Hong: I think entrepreneurs want to make money. It's not that they do it for the money, but they want to make money. Because money is the measuring stick; it's how they know if they've won or not. And I think a lot of what drives entrepreneurs is the kind of legacy they are going to leave. They want to make a mark in the world and feel like their life mattered. Entrepreneurs are the kind of people who love ideas and want to build things, and add value to the world.

Livingston: Now that you're out of the maze, do you get asked out on a lot dates through HOT or NOT?

Hong: Yeah. I actually stopped using my dating service a long time ago as a way to find my own dates, because everyone on there knows who Jim and I are, and many of the ones who seek us out are crazy. I would often get random emails from women sending me naked pictures and all sorts of weird stuff. A lot of them want to date us because they have low self-esteem and they think dating us will suddenly make them hot and cool. Crazy, psycho girls can be fun to date for a while, but I'm a little older now and I'm looking for something a little more serious.

The ironic thing is that from running HOT or NOT, I care less about looks now. When I was a dork, I never really dated anyone who was hot. The models—they weren't going to date me. So you always aspire to it, they're like the untouchables. All of a sudden, HOT or NOT happened, and I was starting to date all these attractive women. I got a taste of it and I realized that looks don't make up for a good personality. Many of these girls were annoying. They were fun to hang out with, but I couldn't have a conversation with them. I'm sure there are smart and hot girls, but if you look at the hot ones first, it's harder to figure out if they are smart too. That takes time.

One of the things that I think is dogma within venture capital is that you don't want to manage what they call the "living dead." I don't know what the numbers are now, but back when I was working with venture capitalists, their rules of thumb were: typically one out of ten companies is a really big hit; roughly three out of ten go belly up pretty quickly, and you get rid of them. The other five to six are what they call the "living dead." They grow nicely, organically, but don't generate spectacular returns, and they take management time and energy. Those are the kinds of companies they prefer not to deal with, because it simply doesn't make sense. They have a fiduciary responsibility to their limited partners to generate a significant return, so they want to deal with firms that will tend to do that.