in contrast to some of the characters with whom he was surrounded. Working as both a startup founder and as a Big Tech employee, he had an awareness of the people around him that I sometimes don’t see in other founders here locally. In my line of work, I have an opportunity to work with new startup founders pretty regularly, and it takes a special set of skills, both knowledge-based and people-based, to successfully lead a company or a team past a set of problems and toward an eventual solution. Founders and team leaders don’t have to be perfect, even though much of the hype around entrepreneurship demands it.

Overall, 10/10, would highly recommend to anyone who wants to take a peek behind the curtain of Silicon Valley. Entrepreneurs and startup founders should give Chaos Monkeys a read, regardless of their interest in becoming part of the Bay Area entrepreneurial ecosystem. Even though the book is a few years old at this point, it was a reminder of some of the nastier behaviors and personalities that we’ve tried to work out of our local ecosystem, but tend to pop up time and again due to the types of personalities drawn to professional entrepreneurship. There’s always work to be done to ensure the story told in this book doesn’t happen locally.