Mastering the Male Market Thrillist founders Adam Rich and Ben Lerer talk about the inspiration for their guys' night out e-mail newsletter.

Entrepreneur: What was your goal from the beginning?

Ben: We wanted a voice that we could trust but we didn't want to know who that voice was. The attitude is really where it has to be. We've never had a masthead.

Adam: From the beginning one thing we knew is we wanted Thrillist to feel like it was your friend talking to you but maybe your friend who had been in the city a couple of years longer than you or maybe knew more people. Guys in general don't want to be made to feel that they're inferior to other guys. There's a competitive element to guys our age.

Ben: People make assumptions by the way they look or the way they talk. The voice speaks so much louder than the actual person talking. We're not looking to run around as the center of attention. We prefer everyone to have a great time and have our sponsors be the center of attention because obviously in the long run, it depends on our sponsors being really happy. It's important that the sponsors are the kind of brands that we think will reflect well on Thrillist the same way that we reflect well on them. Dos Equis is a great brand, Skyy is a great brand. They're brands that are mainstream but they are cool and they're successful and professional and it reflects well on a small business like us to be working with such high quality brands to be working with these wildly successful companies and have them trust us to represent them is really big for us and we're happy to put that out in front.

Adam: There's a real synergy and there's also a kind of ironic thing to it because they're really excited about us because they're big successful and established, whereas we are so little and kind of on the edge. We don't like to be so little we hope to be bigger. They like to associate themselves with a little up-and-comer. We're proud to have caught the attention of a really successful industry player. That has worked to the benefit of the partnership.

Entrepreneur: In what other ways do you work with the sponsors?

Ben: The biggest relationship that we have is advertising. Sponsors go on and buy media. Sponsors can buy allied info e-mail--dedicated e-mail where we lend our editorial voice to a sponsor's message and we send it out to our. Our editorial team tries to glean what is most appropriate. We actually get to swap out the best parts of the advertiser's campaign and put them front and center coming from a voice that our guys have grown to trust because it's the editorial voice of Thrillist.

Adam: It sort of presents that with the sensibility that we do to everything else at Thrillist.

Ben: We also do standard banner display advertising because Thrillist is a subscription model and not people who are kind of lost on the internet like other web properties where people are kind of just sharing links not really necessarily feeling any kind of connection to the brand that's speaking to them. We find we get great responses to the advertising. Even display advertising gets higher click-through and better performance in general because people are in an environment where they feel that everything we write about is a recommendation and not a review. It's a really positive environment for advertisers where they are being set alongside something that we are saying is really cool so they're always in an environment they know that people are it's a positive feel and it's action-based. It's go here, do this, buy this. And all that positive action really rubs off on the advertisers. So we have text ads and banner ads on e-mail. That has been our primary model to date.

Producing events is part of the bigger picture and selling advertisers to those events. We're starting to kind of grow beyond just e-mail. E-mail has been amazing to us; it will be part of our business forever but we feel we can better serve some segments of our audience--people who love e-mail but want more. We have people who read Thrillist every day and use it to plan their social calendar but still have to go to Citysearch to get the phone number. We should be able to provide that, and on the website we're going to build out the city guides in a way where people can hopefully not use any of the other more general things. They can use Thrillist and go through a city guide to get the information they want more quickly in a voice that they trust and get all of the information more efficiently than they are today. So we are going to be adapting a slight web model, and in the future we're looking how to expand content.

Entrepreneur: How are you in the know?

Ben: we're not necessarily in the know as individuals. We're very proud and we love it and when we started it I think we were really in the know but we probably work too hard to actually know what's going on. The idea was kind of predicated on us having a team of people in each market that their basic task--their entire job--is to be in the know. So each city gets a full-time editor whose job is to write 800 words a week which is not a lot of content to actually produce. They have the rest of the time to spend finding the best stuff and combing the city, whether it's walking around, on the phone, tipsters, scouring the internet, playing with delicious flicker web application to find content. We can't do what we do without being plugged in unless we have someone who has been there for years who knows the restaurants--not just what opened but what was there before and what was there before that. So they really understand the city. They're speaking from the perspective of someone who really understands the market. It's crazy for us to think about. It feels so New York to us but we surveyed our entire audience. More people from California responded than New York.
By September we'll be in Miami and by the time this comes out probably another city. Our new website launches in September.

Four or five months ago, we were half the size we are now from employee perspective, half the size from an audience perspective, less than half the size from an advertiser perspective. Things are changing so rapidly that I don't know what. things are really happening at a breakneck speed this year.

Entrepreneur: Did you expect this kind of growth?

Ben: No, we actually already have a bigger audience and more advertising revenue this year than we predicted for the whole year. We're 40-50 percent ahead of what we projected for 2008.
Adam: when we started out, we were working really hard because it felt like we were working our tails off. We were working so hard at figuring all of this stuff out. As we figured more stuff out, things have become less stressful land we've been growing faster so the whole thing has a surreal quality to me in the last year.

For the demographics we service, getting the tone just right and the things we talk about and interest areas locked down, it's critical. That's one of those instances in execution where if you miss, you are going to put yourself just like the rest of the pack. There are other men's things out there that are stumbling through things and don't have a firm grasp on what they are and we really worked very hard to make sure that was never the case for us.

Entrepreneur: Who is your target demographic?

Ben: from the advertising perspective, 21-34 and male. Typically guys like us. Guys living in big cities who work hard and play hard. The editorial does a really great job of writing really funny slapstick humor that is also incredibly clever and has several layers of jokes in there. You'll find that our average reader is very well educated, really intelligent. They're successful people with a sense of humor who are all about fun. We started it because we were living in New York and we were pissed off that finding fun stuff to do was so difficult because there wasn't a trusted voice that gave us information about guy-related content. We couldn't trust the information that we were getting because it wasn't coming from someone with the same interests that we have. Frankly, we have no business starting a company or writing content for anybody and the idea is not ground-breaking. We worked hard and we wanted to make it work and the execution is really the difference between the millions of ideas. The best advice we ever got was when we started the company, we tried to talk to smart investor people and smart business people, whoever we could get our hands on, we'd go and tell them our idea and everybody said, "That's such a great idea, you'll do great." And then we sat down with someone and his response was, "That's just an idea. Go out and do it." A great idea is 10 percent of it; execution is the other 90.

Adam: Everyone was all smiles and pats on the back and no one ever wanted to tell us that it's more than just coming up with a concept.

Entrepreneur: How did you take the advice?

Adam: We basically just took all the money we could scrape together. We had full-time jobs. We hired our first writer on a part-time basis who wrote constantly for six months. It was just an exercise. Probably about six to eight months after we came up with the concept, we started doing actual work. We worked very hard but we also had very little time. We worked on Sundays and two nights a week but it wasn't enough to get the ball rolling. We outsourced the web design to a company in Argentina. We worked nights and weekends. We rolled it out very slowly.

Ben: Then we raised money in August 2005 and the money was to help us get off the ground in October 2005 which is when we went official to the public and launched the newsletter. Our investor forced us to do things slowly and didn't give us a bunch of money. They said go out and build a product that people will like and once we see that the list is growing organically on its own and the content is working. Very early on we were self-sustaining as a business. We had very low overhead and we were generating real revenues pretty quickly. And so we've always had the opportunity to be in the black and reinvest in the business.