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. 

If you want an introduction to DARPA and how it has managed to play such an outsize role in the creation of the technologies of the future, start with this book on its best-known and most influential project, ARPANET. ARPANET went online way back in 1969, when, for the very first time, two computers of disparate types connected over a dedicated phone line to exchange data.

This book tells the story of how the project came together and how it birthed the internet, offering a book-length case study of how DARPA creates wizardry on a relative shoestring. There are lots of great details here, such as the poor soul who kept getting harassed by one of the first dial-up modems calling the wrong number. 

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.

Artificial intelligence, or AI, is the hot topic in the news today, but seldom do we see pundits try to explain it by drawing parallels to other communications or technological revolutions. Wheeler focuses, amongst others, on two paradigm-shifting revolutions: the invention of movable type (printing press) in the 1400s and the invention of the telegraph in the 1800s.

These two technologies upended the world and provided the foundation for massive changes brought forth by other events, including globalization, the Renaissance, scientific revolutions, and more. Wheeler does a great job of revealing the impact of these revolutions on all levels of society and provides a template for how to better understand the technological revolutions we are in the midst of today.

Tech analyst and investor Azeem Azhar concisely pulls together his take on how the arc of technology has moved from linear to exponential both in its development as well as its impact on society and business.

Azhar brings great insight into how exponential growth – creating an “exponential gap” – has put strains not only on businesses, but also on government and society writ large.