Anna Wiener On Uncanny Valley And the Intoxicating Promise of Tech

Of course. I’m a pretty conflict averse person so writing this book gave me shingles. [Laughs]

Literally, or…?

Yeah. I’m a very anxious person to begin with, that’s the baseline. But writing this I got so stressed out about the ethical considerations to make: who has power, who doesn’t have power, do I have power? That’s sort of new for me in this respect. One night I took a bath to relax and I was like I’m going to get high and take a bath, I’m going to relax and re-approach this project with clear eyes. And I got out of the bath and was like, I think I had a bad reaction to the salts and then it turned out I had shingles.

Oh my god.

I do not recommend getting stoned and Googling “body rash.” [Laughs] But, yes, I have thought a lot about that. My whole approach has been to treat it with generosity, that’s where I wanted to come from, was a place of generosity as much as possible and not from contempt. Executives and people with names [in the book] are specific people, there are composite characters who kind of compose the rest of the companies. I interviewed a lot of my old coworkers, I got direct quotes from people, people who are named in the book all read their sections and gave me edits.

I’m not that worried about what the companies think, I’m much more concerned with the judgment of my peers. I’m also aware that the culture sort of encourages a certain style of fealty or commitment to the cause of the company and so writing this is like breaking a pact. [Laughs] So I assume some people will feel betrayed. It’s an indictment of the culture, not an indictment of any individual perhaps with some minor exceptions. I tried not to think about it too hard because I think a problem I have in the world as a person is I’m a little bit of a pushover and I think that it can be easy for me to let someone else the narrative. So I didn’t reach out to coworkers until I was halfway through writing just to be like, okay, I need a gut check and I just needed to get down where I stood before I start to question it.

If you’re in an industry where there’s nothing but money, nothing but opportunity, it seems like a place you can make yourself fail-proof

I feel like that sort of start-up-y, specific, “we are family” rhetoric, you know “we have merch and people get tattoos of the logo thing” is kind of bleeding out from start-up culture and maybe any workplace that uses Slack heavily? Maybe that’s a generalization…

I have friends in the restaurant industry who say that this is sort of what happens in food service as well. You have the family meal, you have the family rhetoric and an emotionally volatile and intense environment. It’s obviously a narrative that’s used to exploit people, to take advantage of people’s desire to be part of something and people’s fear of any sort of precariousness. It’s interesting that it’s happening in media because it’s such a fluid [industry], I feel like people are moving around all the time.

I think in media it goes back to this idea that you’re supposed to feel forever grateful that someone is paying you to do creative work.

I mean I do feel grateful. I know as a labor/power dynamic that’s super fucked up. I’m curious about what you just mentioned about Slack.

Well, I think that Slack demands your time in a way that is all-consuming. It maybe doesn’t necessarily connect directly to those feelings of the company as a family, but it feels like you’re in a group chat with your coworkers all the time? And it doesn’t really turn off? You have to take steps to turn it off.

It’s sort of like the forum dictates the style of communication. In Slack people behave very casually, especially in the younger workplace because it’s people who were raised using AIM and text. I often have felt some anxiety over just how much I reveal of myself through those channels. It’s not that I’m embarrassed, I am who I am, I’m pretty consistent. But it’s stored forever, I don’t know who owns that, I don’t know who the administrators are or who in the company can see your private chats. There’s always some administrative tier that can look at anything. We just saw that with this story about [the luggage company] Away. I think when you’re being casual in the workplace, everything starts to break down around communication.

You mentioned not wanting to approach these companies you worked for with contempt. You do criticize these places in the book but something you also do is kind of draw out how intoxicating this industry can be, writing a lot about wanting to belong in these spaces. I’m curious why that kind of environment sticks with people? Why do you think it’s so prevalent in start-up culture?

I think in start-up culture, it’s a very young culture. For a lot of people it’s their first job right out of college, there are a lot of executives for who management is a novel idea, a lot of founders who are in their early twenties. A lot of people move [to San Francisco] to work at these companies, so you have an immediate social group at your company and you’re there all the time anyway. I think also young people in these jobs tend to not have any dependents or family to go to at the end of the day, so it kind of fills in for everything.

I tried not to be the killjoy, which, of course, the minute you say anything you’re the killjoy forever.

I think one thing, and I don’t have numbers for this, but anecdotally my feeling is that the higher risk the start-up the more privileged the employees are going to be? So that’s when I think about dependents. I’ve weirdly only had the experience of working at two companies in San Francisco that were doing well and I think that when a company is doing well, you think it’s because of something you did and that sort of social affirmation is really intoxicating. I think as a culture we tend to conflate moral value with economic value. I think that that can feel very affirming especially if you’re someone like me having come from an industry that is sort of embattled. I also just wanted to avoid this feeling of failure. So if you’re in an industry where there’s nothing but money, nothing but opportunity, it seems like a place you can make yourself fail-proof, especially when every other industry around it seems to be incredibly precarious.

You have these moments in the book where you kind of take stock in terms of the ways in which working in this industry has kind of changed you, even kind of cosmetically. You talk about buying a lot of fleece and workwear, paying a hypnotist $200 for a session. What did it feel like to kind of step outside of yourself and take note of those changes, that you were assimilating a way in these spaces?

I’m just guilty thinking about all the Patagonia I have stuffed in my tote bag [Laughs] I think there are a bunch of shifts I experienced. I was the fourth woman at a company with 20 people and they didn’t hire a fifth woman for a little while, so I definitely tried to dress the sort of California, outdoors-y, gender-neutral look. If I went in wearing a blouse or something someone would ask what I had going on later. And I’m not into fashion, I don’t know anything about clothing, so for someone like me to feel overdressed… [Laughs] I think part of that was just me trying to strip away any markers of hyper-feminine, gender representation. Not all the time, but there’s really no reason someone like me should be wearing work boots. All my coworkers wore these work boots because they lived in Berkeley and I got the work boots thinking this is the look here, but I felt so foolish wearing my farm clothes to this climate controlled office where you couldn’t even open the window.

I do think some of the narratives about people in tech trying to minimize their clothing choices by only having 8 shirts are a little overstated, but there is something to that. Everlane was big in San Francisco before it was probably big anywhere else. There was a point where I was like: we’re all wearing the same sweater! And it’s kind of all of our “nice” sweater? I was thinking about American Apparel recently because [the writer] Emily Gould wrote a little obituary for them, and I was thinking about how American Apparel were these basics that were kind of sexy somehow. And Everlane are these basics that are sort of professional. Then I was like, have I ever seen anyone have a good time in an Everlane shirt? [Laughs] Like actually, have you ever seen someone have fun wearing Everlane?

No, no.

I’ve seen people present a really nice slide-deck wearing Everlane.

I think also computers and the Internet have become work. I can’t remember the last time I fired up a browser and was like, I want to explore!

That point about underplaying the feminine aspects of yourself, in the book you describe this kind of ambient sexism that permeates these companies. There was that line you wrote where you were getting lunch with someone and you pass by a strip club that people would go to after meetings. It’s such a small kind of example of how normal this culture is.

It’s such a weird strip club, can I just tell you about it? It’s called the Gold Club and the only time I’ve been there they were playing a remix of that Peter Bjorn & John song, [starts singing “Young Folks”] and there is the most bored looking stripper you’ve ever seen stripping. It was kind of incredible. I was like, this makes sense. Everyone was eating salad from the lunch buffet. I did go in the afternoon with a friend because I was like, what is this, I need to know.

But the sexism, much of it is not malicious, it’s just so engrained. And I will say coming from book publishing I worked in an office with all women and I didn’t really think much [about] it. I feel like I was acutely aware of being an outsider and I tried not to be the killjoy, which, of course, the minute you say anything you’re the killjoy forever.

I feel like there’s a very low bar in these spaces when it comes to being the killjoy.

Yes, all I wanted was for people to not say bitch in the chat room or post photographs of their girlfriends in bikinis. I want to give you anecdotes but there’s a lot I didn’t put into the book deliberately, just feeling like it wasn’t my story to tell. When I brought it out on proposal I met with a bunch of editors, it was the first half of the book, [and] they’d ask, “so what happens next?” And I got this feeling that some of them were like, we’d like it if you were a little bit more sexually harassed.

I mean I feel like “being a woman in tech” is kind of a buzzy topic, but when you do point out sexism here the kind of ingrained, casual nature of it feels very realistic.

And it’s so broad. I’ve had a couple people be like, “so, being a woman in tech, tell me about that?” It’s like, help! It’s hard. I wanted to be honest about my own experience, which I feel is actually quite lucky. There’s pervasive sexism and I do not feel like I experienced the worst of it, but I did hear about the worst of it. There were a few things I heard about toward the end of my tenure in the industry where I was just like, fuck this, I’m done. And it’s the specific incidents, but it’s also the way those incidents have been treated by a company and the way that people who are culpable for really significant transgressions are recirculated and forgiven.

There are very public cases of this of people who are accused of sexual assault who get ousted from their own company and then you realize it’s purely cosmetic and they actually then fundraise for a new company or become a VC. But when it happens to people that you know, for me I was just like I don’t why I’m helping these companies. It’s sort of the reverse of what the book is doing, which is using personal experience to illuminate structural situations? I guess I had been living with the structural situations in the back of my head and it took personal experience to really draw that out for me. I think that the people who have the most interesting answers to these questions are women in the engineering divisions. I think tech is still a little bit stuck in the corporate feminism narrative. Maybe we’ll dig ourselves out of that grave one day soon?

You write about moving to San Francisco to work in tech and you say that at the time it was considered sort of corny to be optimistic about the Internet. For you, was there ever a moment for you where it didn’t feel corny, where you were earnestly excited about the Internet and its possibilities? I think every year my friends and I are like, “oh I wish we could get back to the ‘old Internet’” but then what is the old Internet? Are we talking about the Internet a year ago, are we talking about the Internet five years ago?

I have a similar yearning for it. It’s this feeling of people sort of experimenting. I think the problem with the Internet now is that it’s corporate, it’s aesthetically homogeneous, it is highly surveilled, everything is an ad network, and anything that isn’t an ad network or corporate immediately dies. We have a sort of Internet monopoly situation. I’ve even noticed that the number of websites that I read has just dipped dramatically in the last few years. It’s not for lack of interest, I just feel sort of like I’m stuck in a mall and I can’t find the door out.

I personally feel trapped in the major social networks and when I worked at a company with Slack. I think also computers and the Internet have become work. I can’t remember the last time I fired up a browser and was like, I want to explore! Even Google the search engine makes it incredibly hard to discover things outside of the mega mall. Maybe what the yearning is is for something not corporate, not surveilled, not reliant on ads.

I don’t think most people know when they’re using an app that anything they’re doing can probably be seen by employees

Do you think people are growing increasingly aware that there are people behind the internet?

Maybe. I still think there’s too much focus on the executives and the narratives about the executives have sort of shifted. That’s been interesting to watch. It’s gone from “don’t bully Mark Zuckerberg, he’s just a boy!” to really people wanting to hold him to account. I’m more interested in stories about rank and file employees, what it’s like to be inside of these companies, who’s making these decisions and who actually has agency. I do think the work in organizing that’s been happening has given a face to some of these organizations. The Verge did a bunch of reporting on content moderators Facebook was using, [reporter] Adrian Chen has written extensively about this as well.

The thing I thought a lot about at one of the companies I worked for, but it’s an industry problem and not specific to anyone, is this sort of casual and one might even say reckless treatment of employee permissions. So, who inside of a company can see what. I understand that’s often really valuable at a small company so people can jump in and fix something or solve a problem. But I don’t think most people know when they’re using an app that anything they’re doing can probably be seen by employees or that information is potentially being sent to a third party company. The smaller the company, the more likely everyone can see everything.

There’s that moment in the book where you’re asking your friend Parker, “do I work for a surveillance company?” And you touch often on this kind of naïveté at these companies, people unsure what to do with Gamergate for example. How did it feel to kind of look on those moments in retrospect?

I just think everyone was in over their heads and I think it’s such an insular world, or at least it was when I was working there, people really did not think about the broader repercussions of how this works. I wasn’t thinking about surveillance at all until the [Edward] Snowden stuff happened and then my friend through the book Noah, one of my coworkers, he was sort of starting to think about [our work] as a surveillance tool and mentioned that to me. I think there are things that are so clear to people on the outside, like it’s actually not a difficult decision to moderate a platform. We shouldn’t have a situation where we have a company like Facebook is moderating free speech but we do have that situation so I think there’s a moral imperative to be more active in what they call a “community” until we fix the concentration and centralization of influence and power.

But I think if you’re inside of Facebook, as people inside of Facebook have said to me, and in good faith, [they’re] uniquely positioned to solve those problems that are unprecedented and they all have the best intentions. We can probably interrogate the phrase “best intentions” for the rest of our lives, but I think it’s just such a small world that’s telling itself that it’s doing the right thing. I don’t think people have malicious intentions, I really don’t. I just think there’s not a lot of context. It’s a really ahistorical industry. It doesn’t even look at itself, so my feeling looking back on it is really just trying to understand the conditions in which we were all so unprepared for it.