Video Transcript

00:08 Adam Rich: I thought to myself, "I think I made a terrible mistake here starting my own thing. I think maybe I should go and see if they'll take me back at this software job where I didn't see a future for myself."

In 2005, Adam Rich quit his job as a software engineer and co-founded Thrillist, a men's lifestyle website and email newsletter.

00:27 Rich: Everybody warned us, "Starting up a business is really hard. You're gonna work lot, there's a lot of hours", and we thought, "Okay, we can do that." But what I don't think anybody really kind of made an issue of, that we found to actually be probably the most strenuous elements of it, was the emotional toll of the project. And I think, Thrillist wasn't a especially emotional one, because one of the strengths of it for us, as first-time entrepreneurs, was that it was a very personal project. But the flip side of that, and how it's double-edged sword, is that just as felt very personally about the product and the successes we saw from it, the failures were that much more painful.

In Thrillist's first three years, its e-newsletter gained 550,000 subscribers.

But in that period, Adam and co-founder Ben Lerer weren't able to get Thrillist to turn a profit.

01:18 Rich: Ben and I were extremely close. We've been friends all through college. He's a year younger than me, and friends after college, and I think it made us very well-suited to sort of launch the shared vision of a project together, but it also made it very tough because we didn't always agree. And there was one instance where we were putting together a piece of content on Chinese New Year's and it was one piece of content out of the five that we were gonna put out that week, but I don't even know what it was that we disagreed about it, frankly, was obviously, so minute disagreement. But we just both dug our heels in and both of us, because we felt this project so personally, were positive that we were the one who is right and the one was wrong. And we were unable to reach any kind of consensus. We were not at a point where we could step away to actually put things in perspective and realize, this is one piece of content out of five for the week. That was really kind of a low point where I thought to myself that this was just too emotionally fraught... An experience, to have it be sustainable.

Adam did not quit.

In 2008, Thrillist turned its first profit.

02:34 Rich: We had celebrated the seventh anniversary of our very first piece of content in May of this year. And I read it to our entire company, a 200-person plus company. And going through it, it was such a terrible piece of content. This was very first thing that we put out there. We took literally a month to get this to where we thought it was perfect and we agonized over every little element of it. And it really served to remind me that it's never a question of do or die on any one little thing, but it's all part of an overall effort, and it's totally understandable to be stressed out about those little things, to have those keep you up at night. But this was the very first thing we sent out there, and looking at it now, it's an utter piece of trash, but here we are, seven years later, and we're successful.

Today, Thrillist has over three million subscribers, with e-newsletters in 21 cities.

In 2011, Thrillist--which now also includes the shopping site, more than $30 million in revenue.