Uncanny Valley

by Anna Wiener

  They were, of course, not lonely. They were focused and content. All three were clean-shaven and had good skin. They wore shirts that were always crisp and modestly buttoned to the clavicle. They were in long-term relationships with high-functioning women, women with great hair with whom they exercised and shared meals at restaurants that required reservations. They lived in one-bedroom apartments in downtown Manhattan and had no apparent need for psychotherapy. They shared a vision and a game plan. They weren’t ashamed to talk about it, weren’t ashamed to be openly ambitious. Fresh off impressive positions and prestigious summer internships at large tech corporations in the Bay Area, they spoke about their work like industry veterans, lifelong company men. They were generous with their unsolicited business advice, as though they hadn’t just worked someplace for a year or two but built storied careers. They were aspirational. I wanted, so much, to be like—and liked by—them.

  Because the role had been created specifically for me, the job was a three-month trial run. The scope and responsibilities were nebulous to all of us: some curating of in-app titles, some copywriting, various secretarial tasks. As a full-time contractor, I would be paid twenty dollars an hour, again with no benefits. The money didn’t look like much up front, but I calculated the annual salary and was gratified to see that it would amount to forty thousand dollars.

  My friends in publishing were skeptical when I told them where I was going to work. They had a lot of questions I felt uneasy answering. Wouldn’t a subscription model undercut author royalties? Wasn’t it basically a cynical, capitalist appropriation of the public library system? Wasn’t an app like this parasitic at best? Was it all that different from the online superstore, and wouldn’t the app’s success come at the expense of the literary culture and community? I didn’t have a good response to most of these concerns. Mostly, I tried not to think about them. Smug and self-congratulatory, I translated most of my friends’ questions to mean, simply, What about us?

  * * *

  The startup’s office was a block from Canal Street, in a neighborhood the CEO called Nolita, the CTO called Little Italy, and the CPO called Chinatown. The surrounding area was tourist-addled even on weekdays, brimming with adults popping overstuffed cannoli and shooting tiny paper cups of espresso while their children eyeballed storefront displays of dusty parmesan wheels. The office was not so much an office as a spare table in the loftlike headquarters of a more established startup, one that enabled people to buy and sell art on the internet, at auction—a business model I did not fully understand, as the fun of auctions, I had always imagined, was the performative, feverish display of wealth and one-upmanship. I did not realize at the time that for people in the tech industry, such expressions of wealth were not just gauche but antiquated. There was nothing more civilized than hiding your money behind a browser.

  The loft had creaky wood floors and a long kitchen counter running along one wall, which bore an assembly of pour-over vessels and sacks of small-batch coffee beans from local roasters. The bathrooms had showers. On my start date, I arrived at the table to find a welcome gift: a stack of hardcover books about technology, inscribed by the founders and stamped with a wax seal of the company logo: an oyster, unavoidably yonic, with a perfect pearl.

  The e-book startup had millions in funding and job titles that suggested a robust and organized workforce, but the app itself was still in private alpha, used only by a handful of friends, family, and investors. There was only one other employee, a mobile engineer named Cam, whom the founders had been excited to hire away from a photo-editing app. The five of us sat around our mahogany table at the back of the loft, drinking coffee, as if in a perpetual board meeting.

  For the first time in my career, I had some expertise. The men asked for my opinions—on the app’s reading experience, on the quality of the inventory, on how best to ingratiate ourselves with online reading communities—and listened for the answers. Despite misunderstanding the technical infrastructure and having little insight into strategy, I felt useful. It was thrilling to watch the moving parts of a business come together; to feel that I could contribute.

  * * *

  To celebrate the CTO’s birthday, we traveled to Midtown to see a movie about counterterrorism specialists. The movie opened with an audio montage of telephone calls made by people trapped in the World Trade Center on September 11. I did not want to continue watching, but more than that I did not know how to exit gracefully without having to explain that I had seen all of it happen at age fourteen, from the window of my high school Spanish classroom, four blocks away from the towers.

  I considered faking something biological: gastroenteritis, menstruation. I considered the Irish goodbye. I resented that I had not done my research on the film, resented that I could not be a normal person with normal experiences doing a normal thing, like enjoying an action movie with my colleagues, without getting mired in unresolved PTSD. I fidgeted so badly that I lost an earring in the theater, and when the lights came up after the credits, the CTO got down on his knees to search for it, beckoning the others to join. I was embarrassed to see them scrambling across the floor, and moved that they would run their palms over the sticky synthetic carpet for me. After waiting for a few seconds, I exclaimed that I had found it, and the boys stood up to button their jackets and heave on their backpacks; nobody noticed when I removed the remaining earring and shoved it into the lint of my pocket.

  We moved into the late winter light, and walked to a Japanese dessert bar around the corner. I had never been to a dessert bar, let alone a Japanese one. The boys were delighted by the variety. They reminded one another that this was on the company card, and overordered. Sitting with the four of them, watching as they dipped their spoons into each other’s desserts, resisting as they pushed their plates toward me to make sure I tasted everything, I tried to imagine what the other patrons thought about our group. I felt like a babysitter, a fifth wheel, a chaperone, a little sister, a ball and chain, a concubine. I felt indescribably lucky. At the end of the night, I walked downtown alone to the farthest possible subway station, savoring.

  * * *

  I befriended Cam, the other employee who was not a founder. During our lunch breaks we would venture forth into the neighborhood and return with sandwiches or leaky plastic containers of Vietnamese takeout, which we would eat in the conference room while he patiently answered my questions about the difference between front-end development and back-end programming. On occasion, we would talk about the burdens and responsibilities of being employees one and two of a startup that, despite not yet having a public product, was already considered hot. “I think this is a really good time for us to join the company,” he would reassure me. “I think we’re very well positioned.” He either did not know that I was a contractor, or was optimistic that I would be hired as a proper employee after the trial period.

  Cam had a gentle, low-key nature. He loved his girlfriend, and her cat, and I loved hearing him talk about them. The only time I ever saw him get worked up was when I organized a company book club and none of the cofounders followed through. They were too busy building the app, they said. Who had time for book clubs? I understood this and did not particularly mind, but Cam chastened them in the company chat room and then took me out for soup. He insisted that they were rude and in the wrong; he insisted that I was working incredibly hard to build the company culture.

  This was only partially true. After the first few weeks, during which I wrote website copy, tried to help recruit engineers from a short list of top universities, and edited the user privacy agreement to make it sound more like a friend than a lawyer, it seemed that mostly the founders were overpaying me to look for a more permanent office space and order them snacks: single-serving bags of cheese crackers, tiny chocolate bars, cups of blueberry yogurt.

  The concept of eating a snack at work was new to me. At the literary agency, eating at work during non-lunch hours was a source of not-insignificant shame, and gnawing at a bagel or
crunching through a bag of bodega pretzels was, I thought, regarded as sloppy and unprofessional. In previous jobs, my inability to keep my homemade lunch untouched until lunchtime was an expression of my lack of self-control, the reason I still had baby fat at an age when the fat might have been postpartum, but instead was just me; I was the baby. The boys, by contrast, snacked throughout the day. They ate chips at their computers and dusted their hands off on paper towels, swished seltzer water and crumpled the cans beside their keyboards. I meticulously noted their preferences and tried to keep things interesting: a box of clementines one week, bags of cheddar popcorn the next.

  With Cam in mind, I took it upon myself to bolster the company culture. I persisted with the book club, and the founders continued to snub it. I organized team outings, including one to a gilded private library that had belonged to a famed financier, a goliath of nineteenth-century banking. We wandered the building, admiring the imposing floor-to-ceiling bookcases, the twisting staircases and gold-painted ceiling, taking photographs and posting them to social media. This was how the app should feel, we all agreed: luxurious, but not intimidating; infinite.

  The private library was a hit, but the truth was that three men in their early twenties with millions in the bank did not need me to take them on reading-themed field trips. It would be more cost-effective for them to order their own snacks. Despite Cam’s encouragement, they also did not need me to build the company culture. They did not really need me for anything. The culture, insofar as our tiny company had one, revolved around the founders. While they sometimes bickered, I never saw anyone leave the conference room angry. They seemed to be happiest unwinding on the overstuffed couch, playing video games together and drinking domestic beers. They did not need to team-build or bond, and mostly that wasn’t what we were doing. We were building a company—or they were, and I was watching.

  * * *

  When we did find a new office space, on a prime block in the west twenties—a part of the city some referred to, in an act of taxonomic hubris, as Silicon Alley—it also belonged to another startup, but this time the circumstances were different. The lease-holding startup was working on something in the media space, and its headcount had grown and shrunk as if the company were weight-cycling. At a team meeting, our CEO gravely noted that the media startup had already pivoted multiple times over. I asked what he meant by this, and all four men looked at me suspiciously. Pivoting meant that they had changed their business model in an effort to generate revenue. Pivoting meant they were worried about runway. Pivoting meant they were a cautionary tale. Only the two cofounders were left, tucked off to the side. Everyone else had been let go once funding ran out.

  The specter of these laid-off employees lingered, a reminder to work harder. Most of our days were spent heads-down at our desks, furiously instant-messaging each other from across the underfurnished office. We took synchronized lunches and talked about strategy. We returned to our computers and assiduously avoided eye contact. We held long and impassioned meetings about partnerships and design, and ordered in pizza when these meetings crossed into night. Everything felt urgent, high stakes.

  One afternoon, the CEO summoned us into a conference room to demo the pitch deck he was making for meetings with publishers. He opened by stating that ours was the era of the sharing economy. Millennials, he said, as if he were not one of them, weren’t into ownership, but experiences. This was not just a new market strategy, but a cultural ideology. Pioneering digital platforms in the sharing and subscription economies enabled people to stream films and albums and video games, rent cocktail dresses and three-piece suits, reserve bedrooms in strangers’ houses, and ride shotgun in strangers’ cars. Music, movies, television, retail, and transportation had been disrupted. The time had come for books. The CEO flipped to a slide that displayed the logos of various successful subscription platforms, with our logo at the center.

  Technology products were lifestyle products, the CEO said. As he continued his pitch, it became clear to me that the utility of the e-reading app was not so much about reading as it was about signaling that you were the type of person who would read, and who would use an app with a cutting-edge reading experience and innovative, intuitive design. The ideal user of the app, I deduced, was a person who thought of themselves as a reader, but wasn’t, not really: licensing cost money, and anyone reading more than a few books a month could generate a licensing expense exceeding the subscription fee. Books were an opportunity, I understood, but not the endgame. It was just one type of content, and only the first step. Expansion: that was the endgame. Probably. I trusted them to figure it out.

  The CEO did not acknowledge that the reason millennials might be interested in experiences—like the experience of renting things they could never own—was related to student loan debt, or the recession, or the plummeting market value of cultural products in an age of digital distribution. There were no crises in this vision of the future. There were only opportunities.

  I tried to determine whether I could believe in this. The CEO was charming, and committed to the company and its vision. Perhaps he and the other two founders were also brilliant. Their investors in Silicon Valley must have thought so. But they seemed to be least interested in the part of the business I cared about most—the books. “Hemingway” had been misspelled in the CEO’s pitch deck: two m’s.

  More relevantly, the model—starting with books, and taking it from there—seemed to hew all too closely to that of the online superstore. I began to wonder why it was, exactly, that they had hired me. I had been operating under the vain premise that it was because I knew something about books: I could be a bridge between the old and new guards. I had fancied myself a translator; I had fancied myself essential. Later, once I better understood the industry-wide interest in promoting women in tech—if not up the ranks, then at least in corporate marketing materials—I would allow myself to consider that perhaps I was more important to the aesthetic than critical to the business.

  * * *

  What I also did not understand at the time was that the founders had all hoped I would make my own job, without deliberate instruction. The mark of a hustler, a true entrepreneurial spirit, was creating the job that you wanted and making it look indispensable, even if it was institutionally unnecessary. This was an existential strategy for the tech industry itself, and it did not come naturally to me. My imagination was still tailored to the parameters of publishing: I suggested that the e-book startup host a reading series, as a form of outreach to the literary community. Perhaps we should have a book blog, I mused. Instead, the startup sent third-wave-coffee trucks to distribute free espresso drinks and pastries at industry conferences, where exciting swag historically meant a cotton tote bag or an advance reader’s copy of a debut work of literary fiction. I had trouble strategizing at scale.

  “She’s too interested in learning, not doing,” the CEO typed once into the company chat room. This was an accident—he meant it only for the other two cofounders. We huddled in the conference room and he apologized sincerely, while I looped the words over and over in my head. I had always been interested in learning, and I had always been rewarded for it; learning was what I did best. I wasn’t used to having the sort of professional license and latitude that the founders were given. I lacked their confidence, their entitlement. I did not know about startup maxims to experiment and “own” things. I had never heard the common tech incantation Ask forgiveness, not permission.

  In an effort to self-educate, I read blog posts about the startup mentality and did my best to imitate it. The CEO had published one a year earlier titled “How to Make an Impact During the First Month of Your Startup Job,” and I resented myself for missing the writing on the wall. Take ownership, he had advised in the post. Be optimistic. Write down your opinions.

  In the end, I resorted to writing long, embarrassing, and unsolicited emails to the founders, declaring my passion for reading. An e-reading app needed a passionate reader on staff, I was s
ure of it—maybe I didn’t know how to be a good startup employee, at least not yet, but surely they would benefit from having me, a focus group of one, on the team anyway. After several long and heartfelt emails and another painful one-on-one huddle in the conference room, it was clear that there was no way I could stay. This was not the right moment in the company’s journey, they said, for someone like me to get up to speed. The areas where I could add value would not be active for some time.

  The cofounders all wanted to help me find a new job. They assumed I wanted to continue working in tech, and I didn’t disabuse them of this. I was reluctant to return to publishing. I had tried to strike out on my own and had failed. Besides, I had been traitorous, joining a startup trying to rock the book world, and did not want to face the possibility that I might now be unwelcome.

  I had also been spoiled by the speed and open-mindedness of the tech industry, the optimism and sense of possibility. In publishing, no one I knew was ever celebrating a promotion. Nobody my age was excited about what might come next. Tech, by comparison, promised what so few industries or institutions could, at the time: a future.

  Most of the founders’ professional network—the other startups in their venture capitalists’ portfolios—lived in the Bay Area. The CPO spoke wistfully of California. “I maintain that San Francisco is the best place to be a young person,” he told me. “You should really try to get out there before too long.” I wanted to tell him that I thought I was still young: I was only twenty-five. Instead, I told him I would try.