Tuesday, October 17th, 2017

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Ben Lerer Wants to Guide You

Ben Lerer and his college buddy, Adam Rich, were looking for some fun things to do in New York City. Frustrated with not being able to find what they were looking for, Lerer and Rich decided to start their own city guide. And in 2005, Thrillist was born. Thrillist is a daily newsletter designed for guys who are fresh out of college and looking for the coolest restaurants, gadgets, fashion, and entertainment spots in whatever city they find themselves. Thrillist started as a New York city guide and has since expanded to other cities across the nation, including Washington, D.C., Atlanta, Miami, San Francisco, Boston, Chicago, Dallas, Los Angeles, Las Vegas, Hamptons and Philadelphia.

I met up with Ben Lerer, CEO of Thrillist, at the company’s main office in the Soho district of Manhattan, NY, to interview him about Thrillist and the makings of a successful entrepreneur.

MC: How did you come up with the idea of Thrillist? What made you decide to start your own online city guide?

BL: The problem that we found was that the city guides that we were reading weren’t really targeted to guys like us; everything was very general, they were just aggregators of content covering everything in a given city, and so we found that we sort of couldn’t trust the information that we were getting. We would go to a city search and we’d spend all day sort of sifting through the crap to find where we actually wanted to go for dinner, or to find a piece of information that we thought was truly relevant to us. Unfortunately, we just didn’t have time for it. At the same time, we looked at the national men’s magazines that everyone’s familiar with-the Maxims and the GQs-and we found that the content that they were covering online wasn’t really relevant to us either, because it was all of the general trend stories, and nothing that really gave us advice on what to do and where to go and we figured if we sort of took a national bend sensibility and connect it to the local level, we’d really be able to create content that resonates with guys like us.

MC: When you started Thrillist, how did you initially get companies to trust and believe in your brand enough to advertise?

BL: That’s the challenge, right? Off the bat, we didn’t actually go and try to find advertising dollars until we already built up an audience where we had a little bit of reputation and a track record, even though it was only in New York at that point. We sort of had some success to build on and since the voice was pretty unique and the offering was pretty unique, we were able to go to smart marketers and kind of innovated marketers and convince them to run small tests with us and the hope and expectation was that if it performed well they’d come back and do more business. The audience was real and was engaged, so they did come back and spend more and as a result we were able to go from there.

MC: I read that you got funding for Thrillist from the very beginning, but when you started the company, how did you go about making this happen, when you didn’t have the track record, previous to getting the funding?

BL: Before we had funding, we sort of self funded it. It was myself, and a buddy from college and we were both working other full-time jobs and while we were working other jobs, we were sort of spending "beer money" on getting the website developed and just getting things off the ground. We were in a position where we were making a little bit of money go a long way, but we knew we did need to go out and raise money. We did all of the basic development and got something out there to prove the concept and once we did that we were able to go out and find the money pretty quickly.

MC: Did you create a formal detailed business plan for Thrillist or just a simple one considering the fact that you’re an online newsletter?

BL: Well, overtime, the business has proven to be much more complex then we had originally envisioned. Just being a newsletter online, we certainly never thought we’d have 40 employees, but here we are; it spiraled over time. With that being said, we had a pretty good sense of the business, we spent less time trying to project all the financials then we did developing the product. Once we had something that we thought was actually good and we had an audience that was engaged in it, we went specifically to an investment fund that had already has experience with a very similar property for women, called Daily Candy. So, we went to them and said "look, we’re not gonna sit here and do a bunch of fancy projections for you. We don’t have any clue what this business looks like in 3 years, but you guys sort of do. How about we partner up?" And they said "yes" and that’s how we were able to get them involved.

MC: So would you suggest that other website owners start that way with not much of a detailed plan?

BL: I sort of get asked these questions a lot with what’s the right order of operations to get something off the ground and I still have no clue. Frankly, I don’t even know how we did it the first time. It just seems like everything happened at the right time and we got really lucky. I think generally, when starting something, you wanna do as much as you can before ever looking to raise any money. A: It’s gonna get you a much better evaluation, B: It’s gonna get people much more interested in what you’re doing because particularly in an economy like this one, people aren’t just gonna throw money at a good idea. The execution is what matters and smart investors know that to be the case, so you need to put some real ‘blood, sweat and tears’ into developing something with value.

Then once you know you got something with proven consumer adoption or proven revenues or what ever it is, you got something that you know is working, then is the time to go out and raise money. But I think going out and raising [money] before you made something work is not a good idea. Anyone who’s starting their own business should be willing to work nights and weekends on their own project and have a full time job to pay the bills so that they can afford to spend nights and weekends working on their own project. I think that’s just the sacrifice that any entrepreneur needs to be willing to make. It doesn’t mean you work 120 hours a week, but you can’t leave your job and then see if it works. You need to be willing to test it and work at it while you’re still locked into another full time gig.

MC: Have you faced a moment while running Thrillist where the business was doing bad and you thought about quitting? How did you turn that situation around?

BL: The only times we ever thought about sort of "bagging it all" was before we actually got started when we were in the “concepting” theme and we started to do more research. I remember one day, four years ago now, when we found that Shecky’s had an e-mail newsletter. Shecky’s is like a little female focused events company that used to sort of have a bar guide, and we saw that they had a newsletter. I remember sitting next to Adam, like beside ourselves, that we thought that somebody had beaten us to the punch and we were out of business and we should never consider launching it [Thrillist]. Clearly, we realized that it was a different value proposition and we thought that we would do some things differently then they did. Only very early on did we question ourselves that much and fortunately we had friends and family to push us to keep going.

I think since we officially launch, and certainly since we raised money, we never looked back for a second and the business has never been in a position where we were struggling even close to enough that we ever considered the possibility that this wasn’t going to be successful. We knew it or we were at least inexperienced and blind enough to be the confident that it was going to work, that we never considered the possibility of failure.

MC: Do you make sure to personally visit all the places that you feature in Thrillist New York? Do your employees based in the other locations make sure to personally visit the places they cover?

BL: I don’t have anything to do with editorial these days, so I don’t visit anywhere–I don’t even read Thrillist until it comes out after. I read it the same time you read it in the morning. Our editors are responsible for either going first hand and seeing it, or getting tips from a network of freelancers whom they trust, before we cover something. Sometimes we cover a restaurant the day before it opens, but we know of the chef and the restaurant or behind it and there’s every indication that it’s going to be cool and worth checking out. Sometimes you have to just take a leap of faith, but for the most part we seem to be pretty good at picking winners. I think that there’s no exact formula for how to make something work. We do pretty thorough research and make sure that we’re very well educated about what we’re talking about, even though we’re not ready for CNN, we consider this to be real reporting and take pride in having the best information and really good fashion information about the topics that we’re covering.

I personally don’t have to check anything, but early on, Adam and I put our personal stamp on something, liked it and wrote about it. But overtime, to scale the business, that doesn’t work. We have a senior editorial team that monitors the things we’re doing and we have a general editorial team that’s writing and creating these articles. They understand the sensibility of the brand and generally have a similar set of tastes.

MC: How did you go about growing your company from two people to 40 people? What were the basic steps to do that?

BL: We didn’t raise a lot of money, so we were never in a position where we could go out and say “okay, we’re gonna hire 10 people and then we’ll hope to grow into the staff.” We basically said–it was the two of us–"to make the product better we’ll need more help writing.” Then it was the three of us. Then we said "we need to start making money to support the three of us. So let’s bring in a sales person." Then we started selling, and the sales person said "I’m selling really well; we need a bigger audience.” So we said "okay, let’s bring in a partnership person who can help us form partnerships to grow our audience.” Then we said "okay, now the audience is telling us that they want more. Let’s launch some new cities.” Then we hired some editors. It all was very organic. There was never a road map for how this was supposed to look, from a staffing standpoint. We always hired someone when another person is doing two people’s jobs. We figured out what two jobs their doing and what job they wanna keep and what job they don’t wanna keep, and we hire someone to take the job that they don’t wanna keep. That’s the way we’ve been growing over time.

MC: What are some tips you can give to other entrepreneurs looking start their own website and make it successful?

BL: There’s a few pieces of advice that I hold near and dear that I think are key lessons for us. When we pitch the company to about 30 friends and family who were successful in various ways and the first 29 of them said "what a great idea. You guys are so smart. Good luck, do it, I‘m sure you‘ll be successful.” So we thought great, we’re on top of the world and everyone thinks we’re so smart. Then we went to another guy and bought him the idea and he said "and?…get the hell out of my office! You guys haven’t done anything. You have an idea. The idea is five percent, execution is 95 percent." What he basically said is that if you want to make something of this idea, you have to make something of this idea. You have to do it. Don’t be scared, don’t hope that anybody else is going to do it for you, don’t hope that anyone is going to give you money for free. You have to earn it and if you wanna do it go out and do it.

That lesson was basically, execute. Don’t ever hope; make your own way. That was one really great piece of advice. Another good piece of advice was spend every dollar like it’s your own. If you raise money, even if you just pool money, understand the value of a dollar and spend every dollar like it’s money coming out of your bank account that you’re not gonna get to spend on dinner with your girlfriend or tickets to the Yankees game. That money is real and you should treat it like it’s your own and don’t be afraid to invest in something that you believe in. Those are the best pieces of general advice.

Another piece of advice is if you start doing something and it doesn’t feel right at some point, you don’t have to suck it up and go down that path and deal with it and run the thing into the ground. If you make a decision and it’s the wrong one, you can change your mind. Don’t be afraid to change your mind if your gut is telling you that you’re doing something wrong.

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