Four Years in Startups

Depending on whom you ask, 2012 represented 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 co-workers, high on the fumes of world-historical potential, breathlessly called the ecosystem. Everything was going digital. Everything was up in the cloud. A technology conglomerate that first made its reputation as a Web-page search engine, but quickly became the world’s largest and most valuable private repository of consumer data, developed a prototype for a pair of eyeglasses on which the wearer could check his or her e-mail; its primary rival, a multinational consumer-electronics company credited with introducing the personal computer to the masses, thirty years earlier, released a smartphone so lightweight that gadget reviewers compared it to fine jewelry.

Technologists were plucked from the Valley’s most prestigious technology corporations and universities and put to work on a campaign that reëlected the United States’ first black President. 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. It was the dawn of the unicorns: startups valued, by their investors, at more than a billion dollars. The previous summer, a prominent venture capitalist, in the op-ed pages of an international business newspaper, had proudly declared that software was “eating the world.”

Not that I was paying any attention. At twenty-five, I was working in publishing, as an assistant to a literary agent, sitting at a narrow desk outside my boss’s office, frantically e-mailing my friends. The year before, I’d received a raise, from twenty-nine thousand dollars to thirty. What was my value? One semester of an M.F.A. program; fifteen hundred chopped salads, after taxes. I had a year left on my parents’ health insurance.

I was staving off a thrumming sense of dread. An online superstore, which had got its start, in the nineties, by selling books on the World Wide Web, was threatening to destroy publishing with the tools of monopoly power: pricing and distribution. People were reeling from the news that the two largest publishing houses, whose combined value pushed past two billion dollars, had agreed to merge. In the evenings, at dive bars, I met with other editorial and agency assistants, all women, all of us in wrap dresses and cardigans, for whiskey-and-sodas and the house white. Publishing had failed to innovate, but surely we—the literary, the passionate, lovers and defenders of human expression—couldn’t lose?

One afternoon, at my desk, I read an article about a startup, based in New York, that had raised three million dollars to bring a revolution to publishing. It was building an e-reading app for mobile phones which operated on a subscription model. The pitch—access to a sprawling library of e-books for a modest monthly fee—should have seemed too good to be true, but the app was a new concept for publishing, an industry where it seemed as if the only ways to have a sustainable career were to inherit money, marry rich, or wait for our superiors to defect or die.
My interviews with the e-book startup were so casual that at a certain point I wondered if the three co-founders just wanted to hang out. They were younger than I was but spoke about their work like industry veterans, and were generous with unsolicited business advice. I wanted, so much, to be like them. I joined at the beginning of 2013.

The job, which had been created for me, was a three-month trial run. As a full-time contractor, I would be paid twenty dollars an hour, with no benefits. Still, the annual salary amounted to forty thousand dollars. On my start date, I arrived at the office, a loft a block from Canal Street, to find a stack of hardcover books about technology, inscribed by the founders and stamped with a wax seal of the company logo: a mollusk, unavoidably yonic, with a perfect pearl.

The e-book startup had millions of dollars in funding, but the app was still in “private alpha,” used by only a few dozen friends, family members, and investors. For the first time in my career, I had some semblance of expertise. The founders asked for my opinions on the app’s user interface and the quality of the inventory, and on how we could best ingratiate ourselves with the online reading communities, the largest of which would soon be acquired by the monopolistic online superstore. One afternoon, the C.E.O. summoned the other two founders and the staff of three to a conference room to practice his presentation to publishers. He opened by saying that this was the era of the sharing economy. Music, movies, television, retail, and transportation had been disrupted. Apparently, the time had come for books. He flipped to a slide that displayed the logos of various successful subscription platforms, with ours at the center. “Hemingway” was misspelled in the pitch deck: two “m”s.

After the first few weeks, it seemed that the founders were paying me mostly to look for new office furniture and order them snacks: single-serving bags of sliced apples, tiny chocolate bars, cups of blueberry yogurt. “She’s too interested in learning, not doing,” the C.E.O. wrote. He meant to send the message to the two other co-founders, but mistakenly posted it in the company chat room. He apologized sincerely, while I looped the words in my head. I had not understood that the founders hoped I would make myself indispensable. I had never heard the tech incantation “Ask forgiveness, not permission.”

Soon afterward, the co-founders informed me that the areas where I could add value would not be active for some time. They assumed that I wanted to continue working in tech, and I didn’t disabuse them of this notion.
One of the e-book startup’s co-founders helped arrange an interview at an analytics startup in San Francisco. The role was in customer support, which I was not particularly excited about, but it was an entry-level position 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 night before the interview, in a bedroom I’d rented through a millennial-friendly platform for sleeping in strangers’ bedrooms, I read puff pieces about the analytics startup’s co-founders, now twenty-four and twenty-five, with one Silicon Valley internship between them and a smart, practical dream of a world driven by the power of Big Data. A renowned seed accelerator in Mountain View had offered funding and connections in exchange for a seven-per-cent stake, and the C.E.O. and the technical co-founder left their college in the Southwest to join. The startup had twelve million dollars in venture funding, thousands of customers, and seventeen employees.

In the office, the manager of the Solutions team, a hirsute man with a belly laugh, presented me with a series of questions and puzzles. A wiry sales engineer showed me how to write a function that rearranged the characters in a long string of letters. The technical co-founder watched me complete a reading-comprehension section from the LSAT.

The offer included company-paid medical and dental coverage and a starting salary of sixty-five thousand dollars a year. The Solutions manager did not mention equity, and I didn’t know that early access to it was the primary reason people joined startups. Eventually, the company’s in-house recruiter recommended that I negotiate a small stake, explaining that all the other employees had one.

Friends at home told me that they were excited for me, then asked whether I was sure I was making the right decision. The media tended to cover tech as a world of baby-faced nerds with utopian ambitions and wacky aesthetic preferences, but to my friends it was a Wall Street sandbox. I stuck to the narrative that working in analytics would be an experiment in separating my professional life from my personal life. Maybe I would start the short-story collection I had always wanted to write. Maybe I would take up pottery. I could learn to play the bass. I could have the sort of creative life that creative work would not sustain. It was easier to fabricate a romantic narrative than to admit that I was ambitious—that I wanted my life to pick up momentum.
Startups in New York were eager to create services for media and finance; software engineers in the Bay Area were building tools for other software engineers. The analytics platform enabled companies to collect customized data on their users’ behavior, and to manipulate the data in colorful, dynamic dashboards. I’d had some guilt about the opportunism of the e-book startup, but had no qualms about disrupting the Big Data space. It was thrilling to see a couple of twentysomethings go up against middle-aged leaders of industry. It looked like they might win.

I was employee No. 20, and the fourth woman. The three men on the Solutions team wore Australian work boots, flannel, and high-performance athletic vests; drank energy shots; and popped Vitamin B in the mornings. The Solutions manager assigned me an onboarding buddy, whom I’ll call Noah—employee No. 13—a curly-haired twenty-six-year-old with a forearm tattoo in Sanskrit. He struck me as the kind of person who would invite women over to listen to Brian Eno and then actually spend the night doing that. I spent my first few weeks with Noah carting around an overflowing bowl of trail mix and a rolling whiteboard, on which he patiently diagrammed how cookie tracking worked, how data were sent server-side, how to send an HTTP request. He gave me homework and pep talks. Our teammates handed me beers in the late afternoon. I was happy; I was learning. The first time I looked at a block of code and understood what was happening, I felt like a genius.

Anna Wiener –

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