Uncanny Valley

by Anna Wiener

  Besides, early employees were trusted like family. It was assumed we would only look at our customers’ data sets out of necessity, and only when requested by customers themselves; that we would not, under any circumstances, look up individual profiles of our lovers and family members and coworkers in the data sets belonging to dating apps and shopping services and fitness trackers and travel sites. We would not, out of sociological curiosity, surf through data sets of neighborhood-watch platforms and online programs for Christian men trying to kick their masturbation habits. We would not pry.

  It was assumed that we wouldn’t check back on past employers to see how they were faring without us. It was assumed we would never discuss the glaring inconsistencies between the public narratives spun around our startup customers and the stories that their data told: if we were to read breathless, frothy tech-blog coverage about companies we suspected were failing, we would only smile and close the tab. It was assumed that if we had a publicly traded company using our software—and, if so moved, could chart the overall health of that public company based on its data set, or build out predictive models of when its overall value might grow or recede—we would resist buying or selling its stock.

  Our tiny company of twentysomethings operated on good faith. If good faith failed, there was a thorough audit log of all employee behavior: the founders had implemented a product on our own back end, which tracked the customer data sets we looked at and the specific reports we ran. But nobody ever used the words “insider trading.” Nobody had a press contact. There was no policy on leaks. Not that we needed one—we were all, as the CEO liked to remind us, Down for the Cause.

  San Francisco was an underdog city struggling to absorb an influx of aspiring alphas. It had long been a haven for hippies and queers, artists and activists, Burners and leather daddies, the disenfranchised and the weird. It also had a historically corrupt government, and a housing market built atop racist urban-renewal policies—real estate values had benefited as much from redlining as from discriminatory zoning practices and midcentury internment camps—but these narratives, along with the reality that an entire generation had been prematurely lost to AIDS, undercut its reputation as a mecca for the free and freakish, people on the fringe. The city, trapped in nostalgia for its own mythology, stuck in a hallucination of a halcyon past, had not quite caught up to the newfound momentum of tech’s dark triad: capital, power, and a bland, overcorrected, heterosexual masculinity.

  It was a strange place for young and moneyed futurists. In the absence of vibrant cultural institutions, the pleasure center of the industry might have just been exercise: people courted the sublime on trail runs and day hikes, glamped in Marin and rented chalets in Tahoe. They 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. They looked in costume to LARP their weekend selves.

  The culture these inhabitants sought and fostered was lifestyle. They engaged with their new home by rating it. Crowdsourced reviewing apps provided opportunities to assign anything a grade: dim sum, playgrounds, hiking trails. Founders went out to eat and confirmed that the food tasted exactly how other reviewers promised it would; they posted redundant photographs of plated appetizers and meticulous restaurant-scapes. They pursued authenticity without realizing that the most authentic thing about the city was, at this moment in time, them.

  The city’s passive-aggressive, progressive, permissive politics tended to rankle transplants, but tech’s self-appointed representatives weren’t for everyone, either. Every three months a different engineer or aspiring entrepreneur, new to the city, would post a screed on a blogging platform with no revenue model. He would excoriate the poor for clinging to rent control and driving up condo prices, or excoriate the tent cities by the freeway for being an eyesore. He would suggest monetizing homeless people by turning them into Wi-Fi hotspots. He would lambaste the weak local sports teams, the abundance of bicyclists, the fog. Like a woman who is constantly PMSing, a twenty-three-year-old founder of a crowdfunding platform wrote about the climate. The extension of casual misogyny to weather was creative, but the digital ambassadors didn’t seem to like actual women, either: they whined that the women in San Francisco were fives, not tens, and whined that there weren’t enough of them.

  Like most of the larger, older, serious hardware corporations, the major internet upstarts had hunkered down on the suburban Peninsula, thirty miles south. Their campuses offered candy stores and rock-climbing gyms, bike-repair shops and doctors’ offices, gourmet cafeterias and hair salons, nutritionists and day cares. They offered no reason to ever leave. The campuses were accessible by public transportation, but public transportation did not offer Wi-Fi. Every weekday, private shuttles looped through the city’s residential neighborhoods, pausing at public bus stops to pick up commuters.

  The commuters wore corporate identification badges clipped to their belt loops or draped on top of their jackets, like children trying not to get lost in a mall. They stood in line for the shuttles with their backpacks and reusable coffee cups; some slung bags of dirty laundry over their shoulders. They looked tired, resigned, sheepish. Mostly, they looked at their phones.

  Transplanted startup workers bemoaned the transit infrastructure, an old system riddled with inefficiencies that shut down almost entirely at midnight—not that anyone making a midlevel tech salary was taking the bus. A glut of transportation apps had sprung up to replace San Francisco’s poky streetcars and unreliable taxi fleet. The largest was an on-demand ride-sharing startup, a company committed to domination at all costs, including profitability.

  The ride-sharing startup’s main competitor had a near-identical business model but much cuter branding. The cute competitor required its drivers—contract laborers commandeering their own personal vehicles—to hook large fuchsia mustaches, made of synthetic fur, to their grilles and greet passengers with a fist bump. Improbably, this worked. The company knew its audience: San Franciscans, living in neighborhoods where every other storefront had a pun in its name, were corny.

  I abandoned my expectations for how cities should be. Bars and cafés opened late and closed early; traffic seemed to slide backward, downhill. The city dealt in improbable couplings. A pay-as-you-wish yoga studio shared a creaky walk-up with the headquarters of an encrypted-communications platform. A bodega selling loosies sat below an anarchistic hacker space. The older office buildings, regal and unkempt with marble floors and peeling paint, housed orthodontists and rare-book dealers alongside four-person companies trying to gamify human resources or commoditize meditation. Data scientists smoked weed in Dolores Park with Hula-Hoopers and blissed-out suburban teenagers. The independent movie theaters played ads for networked appliances and B2B software before projecting seventies cult classics. Even racks at the dry cleaner suggested a city in transition: starched police uniforms and synthetic neon furs, sheathed in plastic, hung beside custom-made suits and machine-washable pullovers.

  Homeless encampments sprouted in the shadows of luxury developments. People slept and shat and shot up in the train stations, lying beneath advertisements for fast fashion and productivity apps, as waves of commuters stepped delicately around them. I woke up one morning to the sound of someone howling for mercy on the corner of my block: a woman screaming bloody murder, dragging one leg, wearing nothing but a torn T-shirt emblazoned with the logo for a multinational consumer-electronics company.

  This concentration of public pain was new to me, unsettling. I had never seen such a shameful juxtaposition of blatant suffering and affluent idealism. It was a well-publicized disparity, but one I had underestimated. As a New Yorker, I had thought I was prepared. I thought I’d seen it all. I felt humbled and naïve—and guilty, all the time.

  * * *

  I moved into an apartment in the Castro, joining
a man and a woman in their late twenties, roommates who had wiggled their way onto a hand-me-down lease. They were tech workers, too. The woman worked as a midlevel product manager at the social network everyone hated; the man as a data scientist at a struggling solar-energy startup. They were both endurance runners; the data scientist kept a road bike in his bedroom. They had no body fat. They had no art in the apartment, either. On the refrigerator was an impressive collection of novelty magnets arranged in a perfect grid.

  The apartment was gigantic, a duplex with two living rooms and a view of the bay. Both roommates claimed they wanted to live independently but couldn’t abandon the rent control. With a combined household income that easily topped four hundred thousand dollars—not including the product manager’s stock—we were not people for whom rent control was intended, but there we were. When I signed a sublease in exchange for the keys, my new roommates congratulated me on my good luck.

  I got along better with the product manager, though we occupied different spaces: I was in the startup world, land of perpetual youth, and she was an adult like any other, navigating a corporation, acting the part, negotiating for her place. She was classically trained in violin and collected leather-bound antique books, like a Chekhov character. I felt uncultured by comparison, with my colorful contemporary paperbacks and penchant for overwrought indie rock. She seemed to find me amusing, maybe a little pitiable. I admired and did not understand her. Mostly, we talked about exercise.

  The bedroom I sublet had an air mattress and a fire escape. One by one, I moved my boxes out of the startup’s supply closet. I stacked the books on the floor, unrolled a camping blanket onto the bed, hung my blouses and wrap dresses in the closet. My clothes looked like they belonged to someone else, probably because they did. After a few weeks, I folded them back up and sent them to a publishing friend in New York, who still dressed up for the other women in her office.

  The fire escape offered a private passage to the roof, and from time to time I would climb up to take stock. I would gaze out over the pastel Victorians, the rustling magnolia trees, the fog rushing over the hills, the container ships skimming the bay. Every so often, I felt a wave of affection for San Francisco, a thrill like hope—a sense, however small, that it could eventually become home.

  * * *

  When the product manager turned thirty, she hosted a wine and cheese party at our apartment. The data scientist and I were invited. I marked it on my calendar, as if I would forget.

  The product manager’s friends arrived promptly, in cocktail attire. She was intimidating in black silk. Hundreds of dollars’ worth of cheese had been procured, and classical music streamed through the house. A man opened a bottle of champagne, which he reassured us was from France. People clapped when the cork popped.

  Feeling like a child at my parents’ party, I sent myself to my room, locked the door, and changed out of work clothes—baggy sweater, high-waisted jeans—and into a very tight dress. I had gained five, eight, ten pounds in trail mix. When I reentered the living room, I sucked in my stomach and slid between people’s backs, looking for a conversation. On the couch, two men in suit jackets expounded on opportunities in cannabis. Everyone seemed very comfortable and nobody talked to me. They tilted their wineglasses at the correct angle; they dusted crumbs off their palms with grace. The word I heard the most was “revenue.” Maybe “strategy.”

  This was the nascent neomillionaire class, I realized. They weren’t all rich, not yet, but they were right on track. My coworkers were also aspiring, but they had a different style. Not one of them would be caught dead wearing a tailored suit to a house party.

  I wound up on the roof with a cluster of men. In the distance was the tip of the famous rainbow flag on Castro Street, whipping. I felt a twist of homesickness, the jolt of being three thousand miles away from my mother.

  “We’re looking to buy in Oakland,” one of the men was saying.

  “Too dangerous,” said another. “My wife would never go for it.”

  “Of course not,” replied the first, absently swirling his wine. “But you don’t buy to live there.”

  By the time the last guest filtered out, I was already in leggings and a sweatshirt, half-drunk and cleaning: scooping up cheese rinds, rinsing plastic glasses, sneaking slices of chocolate cake with damp hands. The product manager came to say good night, and she was beautiful: tipsy but not toasted, radiant with absorbed goodwill. She repaired to her room with her boyfriend. From down the hall, I could hear them as they quietly undressed, eased into bed, and turned over into sleep.

  * * *

  Most nights, I worked late. The neighborhood around the office emptied out after dark. An off-price department store glowed on the corner. Men in shredded pants shuffled in front of the train station, shouting down nobody.

  I downloaded the ride-sharing apps that everyone had said I would want, but which I had resisted. I found the premise creepy: I had never wanted to get into strangers’ cars, hated hitchhiking, had been told my entire life never to do so. Being chauffeured by other adults in their own vehicles didn’t seem luxurious to me, it looked like carpooling. Carpooling, however, was meant to be a social good with an environmental benefit. It seemed cynical and backward to pay a private company to brute-force carpooling by putting more cars on the road.

  But the buses had delays and broke down; the light rail back to the Castro came every forty minutes. A car, by contrast, was a tunnel to home. I found myself ducking into strangers’ sedans on a nightly basis, meekly extending my fist for a tap, chattering on mindlessly from the back seat. Clutching my keys, crossing my fingers.

  As part of the onboarding process, the operations manager set me up on lunch dates with coworkers from across the company. I went out with an account manager whose desk faced mine in the cluster. He often air-golfed, perfecting his swing, while on the phone with customers. He called the Mission “the Mish,” but I liked him a lot. He was easy to talk to; he was easy to talk to for a living.

  The account manager and I procured large, sloppy sandwiches and sat down in a plaza between two hotels. We gazed out at the underdressed tourists. I asked how he had chosen to work at the analytics startup—he’d studied history, after all. It wasn’t a major I associated with upselling. “Come on,” he said. “I heard there were a bunch of twentysomethings crushing it in the Valley. How often does that happen?”

  Relatively often, I had assumed. The plaza was full of people who looked just like us: white and young and exhausted, coasting on caffeine and simple carbohydrates. The previous year, a thirteen-person startup, the maker of a photo-sharing app, had been acquired for a billion dollars by the social network everyone hated. Their office was three blocks away. “This is a get-rich-quick scheme,” the account manager said. “We built a tool that’s, what, five, ten years in the future? Nobody has ever seen something like this before. The product practically sells itself.”

  I had not fully grasped how rare the analytics startup was. Ninety-five percent of startups tanked. We weren’t just beating the odds; we were soaring past them. This was what everyone who trekked out to the Bay Area wanted, but it was not actually supposed to happen. The CEO of the e-book startup had been right: the analytics startup was a rocket ship. Despite its size and age, the company was already well regarded and legitimate, marked to become a unicorn. We were hurtling toward a billion-dollar valuation. Our revenue soared every month. We were winning, and we would be rich.

  “This company is going to be worth a gajillion dollars,” the account manager said, taking a bite of potato salad. “We’re ripping up and to the right. We have the best and the brightest. We’re on an immutable path toward success. We’re all just fucking ready to give whatever needs to be given to make this thing happen. All anyone is asking is for us to pour our hearts and souls into this unstoppable behemoth.” He drained his iced coffee. “Frankly,” he said, “I think it’s a pretty good bargain.”

  * * *

  I went on anothe
r arranged lunch, with the CTO. We had never spoken; I didn’t know what to expect. According to my teammates, the CTO was brilliant and difficult. An autodidact, he hadn’t graduated high school, but he could single-handedly design the sort of complex database infrastructure that, elsewhere, would have taken a team of experienced computer scientists. I didn’t know whether this was hyperbolic, but it didn’t matter: he was the only employee to whom the founders deferred. This wasn’t just programmer supremacy, despite its popularity. He was the only one who really understood the core technology. The company wouldn’t exist without him.

  The CTO was in his early thirties, with untended facial stubble and beautiful, wide-set eyes. He often smelled like menthols. While the other engineers had condos in the Marina or renovated Victorian apartments lining Dolores Park, he lived in the Tenderloin, a high-crime neighborhood with a concentration of SROs and open-air drug markets—on purpose, Noah had once said, eyebrows raised in admiration. The CTO shuffled into the office every afternoon with headphones on, holding a paper cup of coffee and avoiding eye contact. He almost always wore a T-shirt with the company logo on it and an unbranded navy-blue hoodie.

  We ordered salads at a faux-French café in the financial district and sat at a rickety table outside, watching the midday stream of men with briefcases and women in shift dresses. They looked so much older than we did, in their inoffensive textiles and fake alligator loafers. They looked straight out of another era, like the nineties. I wondered how we looked to them: two round-cheeked slobs in T-shirts and sneakers, eating slices of grilled chicken like teenage miscreants with a stolen credit card. I nudged my backpack under the table, out of view.

  My coworkers had warned me that the CTO was inscrutable and reticent, but after a few minutes I wondered how hard any of them had tried. I was surprised to find that he had a dark, sarcastic sense of humor. We had more in common than I would have guessed: compulsive reading habits; insomnia. While I usually spent sleepless nights staring at the ceiling and worrying about my loved ones’ mortality, he worked on programming side projects. Sometimes he just passed the time between midnight and noon playing a long-haul trucking simulator. It was calming, he said. There was a digital CB radio through which he could communicate with other players. I pictured him whispering into it in the dark.