Portfolio.com: Are you specifically looking for New York-based startups?

Wilson: We want to be able to invest as close to home as possible, as often as possible. We have been living and working in the New York market for a long time and we know a lot of people here. So if we need to bring in a V.P. of sales or a C.F.O., here in New York we have a really good sense of who those people are, and we can be much more effective doing that. And the other thing is, we can see them. We can have breakfast with them once or twice a month. We can go to meetings with them, and help them in ways that it's harder to do if they're not here. So, we'd love to make every investment here in New York, if we could. We don't, but that would be a great thing if we could.

Portfolio.com: So basically, you just love New York too much to leave.

Wilson: I grew up in the business here in New York. After I got out of business school in the mid-80s, I started doing venture capital in New York and made a home here. And I've figured out how to do it here. In some ways it's better to do it here because in Silicon Valley there are 500 venture capital firms, 100 of which are household names in the technology industry. Here in New York, there are maybe 20 or 25 venture capital firms and maybe five are household names. And so when you can be one of them—and we are one of them—it's a competitive advantage.

Portfolio.com: So would you say you like being a big fish in a small pond?

Wilson: That has helped us a lot. Union Square Ventures in only three-and-a-half years old, and I think that we have established ourselves in our sector as one of the go-to firms across the entire country. And I think one of the reasons we were able to do that here in New York is we were able to quickly assemble a high quality portfolio and make a name for ourselves in a way that would have been a lot harder for us to do in Silicon Valley.

Portfolio.com: Do you see a cultural difference between the tech scene in New York and the tech scene in Silicon Valley? Are West Coast startups more engineering-based, given their proximity to big research universities like Stanford?

Wilson: I think that there is [a difference]. In Silicon Valley, everyone is in the business. So your kids go to school, and the other parents in the school are in the technology business. They're either venture capitalists or entrepreneurs or they work in portfolio companies. So it's a little incestuous. That's a positive and that's a negative. Here in New York you're going to have a much more diverse set of people that you might know. So you can get away from the business a little bit here in New York. It's much harder to get away from the business in Silicon Valley. Again, that's a good thing and a bad thing.

I don't totally agree about the engineering cultures being that different. Google has built an enormous engineering organization here in New York. I think there may be 500 or more engineers working for Google here in New York now. So there are a lot of high quality engineers here in New York, and the companies that we invest in here in New York have great engineering teams. Everyone says that [Silicon Valley has better engineers], but I'm not so sure that's true. I think that the differences have more to do with the kinds of people and what their everyday lives are like in the startups here in New York and the startups in Silicon Valley.