As a contributing writer for The New Yorker, Anna Wiener files dispatches from San Francisco that home in on the Silicon Valley’s human stories with a subtlety elided by consumer data sets and algorithmic models. Contextualized by her own professional experience at a succession of Bay Area internet platforms, she’s plumbed LinkedIn-friendly headlines about earnings reports and funding rounds in order to interrogate the culture: the restrictive gatekeeping of seed accelerators and venture capital, the unlikely marriage of California bohemianism with corporate libertarianism, and the lonely homogeneity of modern, online cities. By analyzing the structures behind the tech industry’s most valuable and ubiquitous products, she conveys these phenomena as natural, if not inevitable, byproducts.

Wiener’s memoir Uncanny Valley maps her own coming-of-age during the Valley’s 2010s rush, as well as the industry’s simultaneous loss of innocence. Frustrated at her dead-end assistant job with a New York literary agency, she jumps at the opportunity to join a short-lived ebook start-up, then sets west to work at a series of big-data SaaS (Software as a Service) companies that promise excitement and equity in exchange for cultish devotion. As a support specialist, she inadvertently finds herself witness to Gamergate, Pizzagate, data breaches, and the ad-tech surveillance boom that fed the 2016 election. The Bay Area, and soon the nation, are seized by palpably unsustainable wells of funding, and the visible indicators of gaping income inequality in the city itself are viewed as markers of progress. Eschewing the caffeinated, self-referential keenness that defined the decade’s online writing, Wiener is cerebral and diagnostic in her observance of escalating corporate surveillance.

I first emailed Anna in early 2016 to express my appreciation of her n+1 story on start-up burnout; at the time I’d been pulling eighty-hour weeks at a doomed Flatiron District data start-up, and her portrayal of infantilizing conformity, circular marketing speak, and opaque executive boys’ clubs seemed remarkably true to my own experience. In December 2019, we met at a bar in her native Brooklyn neighborhood, which, like San Francisco, has been transformed by coworking spaces, fluorescent fast-casual chains, and a shiny new arena that houses a professional basketball team owned by a consortium of local tech czars.

INTERVIEWER

I’m interested in the idea of a professional meritocracy. You write about, on the one hand, being conditioned by traditional liberal arts values, and then landing in Silicon Valley where the “meritocracy” is almost flipped. It’s less about degrees and accomplishments than hustle, ambition, and the ability to sell oneself. Looking back, which of those, if either, do you find more empowering?

WIENER

I wouldn’t call either one empowering. I think they just have their own rules, their own networks. In practice, the two value systems aren’t that different—it seems to come down to marketing. Publishing has a ton of problems. Gatekeeping, tiny networks, compensation low enough that, when combined with the emphasis on cultural capital, is prohibitive and exclusive. I’m a beneficiary of this—I went on five networking coffee dates, a chain of referrals, before being sent the job listing for the assistant position I took in publishing.

Both industries are pretty homogeneous. In tech, meritocracy seems to be used as a cover story for social inequities. Not everyone has the opportunity to prove themselves in the same way. My sense is that underrepresented minorities in tech don’t get a pass so easily—I think you’ll tend to find that those groups are heavily credentialed. At the first start-up I worked for in San Francisco, the job listing for customer support representatives came to read, “Relevant work experience or a degree from a good college.” The CEO, it’s worth mentioning, had left college to found the company at age nineteen or twenty. It’s like the difference between someone who went to Yale and someone who dropped out of Stanford. I think both of these industries inherit the problems of a larger social landscape.

Something that’s really valuable in publishing is the idea of taste. The concept of taste is riddled with sexist, racist, classist assumptions. But for a lot of people, it comes down to an individual feeling, an individual orientation toward a form of cultural production. It’s not measurable. Like you said, in tech it’s more about your capacity for hustling, less about who you are than what you say you can do, what you generate or say you’ll generate. Both strike me as forms of storytelling, in the branding sense.

INTERVIEWER

One phenomenon you witnessed firsthand during Silicon Valley’s 2010s boom was overconfident white men being anointed with investor capital, based as much on ambition and pretense as on actual vision and product. I’m comfortable saying that overconfident white men have always benefited from institutional deference. Did you sense that Silicon Valley’s deregulation and lack of oversight exacerbated privilege?

WIENER

Like you, I’m not sure it’s a phenomenon so much as an unbroken cultural tradition—but yes, I think certain characteristics of Silicon Valley served as accelerants. Deregulation and lack of oversight quicken and amplify start-up founders’ visions of the world, and help push new ideas through with speed and a certain degree of impunity.

INTERVIEWER

I don’t mean to paraphrase, but it seemed that the founders of the ebook start-up you worked at in New York had amassed capital by selling themselves as opposed to a product.

WIENER

I think that was a big part of it, but this was also a moment when people hadn’t cracked ebooks—or more specifically, “Netflix-for-ebooks”—yet. Books were another medium to disrupt, or innovate on, or whatever. So it was the idea of the product, but it also mattered that the idea came from three charismatic guys who’d graduated from prestigious private colleges, and had worked briefly at successful start-ups and tech corporations.

INTERVIEWER

Reading, I couldn’t help but consider what an absolute mess things have become. All these young men were gifted millions in venture capital without much to show for it, setting labor rights back God knows how far in the process. I don’t know if it was any better working at IBM or Hewlett-Packard forty years ago, in terms of leverage and stability, but I can’t imagine it was any worse.

WIENER

Today’s iteration of Silicon Valley seems ahistorical, anti-intellectual, irreverent in a way that is more reflective of the current phase of capitalism than of any unique industry value. I feel the industry needs to be more closely tied to both the government and academia, and better integrated—not in the current NSA, Stanford-pipeline sort of way. We’ve lost, for example, the tradition of research labs. In the late twentieth century, the countercultural idealism hardened into a libertarian ethos, an anti-institutional, anti-government stance, and also this new form of hubris that was legitimized by venture capital. I think people are incredibly reluctant to surrender that underdog identity, regardless of how true it was, then or now.

INTERVIEWER

When you took your first role in San Francisco, something that appealed to you was the idea of working for an underdog, one of the scrappy upstarts trying to upstage old-line corporations. Do you still feel that way, or is it more the case that those underdogs have simply evolved into that tier of dominant institutions?

WIENER

Both. I would say I want to be on the side of the underdog, generally, but I’m no longer excited to go to the mat for a business. Employees, of course, are another story. What took me a while to understand was that there is a pervasive, willful reluctance in the industry to acknowledge power, and to acknowledge tech’s transition from underdog to establishment. Among other consequences, that’s resulting in a new political orientation for a lot of people, a rightward swing.

I think when that underdog status is exciting, it’s often short-lived. A lot of one-time underdogs who experience success are unable to relinquish the identity. No one wants to see themselves as representative of the new form of corporate America.

INTERVIEWER

Something that seems representative of your experience working in Silicon Valley was the implicit ways in which workplace sexism occurred, all of which would have been difficult to regulate. The idea of “emotional labor” and women being expected to perform soft-skills work while men were allowed to act like children seemed pretty widespread.

In your book, you write a bit about diversity initiatives and the brand of milquetoast, lean-in feminism that tech later embraced. In organizations like those you worked in, can you imagine any ways in which anti-discrimination policies might actually be enforced given the leadership structures and hierarchies?

WIENER

For meaningful shifts, everything would need to change—stock option distribution, board composition, hiring practices, the exchange of silence or NDAs for robust severance packages. In so many ways, the American tech industry is a reflection or concentration of social issues with deep roots.

The conversation about diversity is, among other things, a conversation about power. You’ll be hard-pressed to find people in leadership roles who are excited to relinquish power—especially in tech, with its stories about meritocracy and homespun genius. This is part of why I find lean-in feminism exhausting. It’s so unimaginative, so flattering to existing power structures. These aren’t problems specific to tech, of course—what we’re talking about are incentives and expressions of capitalism. Capitalism isn’t interested in equity or accountability.

INTERVIEWER

I was struck by your analysis of workers drawn to Silicon Valley in the 2010s. You intersected with a number of professionals from nontechnical backgrounds—teachers, lawyers, career-track academics—who came west to work for start-ups.

Working in tech, I’ve certainly thought about this—would I be doing this if, say, public servants made more money? How much do you think Silicon Valley preys upon this job market?

WIENER

I think that we’re in a moment of transition, institutional erosion, shifting—or crystallizing, depending—social values, changing tides in the economy. Recently I had occasion to think about an engineer I worked with who had a Ph.D. in musicology. He was an expert on medieval polyphonic choral music, if memory serves. In a different economy, I doubt he’d be a programmer. I think a lot of people in tech were prepared for other careers, and would be working in academia, law, public service, the arts, if those industries could offer a sense of stability and momentum.

I don’t think Silicon Valley preys on anyone, but the industry has ascended to a dominant position in society and the economy. People have debt, or dependents, or a need for insurance or work visas. Or maybe they’re relatively unencumbered, but had been working toward the promise of something that no longer existed by the time they arrived. There’s a lot of talent pooled in Silicon Valley, and it’s hard not to look around at a lot of the companies here and feel that it’s a bit of a shame, a waste of potential.

INTERVIEWER

Thirty years ago, folks with liberal arts backgrounds would graduate from college and go to law school without a second thought—it didn’t cost too much, you didn’t even have to practice law afterward, it was just a pragmatic resume-booster for the corporate world. Today, the notion of taking on six figures in debt for any graduate degree is a nonstarter. That blocks off entire industries that competitive applicants would otherwise be drawn to.

WIENER

I think you could refer to it as a brain-drain situation—from public service, from the government, and from other industries that would contribute to a more robust economy and society. I wouldn’t completely blame it on the industry. The tech industry’s not generating student debt. I think what most people want is a dignified, stable, self-directed life, and that’s harder and harder to have without sacrificing leisure time, and maybe even your personhood, to a certain extent. I’m speaking in escalated terms, but I do think it’s fundamentally true.

I find the whole coding-boot-camp economy really interesting. A narrative many of the coding boot camps promote is that they offer a program that’s superior to a four-year college or university, because it will immediately lead to an income jump and a marketable skill. I get that—it’s very valuable for most people who finish these programs. But it also seems incredibly cynical, limited, anti-intellectual. There’s some conflation happening there, of moral value with economic value, that I find alarming. All that said, it’s also a form of social or civic circumvention. Tech is very good at this, I think—upending things, tearing through. What’s lacking is committed, long-term engagement.

Pete Tosiello’s criticism, reportage, and interviews have appeared in The Washington Post, the Los Angeles Times, Vulture, and Pitchfork among many others. He lives in New York City.