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Exploring The 'Uncanny Valley' Of Tech Startup Culture

Screen shot of "Uncanny Valley: A Memoir" by Anna Wiener. (Copyright © 2020 by Anna Wiener. Published by MCD, an imprint of Farrar, Straus and Giroux)
Screen shot of "Uncanny Valley: A Memoir" by Anna Wiener. (Copyright © 2020 by Anna Wiener. Published by MCD, an imprint of Farrar, Straus and Giroux)

A new memoir reveals an unsavory depiction of tech startup culture. We’ll examine the influence of Silicon Valley’s most powerful companies — and how the public’s view of Big Tech is changing.


Anna Wiener, contributing writer for The New Yorker, covering Silicon Valley, startup culture and technology. Her new book is “Uncanny Valley: A Memoir.” (@annawiener)

From The Reading List

Excerpt from “Uncanny Valley: A Memoir” by Anna Wiener 

“Depending on whom you ask, it was either the apex, the inflection point, or the beginning of the end for Silicon Valley’s startup scene—what cynics called a bubble, optimists called the future, and my future coworkers, high on the fumes of world-historical potential, breathlessly called the ecosystem. A social network everyone said they hated but no one could stop logging in to went public at a valuation of one-hundred-odd billion dollars, its grinning founder ringing the opening bell over video chat, a death knell for affordable rent in San Francisco. Two hundred million people signed on to a microblogging platform that helped them feel close to celebrities and other strangers they’d loathe in real life. Artificial intelligence and virtual reality were coming into vogue, again. Self-driving cars were considered inevitable. Everything was moving to mobile. Everything was up in the cloud. The cloud was an unmarked data center in the middle of Texas or Cork or Bavaria, but nobody cared. Everyone trusted it anyway.

“It was a year of new optimism: the optimism of no hurdles, no limits, no bad ideas. The optimism of capital, power, and opportunity. Wherever money changed hands, enterprising technologists and MBAs were bound to follow. The word “disruption” proliferated, and everything was ripe for or vulnerable to it: sheet music, tuxedo rentals, home cooking, home buying, wedding planning, banking, shaving, credit lines, dry cleaning, the rhythm method. A website that allowed people to rent out their unused driveways raised four million dollars from elite firms on Sand Hill Road. A website taking on the kennel market—a pet-sitting and dog-walking app that disrupted neighborhood twelve-year-olds—raised ten million. An app for coupon-clipping enabled an untold number of bored and curious urbanites to pay for services they never knew they needed, and for a while people were mainlining antiwrinkle toxins, taking trapeze lessons, and bleaching their assholes, just because they could do it at a discount.

“It was the dawn of the era of the unicorns: startups valued, by their investors, at over a billion dollars. A prominent venture capitalist had declared in the op-ed pages of an international business newspaper that software was eating the world, a claim that was subsequently cited in countless pitch decks and press releases and job listings as if it were proof of something—as if it were not just a clumsy and unpoetic metaphor, but evidence.

“Outside of Silicon Valley, there seemed to be an overall resistance to taking any of it too seriously. There was a prevailing sentiment that, just like the last bubble, this would eventually pass. Meanwhile, the industry expanded beyond the province of futurists and hardware enthusiasts, and settled into its new role as the scaffolding of everyday life.

“Not that I was aware of any of this—not that I was paying any attention at all. I didn’t even have apps on my phone. I had just turned twenty-five and was living on the edge of Brooklyn with a roommate I hardly knew, in an apartment filled with so much secondhand furniture it almost had a connection to history. I had a fragile but agreeable life: a job as an assistant at a small literary agency in Manhattan; a smattering of beloved friends on whom I exercised my social anxiety, primarily by avoiding them.

“But the corners seemed to be coming up. The wheels were coming off. I thought, every day, about applying to graduate school. My job was running its course. There was no room to grow, and after three years the voyeuristic thrill of answering someone else’s phone had worn thin. I no longer wanted to amuse myself with submissions from the slush pile, or continue filing author contracts and royalty statements in places where they did not belong, like my desk drawer. My freelance work, proofreading and copyediting manuscripts for a small press, was also waning in volume, because I had recently broken up with the editor who assigned it to me. The relationship had been fraught, but reliably consuming: the editor, several years my senior, had wanted to get married but wouldn’t stop cheating on me. These infidelities were revealed after he borrowed my laptop for a weekend and returned it without logging out of his accounts, where I 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.

“I was oblivious to Silicon Valley, and contentedly so. It’s not that I was a Luddite—I could point-and-click before I could read. I just never opened the business section. Like anyone else with a desk job, I spent the majority of my waking hours peering into a computer, typing and tabbing through the days, the web browser a current of digital digression running beneath my work. At home, I wasted time scrolling through the photos and errant musings of people I should have long since forgotten, and exchanged long, searching emails with friends, in which we swapped unaccredited professional and dating advice. I read the online archives of literary magazines that no longer existed, digitally window-shopped for clothing I could not afford, and created and abandoned private, aspirational blogs with names like A Meaningful Life, in the vain hope that they might push me closer to leading one. Still, it never occurred to me that I might someday become one of the people working behind the internet, because I had never considered that there were people behind the internet at all.”

Excerpted from Uncanny Valley: A Memoir by Anna Wiener. Copyright © 2020 by Anna Wiener. Published by MCD, an imprint of Farrar, Straus and Giroux. 

The New York Times: “‘Uncanny Valley’ Charts a Tech Pilgrim’s Progress” — “Even at the end of a decade marked by surveillance capitalism and Russian trolls — a period of time when techno-utopianism curdled into disillusion — Silicon Valley has shown itself more than capable of delivering on one of its core promises: a frictionless convenience, at least for those who can afford it.

“The journey from feeling to wanting to procuring used to take deliberation and time; now the experience has been squeezed into a seamless moment of scrolling and clicking, without any obligation to interact directly with another human being. Two decades ago, the novelist and former software engineer Ellen Ullman anticipated that the internet would bring about the ‘suburbanization of existence’ — a libertarian idyll or libertarian hellscape, depending on how you might fare in an increasingly private and privatized world.

“In her extraordinary new book, ‘Uncanny Valley,’ Anna Wiener recounts what made her, a 25-year-old woman with an ‘affectedly analog’ life in New York City, abandon her job at a literary agency in 2013 to work for tech start-ups, and what eventually — five years later — made her leave the industry. Money was certainly part of her original decision, but not all. At the literary agency, she was subject to the low pay and genteel exploitation of a shrinking industry; even more alluring than the offer of a better salary was tech’s ‘optimism and sense of possibility,’ how it ‘promised what so few industries or institutions could, at the time: a future.’”

San Francisco Chronicle: “Review: In ‘Uncanny Valley,’ Anna Wiener unpacks strange world of tech startups” — “Languishing in your mid-20s is excruciating. Eating lunch out of a Tupperware container at her desk at a successful literary agency in Manhattan, Anna Wiener, bogged down by a palpable sense of entropy, writes that ‘nobody my age was excited about what might come next.’

“She’s a 20-something living in Brooklyn around 2010, inhabiting a life she deems ‘affectedly analog,’ working in publishing — ‘where new ideas rarely emerged and were never rewarded’ — for less than $30,000 per year.

“’The situation was not sustainable,’ she writes. ‘I was not sustainable.’ Silicon Valley technology companies, by comparison, ‘promised what so few industries or institutions could, at the time: a future.’

“Operating against the backdrop of a sense of possibility entices her. She flirts with working at a startup, and eventually does. ‘I wanted my life to pick up momentum, go faster.’

Slate: “The Loop in the Kingdom of Vectors” — “In the early 2010s, Anna Wiener had an assistant’s job at a literary agency in New York. She dated the kind of artisanal Brooklyn men who ‘made chapbooks or live-edge wood furniture,’ and, she maintains, she didn’t even have apps on her phone. She was broke, working in an industry with notoriously low pay and sparse opportunities to move up. When she read about a new startup that had landed $3 million in funding to offer e-books on a subscription model, she decided she wanted in.

“Uncanny Valley, Wiener’s memoir of several years working in the tech industry—at first in New York, but soon in San Francisco—is a book that shares the in-betweenish quality its title describes. (The Uncanny Valley refers to the unsettling feeling provoked by representations of human beings that come close to resembling real people while remaining discernibly artificial.) Is it the story of a young woman figuring out what to do with her life, or is it grunt’s-eye view of an industry with immense economic power and social influence?

“Wiener worked for three companies in customer service positions, relatively low-status in a culture that prizes technological and engineering expertise above all. She had no interest in learning to code. When she tried, she had some aptitude but found herself ‘thinking about all the other things I would rather be doing, like reading a novel, or writing postcards to my friends, or exploring a new neighborhood on my bike.’”

This article was originally published on WBUR.org.

Copyright 2021 NPR. To see more, visit https://www.npr.org.

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