The greatest tech books of all time

1

Close to the Machine: Technophilia and Its Discontents

by Ellen Ullman

Not only does Ullman tell us what it was like to be an engineer during the dot-com bubble, but she does it in prose that many professional writers envy. The programmers in her milieu live in a strange place, longing to slip the bounds of humanity through their code; at the beginning of the book, Ullman and two other programmers haven’t left the building where they are working in three days.

The end users, who are only too human, are a source of contempt for these programmers — and Ullman’s attempt to bridge these two groups with a program makes her increasingly troubled. Because far from the machine, away from the sterile comforts of logic, there are people: AIDS patients, who the program is meant to help. For better or worse, we’ve all gotten closer to the machine since Ullman first wrote, but this memoir is perhaps the most powerful book ever written about technology. — Liz Lopatto

2

Technopoly: The Surrender of Culture to Technology

by Neil Postman

In Technopoly, Postman lays out the case that America is a “totalitarian technopoly,” with humans getting squashed beneath the thumb of Big Tech. Systems of meaning have lost all authority — and so now, there is no reliable way to order information into meaning because it is impossible to know which information to discard. With social institutions shaken from their mooring, people trust themselves so little that they are always looking for the authorization from their technological toys — doctors who won’t treat symptoms but will treat blood tests, for instance. Darkly funny, Postman argues that we have made ourselves subservient to our tools. — LL

3

Uncanny Valley

by Anna Weiner

This book stands out among the Silicon Valley memoirs because it doesn’t really have a happy ending. Come to think of it: it doesn’t really have a happy beginning or middle, either. Instead, what we get is a heartbreakingly personal story about what it’s like for a woman who isn’t a developer to work at tech startups that worship bros with engineering prowess and the ability to code. It’s also a story about change — the change that comes from moving across the country, getting a new job with new co-workers, or the creeping realization that the relentless optimizing that the world had about the tech industry (and that the tech industry had about itself) in the early 2010s may not actually be warranted. — Mitchell Clark

4

This Machine Kills Secrets: Julian Assange, the Cypherpunks, and Their Fight to Empower Whistleblowers

by Andy Greenberg

This is a swashbuckling thriller filled with hackers, whistleblowers, idealists, and some truly reprehensible people. From Daniel Ellsberg to WikiLeaks, the book connects the lesser-known elements that blew up geopolitics and continue to warp our society today. The stories of the cypherpunks mailing list and the ’90s “crypto wars” (that’s cryptography and not monkey jpegs) are woven through riveting portraits of charismatic villains and flawed heroes. The one caveat here is that every version of the book on the market deadnames Chelsea Manning, who publicly changed her name and pronouns the year after publication. (“I definitely don’t feel great about that,” Greenberg told me via email. He explained the book hasn’t been reprinted, so there’s been no opportunity to address this.) It’s a good book if you want to be entertained, and it’s a great book if you want to better understand a radical, slightly grimy slice of tech culture that has loomed large over Silicon Valley for decades but has gone mostly unnoticed elsewhere. — Sarah Jeong

5

Hamlet on the Holodeck: The Future of Narrative in Cyberspace

by Janet Murray

It’s hard to overstate Murray’s influence on how people think about video games and the web. Written in the era of Doom, Myst, and the text-based precursors to massively multiplayer games, her work contains the early threads of debates over agency, immersion, and emergent narrative that we’re still arguing about today (plus, as its title suggests, a lot of bonus references to Star Trek). But Hamlet on the Holodeck isn’t just worth reading to vindicate Murray as right or see what she got wrong. It’s a treatise on the potential of computer storytelling from a moment that’s both strikingly similar and remarkably different from our own, as memorable for its descriptions of now-forgotten experiments as its prescient attention to forms like chatbots and multiplayer social worlds. — Adi Robertson

6

Super Pumped: The Battle for Uber

by Mike Isaac

We’ve had enough examples of founder worship gone wrong that you’d think we’d have learned our lesson. But Super Pumped, the thrilling portrait of Uber under the reign of its aggro bro CEO Travis Kalanick, is unsparing in its detail and delicious in its office drama. The startup Isaac paints is one that is guided by growth rather than any direction from a moral compass. But it’s Kalanick’s conflation of ego and ambition that eventually led to his employees turning on him. In the end, Kalanick saw himself and Uber as singular — and I don’t think he was wrong. He was just astonishing in a different way than he’d hoped. — Kevin Nguyen

7

Broad Band: The Untold Story of the Women Who Made the Internet

by Claire Evans

I’ve read many, many books about computer history at this point, and still, most of the stories in Broad Band were new to me. In some ways, that’s the point — true to its subtitle and meant to do more than just reinforce the legends of all the dudes we already know. By giving the women of computer science their due, it manages to capture something that a lot of other histories don’t. Yes, it goes into exciting and groundbreaking inventions and talks about the very smart and semi-famous people who made them, but it also delves into the less well-known parts of computer history — the communities that supported those inventions and the (sometimes offline) infrastructure that made them work. It’s a book about missing pieces, the silent or underappreciated systems and people that made it so technology could continue to leap forward and that made the internet we call home worth using in the first place. — MC

8

The Boy Kings: A Journey into the Heart of the Social Network

by Kate Losse

Part memoir, part company portrait, The Boy Kings occupies an era of Facebook long before Cambridge Analytica revealed what Mark Zuckerberg’s empire — and Big Tech at large — had wrought. But in The Boy Kings, we see the early days as the company pursued its techno-utopian ideals. Losse herself only stumbled into the job and always maintained an anthropological distance from her work. There are plenty of lavish, frat-y startup anecdotes. But the enduring heart of the book is Losse’s access to a younger, more naive Zuckerberg — she was so close to him that her job transformed into being his ghostwriter. Here, the CEO is revealed to be entitled, un-self-aware, and vague in his vision for the future. While other Facebook employees hail him as an emperor, Losse instead figures out quickly how he pretends to be one. — KN

9

Common as Air: Revolution, Art, and Ownership

by Lewis Hyde

A lot of us looked at the overheated anti-piracy rhetoric of the 2000s, cracked some jokes about those corny “You Wouldn’t Steal A Car” ads, and moved on. But Hyde encountered the decade’s push for ever-broader intellectual property rules and saw something deeply pernicious: an erosion of our common culture borne of treating knowledge like mere private property. His response, Common as Air, is one of the most eloquent and rousing defenses of the public domain you’ll ever read. On top of a thoughtful argument about a powerful organizing principle of modern media, it’s a book that can make you excited about the prospect of artists building off each other’s ideas. If watching corporate juggernauts reduce every book, game, and movie in existence to eternally “exploitable IP” makes you a little queasy, it’s the perfect antidote. — AR

10

Like, Comment, Subscribe: Inside YouTube’s Chaotic Rise to World Domination

by Mark Bergen

What is YouTube, really? A video hosting platform? A social network or a search engine? The world’s largest music service or a replacement for television entirely? The tensions between all of these things, YouTube’s leadership, and YouTubers themselves are masterfully laid out in Like, Comment, Subscribe, which is among the very best books of its kind. Yes, it is a tumultuous history of YouTube, from its shaky startup days through to its dominating position as an institution of both the internet and the global cultural economy, but it is importantly also a history of the YouTube creator and how the platform’s shifting goals and metrics have built and destroyed entire content empires in the blink of an eye. — Nilay Patel

What did we miss?

Any list is bound to inspire some debate. (Heck, you should have seen how long we debated.) So if you think there’s a great tech book we’ve missed, let us know, and make your case. We’ll publish our favorite responses in a follow-up.

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A People’s History of Computing in the United States

by Joy Lisi Rankin

In this history of the early users of computers in the 1960s and 1970s, Rankin emphasizes that the history of technology isn’t the history of the Great Men who created products — but of the people who made communities with them. 

New Money: How Payment Became Social Media

by Lana Swartz

What is money if not the original social network? Swartz’s observations of how digital money works as a creative (and destructive) force are a must-read for anyone who makes money online.

The Soul of a New Machine

by Tracy Kidder

In his chronicle of a group of super computer engineers from the late ’70s / early ’80s, Kidder never shies away from the nitty-gritty of engineering and computing, and his confidence in the mechanical keeps Soul of a New Machine enduring over four decades later.

Spam: A Shadow History of the Internet

by Finn Brunton

So obvious that it is mostly unremarked upon, Brunton argues that spam messages tell us all about modern society, revealing that a lot of modern life is computers just talking endlessly to each other, cutting out the human middleman.

Being There: Putting Brain, Body, and World Together Again

by Andy Clark

What if your body is part of your mind? Where is the barrier between the world and the mind anyway? Clark’s study of thought weaves together what it actually is to think, which is much more complex than just neuronal activity.

Spelunky

by Derek Yu

Spelunky has always been a bit of a gamer’s game: mechanical, nostalgic, somewhat inaccessible, brilliant. Though developer Derek Yu is extremely specific in this book about the thoughtful choices he made with the game, the design lessons speak to much larger themes and conflicts in art-making.

The Attention Merchants: The Epic Scramble to Get Inside Our Heads

by Tim Wu

Wu thinks advertising is the web’s original sin, and in this history of advertising and propaganda, he makes a case that we’ve hit a new inflection point in the industrial control of our minds.

Distributed Blackness: African American Cybercultures

by André Brock Jr.

In this excellently researched study, Brock Jr. emphasizes the role that Black users play in online culture and the joy and playfulness these users bring to online spaces.

The Extreme Self

by Shumon Basar, Douglas Coupland, and Hans Ulrich Obrist

Have you ever felt bullied by a picture book? In this graphic novel, Basar, Coupland, and Ulrich Obrist push and pull at what it is to have a self at all.

Small Fry

by Lisa Brennan-Jobs

Catchy as a glimpse into the family life of Steve Jobs, but Brennan-Jobs possesses a compelling story all her own. A carefully observed memoir, she casts a sharp, specific portrait of burgeoning Silicon Valley in the ’80s against the universal story of longing for a father’s love.

The Hacker Crackdown: Law and Disorder on the Electronic Frontier

by Bruce Sterling

What do you get when a glitch takes down America’s biggest phone network, the Secret Service raids a tabletop RPG maker, and the US government declares war on hackers? A wry and surprisingly twisty nonfiction caper about ’90s phone phreak culture by science fiction author Sterling.

Orality and Literacy: The Technologizing of the Word

by Walter Ong

What if online culture is more like oral culture than literate culture? Ong persuasively argues that communication shapes thought, and after reading him, it’s hard to escape the notion that the changes to consciousness from digital communication may make us more like the ancients than like our parents.

Disciplined Minds: A Critical Look at Salaried Professionals and the Soul-battering System That Shapes Their Lives

by Jeff Schmidt

Though Schmidt focuses primarily on physicists, this study of how white-collar professionals are selected and shaped for certain kinds of creativity and incuriosity clearly explains why most people in the tech industry have such limited imaginations. Of course all the “contrarians” think exactly the same — they were selected that way.

Readme.txt

by Chelsea Manning

If the only thing you know about Manning is that she’s a whistleblower, you’ll find a much richer story in the details of what led her to that decision and the horrific consequences that followed, as well as her journey toward understanding her gender identity.

Death by Video Game: Danger, Pleasure, and Obsession on the Virtual Frontline

by Simon Parkin

A compellingly and curiously researched book about great feats of video game obsession, written with the careful eye of a critic.

Life In Code: A Personal History of Technology

by Ellen Ullman

This essay collection gives you a 20-year view of the tech industry from one of its best chroniclers. The essay about Y2K is particularly insightful, as are her comments about tech culture, who makes it, and who gets excluded.

Bad Blood: Secrets and Lies in a Silicon Valley Startup

by John Carreyrou

Carreyrou lays bare the downside of the tech hype cycle: not everything is marketing, and when Elizabeth Holmes doesn’t deliver on her promises, real people get hurt.

There Must Be a Pony in Here Somewhere: The AOL Time Warner Debacle and the Quest for the Digital Future

by Kara Swisher

In this compulsively readable history of the AOL / Time Warner merger, Kara Swisher dishes the dirt on the egos of the dot-com boom and the easy money that came with it.

The Twenty-Six Words That Created the Internet

by Jeff Kosseff

Kosseff will take you through two decades of fights over Section 230, a law whose effects are felt in nearly every corner of the internet. Beyond the legal arguments, Kosseff captures the limits of abstract principles in the face of people doing awful things online — a problem that’s existed almost as long as the web itself.

Everything I Need I Get from You: How Fangirls Created the Internet as We Know It

by Kaitlyn Tiffany

A reclamation of fandom (and a surprisingly robust deep dive into the annals of One Direction Tumblrs), former Verge staffer Tiffany brightly and breezily argues how the seemingly niche contours of stan culture shaped the greater internet landscape today.

Videogames for Humans: Twine Authors in Conversation

edited by merritt k

Hypertext design tool Twine fostered a singular world of experimental, deeply personal video games. Videogames for Humans is a series of essays taking a close lens to those works — producing the kind of literary analysis not enough games receive.

Algorithms of Oppression: How Search Engines Reinforce Racism

by Safiya Noble 

“Systemic racism” is often hard to pin down as a nefarious and often opaque form of discrimination. But in Noble’s thoroughly researched book, she’s able to nail down one specific and troubling system: the search engine.

Dealers of Lightning: Xerox PARC and the Dawn of the Computer Age

by Michael Hiltzik

Xerox’s Palo Alto Research Center is the birthplace of ethernet, desktop computers, and the laser printer, and Hiltzik’s account of its heyday might leave you impressed they pulled any of it off. Dealers of Lightning profiles a team of visionaries who helped create computing as we know it — while fighting their own company every step of the way.

Weapons of Math Destruction: How Big Data Increases Inequality and Threatens Democracy

by Cathy O’Neil

If you want to understand how algorithms shape modern society in ways that are hard to avoid or contest, this is a great way to familiarize yourself with how data can work to make life less fair.

The Deal of the Century: The Breakup of AT&T

by Steve Coll

It feels like tech antitrust is a hot, trending topic. But maybe tech and antitrust have always gone hand in hand. AT&T, after all, was and is a kind of tech company, and the things that make tech companies large and successful are the same things that attract the attention of regulators.

No Filter: The Good, the Bad, and the Beautiful

by Sarah Frier

Influencers exist because they were deliberately courted, and Frier’s account gives us a history of how some nerds attempting to build a photo business built the foundations of the creator economy.

Countdown to Zero Day: Stuxnet and the Launch of the World’s First Digital Weapon

by Kim Zetter

This book recounts the tale of the Stuxnet malware: why it was made, how it was delivered to a secure nuclear facility, and the cat and mouse game researchers played to pick it apart and understand it. It also asks the terrifying question: what doors did the first major cyberweapon open?

Crash Override: How Gamergate (Nearly) Destroyed My Life, and How We Can Win the Fight Against Online Hate

by Zoë Quinn

Quinn’s breakup was so bad the UN got involved. In Crash Override, she writes about being at the center of a storm of sexist harassment during Gamergate — and gives us a portrait of what it is to be targeted by the entire internet as you try to exit an abusive relationship.

Who Controls the Internet? Illusions of a Borderless World

by Jack Goldsmith and Tim Wu

Published in 2006, the book is clearly intended as a response to contemporary technolibertarian hype of an ungovernable internet — the thesis is that the internet is, in fact, effectively and actually subject to specific organizations, infrastructures, laws, governments, and borders. In 2023, this is no longer a provocative counter-revolutionary salvo, but the book remains a vital history of the internet.

You Look Like a Thing and I Love You: How AI Works and Why It’s Making the World a Weirder Place

by Janelle Shane

Shane’s primer treats AI like a large, surprisingly clever, but frequently discombobulated pet. It’s an affectionately down-to-earth introduction to the year’s most hype-prone field of tech, complete with charming illustrations.