Q+A: Mike Crocker, Choose A Challenge

Giving college students the chance to travel around the world while also fundraising for charities is how Choose A Challenge is disrupting the student travel market. Over 10,000 students have been able to go abroad through Choose A Challenge and they have raised $25 million for charities worldwide. Started by two individuals, the company began in London and has grown to include their DUMBO office. 

We sat down with Mike Crocker, VP of Marketing at Choose A Challenge USA, to talk about the company’s impact on college students, their work with charities, and how Mike went from being a news reporter to guiding students on expeditions across the globe with Choose A Challenge.

What is Choose A Challenge?

Choose A Challenge is a travel adventure company geared towards college students. Our goal is to take more college students abroad to help them see the world and become more cultured and more worldly. What makes us different is that we involve charity partners. Students fundraise the cost of their travels, which makes international travel especially, more affordable. It’s an experience that differs from study abroad, where you go over a long series of months, to being able to go on a shorter trip to some of the most iconic places in the world for a fraction of the cost.

And how does it work, exactly?

Let's use a long-time participant, Jeremy, as an example.

The process begins with the initial meeting on campus. We usually have a student who is that school’s leader, as Jeremy has been for the University of Connecticut. We promote the meeting along with the student leaders. At the meeting, Jeremy is there, and a Choose A Challenge staff person is there, someone who has been on a trip or more and is just out of college. We give a presentation and then interested students–like Jeremy when he first started–sign up. Once they sign up, and they connect with a charity in their community. For example, at UConn we partner with Make A Wish Connecticut. The students also get a personalized message from someone on staff who will be with them to prepare for the trip.

Part of preparing for the trip is fundraising. Each trip has a fundraising target for the student to raise. Jeremy, for example, went to Machu Picchu and that target is $4,000. It seems like a lot of money. but half of that is going to pay for your trip, which includes flights, food, in-country transport, and is as close to all-inclusive as you can get. The remaining half goes to the charity, in this case Make A Wish Connecticut, which benefits your own community. In terms of pricing, we really try our best to get it as close to what it would normally cost and the benefit is that you also get to donate to an amazing charity.

Jeremy is on the UConn team and there are normally teams of 20 or so, which means there are 19 other people doing the same thing as him. They can come together on group fundraisers and if they want even more help, they can contact our team for support.

When it comes for trip time we give them everything they need to know beforehand, and give them some cool blog content from actual past participants that give them the good inside stuff that maybe we didn’t think of. We try to have it be as authentic as possible. Once the students raise the money, the charity signs off on the student hitting their fundraising goal. We get them ready to go and we’re even there at the airport to see them off and sometimes even go with them on the flight. The whole nine. Especially because if it’s their first time out of the country, it can be a little scary, and we want them to have a friendly face to help them out. People come back humbled, changed, or just happy with a cool trip.

Jeremy has been on three out of the four trips we offer. He graduates in December and the amount of money he’s personally raised for Make A Wish is somewhere around over $13,000 just as an undergrad. That’s super impressive. As part of our alumni network, we also invite him to events and provide testimonial content. We have alumni student leaders come to the next college meetings we have at their schools and to help give newly interested students and newly recruited leaders tips. Keeping our alumni around helps us keep our trips authentic and provide a real resource for new students who are interested in going on our trips.

Our goal is to take more college students abroad to help them see the world and become more cultured and more worldly.

What kinds of trips does Choose A Challenge offer?

It’s embedded in the name. We want to offer trips that are a challenge, so they are travel adventure trips to iconic places around the world. We wanted to make accessible trips to places that normally you wouldn’t think are possible to go to as a college student. Most of our trips range from five days to sixteen days.Some examples are Mt. Kilimanjaro, Everest Base Camp, the ruins of Machu Picchu and running the Edinburgh Marathon. If some of the students want to continue their adventure, they can elect to go on extension trips that we offer as well. For Mt. Kilimanjaro, the extension trip is a two day African safari where you can see the Big Five and then go to the beaches of Zanzibar, going on cruises, swimming with the turtles, and more.

The shortest trip we offer is a marathon trip like to the Edinburgh Marathon, which is a five day trip. We just had a group from the University of Connecticut come back from there. They get to do a bunch of sightseeing, culture stuff, and then they run the big race on Sunday.

How does working with the charities come into play?

It’s three parts. Choose A Challenge puts the trips together. We’re the travel experts since we’ve been there before and have guides that do this hundreds of times a year. The charity comes in and they have the students fundraise the cost of their trip. The student fundraises for the charity and then they take the trip with us. Each one makes the other one work. The student comes abroad, the charity helps them fundraise the cost of their trip, and then we actually put on the trip.

Mike talking with the DUMBO BID
Mike talking with the DUMBO BID

How did Choose A Challenge start?

Ten years ago, two best friends climbed Mt. Kilimanjaro and they were with a group of people that all got together and reflected on how it was an expensive trip to take. So, then they worked with the charities and asked “Hey can we do something where we fundraise the cost of this trip, do it for a good cost, and then work it out?”. They were able to figure it out this business model at the summit of Mt. Kilimanjaro.

We've been around for a decade in London and three years here in the US. We’re expanding all the time. Overall as a company, we’ve brought 10,000+ students abroad and in the US alone we’ve raised well over $1 million here. With the UK combined, we’re at $25 million. We work with a lot of different charity partners to make those numbers realistic. Our goal at the end of every year is to be continuously growing. Us being out here in DUMBO for this number of years is a good sign of growth.

Could you tell us a bit about your journey?

I started out working in film and television and then I slowly found myself getting into television news. I started as an intern, then a beat reporter and then I slowly became a television news reporter. I got to cover things like local elections and even cool things like the New York Knicks are in the playoffs and I’m in the locker room and talking to them. All I knew was how to be an effective TV sports and news reporter. It’s what I loved. Then you know you just find your way on a different path when the opportunity approaches you.

I remember I was around people who were my age who had just an idea of a company they wanted to start. One of my friends who I was working with had this idea that he would talk about and then one day he wasn’t at work. We go “Where’s Steve?” “Oh somebody picked up his company and then they backed it”. That was the moment for me where I picked up the entrepreneurial start-up spirit.

I was itching to travel because in the news it’s tough to take off time. I saw the opportunity at Choose A Challenge on AngelList and went “Wow if I was in college I would love to take advantage of this.” then I hit apply and didn’t think anything of it. The CEO then reached out, then four interviews later they wanted me to be the first US hire they had out here. That was a cool experience for me because it was like “Hey this is an idea. There’s people that believe in it and it can actually become a business out here”. There also wasn't as much risk because they were well known in the UK.

As much as I was buying into them, they bought into me as well. They told me flat out that they wanted someone who could tell our story out here in the US and can speak knowledgeably about it and gets people excited. To tell this brand’s story has been one of the most beneficial experiences for me. They knew I didn’t come from a traditional marketing background but they invested in me and that was reason enough to move forward with these guys and build this company into what it is today.

Mike at Mount Kilimanjaro
Mike at Mount Kilimanjaro

Do you have any memorable moments from the trips?

The first big trip I ever did with Choose A Challenge was Machu Picchu. For the students there’s a little bit of nerves on their first trip and it was the same with me because it was my first big trip too. Three or four days in, we’re going through the Santa Teresa Valley, which is this huge open area filled with beautiful untouched nature, and there’s a family of three harvesting potatoes, which is huge in Peru. It was Mom, Dad, and a little girl who couldn’t have been more than five years old. We’re all waving and the little girl comes up and gives us a potato. And we’re like “this is super cute” and we had a little piece of Peruvian chocolate with us, which we wanted to give to her in thanks. I wave over to the parents and stick my thumbs up or thumbs down and they’re like “oh it’s fine!”, so I give her the chocolate and the look on her face just lit up. She takes it and runs back, we think back to her parents, but she comes back with the sack of potatoes and gives it to us. It made me think, it’s the moments in between the trek up to the ruins, which showed me that we’re really just out here and we’re in it.

DUMBO represents our spirit. It’s cool. It’s hip. It’s New York.

Why did Choose A Challenge choose DUMBO?

We knew we wanted to go to New York City. And for a startup, we wanted to look for a place that had a good balance between practicality/affordability and a good representation of your company. DUMBO represents our spirit. We’re young, a startup, and we work in a WeWork right now too. DUMBO has that feel as well. One of the things we wanted to establish out here is to be around people with that young upstart entrepreneurial spirit and DUMBO has that. It’s cool. It’s hip. It’s New York. Our first office was in DUMBO too and we could have moved to Manhattan but we moved right up the street because we’ve planted our roots here.

What’s your favorite place in DUMBO?

I mean Brooklyn Bridge Park has everything. I play my recreational volleyball league down there. I also go to lunch at Bridge Fresh Deli and see J.J. Reddick and he’s my favorite basketball player, which is cool. The team’s favorite lunch spot too has to be Bridge Fresh, Pedro's, or Front Street Pizza, which is a classic. We also go to Melt all the time.

Mentioned in this article

Choose A Challenge Bridge Fresh Market Pedro's Spanish American Restaurant Melt Bakery Front Street Pizza