I used to work at a large multinational media corporation that desperately wanted to be a tech start-up. “Data,” “metrics,” and “product” were the terms du jour: They drove, however ambiguously or cynically, many of the decisions made by the magazine makers and website producers who paid me to line-edit what throughout the industry is now simply called “content.” The company’s coders were poached from prestigious firms to build publishing-focused software, and their offices, located a few floors below ours, offered a cornucopia of amenities that exceeded those of the “content producers”: They had higher salaries, nicer workstations, the presumption of job security, and free snacks. They seemed to be trusted with the future of the company, responsible for creating tools to help us publish our stories and decode the data that came back to us about our readers. In meeting after meeting, low-ranking executives, accompanied by these code jockeys, would instruct editors on how to game SEO and social media algorithms, reminding us about the need to remain vigilant in the face of an ever-changing media landscape. No one really seemed to know how to fix the ailing media company, but that didn’t prevent anyone from religiously paying tithes to the very technologies undermining our shared industry.
When I wasn’t at work stressing out over the ticker counters that gave value to my toil, I was still trapped in this world. I looked at my feeds when I woke up, trawling through the news, memes, and life events; I swiped between photos of strangers on dating apps; and I signed away the rights to my privacy and image with each new app I downloaded. Sometimes I would accept invitations to parties from friends on the very social media apps that were ruining my industry, and I would find myself in penthouses owned by early employees of what were known in the tech world as “unicorns”—start-ups with a valuation of $1 billion or more. Feeling flattered and, at the same time, guilty to be invited, I would spend a lot of time gawking at the excess: free drugs, alcohol, and hired help. I would think that no one, especially no twentysomethings, should be this rich. I still partook in the luxuries on offer. Surrounded by my college-educated peers who had done the smart thing and sold out, I wondered if being an editor and writer was worth the trouble. I knew I wasn’t alone in this, because a lot of my friends who came of economic age after 2008 were asking the same thing. Precarious, overeducated, and complicit in a rigged economic system we knew was undermining our own work, we wondered why we hadn’t all sent in job applications to the next hot tech company. (I did, to be honest, and was rejected.)
In Uncanny Valley, a remarkable memoir of her nearly five years working in San Francisco’s start-up scene, Anna Wiener tells us what happens when you do end up in the tech world—and about the anguish it has caused. A liberal-arts-educated East Coaster and erstwhile denizen of New York’s literary scene, Wiener provides an achingly relatable and sharply focused firsthand account of how a set of “ambitious, aggressive, arrogant young men from America’s soft suburbs,” backed by vast capital investments and armed with data analytics technology, helped to refashion not just our economy but also our culture, aesthetics, and politics with the new digital tools they produced.
At the center of Wiener’s narrative is a story about a generation: For her, the great innovation of the young people behind the continuing second dot-com bubble has been to persuade the rest of the world to fetishize the prophetic power of data and to get us to trade away privacy for optimization. But as an employee guiltily benefiting from this gold rush, she gives us a cautionary tale about the dangerous work cultures these tech companies cultivated as well. While warning about the collection of data and the way it reaffirms some of the most invidious forms of inequality in our society, she examines how tech companies were run on a toxic cocktail of misogyny, prejudice, and rampant surveillance. Unlike several other recent nonfiction dispatches from Silicon Valley, her book is less interested in making sense of the tech boom through the eyes and foibles of start-up founders and more concerned with asking questions from the point of view of the young people they employed. Although her memoir charts her eventual escape from this world, it also reminds us that even if we don’t work in tech and refuse to engage with the world that start-ups have created, we still need something far greater than rejection to resolve these issues. In this way, Wiener’s book, while not explicitly political, gives us a road map to the ways we can turn our growing dissatisfaction with what tech has wrought into the backbone of an ideology.
Before 2013, when she plunged headfirst into the start-up scene, Wiener was an assistant at a middling Manhattan-based literary agency, making $30,000 a year without benefits. This kind of job is not unfamiliar to anyone who has worked in publishing or journalism. It’s an effective dead end: Often the only forms of advancement come from extrinsic forces. One could, as Wiener notes, move up by being able to “[inherit] money, marry rich, or wait for peers to defect or die.” None of these seemed likely to be happening soon, so she began to wonder if securing advance reader copies and enjoying the shabby glow of cultural capital—even while scraping to pay the rent each month—was really enough. Then one day she read an article about an e-book start-up that had raised $3 million in seed funding.
The start-up’s mild form of disruption was simple: Seeking to turn once public goods like library books into a private, curated service, it planned to offer “access to a sprawling library of e-books for a modest monthly fee.” For Wiener, the money that might come from working at such a company had its appeal, and this particular start-up offered the chance to retain a connection to the analog world she loved, so she wanted in. No one can live off “taste and integrity” alone, she tells us, and when she was offered a three-month trial run with the company, she accepted.
Working as a kind of do-it-all assistant for the company’s four-person team, Wiener spent her days not learning a new profession but instead buying the employee snacks, writing copy for the website, and trying to lend her literary taste and expertise to a group of boys who did not really seem to care all that much about books. In one pitch presentation the CEO asked the staffers to consult on, she notes—to herself—that he spelled “Hemingway” wrong. In the same pitch, the CEO insisted that books are not really the point of the app they’re selling; they are monetizing a kind of lifestyle. As Weiner writes, the CEO and by extension his cofounders never really “acknowledged that the reason millennials might be interested” in buying (really renting) these experiences no longer linked to physically owning books had anything to do with “student loan debt, or the recession, or the plummeting market value of cultural products in an age of digital distribution.” They were just worried about making money.
As her trial period ended, Wiener could see she was a bad fit not just with this start-up but maybe with all start-ups. She was criticized for being too nice and not assertive enough (criticisms that followed her on her journey). She wrote the e-book boys a long, heartfelt e-mail hoping to convince them that her skills were indispensable, but they let her go anyway. The guys felt bad—they meant well, after all!—and helped her parlay her experience into an interview with a start-up they thought was more exciting than their own: a data analytics company in San Francisco that industry chatter had anointed as the next unicorn.
Wiener flew to San Francisco, and after a rather humiliating interview (she was given an LSAT practice test because the interviewer didn’t have any questions for her), she landed a customer support gig that would pay her double what she made as a literary assistant. If fitting in was the problem at her first start-up job, Wiener soon realized that she had a whole new world to master: Leaving aside the strange tech lingo and office rituals, the company she was about to work for, with its sexist and often classist workplace, would reveal how rotten the Internet industry had become. The two years she eventually spent at the analytics start-up were an eye-opener not just for her; the period also charted how an industrywide, government-supported embrace of data collection rewired the US economy and redefined life both on- and offline.
Wiener left New York for San Francisco at just the right moment—at least for a young person with literary aspirations. In 2013, Penguin and Random House merged to become one of the largest publishing companies in the world, employing about 10,000 people, commanding a combined value of over $2 billion, and creating a vast conglomerate that could affect the livelihoods of smaller houses, writers, and workers around the planet. But the mega publishing house was no match for what else was happening in the US economy. Not long before, Facebook went public with a valuation north of $100 billion, and Amazon facilitated one-half of all book sales. Amazon was also running an even more “lucrative sister business,” Wiener writes, of “selling cloud-computing services—metered use of a sprawling, international network of server farms—which provided the back-end infrastructure for other companies’ websites and apps.” In earlier eras, this kind of infrastructure might have been built by and for the public, but now it was privately owned and rented out, making it “nearly impossible to use the internet at all without enriching” Amazon. In the ecosystem Wiener was about to immerse herself in, Amazon’s ruthless and ingenious business model was much admired and provided a way to understand the world that start-ups were helping to create. It operated with the idea that there was no “crisis” in this vision of the future, “only opportunities.”
Wiener’s new start-up job focused on helping the data analytics company’s clients troubleshoot problems with the implementation of the company’s products, a powerful suite of tools designed to help websites and apps collect user data. Quickly, Wiener realized the tools for data collection weren’t the only things for sale. For the company’s clients, user data, as much as any of the services on offer, was itself a valuable good that could be packaged and sold. “The right findings,” Wiener tells us, “could be golden, inspiring new products, or revealing user psychology, or engendering ingenious, hypertargeted advertising campaigns.” To turn these insights into an economic windfall, the analytics start-up divided the data that its clients collected into highly granular morsels. Clients could break down and segment user engagement in a way that enabled them to predict user behavior and either sell this information to other companies or retain it for their own projects.
The start-up’s employees were expected not to snoop around the private information that they were enabling clients to collect. But by using a setting called “God mode,” Wiener implies, she and her colleagues could easily “look up individual profiles of our lovers and family members and co-workers in the data sets belonging to dating apps and shopping services and fitness trackers and travel sites” that worked with the start-up. Even if there was an ironclad rule against such prying, Wiener continues, she’d heard stories of people at other start-ups not acting with such discretion. At a ride-sharing company, employees would frequently “search customers’ ride histories, tracking the travel patterns of celebrities and politicians.”
With this power at her disposal, Wiener not only learned how widespread data collection had become but also began to grow a bit paranoid. “It wasn’t the act of data collection” that gave her pause, she writes; she was already resigned to that. What disturbed her was “the people who might see [her data] on the other end—people [like her].” She “never knew with whom [she] was sharing” information, and soon she began to see how the collection was not just a business strategy but something far more dangerous. It created a wealth of unchecked power for those companies that ended up with its vatic information. If they could predict user preferences and behavior, they could also manipulate the entire economy.
Still, in her early days at the analytics company, Wiener tried to brush away many of these fears. The money was just too good, and for the first time in her adult life she was saving and climbing a career ladder. Even when a grave new development connected Silicon Valley with the upper echelons of the US government’s War on Terrorism, she didn’t at first see how the work she did was implicated.
On the day Edward Snowden’s NSA leaks became public, Wiener and her coworkers weren’t particularly interested: “In general, we rarely discussed the news, and we certainly weren’t about to start with this story. We didn’t think of ourselves as participating in the surveillance economy. We weren’t thinking about our role in facilitating and normalizing the creation of unregulated, privately held databases on human behavior.” But Wiener’s growing unease was vindicated. Not only corporations but our government (and others around the world) were now wielding these powers to spy on their citizens and enemies alike on a scale never seen before. “We facilitated the collection of the information,” a former coworker tells her, “and we have no idea how it will be used and by whom. For all we know, we could have been one subpoena away from collaborating with intelligence agencies. If the reports are accurate, the veil between ad tech and state surveillance is very thin.”
After the Snowden revelations, things began to sink in for Wiener, and Uncanny Valley tracks each step she took in connecting the dots. She moves from the rise of cloud computing (“The idea of the cloud, its implied transparency and ephemerality, concealed the physical reality: the cloud was just a network of hardware, storing data indefinitely. All hardware could be hacked”) to the links between corporations and the US national security state (“The servers of global technology companies had been penetrated and pillaged by the government. Some said the technology companies had collaborated wittingly”) to the terrible version of the Internet we all live with now. And while these passages can illuminate for readers the intersections they might not already know, they carry a tinge of paranoia that can veer into near–conspiracy theory. But in fairness to Wiener, she makes clear how jobs like hers incentivize people to be ignorant of the world around them. “It was perhaps a symptom of my myopia, my sense of security, that I was not thinking about data collection as one of the moral quandaries of our time,” she writes. “For all the industry’s talk about scale, and changing the world, I was not thinking about the broader implications. I was hardly thinking about the world at all.”
Apart from her growing fear of the dangerous implications of data collection, Wiener was also confronted with the arrogance, classism, and misogyny of Silicon Valley’s workplaces. Without the aggression and petulance of a workplace culture that compared everything to conquest and brutality, she suggests, her colleagues might have paused to consider whether the products they worked on were directly connected to industry or government surveillance programs.
At the data analytics company, in particular, Wiener got a crash course in the bullying rhetoric and office culture of the start-up world. The company’s internal slogan, “Down for the cause,” was used to chastise her and her coworkers if they failed to live up to the vague mandates of growth and devotion. The staffers were haunted by the company’s oracular CEO, an Indian American college dropout who talked almost exclusively in the language of war. After one happy hour hosted by the company, a coworker attempted to grope Wiener in the backseat of a cab. Another colleague made a pass at her in the middle of the workday and told her that he “loves dating Jewish women” because they are “so sensual.” While such workplace abuses are widespread across all industries, Wiener shows how the casual misogyny and truculence of her workplace—and tech businesses in general—are two of the reasons the Internet has become an unwelcoming place for women, people of color, and those who are down and out. Having refashioned the Internet in their image, start-up executives have made it a hostile environment for everyone else.
Wiener eventually moved on to a third start-up, where she worked as a kind of content moderator, trawling reports of “pornography or neo-Nazi drivel” and determining if the posters violated the company’s free speech policies. For Wiener, this work proved to be the breaking point. The way her peers in tech treated San Francisco was another. On an unnamed blogging platform, a varying set of “engineers and aspiring entrepreneurs” captures the general mood among pigheaded tech bros there. In one post, a man compared the city’s temperamental weather to “a woman who is constantly PMSing.” In another, a tech dude joked about “monetizing homeless people by turning them into Wi-Fi hotspots” and excoriated the poor for “clinging to rent control and driving up condo prices.” One of her first realizations about her new home—and the one that stuck with her throughout her years there—was the depth of its contrasts: “I had never seen such a shameful juxtaposition of blatant suffering and affluent idealism.”
For Wiener, the city, the workplace, and the Internet had an appalling commonality. Wrapped up in the start-up machismo about disruption so prevalent in all these spaces was a stomach-churning disgust for the poor, for women, for basically anyone not employed by a tech company. The coders—many of whom were white and college-educated and were from middle-class homes—preferred a world that reflected their own comforts and needs and then projected those preferences not only into the workplaces that Wiener and many other women and people of color had to share with them but also into the technologies and surveillance tools that helped drive the economy. “Silicon Valley might have promoted a style of individualism,” Wiener observes, but its scale “bred homogeneity. Venture-funded, online-only, direct-to-consumer retailers had hired chatty copywriters to speak to the affluent and overextended…. Homogeneity was a small price to pay for the erasure of decision fatigue. It liberated our minds to pursue other endeavors, like work.”
About four years after moving to San Francisco to enter the tech world, Wiener quit her last job there. She managed to escape with a nest egg of about $200,000 after exercising her stock options, around a year after the election of Donald Trump.
The big-picture takeaways of Uncanny Valley are compelling, though they are not Wiener’s alone: For the last few years, we’ve seen a cottage industry of books detailing the personal and political effects of surveillance capitalism and tech-world excess. But the literary texture of Wiener’s narrative makes it particularly valuable as a primary document of this moment. Her voice, alternating between cool and detached and impassioned and earnest, boasts an observational precision that is devastating. It is whip smart and searingly funny, too. The book contains a six-page tour de force on Internet addiction, algorithms, and all of the attendant feelings of dread that is one of the best summations of an average day online I’ve ever read.
There is also a powerful and often surprising combination of joy and ambivalence running through Wiener’s story. She is careful not to say that all tech is bad, all start-up bros evil, and she marvels at the magic of both understanding and deploying a line of code. She also allows space to those who upend her preconceptions of tech culture, among them her boyfriend Ian, a Google engineer, and Patrick, an erudite young start-up founder she befriends. That Wiener squeezes all of this—along with passages on urban theory, tracts on electronic dance music, and thoughts on contemporary novels—into some 275 pages is quite a feat.
Still, it’s impossible to leave this book not feeling drained spiritually and politically, even as its wealth of knowledge helps orient the reader in a world so closely tied to the ups and downs of Bay Area billionaires. Throughout Uncanny Valley, there is a sense of crushing defeat. The world that Big Tech has given us feels almost foreordained, with few alternatives to serve as a counterweight to its dominance over the tools that facilitate everyday life. Wiener found her escape route, eventually becoming a writer for The New Yorker, where she quickly established herself as a trenchant observer of the tech industry. In this way, one can read Uncanny Valley as a Künstlerroman, a tale of our heroine returning to her literary ambitions after all. But like a lot of recent books on the hellscape that is the Internet, her personal story gives us little room to imagine how we all might escape this new, malignant, corporate-controlled space, where data collection, advertising, and surveillance are the status quo.
For Wiener, this may be part of her goal. The clarifying anger that infuses her book also points to the larger politics that we will need if we are to make the Internet a more humane gathering place. Breaking up the Silicon Valley monopolies, unionizing their workplaces, and imposing effective new government regulations need to happen to begin fixing the Internet (and the world). Yet while she only briefly engages with the prospect of tech unionization, the entirety of the book is spent grappling with the limits of her coworkers’ and her own political imagination in the face of the tools they’ve created. She shows us all this because she knows something has to change. Uncanny Valley may tell the story, from one woman’s perspective, of how the tech industry has come close to ruining the world. But Wiener’s book is also proof that it hasn’t succeeded yet.