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15 January 2020

Anna Wiener’s Uncanny Valley: an insightful memoir of San Francisco startup culture

Wiener is a keen social observer and scene-setter, especially attuned to the hypocrisies of the hubristic young men of Silicon Valley.

By Alice Robb

When Anna Wiener was in her early twenties, her life resembled that of any number of young New Yorkers with liberal arts degrees and writerly aspirations. She answered phones at a literary agency and freelanced as a copy editor, went to parties in Bushwick and dated men who made chapbooks or furniture. After a few years – increasingly frustrated by the rigid hierarchies of publishing, and unable to see a way out of the “assistant class” – Wiener quit the agency and took a temporary job at a start-up selling e-book subscriptions.

It was 2013, and, even in a lowly administrative role, she found the tech world to be everything that publishing was not: fast-paced, optimistic, flush with money and opportunity. After a short stint there, Wiener – “a sociology major with a background in literary fiction and three months of experience in snack procurement” – was thrilled to be hired in a customer support role at an analytics start-up in San Francisco.

She headed west and, over the next several years, immersed herself in the culture of Silicon Valley, riding a skateboard around the office, attending extravagant “off-sites” at swanky restaurants and ski resorts, and acquiring a boyfriend who worked in robotics. She enjoyed the perks of earning three times what she had in New York and the rush of being at the centre of something new. “It was thrilling to watch the moving parts of a business come together; to feel that I could contribute,” she writes. But she was also disturbed by her colleagues’ nonchalance about the potentially nefarious uses of the surveillance software they sold, and the self-important culture that prized blind loyalty above all. “We are at war,” the CEO would say. “Are you Down For The Cause?” The conference room was decorated with sculptural metal letters: DFTC.

In the overwhelmingly male world of tech, casual sexism was “everywhere,” Wiener writes, “Like wallpaper, like air.” (Only 18 per cent of executives at the top US tech companies are women; men own 91 per cent of equity shares in Silicon Valley.) Wiener’s co-workers commented on her weight, lips, and sex life, and the “sensual” nature of Jewish women. One kept a list ranking his female colleagues by their looks. Another regularly asked her to slap him across the face. In 2016, Wiener wrote a critique of the tech industry for the literary journal n+1, which went viral and netted her a book deal. (Wiener no longer works in tech, but covers it for the New Yorker.)

Wiener is a keen social observer and scene-setter. She has an eye for telling details about people and places, and is especially attuned to the hypocrisies of hubristic young men. Her bosses at the e-books start-up say they are too busy to join a book club, and spell Hemingway with two “m’s”. Tech bros in San Francisco “dressed for work as if embarking on an alpine expedition: high-performance down jackets and foul-weather shells, backpacks with decorative carabiners. They looked ready to gather kindling and build a lean-to, not make sales calls and open pull-requests from climate-controlled open-plan offices.” Dating apps in the valley were “flooded with milquetoast strivers who earnestly listed business-management guides among their favourite books and arrived at dinner wearing backpacks stamped with the names of their employers”.

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She elegantly captures the vertigo of spending most of her waking hours online, of how she “careened across the internet like a drunk”: toggling between pictures of acai bowls, interviews with writers, and videos of strangers’ marriage proposals; sending emails and chatting with confused customers until “I felt like a piece of software myself”.

Wiener is also a witty and stylish writer. Women in tech meet-ups at a corporate wine bar “bore the metallic taste of duty”. The internet is a “collective howl, an outlet for everyone to prove that they mattered”. A young man interviewing her for a job was “confidently unprepared”. (Instead of asking questions, he gave her a law-school entrance exam and went back to work.)

She can distil an interaction or even a whole culture into a quotable line or two. On the defeatism of publishing: “no one I knew was ever celebrating a promotion. Nobody my age was excited about what might come next.” On an awkward friend-date: “We finished our drinks, and with a seamless, unspoken intimacy, both declined the waiter’s offer of a second.”

But these observations sometimes substitute for deeper analysis; Wiener drops tantalising morsels and immediately moves on. Among countercultural types in the Bay Area, “Some of the women instituted systems of gender reparations with their male partners.” I could read several pages about what this means and how it works, but unfortunately, that is all we get. Elsewhere, she mentions a colleague who identified as a Japanese raccoon dog, wore a tail to work, and was known by his online handle, “a cute nickname that invoked a bear cub” – and leaves it at that.

As a memoirist, Wiener maintains a cool distance from the reader. Her account of discovering a boyfriend’s affair – surely a traumatic, or at the very least emotional, event – is curiously dispassionate. He forgot to log out of Facebook on her computer, she writes, and she “read a series of romantic and brooding private messages he exchanged with a voluptuous folk singer via the social network everyone hated. That year, I hated it extra.”

Wiener never names the tech companies she works for or the apps she uses, instead giving them creative epithets: Airbnb is “the millennial-friendly platform for renting strangers’ bedrooms”; Google is “the search-engine giant down in Mountain View”; LinkedIn (I think) is “a website where people voluntarily posted their own résumés”. At first, I found this decision provocative and funny; by the 300th page – and the 13th repetition of “the social network everyone hated” – it was tiresome and occasionally confusing. (Maybe everyone in San Francisco knows the location of Google’s headquarters, but I had to look it up.)

Wiener has obvious – and justifiable –scorn for the Californian obsession with “lifestyle.” But she devotes so much space to cataloguing what people wear and eat, and even – if she doesn’t know them well – what she imagines they might wear or eat, that I wondered if it had rubbed off on her anyway. She recalls the silk blouses, heeled boots and wrap dresses favoured in the publishing industry; the logoed hoodies, T-shirts and articulated-toe sneakers popular in Silicon Valley. She notes the superiority of office snacks in start-up kitchens, and the Wagyu beef and black sea bass at a company dinner.

When she meets a gentle 26-year-old with a penchant for psychoanalytic language, she pictures him making a stir-fry with the vegan meat substitute seitan. What are we supposed to infer about his character? I still don’t know. Plenty of New York writers eat seitan, too. I sometimes felt like I was reading a series of well-written in-jokes I didn’t quite get. “I began wearing flannel,” she writes, in a passage on her transformation into a tech worker. Does flannel somehow signify a change in her belief system? A concession to chilly weather?

I didn’t want to be learning, two-thirds of the way through the book, that she meets many people with similar-looking eyeglasses. I didn’t want to still be guessing, on page 280, what the “highly litigious Seattle-based conglomerate” is. It’s pleasant, for a while, to coast along on the charm of Wiener’s prose – but by the end, her charm had begun to cloy. 

Alice Robb is the author of “Why We Dream” (Picador)

Uncanny Valley: A Memoir
Anna Wiener
Fourth Estate, 304pp, £16.99

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This article appears in the 15 Jan 2020 issue of the New Statesman, Why the left keeps losing