The Trip Tribe founder connects like-minded travelers for unforgettable group vacations.
From a co-working space in Dupont Circle, former White House national security official David Aidekman, 39, dreams up new adventures for his company, Trip Tribe. Launched in 2012 with his wife Meg, the retreat planning website is now the leading site of its kind in the world.
How did the company first get started? It was a series of very happy accidents that turned a very intense hobby into a small business, which turned into a slightly bigger business, which turned into a tech company, which turned into a startup. Meg and I were organizing group vacations and learning a lot about the industry when I became part of another travel business, getting involved in group vacations in Europe and the Caribbean. We saw a huge opportunity to build it to Internet scale and set ourselves on a path to expand.
What did you think was missing with regard to group trips? The whole genesis of our business is that the people you go with makes or breaks whether you have a good experience. So, we created trips that were about connecting the right people with each other, building amazing groups and making lifelong friends.
Is it usually people who know each other or do you bring people together who have never met? It’s a mix. Most of our bookings are individuals and pairs — not necessarily couples but maybe two friends — who wish to join a larger group. A lot of our trips are suited for groups. You don’t necessarily go on a yoga retreat by yourself, or white water rafting or a cycling tour around Europe. Whether you know people or want to meet people, we make that easy.
Is there a certain age group or target audience? No. It’s all over, from young professionals to retirees.
What categories of trips do you offer? Yoga, wellness and fitness is one of our biggest categories. Next we’ll have hiking, cycling, food and wine, boating, skiing, golf and over time we’ll cover the whole landscape of group vacations.
Did you face any unexpected challenges getting a startup off the ground? Oh, all the time! We learn something every week. In my past career I had been accustomed to massive operations with tons of resources and a massive budget. I came in, starting as the only full time person and tried to build a team and build out capabilities and technology on a shoestring budget. That was a challenge and it’s always a challenge because your ambitions are always bigger than the resources available.
What do you think Washington, D.C. has to offer the startup scene? It has tons of intellectual power. There are a lot of smart people who either come here or are immersed in the culture of trying to change the world or transform things. There’s a lot of energy and ambition and, secondarily, for a small company looking for resources and capital, there’s wealth in the area. Fifteen years ago, there wasn’t a lot focused on little technology startups, but I think now there’s a fair bit of attention on that, plus awareness and willingness to invest.
You must love to travel. What’s been your most memorable trip? Our honeymoon two years ago. We sailed around the coast of Turkey.
Where would you like to travel next? Africa. I’d like to go on safari. I’ve never been.
This article appeared in the November 2015 issue of Washington Life.