How a Canceled Trip Created Treehoppr

Three years ago (almost to the day), I canceled a trip to Iceland. The next day, unknowingly, I began my journey toward Treehoppr.

I bought the ticket. I had never booked a trip so spontaneously before. Minimal research, minimal planning, just a desire to go somewhere new and see something different. A wave of excitement crashed over me. I started picturing myself eating seafood in Reykjavik, hiking alongside Asbyrgi Canyon, floating in the Blue Lagoon. I went to bed knowing that, in two weeks, I would land at Keflavík Airport ready for the trip of a lifetime.

I woke up to different thoughts. Reasonable Kevin joined the party and made some decent arguments against the trip: 1) You have a rent payment coming up. You can’t afford the $1,200 trip you just booked. 2) Your boss will hate you if you take a week off from work right now. 3) You’re going on this trip alone? Are you crazy?!

So, I canceled it. It was a terrible feeling. I got most of my money back (minus the hotel), but the thing that bothered me was knowing that my responsibilities got in the way of something that I always wanted to do. I felt like a reasonable adult and I hated it.

I wondered, though. Do other people have the same hesitations toward travel? Do other people fret over taking time off work? Do they debate the amount of money they’ve saved or the research they’ve done? Millions of us around the world identify as travelers, but are we able to travel as often as we’d like? Or are we limited by our own inhibitions? The entrepreneur within me sensed a product buried beneath those questions; so, I started digging.

In the months following my canceled Icelandic adventure, I picked up every literary piece I could find on the travel industry. I delved into dozens of studies regarding the correlations between travel and mental health, productivity, economic growth, etc.. I read books examining the psychology and behavioral patterns of travelers. If you’re ever looking for some light reading, give “Economic Psychology of Travel and Tourism” by John C. Crotts a whirl; it’s fascinating (even more captivating considering it was written in a pre-internet era). People are better when they travel. Everything I read seemed to draw that conclusion. So why do most of us only take one or two trips per year?

My curiosity grew. On to step 2: interviews. I sat down with travelers and asked them about their experiences, what they liked and disliked most about wandering the globe. I found out that I was not alone. The most common statement I heard during those sit-downs was “I would love to travel more, but…” The subsequent assertion varied, but that small snippet indicated that there are pain points in the travel experience. Whether it be cost, or time, or lack of preparation, people feel inhibited from traveling as often as they’d like. That was all I needed to hear.

I started piecing together the first version of Treehoppr after that. It was an exciting time. Doug, my co-founder, joined me and we hacked together this ragtag consumer platform which combined trip planning tools and automated savings plans. It allowed travelers to hone in on itineraries they might be interested in based on their personality traits and incrementally set aside money for those trips. We stepped back, and said, “Damn, this is cool. I like this.” Then, we said, “Is it different?”

It wasn’t. If you go on AngelList today, click on “Jobs By Market,” and select “Travel,” you’ll find over 24k startups listed. 99% of them are doing exactly what Doug and I were trying to do with that first version: solving pain points in the consumer travel experience with an “innovative” online platform. What we had was good, but scaling it and differentiating ourselves in such a saturated market would take a miracle.

We had to go one step further. Back to the drawing board. After an afternoon whiteboarding with our mentors back in Boston (shoutout to the guys at Mavrck), it dawned on us: B-B! Few business-to-business platforms exist for travel, and even fewer involve any aspects of leisure travel. Was there a way we could wrap our software into a platform that would bring value to organizations? Could we link leisure travel to employee wellness and appeal to businesses as a hiring and talent retention tool, as a unique way to tap into employee interests and improve productivity? “Travel benefits” were born.

Treehoppr shed its consumer travel facade and became an employee wellness company overnight, dedicated to ending the stigma surrounding paid time off and to making travel a more integral part of corporate cultures. Our founding team came together quickly; Zoe, Chelsea M., Chris, and Chelsea F. all joined within a one month span. We reskinned our platform, added some business-friendly functionality to it, put together marketing materials, and reached out to organizations with our new value-prop; it’s been a whirlwind ever since.

Incredibly, three years have passed since my canceled trip. I still haven’t been to Iceland, but I can smile about that now. That moment lead me to Treehoppr, to this idea, to this team, to this feeling of fulfillment that I get every day I step into the office. The road here has been tumultuous, riddled with ideas, interviews, questionnaires, long nights, red bulls, coding classes and bootcamps, pitches, partnerships, passion, persistence, successes, and an ABUNDANCE OF FAILURES, but I wouldn’t trade any of it. I’m so proud of this team and all that we’ve accomplished so far. I’m excited for where 2018 will take us and, even more so, for where what we’ve built will take all of you. As the new year rings in, make a promise to yourself. Don’t let your hesitations hold you back. Find new and beautiful places to go and get lost in all of them.

Hey Iceland, btw, I’ll see you in April.

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About Kevin Corliss

Kevin is CEO and co-founder of Treehoppr where he's in charge of strategy and marketing. Kevin is an outdoor enthusiast and travel addicted. Contact him via email at