his and Jessica’s [Livingston, YC Partner and Paul Graham’s wife] deciding to let me watch the program.
X: What was your pitch to them?
RS: The Benchmark book used a fly-on-the-wall approach that tried to give the reader a vivid sense of what happened. I reused the pitch from eBoys with Paul Graham and the other partners. Which was: this is a historically interesting moment, and journalists shouldn’t get to be the only ones who do the first draft of history. Historians should get to too.
X: So you think of yourself primarily as a historian? You’ve published in a lot of journalistic outlets, such as the New York Times.
RS: I was trained as a historian. I think I have a historian’s sensibility. So I practice journalism, but I think at heart I remain a historian.
X: Did the partners buy your pitch, or did it take some persuading?
RS: I don’t know what went on—it was a pretty short exchange of e-mails. The only objection initially was that the timing was not right, because they had already given permission to a group of filmmakers to film during the Summer 2011 batch. Paul had initially said “I can’t have you both here at the same time, so it’s not going to work.” And I thought that was the end of it. Then he came back a few weeks later and said he had given it more thought, and there was going to be a large batch, so there would be lots of companies for each of us to follow.
So I started with the expectation that I would have the filmmakers there too. Which would not have been ideal, because I think the presence of cameras would have made everyone self-conscious—more so than just a writer with a tape recorder. As it turns out, the filmmakers apparently had difficulty getting the funding they wanted, so it was just me.
X: Speaking of self-consciousness, do you think you got a good look at how Y Combinator really works? The presence of an outsider always changes things a little bit. Do you think the YC partners and the founders behaved around you the way they naturally would?
RS: It’s hard for me to judge. Certainly, as time went on, I think everyone became more comfortable with my presence. Because most of the situations I was sitting in on involved three, four, five, or more people, the numbers were in my favor. I don’t think I stuck out as much as I would have in one-on-one conversations.
X: Also, I’m assuming the startups all knew that you were working on a book, and that the details wouldn’t come out for a year or more.
RS: Yes, that was something that was important to the partners. They understood that this was a different sort of thing from a feature story. There would be that delay, and that meant that things that obviously were very sensitive at the time, were they to be made public, would not be so sensitive a year or a year and a half later.
X: Did you have full editorial independence?
RS: Yes. The only restriction that was imposed on me—and I didn’t realize it when we started, but I understood the necessity for it—was that I could not record or use the Tuesday guest appearances. Those are off the record permanently. They have a tradition of enjoying complete blanket protection of what is said, and Paul Graham didn’t want to impinge on the speakers’ comfort in any way.
X: Did you have a picture of Y Combinator and what it’s like to be a YC startup before you started the project, and if so, how did that picture change as you went on?
RS: Because I took an anthropological approach, I did not have a model in my head that I needed to adjust and edit and update. I was ready to observe whatever unfolded. Also, I was so busy trying to follow as many of the companies as I could that maintaining some mental model wasn’t really the thing I was worried about.
I had this challenge of following what started out as 64 companies, and I knew I couldn’t follow them all. So how would I know which ones would produce the most interesting stories, the stories that would have the most representative characteristics? That’s what I struggled with.
X: How did you resolve that?
RS: It was partly affected by who was willing to work with me. Probably four-fifths of the companies actively reached out to me saying they wanted to help. That still left a lot. So one of the things I tried to do was focus on the companies whose products or services would be ones general readers might encounter. There were some very specialized companies, serving narrow, vertical markets, where it would be very hard to describe what they were doing. There were a number of companies in the batch who are what I call D2D, developer-to-developer. Some of them were included in the portraits in the book but there were many that I could not include.
But I felt myself fortunate that the class had expanded in size. It effectively doubled between 2010 and 2011, which gave me that many more possibilities.
X: Can you contrast your experiences with the Benchmark Capital book and your experiences inside YC? What struck you most about the ways startups have changed since 1998?
RS: One of the things that struck me, of course, was how young the founders were, and the absence of a requirement that they put in time at one of the technology powerhouses before they would get investors to back them. Back in the late 1990s, you would see engineers leaving Microsoft, HP, Oracle, or Cisco to start their own companies, but they had
