“These companies can really infiltrate your identity”

Anna Wiener. Photo: Russell Perkins

Silicon Valley has mostly been chronicled by founders, investors, and tech-utopian true believers. By that measure, Anna Wiener’s new memoir of working for start-ups, Uncanny Valley, in not really an insider's account. True, Wiener worked for a variety of tech companies beginning in 2013, but her customer-support jobs were viewed as superfluous to the “real” work of CEOs and engineers. This position of insider-outsider allowed Wiener to impartially observe the hidden workings of companies that have taken over virtually every aspect of the economy and transformed our public and private lives.

Bookforum spoke to Wiener by phone about the limitations of start-up ideology, power, and the interchangeable nature of the great men of tech.

When did it become clear that you wanted to write about your experience in Silicon Valley?

The book emerged slowly from a piece that I wrote for n+1 in 2015, which was published in 2016. Initially it was supposed to be a review of a book called Lean Out, which was a response to Sheryl Sandberg’s Lean In. I was seeding it with anecdotes from my life out here, and was just having so much fun writing it. The review part of it fell away, and I just wrote this dispatch from my life. Then I backed off for a while—I still worked in the industry and I felt too close to it, but I knew I wanted to do more at some point.

After the 2016 election, it just started to feel more urgent, like something had ended. It felt like this was a really specific era for tech especially, and I wanted to capture it before things changed, particularly from the perspective of an ordinary employee––rather than the vantage point of an executive, or as a pundit. I landed on memoir because it felt like fiction was not going to be the most useful form. As a woman in a nontechnical role, especially as a low-level employee, I felt that if it were fiction, it would be mistaken for satire, or people wouldn’t take it seriously.

What do you think changed in Silicon Valley after 2016?

I think the election catalyzed a wave of critique and scrutiny. I think a lot of people felt betrayed by the industry. I don’t think much changed structurally; the problems that the election helped surface have very deep roots. I think it was more about where people were training their attention, the stories the media was telling about Silicon Valley, and the stories Silicon Valley companies were telling about themselves. In the public eye, the tech industry went from looking like a decadent, goofy, anomalous culture, to looking more like a mutation of hyper-capitalist ideology––or, depending on your perspective, the natural progression and endpoint of American capitalism.

What brought you out there initially?

I just wanted to find my place in the world. I wanted to feel like I was on a track, any track, really––that I was going somewhere. I couldn’t see a future for myself in publishing that looked stable, compelling, or independent. Tech, on the other hand, offered nothing but future. I think I shared some qualities with the archetypal start-up founder, like impatience and feeling like I had more to contribute. I was enthralled with the speed and momentum that the industry offered––these guys had an idea and were given license to experiment with it. What’s thrilling about the industry, especially to someone in their twenties, is also what makes it so dangerous: inexperience, wild ambition, and lack of expertise cut both ways. My personal story is not particularly flattering: I wanted to feel like I was doing something right, and being at a company that had been given a stamp of approval in the form of $3 million in venture funding felt intoxicating. I was making more money. There was latitude. I felt like I had been approved.

You’re incredibly self-aware in the book. How hard was it to get to a place where you could be honest about your relationship to certain unhealthy power dynamics, and how did you make decisions on what to include when writing about it?

The self-criticism isn’t a deliberate layer—it’s just how I move through the world. That degree of self-consciousness isn’t a recipe for happiness, but it’s true to my experience.

I think a huge problem in tech is an aversion to conversations about, and the analysis of, power. In a lot of ways, I succeeded in tech despite myself, and I think a large part of that had to do with being white, well-off, and socialized in a particular way. I was never important in the industry, which is of course part of the point of the book, but I still hope it’s useful for someone like me to dissect some of these power dynamics and to consider what they might reveal about the broader culture.

How does your book differ from the typical stories we tell about the tech industry?

Most stories about Silicon Valley are told by founders, executives, people in positions of significant power––people who want to give business advice and flatter themselves. There are also plenty of technophobic narratives, or scathing, damning indictments of the industry; there’s a lot of really important academic inquiry. But I’m not an academic, and I’m not interested in triumphalist narratives about innovation and boy genius, and I didn’t want to write something polemical. I wanted to tell the story of an average employee: someone who had bought in, then bowed out. My goal was to write about this time and place from the perspective of someone that’s not particularly special in this industry, which is one that tends to focus on people around whom capital and power are pooled. There’s a mystification happening there that doesn’t really serve anyone except those individuals. I hope my book is a counterweight to a lot of the literature about Silicon Valley that was published in the last decade.

At one point you write that “everyone was doing what they could to keep a toehold on the city, to keep a part of the culture sacrosanct; to build what they believed would be a better world.” Later, you recall a friend describing his work in the tech industry “as both a personal defeat and a concession to his hometown’s new identity.” Are most tech workers, whether they’ve given into the aware of the disparity between their ambitions and reality?

I think some are. This is an industry that’s full of really smart people who are aware of what’s happening in the world around them. I think that’s part of why these companies have such intoxicating corporate cultures, to say nothing of the high salaries: it breeds contentment. These companies can really infiltrate your identity. For many, though, I think there’s some degree of willful passivity or detachment––or the belief, which I’ve heard from a few Facebook employees, that they can change things from within, and have a greater impact by trying to do good inside a company, rather than leaving. I also think there are plenty of other reasons people stay in these jobs that I don’t want to discount, reasons that are more structural in nature: visas, debt, dependents.

It seems like most of the companies you write about lack things like reporting lines, real management, or HR, which leads to toxic environments that prioritize the comfort of white men over other employees. Do you think things will ever improve?

How a company treats its employees tells you everything about the company, and I don’t mean the perks. Do they fire whistle-blowers, or people who agitate, or demote women who complain about harassment, or place sexual abusers on paid leave? I do think there are some things we haven’t tried that are compelling, like more leadership from employees, more ownership by employees of internal processes, or giving employee board seats. It doesn’t matter how many design ethicists or diversity and inclusion specialists a company hires if those people don’t have agency and influence internally. We also haven’t tried regulation, for the most part. We haven’t reconsidered the business models, or the role of venture capital, or the emphasis on global scale and rapid growth. I think the more we can just acknowledge that these are businesses, the better, but that’s the bare minimum. I have to hope things will get better. I have to believe that, because otherwise what’s the point?

Speaking of businesses, there are no named companies in the book, but it’s fairly obvious which companies you’re writing about. How and why did you make this call?

It was a stylistic choice. Mostly, I felt the names of the companies didn’t matter. This book is a not a tell-all—someone will write the great GitHub tell-all someday, but I’m not interested in that project. I thought that simply describing what the start-ups did would be more effective and would point to the interchangeability of many of these companies, in terms of their culture and leadership. Again, my hope is that it counterbalances the individualism that the industry exalts.

The CEOs that I worked for could easily have been a number of other people. They were behaving within a system, one with its own interests and constraints. When my friend Moira lived in San Francisco, we would take these long walks around the city, and I remember one conversation in which I pitched her my theory that Mark Zuckerberg’s goal was to become a great man of history. What else could the endgame be? I’m not sure she disagreed, but she sort of smiled, and rolled her eyes, and said, dryly, “If Mark Zuckerberg didn’t exist, the industry would invent him.” I think about that all the time.

What traits, if any, might these CEOs share that seem to make them interchangeable?

I don’t want to psychoanalyze, but one narrative that I don’t think is helpful in tech is this idea of the scrappy, merit-based success story. A lot of people who run companies come from privileged homes, have been given the benefit of the doubt most of their lives. They’re familiar to me—I’m one of them. There are also a lot of people who have been told they’re smart their entire lives, and they’ve had success in the industry, are given money, and are surrounded by people who are telling them they’re doing everything right. It’s not based on experience, but on vision: an abstract idea of the world. Everyone’s ambition is rooted in something personal, but tends to take on a more universal story.

Eric Farwell is an adjunct professor of English at Monmouth University and Brookdale Community College in New Jersey. His writing has appeared in print or online for Esquire, Salon, the Kenyon Review, the New Yorker, McSweeney's, the Village Voice, and Vanity Fair, among others.