An Interview with Anna Wiener

Anna Wiener is a New Yorker contributor who writes about tech culture. Her work has appeared in The New Republic, The Atlantic, The Paris Review, and others. Wiener’s first book Uncanny Valley, a memoir about her time working for Silicon Valley startups during the age of the unicorns, came out on January 14, 2020. Below is a transcript of a conversation which took place on January 16, 2020 between Wiener, former Advocate president Natasha Lasky ’19, and Features Board member Emily Shen ’20. This interview has been edited for length and clarity, and transcribed with the help of, a machine learning powered personal assistant that provides speech to text transcription.

ES: Something featured in the book is your complicated relationship with the CEO of the data analytics startup. In that job, you likened yourself to a bot in describing how you catered to your mostly male customers’ requests. Later, when you are promoted, the solution manager describes your male coworker as strategic and you as someone whose strengths are that you “love our customers,” putting words in your mouth and almost commodifying your feelings. There were times where your care for your co-workers and CEO was seen as a liability, but it was like that was supposed to be transposed when it was effective, on to customers.

AW: But still undervalued.

ES: Yeah. And I wanted to know what you thought of that. When you said “bot,” it made me think of how AI is feminized a lot in media, and how you were kind of being like Scarlett Johansson’s character in Her — expected to serve people and not only do that, but in an emotional way.

NL: Not even just in media — the personal assistant on your phone, Siri.

AW: Alexa, perform affective labor. I don’t know if you have these men in your life —

ES: Probably, yes.

AW: There are men who will text me in ways that make me feel like a bot. They need some support — some emotional support. And I used to be much more willing to provide that when I was younger.

I think that soft skilled labor tends to be a way to devalue work done by women and other underrepresented minorities in tech. It’s not specific in tech — it happens everywhere — but it's amplified in tech, specifically when you're working in a company like I did, which is a b2b software product. You’re surrounded by men in your workplace, or I was, and most of the customers are men. For me, the thing that got complicated was that I saw that when I did these sort of maternal things, people liked it. And that seemed to be a way to feel valued — to play up that side of my personality. To some extent we all enjoyed it, too. So how do you talk about that?

NL: Having a certain amount of privilege and also being a woman — you can reap the small benefits of patriarchy if you perform in the proper way. And sometimes there's joy in that even though it may feel empty in some way.

AW: I like that. Reap the small benefits of, or eat the leftover scraps of.

NL: It does feel like being a pet in some way — like a conditional acceptance.

ES: You’ve been asked a lot about your decision not to name any of the companies you discuss in Uncanny Valley.

AW: It’s a purely stylistic choice. I think it’s important to remember what these companies do rather than whatever cultural association someone might have with the name, and it also gestures towards the interchangeability of these companies. In terms of what I’m writing about, the companies themselves don’t really matter because I think the situations that arose from these environments are reflective of a bigger structural narrative. I also just don’t really like the names of a lot of these companies; I think they are hard to read on the page for me.

NL: It’s interesting that you say that especially with regards to interchangeability. I think of the e-book founders, in the way that you describe them, as being this hydra of interchangeable white men. Why do you think startup culture functions this way in terms of interchangeability and culture?

AW: I think it has to do with the values of the industry. The business model favors speed, monopoly as a sort of endgame, efficiency, optimization, scale. On the cultural side, the industry loves the story of the contrarian, visionary young white man. There's this feeling that people who are younger have come into the technology at the cutting edge, so they represent something about the speed of the development of technology. When you have these workplace environments where optimization, speed and scale are the primary goals, and everyone is also quite young and figuring out how to be a boss at the same time that they're figuring out how to be a person, you get a somewhat fairly standard output, right?

I also think that this can vary depending on what type of company. There are some companies in Silicon Valley that are operating within highly regulated industries, like financial tech. I would assume that those companies tend to have a more mature and more businesslike culture. That's just my assumption; I haven't worked in one of those.

ES: On tech culture being homogeneous, everyone's always talking about disruption but doing things in a very similar way. The success story of a startup has been very codified: seed from Y Combinator, raise additional funding from Accel, grow, exit. Everyone kind of follows the same path, yet is convinced that they’re different. People in Silicon Valley like to see themselves as different.

AW: It’s so interesting you bring up Y Combinator, because I think that's actually a great example to use when thinking about this question. It’s this network of entrepreneurs who essentially help each other out. One of Y Combinator’s greatest selling points is its network. Paul Graham is one of the founders of Y Combinator; his influence is deeply felt in that sphere. Joining the Y Combinator network is a way of becoming even more insular. It’s a place where people are reinforcing each other.

There is a sort of set of ideas — you can even call an ideology — about entrepreneurship, company culture, and scale that I think can lead to homogenous workplaces. I have a scene in the book where my team manager brought us all into a room and said, Write down the names of the five smartest people you know, and then asked us, Why don't they work here? I thought this was just something that had happened at my startup, because there was such an intense culture, but then a friend of mine read the book and texted me the other day and said, I can't believe that this happened to you too. This must have just been a blog post that everyone read.

ES: It makes me think of how technical interviews are structured. Everyone decided that the best way to interview software engineers was to put them through these brain teasers, and they've evolved from brain teasers to be these algorithms problems that are still very cerebral. Across the industry, every technical interview is nearly the same. And it's become the standard. It’s weird because Silicon Valley rejects institutions. The best CEO is someone who's dropped out of college, but they've formed institutions and practices that have grown to become their own.

NL: The scourge that is venture capitalist Twitter is virtually indistinguishable from the sort of self-help nonsense spewed by capitalists like Andrew Carnegie.

AW: These new institutions are also just replicas of fairly old and conventional business philosophy, like Harvard Business Review distilled into CliffsNotes. I feel like that ties into this sort of ahistorical, anti-intellectual, anti-academic kind of mentality. And obviously the person with no experience has to fit into a certain framework — they've dropped out of a really good college, probably have some financial security outside of work, and are really confident and have like, nice skin.

NL: There is a widespread disdain for universities, if it's not an Ivy League school you're dropping out of. But at the same time, so many corporate facilities are modeled on college campuses and sort of use the structures of college applications to facilitate deciding whether or not someone is all around smart enough to work for them.

AW: There’s a lot of excitement among the VC Twitter set about this one startup called Lambda School. They claim to be attacking an important problem: people who are saddled with student debt and are in jobs that are not highly valued. It’s all about economic mobility, and it’s hard not to be on board with that. Where I chafe against it is how it's positioned as an alternative to higher education that is superior because it directly leads to employment — not just employment, but a high-paying job in tech. I feel that Silicon Valley is really good at circumventing social issues and creating alternatives that are private and monetized and tend to focus on the individual capacity for change. And so to me, this isn't really tackling student debt. Can businesses engage with social crises, such as the student debt crisis? Or are they incentivized to only act in these circumventory, atomized ways?

I also just feel like any value system where the end of the idea is that the usefulness of knowledge in society is correlated to one’s income or economic utility — if you continue that to its endpoint, it’s an incredibly grim vision for society.

NL: In other interviews, you’ve spoken about your willingness to empathize with people who others may not be as keen to empathize with. What do you think is the political utility of writing about Silicon Valley in such a humanizing way?

AW: I don’t personally harbor contempt for the people I worked with, or even for. I do think that this sort of structural view that I talked about earlier can be a mode of forgiveness. The flip side is that the structural view can be exculpatory; it can exonerate people who don't deserve it, who aren't necessarily acting due to structural restraints or incentives. I don’t want to let people off the hook who don't really deserve it. Where you draw that line is complicated, and I think that, rightfully so, the book’s been called out for being flattering to power. I think that that's something I've grappled with in writing and something I'm still grappling with as a journalist, and also as a person who lives in this world and who has friends in different corners.

I wouldn't even call it empathy. I wouldn't call it kindness because the book is cutting. It’s critical; it’s not the book I would have written at 25. My hope is that it’s generosity. I want the book to be read by people in the industry. There are enough indictments of tech and those are really valid criticisms, but I don't think that people in the industry read them, and if they do, they feel that they are being unfairly criticized. My hope is that the personal narrative illuminates the structural narrative. I think the structural level is where we need to do the most work. That's collective work, not individual work, but the individual story can maybe be useful and getting people to think about that bigger picture. I also just don’t think cruelty is productive.