Wiener was a customer-support manager, not an engineer or a founder, so she always found herself a little bit peripheral to the big-dreaming action, but she was still present for the glamour and the gold rush. She wasn’t a CEO giving Beyoncé millions of dollars in stock to perform at a party—she was an average employee, interested in finding fulfilling work and worrying less about money than she had been. “I would allow myself to be taken care of,” she decided at one point. “As if I had done something to deserve it.”

I spoke with Wiener over the phone the day before her book’s release. This interview has been edited for length and clarity.

Kaitlyn Tiffany: The aspect of the book that really grabbed my attention was the fact that you weren’t this stereotype of a disruption-hungry bro who wants to make a billion dollars, but you could still be taken in by a lot of the promises of Silicon Valley. What made Silicon Valley so seductive to you?

Anna Wiener: This is a part of the book where I hope the personal story illuminates the structural story of Silicon Valley. For me, the things that were exciting about tech had a lot to do with the fact that I had graduated into a job market that had been affected by the recession dramatically, and I had gone into an industry that felt like it was shrinking. There was a feeling that the sky was always falling.

In tech, it wasn’t so much the products that I was excited about. I wasn’t like, This is the utopian frontier. It was more like, Here’s an industry where there’s a lot of opportunity, there’s a lot of money, there’s a lot of excitement. More than that, there’s a sense of momentum and a sense of freedom for even rank-and-file employees at a start-up. There was something really gratifying about that. It sort of affirmed these stories that I had been told, how I could do something in the world that had an impact. I had always assumed I would feel useful in some sort of way. And in tech, you just feel incredibly useful, because you’ve worked incredibly hard and you’ve been sold a lot of stories about the importance of that work.

It was just that feeling of momentum and of latitude. This industry was only going to grow, and you were only going to find more opportunities for yourself. It just seemed so anomalous in that economy.

Tiffany: Early in the book, you say that what hooked you was “the eagerness and optimism” and “the boyishness.” What was so charming about the boys?

Wiener: As a self-conscious, sort of shy, professionally awkward [woman], for me in my 20s to encounter that young male confidence—I wanted it. I wanted to feel confident; I didn’t want to be insecure. I wanted to feel like the world appreciated me, and that seemed like a pathway [toward] feeling useful or having the feeling of having found one’s place.