Born of founder Ben Lerer and his buddies’ need for better date spots, retail guidance, and watering holes, Thrillist launched in 2005 as a daily newsletter committed to keeping New York’s 20-something men in the know. Each day’s installment boasted (and still contains) one key tidbit on the best outlet or location offering an interesting product or an unusual experience. In under two years, the e-newsletter has begun influencing countless more men with the launch of versions in Los Angeles, “Nation” (so guys stuck in the middle stand a chance at matching their coolhunting coastal counterparts), and most recently San Francisco. We sat down with Lerer to discuss the highs and lows of expansion, and how tough it is to find his patented “Thrillist guy” in Chi-town.
Describe your exact role at Thrillist these days: What’s your day-to-day like, versus what it was like when you first launched?
I guess it’s probably changed a lot. Personally, I used to have a daily deliverable. There were certain things I was responsible for doing on a daily basis, whether that was ad sales, accounts that I worked, people that I worked with, or in editorial. There was a time when I obsessed over every line of every piece that went out. Now that we’ve been growing, my role has changed a little bit because I’m not as obsessed with all the little details. Although I’d like to be, it doesn’t make sense. I’ve broken the company into four divisions, with technology and content and marketing and sales. My role now is just kind of making sure that the people who run each of the divisions are happy and having fun and we’re still kicking butt.
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Who’s obsessing over all your editorial these days?
Adam, who’s my partner from the beginning. He’s the editor-in-chief now. It’s funny: he’s kind of grown into an editor because when we started, neither of us had any experience in editorial, and now he’s gotten really good at it — more than really good. Now he has really become the direction of the voice, and he’s the top editor at the end of the day. Most of the editors choose topics and make sure that we stay consistent between the cities, voice-wise. Then we have an executive editor named David Blend who was our New York editor for the first two years, [who] really came in and taught Adam how to take what was in Adam’s mind and put it on paper. [David] has been kind of a driving force on the editorial side and someone we kind of love desperately, and who has been incredible from the beginning. Each of the editions has one editor, so when we launched San Francisco we had brought in a guy Patrick Heig — he’s our everything in San Francisco. He’s the guy who runs the show out there, picks all the topics, who hires the freelancers, who works with the tipsters, who works with the PR companies, and he’s become the face of Thrillist in San Francisco. We have the same thing in L.A., same thing with New York with Steve [Bryant], and the same thing for our national edition, with a guy named Ben Robinson, who is also somewhat new — he’s kind of our national editor. He’s based in New York as well.
So, Patrick in San Francisco. How did you find him?
There’s a magazine in San Francisco called Todo Monthly. It’s a kind of hipster magazine that comes in the back of taxis — it’s a little hand-held kind of book — and he was a writer there for a few years. Adam went to high school with a guy named Michael Moskowitz, a great guy out in San Francisco who’s the founder and the publisher of Todo. Michael said, ‘I’ve got this guy Patrick, writing for me for years, and I don’t have a full-time thing for him and frankly I don’t think he wants to write full-time for me, but I think Thrillist is the kind of thing he could wrap his head around forever.’ He is as natural a fit as I could ever find, that I could ever imagine for any job in the history of the world. Everything about him: He looks the part, sounds the part, he sounds like a Thrillist guy. Hanging out with him, he’s what Thrillist is all about. We’re really lucky to have him.
That prototypical Thrillist guy: What does he look like, sound like?
I think the idea is you’re young, you’re hungry, you’re hard-working, you’re pretty smart. You work hard, you play hard. You, sometimes you have to wear your suit, and get all dressed up, but you probably prefer to be sleeping on the sofa watching football. A guy you went to college with or you went to grad school with.
How did you pick San Francisco as the next market for Thrillist? After launching New York, national, then L.A. editions?
We went national second, not necessarily because we thought that national was the next strongest market for us, but because we were kind of scared of letting the voice out. National we could run from New York and keep a very close hand in what was going on, and make sure that the consistency was there.
So it was strategic?
Exactly, as far as training an editor, and just getting the voice, being able to replicate the voice, when it wasn’t just David writing and Adam editing. Now that the structure was going to change, [it was] trying to find just how to train the person, how to recruit the right person for the job, and how to develop a network of contacts that, if we were doing it in L.A. first, would have been a little bit out of our league. We went to L.A. second, kind of blindly. We just said, “Why not L.A.?” It seems like the natural move, since L.A. and New York are the two biggest cities.
San Francisco was a little bit more strategic: One reason is that Adam is from San Francisco, so it was not as far from home in some ways as it might seem. Also, it’s a city where we saw that there was a real hole, media-wise, for anything like what we were doing. Daily Candy is obviously out there doing their thing, they’ve had a lot of success there. There are a lot of people working in technology and media out there, with Apple and Google. We thought that in New York, we’re really strong with that community — same goes for L.A. — and we thought that that kind of a guy would be into what we’re doing. Also, we’re out on the West Coast a lot. For business purposes, it’s a short trip. It’s easy. So Chicago is next.
When do you expect to launch in Chicago?
We don’t know. We’re ready from a technical standpoint and we’re ready from an advertising standpoint. I think [with] content, we just want to make sure we get San Francisco very comfortably on its feet before we take the leap [to Chicago].
Do you have an editor yet for Chicago?
We don’t quite have our editor, we’re looking around. In the past, we’ve hired people when a job opportunity presented itself: We need a new salesperson, we need a new this, we need a new that, and we’ve hired not necessarily the first person we’ve found, but one of the first people that had the right kind of experience on paper. This is the experience of starting a company when you’re a little kid: [When hiring] you have to know deep down if it’s the right guy or it’s not the right guy. We’ve met a lot of cool, confident people in Chicago, but we want to wait until we find the guy who [is] so Thrillist, they just live and breathe it, and they’re someone who we are really proud to have representing the brand.
Does the challenge of finding your Chicago guy have anything to do with the Chicago market itself?
I would never have said yes until I started to talk to people: Yes. There must be something in the water there. I don’t know exactly why we’re having so much trouble finding a really good Chicago guy, but it could be there’s something bizarre in Chicago and it could also be that we’re getting better at knowing what we want and we’re being more particular: The skill set needs to be more exact, and it needs to be a better fit. In the past we’d just shoehorn people into jobs that weren’t necessarily perfect. Now, we’re able to be a little more deliberate in everything we do and I think [hiring in] Chicago is maybe the first time that we’ve really been quite so careful.
We didn’t interview 60 people in San Francisco — we interviewed five and we met Patrick and it was great. We’ve interviewed a lot of people in Chicago, and we haven’t found a perfect fit. Although we’ve met with tons of really talented, really funny, really interesting people, no one has been Thrillist.
| We’re only as good as our next piece of content. |
You’ve said before that expansion was a possibility when the number of subscribers hit a certain threshold. What did it take, subscriber-wise, to be able to move forward with new editions?
I think it’s less about that now than maybe it was. I don’t even know what the number was, but the idea was about proving the concept in the city before it. We didn’t want to launch the Nation until we knew that New York had worked. We didn’t want to launch L.A. until Nation had steam behind it — we felt like it was really cooking, people were liking it, the product was working. Same goes for San Francisco.
Now we’ve been able to replicate success in several cities because we’re finding the local people there. It’s not about us, it’s about them once we get to the city. We have a nice model and a nice voice, but ultimately it’s about finding the right editor who really just gets it, and understands the city and what people want in the city. I think now we know we’re going to be successful in San Francisco. We know it’s going to work there because we have a great editor, and I think the voice works for the city and we’re finding cool stuff. San Francisco is just an awesome city with a lot going on. There’s just so much cool stuff to discover, and it’s kind of wide open for us.
So, would your direct competitors be San Francisco Magazine and the aly-weeklies?
Those, or city guides. Absolutely.
We never like to think in terms in competition. All that competition is going to do is bog us down and get us worried. It’s a waste of time for me to think about it — we just have to focus on doing the best job that we can do, and not getting caught up in the little details of other people trying to eat our lunch, because it’s just going to drive us crazy.
Describe why this approach works in an online format versus a print format? You guys are daily, and very granular about what you’re choosing; it’s interesting that there seems to be an opportunity online where there isn’t in print.
First of all, everyone is online right now that we’re going after, so it’s a natural fit. The cost to start something up online is so much less than the cost to get something started up in print, so we never even conceived of print early on. Maybe in kind of a pipe dream, but it was never a realistic opportunity, so online was the only place, and I think that it works.
I think the success of Thrillist is based on email, not just online. It’s a habit. Email is a personal thing, it’s a habit, and getting invited into someone’s email box is such a great way to communicate with somebody that I think a lot of Web sites don’t necessarily see. If you’re a Web site you have to remind people — you have to use more marketing to remind people to come back and check you out. With us, if somebody finds us once and decides it’s really interesting, we’re going to come and remind them that we’re around every day. If we remind them often enough, and they don’t like what we’re doing, they will very quickly remove us from their life, which is fine with us, it keeps our list tight, and it keeps it with the people who are signed up for Thrillist are the people who want Thrillist.
What have you covered that has engendered major reader response, positive or negative?
Just very recently in San Francisco, we wrote about a woman who takes old clothing that you have — old jerseys or old t-shirts, things that are no longer wearable — and makes new clothing out of your old stuff. [She] kind of brings it back to life and makes hoodies out of it, and makes new t-shirts, and other cool things. It was a really interesting one for us because, typically, we move the needle so much more for people as our list grows. As we’re in a city longer, we have more people reading, so when we write about things more people respond. But, this was our first or second piece in San Francisco, and we had 4,000-5,000 people reading that day. We ended up really changing this woman’s business in one day.
We did it and she got a lot of pick-up from other places, and that kind of viral effect really took hold, and now the woman can’t fill the orders she’s been getting. It kind of changed her business from what she told us, which is really exciting because it was very early in the edition. We did move the needle in the first week — it was good for Patrick, it kind of got him really energized, so that’s a recent success.
This is an embarrassing one: We wrote about this shirt that looks like you’re wearing tattoos. It’s like half-see-through, a really silly, funny shirt that I saw someone wearing out one night. I thought it was really funny, and I showed it to the editors, and we thought it was really funny. We didn’t actually recommend it as something that you want to go out and buy, it was more of a Halloween costume, but we featured it on Thrillist Nation, and we got skewered by everyone from Gawker to Vh1 online to Best Week Ever, just ripping on the shirt and us for writing about it. I completely understand where they’re coming from, because there is that inherent recommendation [in covering it], there is the endorsement there, but sometimes we’re writing about something that we think is funny rather than really cool.
Do you still have a book project in the works?
We don’t have a book project in the works. We’ve been approached. Right now I just don’t know what our book would be about and I think that that’s a bad way to start a project. We started Thrillist because we wanted something like Thrillist to exist. We were frustrated that there were a bunch of crappy city guides. Trying to diversify Thrillist into a book when we don’t have a passion to write a book about something would be a mistake and would just be kind of greedy of us, in trying to extend the brand and to create like some Thrillist guide to something that we don’t think would really deliver value to people. At the end of the day, that’s what Thrillist is about, it’s a service; we want to provide value. We want people to be able to walk away and feel like they got something out of reading Thrillist. Unless there was something we naturally thought would be a good idea, and we really wanted to do, we wouldn’t do a book.
Any other projects in the works?
Not really. We’ve kind of had our heads down. We’re trying to do one thing really, really well. The expansion we’re looking at is geographic expansion first and foremost: As much as we want to keep growing to new markets, we really want to focus a lot of our attention to making sure that what we currently have is great, because we’re only as good as our next piece of content. We want to make sure that what we send out to our current readers on New York and San Francisco and L.A. and Nation is great.
Have you gone through any fallow period, maybe transitions between editors, when interest waned?
I can’t necessarily pinpoint it with any user metrics. Growth has never slowed — growth has only gotten faster and faster as we’ve grown, and the response has only gotten bigger and bigger. The only time where we’ve ever been able to pinpoint anything like that is internally, when we’re reading.
The company is a pretty good focus group. There are 13 of us, and we’re all in the demo: we’re all between 25-35 and living in New York or L.A. or San Francisco and we’re young guys. Aside from the editorial staff, if we think the content is taking a little bit of a step back, we let the editorial guys know.
We recently made a big transition, where our Nation editor left, and we had a new Nation editor come in, and our New York editor left to become the executive editor, and we got a new New York editor, and we launched San Francisco. So our staff went up with three new people. It was a really big change because it takes a long time to get the voice, to get familiar with the format, the deadlines and the way that everyone works. So it was tough — It was about a month and a half ago or two months ago where everyone was working many, many more hours a day than ever before. Now we’ve kind of settled back in to a good system and everyone is happy again, but we’re always trying to improve and we always find — once a week, in at least one edition — there’s a piece that afterwards people in the office are like, “That stunk.” We try not to let it get us down when we don’t print the best thing we’ve ever printed. In general, I think four to five days we’re sending out really, really great stuff. You don’t need to hit a homerun every day, you just can’t strike out.
Do you ever worry that you might enter a market and saturate it — hit the bottom of the barrel as far as new things to cover?
I’m definitely nervous about it. I don’t think we’re ever going to run out of stuff in New York or L.A., or San Francisco. I worry that there are other cities around the country that may not be able to sustain it. I’m not sure if we can do five days a week in Seattle or Atlanta. We’re not necessarily married to a daily model in every market we’re in if there’s not enough stuff. In New York, I think there are five great things a week, whether we find them every week is another story. Sometimes we don’t find all five things — we do our best to — but I think there’s always going to be enough content. A friend of mine is a big restaurant foodie guy, starting a food Web site. He was telling me that he’s trying to pinpoint the top 1,000 restaurants in New York, and he has a theory that there are never more than 1,000 great restaurants in New York City. I was saying, what about when a new place opens? He was like, “I guarantee you a place that was in your top 1,000, a place closes.” There is so much turnover in everything.
There’s always new stuff popping up [in our current markets], and we’ll have a neverending supply of content. I don’t think the well can run dry, but in other markets, there may never be enough. So we need to be very careful before we make a commitment to a city that there’s enough. When we launch a new city, we actually launch four days a week rather than five, to give ourselves that day of rest, and that day to be sure that we don’t put that pressure on ourselves early on. We want to be sure that there’s a solid four, that everyone’s happy, and that there’s almost more that we want to cover. We want to get the contacts in place and the freelancers and tipsters, so that there’s too much, that there’s not enough days in a week, and when we get there, we know it’s time to go to five.
What would you say is the most challenging aspect of growing Thrillist?
Entering new markets, I think the most challenging aspect of any of this stuff is a) hiring the right person, and b) just for us, emotionally staying strong and staying focused and looking at this from a long-term perspective. We’re growing this thing and we’re really trying to do the best stuff and not letting one day of content that we’re not in love with make us sad throughout the next day. Just staying focused on doing as good a job as we can, and knowing that we can’t be perfect.
Have you ever had to let anyone go?
We have. There have been a few people that didn’t work out for various reasons. It’s not fun. It’s an awful, awful, awful thing, and everyone who has worked for Thrillist we brought in because we obviously thought that they were great. There aren’t any who left that we’re on bad terms with, I don’t think, but sometimes someone’s not quite right.
It’s really very sad and unpleasant. It’s something that we really don’t want to do, which could be part of the reason we’re so careful with who we hire.
How do you cope with that from the standpoint of a relatively young professional who is responsible for this larger organization, including the morale and the direction of the group?
I rely on the investors a lot to give me advice and help to lead me through those situations and handle them in the most professional way possible.
I haven’t had that many jobs. I’ve never been fired from a job before. So, just going through the process of the way you’re supposed to do it and the way you’re supposed to be sensitive: asking [the investors] about the potential questions people ask, the worries any employer has for somebody who’s not going to be there anymore, from a security standpoint to an emotional standpoint, for the person and for the morale of the team.
We really do try to have a team aspect all the time so it’s not at all out of the ordinary after something like that happens, we have a team meeting when everyone can talk about how they feel. The culture of the company is so much of what we’re about and what we do. Letting somebody go can really shake that, so we’re really careful that everyone understands why decisions get made.
Are there any things that have changed in your day-to-day role that you’ve had to let go that you’ve been sorry to part, work-wise?
I loved reading the pieces, but at the same time, it’s stressful. It’s a big time commitment and it’s tough.
Other than that, I don’t really miss any specific thing. I miss the idea of having daily responsibilities and feeling worthwhile. Today, I feel like I didn’t get anything done. There are so many days now where I feel like I didn’t get anything done because I don’t have anything to show for the stuff that I’m doing necessarily. I miss that a little bit, coming home, being like, “I did something great today,” rather than, “We did something great today.” But, I can definitely settle for “We did something great today.”
Tips on taking your venture into new markets:
1) Have realistic expectations.
Sometimes things don’t go as planned, and sometimes you look back and wish something had turned out differently. “You don’t need to hit a home-run every day,” Lerer says. “You just can’t strike out.”
2) Play with the model.
“We’re not necessarily married to a daily model in every market we’re in if there’s not enough stuff.”
3) Lean on the experts.
Lerer says sometimes, he needs a little guidance. “I rely on the investors a lot to give me advice and help to lead me through those situations and handle them in the most professional way possible.”
4) Appreciate team successes.
With the expansion of the business to new editions, Lerer’s had to trade individual responsibilities for ones benefiting his organization. “I miss that a little bit, coming home, being like, ‘I did something great today,’ rather than, ‘We did something great today. But, I can definitely settle for ‘We did something great today.'”
[Rebecca L. Fox is mediabistro.com’s managing editor.]
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