How I Became a Travel Host.

 

Last summer Brad Stuart and I got the chance to travel around the world and make films for WOW Air, having won their global TravelGuide Contest. It was a surreal experience, somehow being chosen from over 30,000 incredible entries, and learning how to produce a full travel program on the road with just two people.

We produced over 110 films in just three months, all while traveling, which pushed us nearly to the limit of exhaustion. The funny thing about doing what you love, you never realize how truly spent you are until you stop.

Coming back there was a lot to process and learn from, and share as well. Lots of people have had questions like how did we win the contest, or what’s the best way to travel like a travel writerhow did we plan our travel vlog, or just how the experience was. This week I sat down with the good people at The Points Guy and answered some of these questions, which you can read on their site, or down below in an extended interview.

A TPG Reader Dishes on Winning WOW air’s ‘Dream Job’ Travel Contest

— As much as the gig was touted as a “dream job,” having to uproot your life for three months and step away from your daily paid work couldn’t have been an easy decision. Was there one particular aspect of the opportunity, or one thing you were hoping to get out of it, that ultimately led you to decide to go for it?
Accepting to do the project was definitely was a decision we had to think hard about. We realized that being gone for three months without working and still having to cover the cost of our apartments in NYC was going to eat up any per diem WOW was offering us. So from the start we realized we needed to really make this project something special, perhaps much bigger then WOW was expecting. We knew we had to create a diverse library of quality content that could really show our potential as travel content creators. The fact that WOW was letting us have complete control over what we produced and how we produced it meant we could make this project as dynamic as we wanted to, so the opportunity to do what we love the way we wanted to for a brand like WOW was definitely the main draw.
— What sort of training, if any, did you get for the “job?” Did you meet a lot of the WOW Air team in person and go over strategy, or did you just sort of get thrown in the deep end and go?
It was nothing less than freighting how much they trusted us, but also extremely liberating and rewarding. After a casual conversation on the phone with the head of their marketing department we were on a plane to go live in Reykjavik for the summer. We went to their offices, met briefly with Skuli the owner of the company who seemed really excited to have us there, and then they gave us the login information for their youtube, instagram and website and told us to go make some fun stuff. There was no review process or any real brand guidelines which, working in advertising, was absolutely petrifying, but again, liberating. Being able to fully control production from beginning to end was what made this experience exceptional for us. We worked together on what cities we wanted to cover, they set up flights and hotels, and the rest of the job was up to us. 
— How hands-on was the WOW team in terms of what you posted? In terms of determining what you wanted to cover in each city, did they have specific ideas in mind, was that all up to you, or was it somewhere in between? 
They chose 4 cities and we chose the rest, other then that they were completely open to whatever we wanted to cover, which I think was the purpose of the whole contest. They wanted real travelers to explore cities and get others excited about travel, which is exactly what we believed in. We didn’t want to make content that was just another voice in the echo of travel videos already out there online. There is this dangerous cycle that happens, where influencers and influential sites like TripAdvisor or Yelp will only send tourists to the “top 10” places in any one city, and then those people end up writing only reviews about the top 10 places, artificially inflating their importance and value. Whatever was the original experience that made it great cannot be sustained, since its just flooded continually with tourists, and it eventually loses all it’s local vibe. So we felt a responsibility to do the work and discover experiences that were lesser know but just as magical. In order to do so we would check the obvious resources like Conde Nast, Lonely Planet, Thrillist and even Atlas Obscura to see what each city had to offer, but then used WOW’s extensive social media platform to talk directly with our audience, which was the key to finding true hidden gems. We would ask locals where they go on a Thursday night to eat, or on a Monday to drink, and got some amazing suggestions that were largely unknown to foreigners and were truly local. While we covered some well known places that had a big draw, sharing these lesser known places was a way to ensure our audience could get an authentic experience that wasn’t blogged to death about online. There is nothing worse then going somewhere new and already feeling like you’ve been there because you’ve seen it so many times online. 
— What was the biggest challenge you faced in dealing with the company? What about from a personal level of having a limited amount of time to shoot a lot of footage: what was the biggest challenge there for you.
WOW was a pretty great partner; they didn’t demand anything from us that we weren’t willing to provide, and in the end got a lot more then they were expecting. For the most part they let us do our thing and manage our time as we needed. Any pressure we felt came from us driving ourselves to produce dynamic content. We ended up making well over 100 films for 10 cities around the world in just under three months, which was insane, but the experience of learning how to produce so many segments efficiently is something that will definitely benefit us in future projects. 
— In what way(s) did the experience most exceed your expectations?
What was most exceptional was being able to do what you love with a best friend. I think we often forget how lucky we are to be living at this time in history, and just being able to travel, make film, and lifelong memories with a friend is the real prize in all this, not to get to Hallmark Card or anything. I didn’t expect it to be so rewarding in that sense, even when we were exhausted from being up all night editing, or having walked 30 miles with a backpack of gear through a city all day, it was that feeling of accomplishing something difficult for something you really love doing that is the perfect recipe for honest fulfillment. 
— What about the opposite end of that question: Were there certain aspects that proved to be particularly challenging or time-consuming? Any aspect of the process that, if given a second chance, you’d try a different way?
Laundry. Do you know that there is not a single laundromat in all of Reykjavik? Not one. I live in NYC and there are TWO, read that, TWO just in my building. Where the hell do these people wash their clothes? We didn’t have one in our little apartment, so we ended up having to wash everything in the tub with a broken broom stick like it was 1926. Joking aside, it was a rough start for sure. We took too much equipment, and didn’t have a working strategy on how to plan our trips efficiently, but what was truly amazing is how streamlined the process eventually became from the experience of working through it. We realized what gear we really needed, how to plan our day efficiently, how to contact places and people to schedule our day, and how to edit everything and deliver, and still have time to throw a few back at Pablo Discobar before the sun set. That’s a joke because the sun doesn’t set in Reykjavik in the summer. 
— If rating the experience from 1 to 10, 10 being the best, where would it fall? 
26. Honestly. It was the most difficult thing I think either one of us ever tried to do, but because it was something we were really passionate about and loved doing it pushed us to the edge, and there we found nirvana. It was unlike any other experience I’ve ever had, and I wouldn’t of traded it for the world. I think what it gave us was well beyond the gift of travel, just merely visiting these cities, which was wonderful. It really taught us how to produce, and how to turn something we really love into something tangible and we can share. 
— Knowing things now that you didn’t know then: Are there questions you’d advise other people applying for similar travel dream jobs like this to ask of the  company providing the tip?
Make sure you really know what you’re getting into and what you want to get out of it, and make sure you communicate that clearly. Companies will dress up free work as a contest, which isn’t to say it can’t be mutually beneficial, but make sure you know the terms and contractual agreements before agreeing to anything. For us it was important that we could use all this work that we were doing to build off of, and banked on the exposure to do similar projects for other brands in the future. Also always ask if there is a place to do laundry nearby. 
— Would you recommend similar experiences to other people? Do you think there’s a certain personality type that’s best-suited for this kind of adventure?
Obviously anyone looking for adventure, loves to travel and make films are prime suspects for a good candidate, but being a good, self-motivated producer will definitely help you get the most out of the experience.  Knowing how to approach people and businesses so they would welcome us and our cameras was key for the success of the project, and as the summer went on we got better at opening doors. We set up private tours of museums, and got access to people and places that would be totally off limits to the average tourist, which made the experiences unique and profound, and in turn elevated the quality of the films from just average travel vlogs to actual curated segments. As an example we shot an entire film about Nobelhart & Schmutzig, a Michelin starred restaurant in Berlin that doesn’t allow cameras inside, so it was a real honor to tell their amazing story, not to mention one of the best meals we’ve ever had. We basically made these experiences happen for us, so the better you are at making your reality the more you’re going to get out of a project like this.
— Were you at all aware that the company was so close to ceasing operations? Were there any signs of strain or inklings about what was to come for the company?
Can’t really say we could, no. At the time they were a fluid, virile company that was forward thinking enough to send two travel maniacs around the world to make films for them. From an advertising standpoint the contest was a genius move. There is a trend happening now where brands will go direct to content creators and influencers to produce media for them, instead of working with a traditional agency, and for someone that works in advertising I really wanted to find out what was the potential of this type of work, and how far we could push the limits. It was a novel approach to a summer ad campaign and the idea was that they were going to keep the Travel Guide website up forever and have new guides each year go to new destinations. It was a fantastic concept, and I think really had the potential to connect with their consumers base.  
— If you had the chance to do it all over again, would you?
In a heartbeat, but in reality, we never really stopped. We may not be creating content for WOW but we’re constantly making new content to continually grow our own brand and channel. We’re just super thankful that we had the opportunity to do so much fun work with them while they were in business, and will definitely miss the fun little airline that did things a bit differently.