100 books like Chaos Monkeys

Kidder’s book follows the lives of a group of brilliant, funny, and maniacally driven entrepreneurs as they race to get their new minicomputer, the “Data General Eclipse MV/8000,” to market.

The technology is totally obsolete – who under the age of 40 has heard of a minicomputer? – but the story is somehow timeless. The book won the Pulitzer and is still a fun and riveting tale of what it takes to get a product to market on an ever-changing technological frontier.

Dan Lyons’ book is the “fish out of water” trope applied to high-tech. Working in high-tech usually means buying into the grandiose vision of transformation that the company’s technology will produce. In industry parlance: you will be drinking a certain amount of Kool-Aid. Dan doesn’t do this. Instead, he applies a certain skepticism to the work his bosses have asked him to do.

It takes a bit of time to develop cynicism and skepticism in high-tech. By its nature, tech companies are optimistic. When you’re fresh out of school, a high-tech company’s vision and working style seem completely natural. But this isn’t Dan’s first job, and he maintains a near-constant level of incredulity at all the high-tech traditions that he sees around him. This is an intense delight to read.

Changing careers from publishing to tech is a path not often traveled. Wiener made this jump from a world legendary for its light pay compensated by romanticism, to an industry best known for generous “perks that landed somewhere between the collegiate and the feudal.” Wiener’s experience makes for one of the most entertaining books I’ve read in years—she is a gifted writer and unafraid to call out the over-seriousness of the tech bro mentality as an ultimately “dreary” worldview. 

This book tells the fascinating story of the visionary pioneers who created the internet. The wizards are the internet’s forefathers. They were determined visionaries and doers. In the 1960s, when computers where regarded as mere giant calculators, J.C.R. Licklider, the first director of the American Information Processing Techniques Office, saw them as the ultimate communications devices. The early internet was devised and implemented in American research units, universities, and telecommunication companies that had vision and interest in cutting-edge research. Licklider, Vint Cerf, Steve Crocker, Len Kleinrock, Larry Roberts, Robert Kahn, and David Clark articulated the vision of a "galactic" computer network—a globally interconnected set of processing nodes through which anyone anywhere can access data and programs.

This captivating book enables a better understanding of the internet. It captures the hard work, genius, fortunate experiences, and early successes of the visionary wizards and their daring, stunningly successful venture that has changed,… show more.

Kara Swisher has spent decades writing about and reporting on the tech kings of the world, including Elon Musk, Bill Gates, and others. Her insights into the rise of tech giants from the early 1990s to the present illuminate the forces that have shaped our world

I loved Swisher’s insight into these powerful men. She’s blunt, funny, and direct in how she exposes their flaws, and the book feels like it’s written by someone who understands and is fed up with these white, controlling male demigods of tech. I imagine the book’s title refers to how she’s burning all bridges by telling all.

As a journalist who was raised pre-internet, I could deeply relate to Swisher’s outrage in lines such as “What struck me was how easily people could be manipulated by fear and rage, and how facts could be destroyed without repercussions.”

Really, any book or essay (or scrap of paper!) by Pico Iyer, the master of flight and finding that quiet, blue place above any clouds. The first three books in this list were to make you want to take flight. This is the how-to manual. Start it on the plane, as the engine roars to life, the wheels begin to turn… and go.

Palfrey is not just a known authority on internet law and emerging media, but also the former head of the prep school Phillips Academy, Andover; the former executive director of Harvard’s Berkman Klein Center for Internet and Society, a research center that studies cyberspace and internet-related legal issues; the head of the MacArthur Foundation; and, I learned before speaking with him, a great-great-grandson of Teddy Roosevelt. This book, newly updated, delves into the myriad permutations of what it means to grow up in a digital world, with your every move captured and publicized. Yes, it focuses on children growing up digital, but it will be of interest to anyone who has questions and concerns about the future of privacy—meaning, just about all of us. 

This is one of my favourite tech criticism books. I love how each of the book’s chapters takes a word commonly used in Silicon Valley (and the associated international startup communities) - such as "failure," "disruption," "drop-out," and "content" and dives into the "intellectual bedrock" at the heart of the discourse which surrounds them.

Daub is a Professor of Comparative Literature at Stanford - so his critical eye and vast knowledge of intellectual history swiftly pull apart the pseudo-intellectualism so many in the startup community use to justify their success and problematic behaviour.

I particularly valued the fact that it’s short, punchy, and acts as a brilliant thought-starter to go deeper into the crucial ideologies which are hugely impacting our world today.

I'm fascinated by the connection between our modern world and how we got here, and this book takes a deep dive into just that. Johnson looks at the most common objects we often accept as if they've been a part of life forever (such as eyeglass lenses), and traces not only how they were created, their impact on our lives.

I find Johnson's writing incredibly informative without being pedantic and always entertaining. He's got an eye for unintended consequences and pays homage to the spirited determination innovators tend to have. As an inventor I note his appreciation for those brilliant mistakes that turn into brilliant technologies, a great lesson in the value of taking chances.

First published in 1958, this is one of Hannah Arendt’s most influential books and in it she attempts to define the human condition in the aftermath of World War II, developing her concept “natality.” 

It’s a challenging book that I’ve wrestled with and argued with and never forgotten. It includes some of her most powerful and frequently cited passages about birth. Lately, I’ve been returning to its opening pages, in which she discusses the launch of Sputnik into space. 

She saw this launch not as an exciting technological breakthrough, but as a fateful repudiation of our earthly existence, an existence that was defined by birth with possibilities and limitations.