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San Francisco is a gold rush town.

There aren’t many books about people in their 20s who move to Silicon Valley with dreams of earning a living wage with healthcare benefits and celebrate living in a ground-level apartment with views of people fighting to enter the locked Porta Potty.

But Anna Wiener isn’t telling the story of a venture capitalist or a 24-year-old wunderkind. She’s telling her story, the story of Uncanny Valley.

Wiener leaves New York City and an entry-level job in the publishing industry to become part of the start-up culture in Silicon Valley. In her paradigm shift from coast to coast, Wiener trades her wrap dress in for a company hoodie and a corporate structure for no job titles and unlimited vacation.

In her memoir, Wiener shows what it is like to be part of the tech industry as a double-minority of sorts—not only is she a woman in tech, but she’s also a woman in tech who doesn’t have a programming position.

Uncanny Valley, her first book, looks at the tech world through the lens of a tech worker in customer support at a time when the industry shifted from unbridled capitalist success to capitalism out of control.

She talked to ÀÏ»¢»úÎÈÓ®·½·¨ contributor April Umminger about billionaires in their 20s, changes in the industry after the election, and her experiences as a tech worker who didn’t do tech. Their conversation has been edited.


ÀÏ»¢»úÎÈÓ®·½·¨: I’m very intrigued by the title of the book. Where does Uncanny Valley come from?

Anna Wiener: "Uncanny Valley" is a phrase that's often used in robotics and in aesthetics. It describes the feeling that a person has toward a robot or an object as it increasingly becomes more realistic.

With respect to robotics, if you are confronted by a humanoid robot, as it becomes more and more humanlike or takes on human qualities, people tend to feel an affinity for it.

But then as it approaches a certain level of life, it can become too realistic. And then there's a dip in that affinity, and there's a sense of revulsion or eeriness.

Suddenly the emotional experience moves from one of affinity to horror that is in direct correlation to how realistic a robot has become.

For me, that was a very similar arc to my own experience of going into the tech industry with enthusiasm and affection and curiosity. Then slowly, as it intensified or I was able to see it more clearly, I began to want to withdraw from it.

GR: Though I can guess after reading your book, what inspired you to write this memoir?

AW: I came into it backwards, as I tend to do things. I wrote the piece for N+1 that was supposed to be a review of a book called Lean Out, which was a kind of retort to Sheryl Sandberg's Lean In.

I started sprinkling anecdotes from my own life and from my experience working at start-ups into this review. Then it morphed into just being anecdotes, and then it became the piece from which the book emerged.

It was sort of an accident, but once I started writing it, I realized how much fun I was having documenting that world and processing my own experiences.

And then the election happened in 2016, and I felt like something had ended, that some era had come to a close. It suddenly felt more urgent than it had before to really document what had just happened and what had ended.

It seemed like there was an abrupt door slamming shut to a period of time.

GR: In your book you talk about an era coming to an end and people having their eyes opened in different ways. But what shifted so dramatically here?

AW: The industry suddenly found itself under the spotlight, and suddenly it was being criticized, scrutinized from all angles in a way that it previously hadn't experienced. A lot of attention was being paid to Silicon Valley in a very new way.

There was this sense of accountability that hadn't existed before—or the sense that there should be some accountability and the unchecked momentum of the industry was being questioned as a moral good.

The industry had all these narratives about itself that was easy to buy into. In 2016, people started to call those narratives out.

GR: Just seeing the way things are evolving in tech with artificial intelligence, machine learning, facial recognition, etcetera, do you think things have changed?

AW: In the industry?

GR: Yes—do you think there is more accountability? From an outsider looking in, it still seems like technology is running at a speed faster than checks and balances.

AW: I would agree with that statement. But now there's a question of accountability, and I think that's the first step; that's more than we had previously.

Also, what changed is this feeling that what was happening in Silicon Valley was isolated. For a long time it felt like its own ecosystem. And after the election, suddenly the whole world came flooding in.

The shift was maybe one more of affect than of something more tangible or concrete.

I wrote in the book that it did feel like someone had flipped the lights on at a party and caught everyone in the middle of things that they might only do in the dark.

GR: You are very careful with your phrasing and identification of companies in this book. Was it lawyered to death to keep the names out?

AW: The book was vetted by lawyers, but the reason I left out company names and executive names was more of a stylistic decision.

It didn't matter who the companies were—the experiences I had were very universal. I didn't want this to become a book about any particular company. I wanted it to be more about this feeling of trying to find your place in the world in your 20s.

GR: There are many different ways to read your story, and in one way I could see it as a coming-of-age story, where your awareness was changing even though your situation was staying the same. Have things changed? Do you see tech itself evolving or becoming more emotionally intelligent?

AW: Yes, I do think the industry is changing.

With increasing criticism there has been more conversation. I wouldn't say that we've entered a golden age of tech introspection, but people are talking about things I don't think they were talking about six years ago. I find that very hopeful.

In a way, it's becoming more itself, and that is for better and for worse.

Some of the employee organizing has been interesting and the way people are starting to realize that if they're building these tools, they should have a bigger seat at the table.

But, like I said before, it is a relatively young industry. It's sort of being pushed to grow up.

[Laughs.] I'm not saying that it is. We may have an adolescent situation here.

GR: You mentioned the book Lean Out, and when I was reading this, I was thinking about Sheryl Sandberg and her messages in Lean In. How was that book received, and how do you hope yours changes the conversation around women in tech or tech in general?

AW: I will admit that I wasn't paying a ton of attention to Lean In when it first was published, but it shaped a certain discourse.

I don't know that my book and Lean In are particularly in conversation with each other. I do think Sheryl Sandberg perhaps promotes a certain idea that I might describe as corporate feminism, where she is probably very inspirational or aspirational for people who have executive-level ambitions.

My book is really speaking to the experience of an ordinary, average, rank-and-file employee. The biggest difference I might draw out is that Lean In is a book about succeeding within a certain system and my book is more about questioning that system and who it is working for.

GR: You mentioned your former CEO from the analytics company quite a bit. What message would you want him to take from this and your time working for him?

AW: Excerpts from the book ran in in September, and we had a brief email exchange after that.

In the book, I err on the side of, I hope, compassion, and I'm trying to understand where he was coming from. I think it must be incredibly difficult to become a CEO at the age of 24 with no prior work experience and very little life experience.

He was a really smart young person with an idea that appealed to investors. But then he's also 24, and he has $12 million and needs to build a company quickly and grow it very quickly. Anyone in that position needs a lot more structure than the industry tends to provide.

As a takeaway, my hope is that he'll look at some of the structures that helped him in his own role and the way that he structured our company and behaved toward employees. My hope is that we can look, on the structural level, at what's going wrong when you give a 24-year-old $12 million.

I also hope that he sees that what's happening inside of these companies is really more than just business—that it really does affect employees on an emotional level.

I'll be very curious if he does read it and if I hear from him.

GR: That is a good segue into Silicon Valley and how it is different from and similar to other big coastal cities, or anywhere. In terms of the good ole boy’s club that you describe, some of this struck me as same story, different time, different place. How do you think Silicon Valley and the gender dynamics you describe in Uncanny Valley are unique?

AW: [Laughing.] Tech is a relatively young industry, and my thought that those dynamics would be limited to this industry is just like something from someone in tech, who thinks that they've discovered everything.

There is a lot of commonality, and it’s not unique to tech.

My feeling about tech is that it's like capitalism on steroids. It has inherited the social problems of any other industry, but it seems to be accelerated and amplified and maybe intensified in part due to some of these narratives I mentioned earlier. The founder genius narrative. The disruption narrative. This idea that it has a moral superiority because it is economically successful.

There are cultural and aesthetic differences, but a lot of that experience is probably very consistent across other industries.

GR: You went from publishing to writing to tech to writing. Are you still a big reader? What books are you reading now?

AW: I just started reading The Factory by Hiroko Oyamada. I also just read the new Jenny Offill book, which comes out in February, called Weather, which is about climate change. She somehow managed to write this short, beautiful little book that is devastating but also very funny. It left me with no hope, but it spoke to a certain type of anxiety that exists in the culture right now that I hadn't quite seen articulated in literature.

GR: What books would you recommend for people who want to learn more about tech culture or the sorts of issues you explore in Uncanny Valley?

AW: For people who want to read more about our relationship with the work for technology, I really love Jenny Odell’s book, How to Do Nothing. Katherine Losse wrote a book about being an early employee at Facebook, The Boy Kings, and that's very illuminating in hindsight. I love Ellen Ullman’s Close to the Machine, which is about her experience as a computer programmer in the late '90s in Silicon Valley.

There’s a whole genre of workplace novels that I think can be interesting and really fun. It’s a little tangential, but as people learn more about the industry's origins, From Counterculture to Cyberculture, by Fred Turner, is a book that I loved.

GR: Who do you hope reads your story, and what do you hope they take from this period in the tech industry?

AW: This is a book largely about work and about a certain generational attitude toward work. Like you said, it's more universal than just a Silicon Valley start-up universe.

I do hope that tech workers read it.

I have received a lot of emails about other stuff I've written about my experience working at start-ups. I've received a lot of emails from other tech workers, from companies I've worked for, and companies I've never heard of expressing solidarity or a recognition of their own experience in my writing. That means the world to me.

I hope that it speaks to people who are trying to build a meaningful life in a way that seems like it's getting harder and harder to do, and that's not generational at all.

I'm hoping it starts conversations that I wouldn't know to start.