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

Apr 26, 2019

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On March 28, 2019, WOW air — the low-cost airline that made Iceland an attainable bucket-list travel destination — shocked the world when it announced that it was ceasing operations and canceling all remaining flights effective immediately, leaving thousands of passengers stranded in cities and countries that were not their own.

But few people were as saddened to hear the news as Roberto Serrini, a New York City-based filmmaker (and devoted TPG reader) who spent last summer lugging his camera, and best friend, Brad Stuart, around 10 cities and exploring the world of WOW as the winner of the airline’s Travel Guide competition.

Serrini and Stuart saw the gig, which the airline described as, “a 3-month paid summer job, where you will move to Iceland and travel the world with your best friend,” as an opportunity to indulge their shared passion for travel while creating content that would offer would-be travelers the chance to discover off-the-beaten path places.

And it all happened in a bit of a whirlwind: Just two weeks after submitting their application video, Serrini and Stewart learned they had won. They had just one week to pack up and move to Reykjavik.

The Points Guy spoke with Serrini about the WOW air experience, whether he saw any warning signs that the company was in trouble and the serious lack of laundry facilities in Reykjavík. This interview has been edited and condensed.

What sort of training did you get for the “job?”

“It was nothing less than frightening 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 Reykjavík for the summer. We went to their offices, met briefly with Skúli Mogensen, 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?

“They chose four cities and we chose the rest. Other than 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 the original experience was that made it great cannot be sustained, since it’s just flooded with tourists, and it eventually loses all its local vibe. We felt a responsibility to do the work and discover experiences that were lesser known, but just as magical.”

(Photo by Roberto Serrini)
Rob and Brad explore Edinburgh for WOW air.

What was the biggest challenge you faced dealing with the company?

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 than 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 ways did the experience 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 and make films and lifelong memories with a friend is the real prize in all this, not to get all 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.”

(Photo by Roberto Serrini)
Chowing down in St. Louis.

What was the most challenging aspect of the job?

“Laundry. Do you know that there is not a single laundromat in all of Reykjavík? Not one. I live in New York City 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, 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 Reykjavík in the summer.”

Were you at all aware the company was close to ceasing operations? 

“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 who 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 consumer base.”

(Photo by Roberto Serrini)
Chasing waterfalls — and rainbows — at “home” in Iceland.

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.”

Though WOW air’s Travel Guide website folded with the company, Serrini and Stuart will be posting all of their travel videos to their own TravelClast YouTube channel.

All photos provided by Roberto Serrini.

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