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Macmillan Childrens Publishing Group

Uncanny Valley

A Memoir

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 stressful, but reliably consuming: the editor, several years my senior, had talked about marriage but wouldn’t stop cheating. 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 endless, searching emails with friends, in which we swapped inexpert 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.

In the manner of so many twentysomethings living in North Brooklyn at a time when an artisanal chocolate factory was considered a local landmark and people spoke earnestly about urban homesteading, my life was affectedly analog. I took photographs with an old, medium-format camera that had belonged to my grandfather, then scanned those photographs into my dying laptop, its internal fan whirring, to upload to my blogs. I sat atop busted amplifiers and cold radiators in Bushwick practice spaces, paging through back issues of prestige magazines, watching various crushes suck on hand-rolled cigarettes and finger their drumsticks and slide guitars, listening attentively to their noodling in preparation for my feedback to be solicited, though it never was. I went on dates with men who made chapbooks or live-edge wood furniture; one identified as an experimental baker. My to-do list always included archaic chores like buying a new needle for the record player I rarely used or a battery for the watch I never remembered to wear. I refused to own a microwave.

Insofar as I considered the technology industry of any importance to my own life, it was only because of circulating concerns specific to my professional world. An online superstore that had gotten its start in the nineties by selling books on the World Wide Web—not because the founder had a love of literature, but because he had a love of consumers, and consumptive efficiency—had expanded to become a digital bargain basement dealing in appliances, electronics, groceries, mass fashion, children’s toys, cutlery, and various nonnecessities manufactured in China. Having conquered the rest of retail, the online superstore had returned to its roots and seemed to be experimenting with various ways to destroy the publishing industry. It had even gone so far as to start its own publishing imprints, which my literary friends scorned and derided as cheesy and shameless. We ignored the fact that we had many reasons to be grateful to the website, as the publishing industry was being kept afloat by bestselling novels about sadomasochism and vampires who fucked, hatched in the incubator of the online superstore’s marketplace for self-published e-books. Within a few years, the founder, a chelonian ex–hedge funder, would become the wealthiest person in the world and undergo a montage-worthy makeover, but at the time we weren’t thinking about him. All that mattered to us was that the site was responsible for half of all book sales, which meant it had wrested control of the most important levers: pricing and distribution. It had us in its grip.

I did not know that the tech industry fetishized the online superstore for its cutthroat, data-driven company culture, or that its proprietary recommendation algorithms, which suggested vacuum cleaner bags and diapers alongside novels about dysfunctional families, were considered cutting-edge, admirable, and at the fore of applied machine learning. I did not know that the online superstore also had a lucrative sister business selling cloud-computing services—metered use of a sprawling, international network of server farms—which provided the back-end infrastructure for other companies’ websites and apps. I did not know that it was nearly impossible to use the internet at all without enriching the online superstore or its founder. I only knew that I was expected to loathe both, and I did—loudly, at any opportunity, and with righteous indignation.

On the whole, the tech industry was a distant and abstract concern. That fall, publishing was reeling from the proposed merger of the two largest houses, which together employed some ten thousand people and whose combined value pushed past two billion dollars. A two-billion-dollar company: the power and money were unfathomable to me. If anything could protect us from the online superstore, I thought, it was a two-billion-dollar company. I did not know about the twelve-employee unicorns.

Later, once I had settled into my life in San Francisco, I would learn that the year I spent drinking in dive bars with friends from the publishing industry, moaning about our impossible futures, was the same year many of my new friends, coworkers, and crushes swiftly and quietly made their first millions. While some of these friends were starting companies or embarking on two-year, self-imposed sabbaticals in their mid-twenties, I was sitting at a narrow desk outside of my boss’s office, tracking the agency’s expenses and trying to determine my value using my annual salary—increased, the previous winter, from twenty-nine thousand dollars to thirty—as a unit of measurement. What was my value? Five times as much as our new office sofa; twenty orders of customized stationery. While my future peers were hiring wealth advisers and going on meditation retreats in Bali to pursue self-actualization, I was vacuuming roaches off the walls of my rental apartment, smoking weed, and bicycling to warehouse concerts along the East River, staving off a thrumming sense of dread.

It was a year of promise, excess, optimism, acceleration, and hope—in some other city, in some other industry, in someone else’s life.

Lightly hungover one afternoon, eating a limp salad at the literary agency, I read an article about a startup that had raised three million dollars to bring a revolution to book publishing. The story led with a photo of the three cofounders, men who smiled widely against a pastoral background, like fraternity brothers posing for a graduation shot. All three wore button-down shirts; they looked like they had just shared a good chuckle. They looked so at ease, so convincing. They looked like the sort of men who used electric toothbrushes and never shopped at thrift stores, who followed the stock market and kept their dirty napkins off the table. The sort of men around whom I always felt invisible.

According to the news item, the revolution would come via an e-reading app for mobile phones that operated on a subscription model. This sounded niche to me, and the app’s pitch—access to a sprawling library of e-books for a modest monthly fee—seemed like the sort of promise that came with a lot of fine print. Still, something about the idea appealed.

The e-reading app was a new concept for publishing, where new ideas rarely emerged and were never rewarded. It didn’t help that publishing felt always on the brink of collapse. It was not just the monopolistic online superstore, or the two-billion-dollar merger, though these compounded and accelerated our anxieties. It was also the mores. The only way to have a successful and sustainable career in the publishing industry, it seemed, was to inherit money, marry rich, or wait for peers to defect or die.

Among the assistant class, my friends and I wondered whether there would be a place for us as the industry continued to shrink. A person could live on thirty thousand dollars a year in New York; millions did more with less. But take-home pay of seventeen hundred dollars a month was difficult to square with the social, festive, affluent lifestyle the publishing industry encouraged: networking drinks, dinner parties, three-hundred-dollar wrap dresses, built-in bookcases in Fort Greene or Brooklyn Heights. It was nice to get new hardcover books for free, but it would be nicer if we could afford to buy them.

Every assistant I knew quietly relied on a secondary source of income: copyediting, bartending, waitressing, generous relatives. These cash flows were rarely disclosed to anyone but each other. It was an indignity to talk about money when our superiors, who ordered poached salmon and glasses of rosé at lunch, seemed to consider low pay a rite of passage, rather than systemic exploitation in which they might feel some solidarity. Solidarity, specifically, with us.

The truth was that we were expendable. There were more English majors with independent financial support and strings of unpaid literary internships than there were open positions at agencies and houses. The talent pool was self-replenishing. Men in beige desert boots and women in mustard-yellow cardigans waited in the wings, clutching their cream-colored résumés. The industry relied, to some degree, on a high rate of attrition.

Still, my publishing friends and I were stubborn. We liked working with books; we clung to our cultural capital. There was a pervasive resentment around paying our dues, but we were prepared to pay them. A selective moral logic seemed to animate the industry: publishing had failed to innovate quickly, yes, but surely we—the literary, the passionate, lovers and defenders of human expression—wouldn’t lose to companies whose executives didn’t even show an appreciation for books. We had taste and integrity. We were nervous, and very broke.

I was very broke. Not poor, never poor. Privileged and downwardly mobile. Like many of my peers, I could afford to work in publishing because I had a safety net. I had graduated college debt-free, by no accomplishment of my own: my parents and grandparents had saved for my tuition since I was a blur on the sonogram. I had no dependents. I had secret, minor credit-card debt, but I did not want to ask for help. Borrowing money to make rent, or pay off a medical bill, or even, in a fit of misguided aspiration, buy my own wrap dress, always felt like a multifront failure. I was ashamed that I couldn’t support myself, and ashamed that my generous, forgiving parents were effectively subsidizing a successful literary agency. I had one year left on their health insurance. The situation was not sustainable. I was not sustainable.

My parents had always hoped that I would professionalize in medicine or law, immerse myself in something stable and safe. They were comfortable—my mother was a writer, and worked with nonprofits, and my father was in financial services—but they emphasized independence. My brother, who had graduated pre-recession, already had a successful career by the time he was my age. None of them understood the slow burn of the publishing hierarchy or the industry’s shabby, nostalgic glamour. My mother often asked, gently, why I was still an assistant—making coffee, taking coats—at twenty-five. She wasn’t asking for a structural explanation.

My desires were generic. I wanted to find my place in the world, and be independent, useful, and good. I wanted to make money, because I wanted to feel affirmed, confident, and valued. I wanted to be taken seriously. Mostly, I didn’t want anyone to worry about me.

Though I had the nagging suspicion that the e-book startup’s cofounders might be jockeying for a place on the wrong side of the issues I cared about—the side of the online superstore, the side that was already winning—at the expense of publishers, authors, and agents, I envied their sense of entitlement to the future. There was something unusual and attractive about people who had a vision for how the industry could evolve and a green light to get it done.

I didn’t know that three million dollars was considered a modest fund-raising round. I didn’t know that most startups raised money more than once, and three million dollars was experimental, pocket change. To me, that amount of money was a flag in the ground, an indication of permanence, as good as a blank check to go forth and take over. The future of publishing was here, I assumed. I wanted in.

* * *

I joined the e-book startup at the beginning of 2013, after a series of ambiguous and casual interviews. I had been primed to have expectations of a certain techie stereotype—antisocial and unwashed, sex starved and awkward—but the cofounders, who would never have referred to themselves as techies, immediately confounded this. The CEO was fast-moving, confident, and chiseled, and the chief technical officer, a soft-spoken systems thinker, was humble and patient. The creative founder, who referred to himself as the chief product officer, was an easy favorite. He had gone to art school on the East Coast and wore jeans that were so tight I felt I already knew him: he was like my friends from college, but successful. I was older than all three of them.

Conversation with the cofounders had been so easy, and the interviews so much more like coffee dates than the formal, sweaty-blazer interrogations I had experienced elsewhere, that at a certain point I wondered if maybe the three of them just wanted to hang out. They had, after all, recently moved across the country. It wasn’t like they wanted to live in New York—it was clear that they would have preferred the energy out west—but they needed to be closer to the industry they were disrupting, to build partnerships. Like the patron saint of mislaid sympathies, I speculated that perhaps they were just lonely.

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 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.

Copyright © 2020 by Anna Wiener