My Soapbox: James Fisher, Roadtrippers

As is often the case, the best place to start discussing Roadtrippers is at the beginning. In 2011, husband and wife James Fisher and Tatiana Parent (aka Danger) set out to create a well-categorized, fully integrated travel tool. The major early emphasis was to build out a skeleton of the American road. To do this they focused on producing rich, often localized content about interesting routes, sites and oddities throughout the American landscape. Essentially, they put the focus on creating great low-frequency content first with the intent to develop a widespread reach with higher frequency city and destination travel content once they’d fleshed out the skeleton.
Recently, James and I sat down to discuss the company’s rapid success at Roadtrippers headquarters in Over-the-Rhine, a building in a constant state of evolution. Running one of the region’s most successful startups has ironically kept Fisher mostly grounded over the last year.
Can you talk about how Roadtrippers got started? Where did the idea come from?
The very broad background is my wife and I were living in Europe—in Berlin—and coming to the states, taking a lot of road trips. We kind of realized that it was actually very hard to find interesting places that met our kind of tastes.
I’m into architecture; she’s into Civil War Battlegrounds and that sort of thing. We both really like to eat at little mom and pop places, stay at local B&Bs. To accomplish that in this road trip contex,t we were using this big arsenal of different resources, none of which talked to each other and none of which talked to my map, my car, my GPS unit or anything like that.
So we were like, crap, what we need is a map with a menu of places and things to do that are incredibly well-categorized. If I say I want to see a diner, I see a proper diner. It’s focused on small business and just shows me the “cool” stuff, basically. I can use it like MapQuest or whatever, but it’s just the interesting or best stuff.
Then we set about building that. We started to fiddle around with it as a personal project, really. Actually we were going to open a B&B in Savannah, Ga., but we got outbid by some asshole at the auction by two grand. So we were like, screw it, let’s see if we can develop this idea a bit further.
So we applied to the Brandery on the last day of applications. We got in and started working on this. We had a bit of a rocky start with a co-founder that didn’t work out really well, so after the Brandery, we didn’t launch off really fast. We rebuilt the platform, so we actually launched in August 2012, about a year from starting working on it seriously to actually launching. I’d say we kind of doubled our time there—that is something I’ve learned some lessons through.
Now we’ve been live for about two years since then, and have grown to the point where in July we had more than three million people use the site and app.
Can you talk about the transition from five to six people in a room together to expanding to 40-plus employees and your expansion in general?
It’s tough—a lot of work. Building a team this big this fast is not something I’ve ever done before. I tend to be the type that just takes everything there is to do and do it myself, which doesn’t scale well. Having other people on board is great, but I still tend to be that kind of person. The biggest learning curve for me is adjusting that and giving more responsibility to others.
I think we’re getting the hang of it, but there’s a lot of complexity going from six people to 47 in 18 months. What I need now is more senior management. It’s me and one other senior guy—well another director-level person and another on the engineering side. That’s what we are hiring at the moment: very experienced senior dudes.
We have a lot of young, talented people that work really, really stinking hard, but it’s just that experience that is the next step—the next sort of teething problem—having so many people that want to go hard, but lack the experience yet to go (roars). They’re all really smart, and it is sort of on me. I need to give them more.
Has such rapid growth changed the culture at Roadtrippers?
So I think the culture at the beginning was six people who spent all their time together, would get drunk together a lot and that kind of stuff. Then as the team has grown, we’ve really tried to keep a good mix, have “mixery” type things going on because you’ll get people clustering into groups. A certain degree of that is inevitable and healthy, but we really want everyone to know everyone, to like everyone and be on an even playing field. But the core groups kind of split off.
The interesting thing with having a bigger team is we just have more capacity to get involved with more things. Like the ArtWorks project and Chelsea’s garden, all these bits and pieces. Now we have the bandwidth to be able to engage more with the city, where before we were just heads down and doing our own thing. But, we only engage in stuff we really like or that fits our brand, our culture, which is all about doing things our own way. Doing things ourselves.
So there’s a lot of renovation going on. How is that going?
We don’t do too much. We’re going through a bit of a planning process at the moment. It’s going well. It’s great to kind of revive this building. This building was abandoned when we moved in, water was coming in through the ceiling. The building would be in much worse shape and probably need structural help from the city if we hadn’t come in and fixed some things.
We didn’t move the company in immediately. My wife and I moved in, and we have an apartment in here. We literally were such a poor startup or whatever that we had $600 and no heat, no power, no water, no insulation. We had to figure out how to get all those things going, and we moved in at the end of November.
I read that about you, that you love being in a place where you have to—what I call “Frankensteining”—take something dead and give it life, make it your own creation.
That’s honestly the reason we stayed. You think about where we were going to be; we wanted to move to Savannah, which has a similar setup. Beautiful historic buildings, affordable—you just need to put in a bit of elbow grease. But when you do the rewards are huge. You have this incredible, beautiful space and become part of something bigger.
I saw the same here pretty quickly. Unfortunately, we’re not so near the sea, but you know, the architecture and layout of the city is superb, it was just like opportunity to me. That’s why we stayed.
You mentioned Savannah again: Was that the plan—to finish up here after the Brandery and move on—or was there always the possibility of staying?
We thought we’d probably have to move to a city where access to capital is easier for the particular type of startup we are. Where we’re like, “Hey, let’s grow a huge audience, invest lots and lots of money before we worry about making any” (laughs), that’s not necessarily the sweet spot for Midwest investors, you know?
So we thought quite possibly we’d have to relocate, but luckily found the right mix of investors that were supportive of our vision and understood the need to focus on building audience first, then monetizing the audience.
The good thing is, if you create a large audience that has intrinsic value, at least the company has a fall-back position. Another travel company or mapping company would be interested in acquiring us if we just couldn’t figure it out—which isn’t going to be the case.
Roadtrippers is adding new functions like following brands, writers or friends; curated trips; turn-by-turn navigation; and also expanding internationally. Where are you as far as those are concerned?
What we’re working on for the rest of the year is the new release for iPhone, which is coming soon. We massively improved the iPhone app, simplified it in many ways. Made it slicker, smoother, a better experience. That comes out in a couple of weeks, and we’re working on turn-by-turn navigation by Thanksgiving.
With that, the idea is our app talks to our web portal, so you have the mapping site on the web. The reason we want turn-by-turn is actually two parts: One, we want to be able to send you on the scenic route, not just give you the option to avoid highways or tolls, but where you actually say, “Take me down the scenic road.” Then, we’ll calculate the best path for you based on, say, your interest for historic buildings or overlooks. Maybe there’s a historic byway and the app can automatically route you that direction. The second reason is if we engage you during your navigation, then we can suggest things for you to do on the way. If we know you’re interested in old diners or something, we can say, “There’s a great one coming up.” Maybe it’s late and you have another six hours driving; we can say, “Hey this hotel will give you a discount,” and put that in your navigation. That’s why we want to focus on nav.
On the web, we want you to be able to save any place you read about. So building a web browser plugin, that sort of thing. Then whenever you read about a place, you can just save it with a click and it goes into your turn-by-turn navigation. The whole thing is about empowering people to get to the places they want to go.
Has recognition like being named one of Time Magazine’s Top 50 Websites of 2014 helped with Roadtrippers’ evolution?
Press things don’t tend to have a big effect on audience. What they do is help with adding credibility, with partnerships, things like that. It is great, but in a nontangible kind of way. I can’t track the exact results of being a “Top 50 website,” but I guess it makes you a little more “legit.” Kind of like you know what you’re doing a little bit.
Do you still intend to keep Roadtrippers ad free?
Relatively speaking. We are working on some ad model stuff, but not in the typical way. More long-term partnerships centered on content. I can’t really go into specifics, but say we have a ton of content on automotive stuff. A brand can pay to own bits of that. A brand can sponsor “RVing” on the site and pays handsomely to do so. They present it essentially; they become part of the experience.
Do you still get to travel often?
Sadly, I don’t. I haven’t outside of business meetings really. Tatiana is traveling a lot more than I am. She just did Route 66 for three weeks with our 10-month-old baby.
I was going to ask about that actually.
Did you see that?
Yeah, when I was finishing up notes, I was looking through Roadtrippers’ Instagram account and I saw …
Bruce Renegade Baby
Bruce Renegade Baby. So what’s that like having a 10-month-old who is cooler and more internationally renown than you?
(laughs) I know he’s a threat already! I’m going to have to alpha-dog him (laughs).
Tatiana’s traveling to Texas for two weeks. We identify these areas where it’s like, “Crap, we have loads of people traveling here, but nothing about these places online.” So we send Tatiana. She’ll literally go explore, just drive around and find stuff, ask everyone she meets, talk to business owners.
When she did Route 66, she was at Cadillac Ranch and had four separate people come up who were using Roadtrippers at that point in time and saw the badge on side of the car. They were like, “Holy crap, I’m using that to get here!” Several of the business owners on that route know us because we’re sending them people all the time. Some of them—the key hotels—have told us anecdotally that we are sending them more guests than Trip Advisor, which is nice.
What’s your dream road trip?
When I was younger my family used to cross Africa. That map behind you is the route, starting in Morocco and going all the way through. The problem is, recently it’s been (stands to explain on the map) the whole of this portion of Africa has been cut off— centrally—since the early ‘90s. Just been war zones one way or another. So you couldn’t actually drive through.
You can now—well you almost can. Unfortunately, Central Africa has kicked off; there is Ebola here (west). Congo is opening up, but I want to get that. I want to go back and see these places that were so important to me growing up, how they’re changed, you know? What’s been happening and, ultimately, how I can help. When I think about where I want to end up if I can make the company successful, I want to go back to where I began and build things there.
What kind of car would be ideal for that?
My LandRover (laughs). My Defender. That would be the one, 1986 old beater.
If you can pile anyone you want in the truck, who do you bring?
Anyone I wanted?
Yeah. Alive, dead, anybody. It’s hypothetical.
Um, for that trip, I don’t know. Who’s the most badass person ever? Jesus I suppose? (laughs) If he is for real, if he’s all he’s cracked up to be—which nobody is—that’s a good question. I don’t know … Jesus. He’d be an interesting bloke.

Read more articles by Benjamin Plattner.

Benjamin Plattner is a freelance writer, University of Cincinnati graduate (B.A. in Political Science) and an uber-votary of coffee, food, drink, music, travel and Cincinnati’s newfound momentum (feel free to contact him to discuss any of these things). He lives in Columbia-Tusculum with his luminous wife Ieva and their canine cohorts Violet and Clover.
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