Seduced by Start-up Land

A new memoir about millennial ambition in Silicon Valley.

Photo: Dina Litovsky
Photo: Dina Litovsky

If you’re a young woman who writes nonfiction books, you will, at some point, be compared to Joan Didion. Or, as author Rebecca Solnit anointed Anna Wiener on the U.K. cover of her new book, Uncanny Valley: “Joan Didion at a startup.” Over Japanese macro bowls in one of the few remaining untrendy restaurants on San Francisco’s Valencia Street, the 32-year-old writer grits her teeth at the comparison. “That’s very flattering, but imagine Joan Didion a start-up. It makes me want to kill myself,” she muses. “She would just be drinking black coffee and wearing a dress and leaning against the side of a conference room and just collecting checks. And someone would say, ‘Joan makes me kind of nervous.’ And someone else would say, ‘Yeah, but we can’t fire her because it would look bad — she’s Joan Didion.’”

Our day exploring San Francisco began at ‘Salesforce Park,’ a futuristic rooftop green space in San Francisco’s downtown. (Wiener recently wrote a piece about the new park for The New Yorkerwhere she works as a contributing writer covering Silicon Valley and start-up culture.) “Let’s meet in the lobby, near the Jenny Holzer [art installation], by the Dollar Shave Club vending machine,” she texts. After pausing to contemplate some peppermint-scented ass wipes from the razor start-up’s vending machine, Wiener leads me up to the park, where San Franciscans are molting their puffer-vest outer skins in the unseasonable January heat.

Uncanny Valley is a memoir about Wiener’s journey through start-up culture during its most bullish and self-aggrandizing era, and how her idealism gives way to disappointment and horror as society starts to suffer the consequences of tech’s unchecked fetish for growth. Initially, much like everyone else, she is excited about the industry’s promise and naïve about its shortcomings. As she moves from a successful e-book start-up to a successful data-analytics start-up to a successful open-source start-up (the software-development giant GitHub), her main focus is doing a good job and appeasing the powerful men she works for. As she strives to find her place in the industry, she finds herself turning a blind eye to some of its greatest moral failings: the proliferation of hate speech, the erosion of privacy, the housing crisis in San Francisco, and, eventually, Trump’s ascension to the White House amid a tsunami of fake news and Russian propaganda. The book is written using vague descriptions instead of company names — Facebook is “the social network everyone hated,” for example — giving the sense that the specifics of Wiener’s life matter less than the ecosystem they represent.

The book is a portrait of the “people behind the internet” at a pivotal moment in American culture. It’s also a coming-of-age story, one that turns on a set of familiar questions: What kind of life do I want to live? What are my personal goals, what do I believe in, and how do I balance the two against one another? Wiener is an insightful and reflective narrator, and yet still she finds herself blindly accepting Silicon Valley’s mythmaking as infallible truth. “I had been seduced by the confidence of young men,” she writes. “I had trusted them to tell me who I was, what mattered, how to live … I did not see that I was in good company: An entire culture had been seduced.”

What brought Wiener to “the promised land for millennial knowledge work” and kept her there for six long years was a combination of personal drive, structural opportunities, and dumb luck. “Everything that has happened to me has been either an accident or just me following my instincts,” says Wiener. “On the other hand, I’m aware that there’s like a certain type of person” — namely white and privileged — “who can get away with that.”

Wiener grew up in Park Slope, the daughter of a financial adviser father and a mother who worked as an anti-gun activist. Her love of books led her to the New York publishing industry, where the mood was as dire as the financial opportunities. Despite initial skepticism about the “online superstore [that was] experimenting with various ways to destroy the publishing industry,” she became increasingly excited by tech’s ability to offer something important that she felt publishing could not: a future. So Wiener moved out to San Francisco and began to chart a course through the burgeoning start-up economy.

As Wiener’s tech career ramped up, she participated gamely in company ski trips and donned cringey company T-shirts that proclaimed: “I Am Data Driven.” She was intoxicated by the sense of forward momentum the industry provided, even though the job itself left much to be desired. The start-up world is not exactly welcoming to women, and she often found herself “trying to be everyone’s girlfriend, sister, mother,” preparing snacks for the “boys” whose engineering abilities are much more valued than her dispensable “soft skills.” And still, as she rose through the industry, Wiener and her young colleagues increasingly found themselves grappling with moral quandaries far above their generous start-up pay grades. As surveillance became one of the era’s great moral tests, Wiener and her data-analytics colleagues were unquestioningly using an in-app service called “God mode,” which allowed them unfettered access to users’ private data. Later, as the world started to observe how ill-equipped tech platforms were to confront the rise of hate speech, Wiener wondered how to confront the increasingly loud rabble of Nazis and MRAs on the platform where she was then working as a reluctant content moderator (one of four for 9 million users). “It was perhaps a symptom of my myopia, my sense of security,” she writes. “I was hardly thinking about the world at all.”

And at first, she says, her life seemed to be moving in the direction she wanted it to go. “I’m making more money. I’m buying my Everlane sweaters and I have a little bump in equity and I’m hobnobbing with people at these company events that are like me, only more successful. You feel valued,” she she says now, over cans of flavored seltzer outside Salesforce Park’s on-site Starbucks. Yet over time, the world — and  the people behind that vast accumulation of data — began to come back into focus. “I started to wonder, What exactly is the project that I’m helping push forward in the world? Who would that be serving, and to what end, and do I actually believe in that?” she tells me.

In 2018, she quit her job and began writing full time. While she didn’t take notes of her years in start-up land, she has always been a compulsive email writer. Some of these were emails to herself, a scrapbook of standard 20-something neuroses: little notes berating herself to lose weight or stop being needy to her friends. But Wiener, who studied sociology at Wesleyan, is also a keen observer of human behavior, and she started noting down details about her colleagues that resonated with her. She showed me one email from 12:03 a.m. in 2016 — what she dubbed  “stoner-insight hour” — observing “how blake from sales would bring meat, [for his] paleo diet, in ziploc bags in the company fridge, cold and wet and lumpy.” Many of these details found their way into the book, in the form of anthropological dissections of Silicon Valley’s different subgroups (the men on the solutions team who wore Australian work boots and chewed powdered Swedish tobacco; the e-book founders who wore modestly buttoned shirts and were in relationships with high-functioning women). They also helped put her back in the mind-set she was in during that time.

The reader is unlikely to indict Wiener for her 20-something myopia — in part because many of us have been equally eager to drink Silicon Valley’s Kool-Aid, and in part because she has written such a thoughtful and self-reflective book. Whether or not she wants to be indicted is harder to parse. “I was ashamed of my own ignorance and, to a certain extent, complicity, though I don’t want to overstate my importance in any of this,” she reflects, as we leave the park to head to our next spot on the tour. “I’m not one of those tech executives who’s like, ‘I recant!’ — people who actually could have done something. But it was helpful to have those materials because they serve as a record of my own optimism, and my own disappointment.”

How do you be a good person in a world where goodness is, increasingly, little more than a corporate-branding exercise? It’s a question that animates much of the book, and one that Wiener still struggles to answer for herself. As we exit the park, we walk past Salesforce’s downstairs lobby, which has a vague national-park aesthetic to it — astroturf, fake trees. “I wonder if Salesforce is one of the companies that tried to do carbon-emission offsets,” she says aloud. She sticks her arm out and hails a taxi to take us into the Mission District. “I try not to take rideshares when I’m downtown,” she explains. Still, she’s wary of my billing her as an ethical consumer, perhaps because she is still trying to disentangle herself from an industry obsessed with hollow virtue-signaling. She describes recently purchasing a CSA of ‘ugly fruit,’ from a company that sends subscribers boxes of rejected produce, despite her fiancé Ian’s insistence that they bring less venture-backed products into their home. “Then, I was at a party and was speaking to a woman who used to work for one of the largest food banks in California, and she [said] that that company is buying extra food that used to be bought by food banks, which they can offer at a higher price mark. So I was like, Ugh, everything is rotten.”

Uncanny Valley is often acerbic and dark, but Wiener tries to see the good in people. At one point, she refers to herself as “the patron saint of mislaid sympathies.” She is always looking for the psychological explanation behind what makes people tick — “the emotional narrative, the personal history, the story on which to train sympathy.” She wonders if the CEOs of the e-book start-up are lonely; she wonders if the terrible CEO of the data company just wants to make his family proud, picturing him as a grown-up version of the nerdy strivers she went to high school with.

She is self-aware enough to be critical of this impulse, seeing it as an “ineffectual attempt to alleviate her own guilt” and avoid placing blame and accountability where they are due. Yet it’s an impulse she can’t quite get shed. “I’m still constantly making up excuses for people who don’t deserve it, don’t give a shit about me,” she confesses. A few minutes later, when we’ve changed the topic, she returns to the idea, still concerned about her moral flexibility. “Now I’m just like: Maybe the book is an expression of a bad personality.”

While the book is full of pointed details, Wiener reserves her disdain for those with real power. “A lot of [my former colleagues] are people who, had there been a more robust economy with better opportunities, would have done literally anything else,” she says. She sees Silicon Valley as participating in a ‘brain drain’ of young talent, while subtly working to undermine essential democratic institutions.“[I]f we had a better social safety net, I don’t think people would be so compelled to work in these industries that can give them such secure jobs.”

Of course, even with a strong social safety net, there are still plenty of people who would happily choose a million-dollar salary at the Social Network Everyone Hated over some more noble pursuit. And Wiener knows that she was lucky enough to have other options. “I feel like I finally found a way to engage with this city that feels right for me, which is writing about it.” In addition to her yearlong contract with The New Yorker, the book’s film rights were recently optioned by Universal.

I ask if she’s heard feedback from many people in the tech world, and she says she hasn’t, though she gave everybody she named in the book a chance to read and give notes. She’s worried that her former colleagues won’t like it. I tell her I don’t think that’s likely — rather, I worry that certain people might like it too much, that the big, bad culpable tech men will read it and end up identifying with her instead of their own avatars. She thinks about it for a minute, before offering up an anecdote from Elif Batuman’s The Idiot. In it, the central character describes watching the movie Dumbo in kindergarten, and being shocked that all the kids in class, even the bullies, rooted for Dumbo and not his tormentors.

Later, she looks up the exact quote from the book and emails it to me. Everyone thinks they’re Dumbo,” she writes. “We are all Dumbo.”

Seduced by Start-up Land