My thoughts about ‘Chaos Monkeys’

Tanmay Goel
5 min readJul 27, 2021
Source: Amazon

So I recently read a book very interestingly titled Chaos Monkeys: Obscene Fortune and Random Failure in Silicon Valley.

Well, read is an understatement. I devoured it.

From the minute I started reading it, I was sucked into the narrative. Now before I say anything else, I should mention that it's well known that this book is riddled with controversy and inappropriate statements, and I do not support those, however, I did feel it was a one-of-a-kind memoir that is very hard to write, and I wanted to pen my thoughts about it, and what are the takeaways one can learn from this book.

Only someone as radical as Antonio Garcia Martinez, could go ahead and write this book, be willing to burn bridges with very important people in the industry, and unapologetically paint himself as the character he was in the book.

The first half of this book deals with the journey of how Antonio transitioned from an investment banker to Silicon Valley. He gives some interesting insights about the investment banking career, and also one of the main reasons many people end up staying in such a high stress, high demand, and high-intensity career. You guessed it right, it’s the money.

Following that he worked in a tech startup, but eventually realized that the leadership was leading the company to an unsuccessful path, and so he decided to apply to Y Combinator, an incubator for some of the biggest startups in Silicon Valley today (Airbnb, Stripe, Coinbase, Reddit) and many more. Once he got in, he convinced two of his co-workers to quit the company and join him to start a company.

Then comes the tale of how they built an ad-tech startup, but it's no less than a thriller. Their journey is always chaotic, dealing with lawsuits from their previous employers, competitors, the VC game and politics, and even the ins and outs of an acquisition. (Spoiler, they eventually get acquired by Twitter)

For an entrepreneur, it’s the most unfiltered primer you can get about the behind-the-scenes that happens while trying to raise funds, deal with outside forces, or handle everything about a business (aside from the actual product itself).

Some filler chapters talk about Antonio’s personal life, these are mostly uninteresting and contain most of the inappropriate content, so I just skimmed through them without paying much attention.

The second half of this book is what I earlier referred to as one-of-a-kind. You will find so many blogs and people talking about a sugar-coated version of what is a Product Manager. I felt Antonio really gave us an unfiltered explanation of what life as a PM is like, especially in a large and established company like Facebook, where he spent the years following his acquisition, trying to build their ad products.

I don’t want to give away a lot of the juicy parts, so I will stop my summarization here.

Here are some of the interesting concepts that I learned through the book, and other potential reasons why you might want to pick it up too.

  • It’s like a history lesson into how some of the biggest startups today were created. What was it like being an early Y Combinator company, and how early Silicon Valley life used to be
  • It navigates through the whole VC dance and politics, which is something I hadn’t even considered that a CEO would have to deal with. How naive I was.
  • I always wondered what happened to companies after acquisitions. Through this book, I realized, that in many cases, acquisitions are like a fancy way to hire good candidates into the company. It really flipped my perspective
  • There come many crossroads in the book where Antonio has to choose between keeping his head down and going with the flow of the company or go against his superiors to do what he believed in. It didn’t work every time, and sometimes even led to disasters, but I think it's commendable that he completely stood by his convictions. Regardless of what you believe in, it’s important to stand behind it. It eases your regrets in later life
  • A complete inside look at the daily life of a Product Manager and what they have to go through aside from actual product stuff.
  • How the culture at Facebook is raised, what it felt like being at FB pre and post IPO, and why Facebook is such a big company under Mark Zuckerberg’s leadership
  • Making decisions in companies like FB have to go through a lot of mid and high-level politics as well as legal, finance, growth and so many other departments before anything is actually signed off on. Things take time, even at some of the biggest companies in the world.
  • Even though Antonio’s life was so crazy and spontaneous, it’s probably because of his personality and character that he butted heads with so many people and made so many interesting friends and enemies in the valley. We should take it with a grain of salt, it’s not the life everyone can live, digest or survive, neither should they.
  • Interestingly enough, the book also educated me on the ins and outs of the digital ads business. It was definitely really interesting to know how companies like Google and FB actually make money.
  • Finally, Antonio lived and breathed digital ads, and that led him to many great opportunities. As a Product Manager, it could be a good idea to find a niche, to improve your chances of being hired in a specialized role.

Finally, my last takeaway is that be careful about what you write online. Even though the book was an NYT bestseller, his misogynistic words got him canceled and fired from a very senior position at Apple before he even started working there.



Tanmay Goel

I like to write about Product, Tech, Culture, and anything else I can think about