Uncanny Valley

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 sure 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.

Everyone I knew in San Francisco had already left. Our college class had graduated straight into a recession, and while most of us trudged to New York or Boston to compete for unpaid internships and other scraps of a ravaged economy, those who moved west refused to bend to despair. They chose instead to hide out for a while, work on their art. They lived in sun-flooded apartments, took part-time service jobs, and had complicated, consuming social lives. They freely experimented with hallucinogens and polyamory; smoked weed and slept in and day-drank; went to BDSM parties and wolfed burritos afterward. They started bands and did occasional sex work. They spent weekends in the mountains or the woods or on the beach, camping and hiking and participating in other wholesome activities that we made fun of back in New York.

This utopia was short-lived. It was being replaced by a late-capitalist hellscape, my friends reported. Rents were spiking. Art galleries and music venues were closing. Bars were overrun with men in their twenties wearing corporate-branded T-shirts, men who never finished their beers and complained whenever anyone on the sidewalk smoked a cigarette too close to the door. Men who wore stability running shoes to nightclubs. Men who said “K” instead of “thousand.”

Dating websites were flooded with milquetoast strivers who earnestly listed business-management guides among their favorite books and arrived at dinner wearing backpacks stamped with the names of their employers. Young CEOs were showing up to sex parties expecting to play only with other young CEOs. My friends, covered in glitter and wearing tiny nut-hammocks and rolling on ecstasy, found themselves marching in the annual Pride parade alongside primary-colored, brand-consistent, family-friendly floats designed by heterosexual digital-marketing managers.

The city had begun to bend to the on-demand desires of recent college graduates with plump bank accounts. Even Oakland was becoming unaffordable for artists and writers working as loosely credentialed yoga instructors or grocery store cashiers. There weren’t any jobs, my friends said, unless you wanted to work for a tech company. It went without saying that none of them did. Within a few years, they departed for gentrifying neighborhoods in New Orleans or Los Angeles, or found their way to graduate school, their flight paths and cross-country road trips doing double duty as funeral marches for a beloved city that, they all assured me, no longer existed.

When I traveled to San Francisco in the spring, to interview for a customer-support position at a data analytics startup, I didn’t mention it to my ex–Bay Area friends. I dreaded how they would react if they knew I was angling for a job in the tech industry, that I had even a shred of interest in joining the people on whom they blamed their displacement—the people who had ruined their fun. I took the train from the airport into the city, feeling treacherous and estranged.

Using the millennial-friendly platform for renting strangers’ bedrooms, I had booked a room in the Mission, in an apartment that belonged to a couple in their mid-fifties. It was my first time using the app, and as I stood on the front steps of an ornate Victorian, I felt like an orphan of nineteenth-century literature, a child on the brink of a new adventure. Welcome home, the home-sharing platform’s marketing materials had gushed, exuding familial warmth with bright, bold colors. But while the website emphasized community, coziness, a richer life through new connections and novel experiences, my hosts greeted me coolly—a reminder that this was, above all, a transaction.

As the husband showed me around my room—guest towels in the hope chest, lemon tree in the backyard—he asked what had brought me to town. I explained with some trepidation that I was there to interview at a startup. I knew that the neighborhood had long been an enclave for artists, activists, and other groups without enough money to hold their own in housing court. I wanted to be sensitive. He nodded knowingly, without judgment, and shrugged. “We host full-time,” he said. “I guess you could say we work for a startup, too.”

Could I? He and his wife had both quit their day jobs, in the nonprofit sector, to provide the trappings of an authentic urban experience—different enough to be interesting, but generic enough to be comfortable—to tourists and interlopers like me. They slept in the basement. They weren’t employees. They were part of the product.

It was my first time paying to stay with strangers. The apartment was clean and welcoming, full of overstuffed furniture and bowls of fruit, but I didn’t know whether relaxing with a book on the sofa or borrowing kitchen implements to slice a ripe peach would be considered a breach of the home-sharing platform’s terms of service—I’d only booked a room, after all. The policy had extensively covered the company’s liability but didn’t offer any specifics on how to behave. To play it safe, I walked carefully between my bedroom and the bathroom, as if the hallway were a grooved track—as if I were trespassing, intruding on a family and a life that did not belong to me.

The interview had been arranged with the help of the e-book startup’s CEO, who advised that big data was a hot space. According to him, the analytics startup—just four years old, founded by college dropouts—had already infiltrated the market with impressive speed and ferocity. The company had twelve million dollars in venture funding, thousands of customers, and seventeen employees. “Our investors say they’re the next unicorn,” the e-book startup’s CEO had enthused, tipping back in his chair. “It’s a rocket ship.” It was easy to get me to want something.

I was not particularly excited about customer support, but it was an entry-level job that required no programming knowledge. As a sociology major with a background in literary fiction and three months of experience in snack procurement, I assumed I was not in a position to be picky. The e-book startup’s cofounders had been adamant that customer support was a temporary state. If I hustled, all three of them agreed, I would quickly find myself in a more interesting, autonomous, impressive role. I didn’t know that in tech, qualifications—at least the traditional ones, like advanced degrees or experience—were irrelevant when superseded by cheerful determination. I was still behaving like a young professional in a world where dues-paying mattered.

In an effort to hype myself up, I developed the theory, however flimsy, that analytics was a natural extension of my liberal arts education. The e-book startup had used the analytics software to track our alpha users through the app, and I had enjoyed looking at some of the data: what our investors were reading, and abandoning; whether or not people read public-domain books with cover art designed by the CPO, which we had added to bolster the library. In a certain light, I tried to convince myself, business analytics could be seen as a form of applied sociology.

The night before the interview, in the privacy of my rental bedroom, I read interviews and puff pieces about the analytics startup’s cofounders, now twenty-four and twenty-five years old. According to the tech blogs, they’d just been two underage students with one Silicon Valley internship between them, and a smart, practical, easily pivotable dream of a world driven by the power of big data. This was a dream that greatly appealed to the admissions committee of a renowned seed accelerator in Mountain View, which offered funding and connections in exchange for a 7 percent stake. The accelerator’s slogan was an inspirational exhortation to founders to make things people wanted—not, I noted, needed. It boasted a handful of success stories—a grocery-delivery app, a livestreaming site, the home-sharing platform—as well as dozens of failures. The CEO and technical founder had left their college in the Southwest to join the accelerator, then enrolled full-time in the ecosystem.

Several months prior, a tech blog had published an article announcing the analytics startup’s first major fund-raising round of ten million dollars. When asked how he would spend the new funding, the CEO made his priorities clear: he would pay the first hundred employees far above market, he said, and spoil current employees to retain them. This was the language of customer acquisition, but I didn’t know. I didn’t think at all about the stratification, either; how the hundred-and-first employee might feel. I’d never worked anywhere with a hundred people—I’d never worked anywhere with twenty. I’d certainly never worked anywhere that wanted to spoil its employees and had the means to do it. Generous, I thought. I found the tenacity winning.