The Stories Silicon Valley Tells Itself in Order to Live: A Conversation with Anna Wiener

By Sam Jaffe GoldsteinFebruary 11, 2020

The Stories Silicon Valley Tells Itself in Order to Live: A Conversation with Anna Wiener
THE CURRENT ITERATION of Silicon Valley, with its billionaire millennials, unicorn startups, and outright fraudsters, has been around long enough that we have begun to write its history. While it is obviously important to learn about the inner workings of tech companies, so much of the narrative still comes from the top down. Between doting biographies of CEOs and best-selling self-help manuals written by those same CEOs, it is rare to find narratives that question Silicon Valley’s view of itself.

Although that is starting to change, it is the hope of former tech worker and author of the new memoir Uncanny Valley, Anna Wiener, that we will start to hear from more of the workers who fill up the tech behemoths that have come to define our everyday lives. Her book is neither a promotional story of how the tech industry wants to view itself nor a rallying cry to burn it all down. Instead, it is a memoir of Wiener’s personal experiences in San Francisco, from which emerges a nuanced critique of Silicon Valley and an argument for why it needs to be brought to heel as its power and influence continues to grow.

I sat down with Anna to discuss her experiences working in Silicon Valley, how much the region has changed everything, and what we should do about it.


SAM JAFFE GOLDSTEIN: There are very different potential versions of this book. You could have written it as a novel, where you leave a crumbling New York City for the gleaming utopia of San Francisco, or you could have written it as a tell-all memoir that names names. 

ANNA WIENER: I thought about writing the book as fiction — you’re afforded more liberties in fiction. But I felt that if I wrote it as a novel, no one would believe it, or take it seriously. I worried that people would think of it as satire. I was also not interested in writing a tell-all memoir. This book is deliberately not salacious or sensationalist — I want to be generous. In terms of naming names, I didn’t feel that the company or executive names nattered. Many of the companies I’ve written about are, I believe, interchangeable with any number of startups from the era covered in the book.

There has been so much written about the tech industry. What do you think the conversation was missing that compelled you to write this book?  

My interest was in writing about Silicon Valley from the vantage point of a low-level employee. In general, most of the stories that come from the tech industry tend to come from founders, investors, and executives: management philosophy, triumphalist stories about innovation and progress. (There are exceptions — including Ellen Ullman’s Close to the Machine: Technophilia and its Discontents [1997], which is wonderful, and Kate Losse’s insightful The Boy Kings: A Journey into the Heart of the Social Network [2012] — and I hope there will be more.) There have been some dishy tell-all memoirs, but I don’t find those interesting or useful. My hope is that the book is a little unsettling to people, and that it helps demystify the industry a bit. It’s easy to forget that there are people behind tech platforms and products, and I’m hoping that the book will illuminate how people in this industry speak, how they talk about what they’re building, the sorts of frameworks — economic logic, “rationality,” et cetera — that form, or are used to justify, their decisions.

It would be very easy for someone to enter the industry skeptical but, because of the money and benefits, become a convert. How did you stay skeptical and walk away?

At the beginning, I bought into the industry’s stories about itself: its exceptionalism and moral superiority, its vision for a new and better world. I thought the industry was the future, and it felt really good to participate. After a while, though, this mentality started to show fault lines. I had a lot of questions, and qualms, about the endgame. Core values started to seem really pernicious. The idea that your economic output is equal to your value as a person, or to your value in society, is both pervasive and dangerous. Of course, this isn’t really new: Silicon Valley is really just a collision, or amplification, of external forces. It’s capitalism on steroids — the most American place.

I suppose I was able to stay skeptical, but continue working, by doing something that shouldn’t have felt novel: I treated my job like a job. At so many tech companies, committing yourself to “the cause,” or hustling in the name of the company, is the baseline expectation. Not doing so feels like breaking a pact. In terms of walking away, though, I want to be very clear about this: I didn’t leave on heroic terms. I left when it became evident that I could make a living in another industry. If that weren’t the case, I would likely still be working at my last startup job, or at another much like it.

Is it weird that it felt sort of liberating to admit that your job is just a job?

Of course! That’s not the dominant narrative. The dominant narratives are self-congratulatory. During the time I worked in tech, people spoke earnestly about changing the world, and many of them truly believed it — this sort of grandiosity is, of course, part of the problem. I do think that most tech workers would benefit from talking about the fact that these are jobs, not world-historical missions. I also have to believe that this would open up more conversations about compensation disparities, equity, who’s getting paid to do what, et cetera.

How do you navigate the ambivalence between the desire of tech startups to provide a public good versus their actual execution of that service?

What tends to happen in tech, generally, is that there is a legitimate critique — of the student debt crisis, say, or media gatekeeping — but instead of engaging with what’s broken, there’s a tendency to circumvent. The people coming up with a solution are not necessarily best equipped to solve the problem at hand; for them, it’s an opportunity. All of this tends to be accelerated, or amplified, by infusions of venture capital.

Even as these tech companies have turned into behemoths, they have hung onto a vision of themselves as disruptive startups. Mark Zuckerberg said he created Facebook to voice his opposition to the Iraq War, which is such a blatant lie.

That was astonishing. He’s been trying to revise that narrative for years. My best guess at his endgame is that he’d like to be seen as a man of history, a favorable world-historical figure. I do wonder where someone like Zuckerberg gets his information, his view of the world. He came of age as a CEO. How might that affect someone’s worldview?

How do you deal with the paradox that so many tech companies emphasize individuality while both their workers and their users get subsumed into a homogeneous network?

Who are these narratives about individuality actually about? Meritocracy, with its libertarian emphasis on individual capacity, is a story that’s often used to pull a scrim over irresponsible allocation of resources, power, and money. It is offered as an excuse for great inequities. You’ll notice that this group of individuals who are supposed to be brilliant all look the same — weird!

In terms of aesthetics, or style, Mark Zuckerberg famously has a closet of expensive gray T-shirts. I think the logic behind this is that a uniform removes the burden of decision making, clearing the way for his brilliant mind. I wonder about the extent to which this mindset pervades the broader culture — look at the popularity of clothing brands like Everlane. Things that were once sensuous and aesthetic are now utilitarian. Perhaps such homogeneity liberates you, the white-collar worker, to be more economically productive.

Are we condemned forever to a clean minimalist aesthetic? 

I’m not sure — this is Kyle Chayka territory. Design, like anything, tends to reflect certain economic realities, so it’s not an accident, in my mind, that in the era of WeWork-y “do what you love” — to say nothing of the ascendance of startup workplace culture, and gig-economy precariousness — people’s offices look like their homes. For a lot of young people, home is probably transient, and minimalism may reflect that uncertainty. It’s also cheaper, in many cases, than maximalism. Whether we’re condemned to it, though? Probably not. Trends change.

A lot of your job in Silicon Valley involved writing for your company’s product users. Did that writing style influence you?

I had a hard time writing creatively when I was working on marketing copy or sending customer support emails. My brain is too porous; I couldn’t separate the two.

Do you think engineering teams need to go back to liberal art schools?

No. I think that’s condescending. A lot of the engineers I know did go to liberal arts schools. A lot of those who didn’t still have a very strong sense of ethics. I wouldn’t locate this in the engineering cluster. I would look at what the industry’s values are, how they are reinforced, and how that leads people to make certain decisions.

As you point out in the beginning of your book, your entire life was affected by the internet. Yet you didn’t understand that there were people behind the network. What did you learn when you came to understand that people were behind it?

It’s much more chaotic behind the screen. These organizations are messy, the products are messy, the code is messy, it’s a lot less coherent than you might think. Most apps are designed to be frictionless, efficient. This doesn’t mirror at all how these organizations function. Human decision making, communication, and collaboration are the engine of the whole thing. The push toward efficiency is corrosive and undermines a lot of what could be much better in tech than what we have.

Were you also shocked by how few people there were?

Sure. Twenty people with $12 million in funding and money pouring in? Gob-smacking, at least to me. Not thinking about the people behind the internet was one thing, but I was also naïve about the business model for most tech companies, specifically those offering free digital services.

Everything has changed thanks to the tech industry. Where do we go now in the aftermath of this cultural shift?

I think we’re still in the shift. We’re still at the beginning of something. Not in the aftermath, not even in the middle. What we have right now is not inevitable, and it shouldn’t be treated as such. What can we envision that’s better? Can it be more ethical, more interesting, more open, and less corporate, less surveilled? It feels pretty grim, but I have to believe it can change.

You bring up the theme of disassociation at the end of your book. Why do you think this feeling is important for us to write and talk about?

With respect to work, I think a feeling of dissociation can emerge from the gap between expectation and reality. More specific to tech, I think it can be easy to lose oneself in a company, undergo a sort of identity transfer. It’s very seductive.

What do you hope to change about the story that Silicon Valley tells itself? 

I’m interested in hearing more from normal employees, rather than from founders, venture capitalists, and executives. Let’s move away from hagiographies, triumphalist narratives, and stories that assign moral value to business success.

Is it time to just log off?

No. I loved Jenny Odell’s How to Do Nothing: Resisting the Attention Economy (2019), and her response to that impulse. It is a wild privilege to walk away from the internet. Of course, there are ways to better engage with digital platforms and products, to manage the demands on time and attention — to resist the push for constant engagement. But personal responsibility is not the answer to privatization, surveillance, corporate greed, et cetera. Wouldn’t tech corporations love for us to think so?


Sam Jaffe Goldstein is a bookseller at Community Bookstore in Brooklyn. You can find him on twitter at @sgiraffe666.

LARB Contributor

You can find Sam Jaffe Goldstein on twitter @sjaffegold.


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