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 mis