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An Interview with Paul Bennett at Context

Today we’re talking to Paul Bennett, the co-founder of Context Travel; a walking tour company that organizes small-group and private tours led by scholars and experts in different topics for intellectually curious travelers. One of our primary goals at Oh Hey World is to connect like-minded people with each other. Being a co-founder of a tech company in the travel industry, one of my personal interests is learning more about other entrepreneurs building travel companies. I came across Paul from a conversation I had with Rovaira at Pulse.ph and reached out to have him answer a few questions.

Without further adieu…

1) What do you do?

I run a global boutique walking tour company called Context along with my wife and co-founder, Lani Bevacqua. We organize small-group and private tours led by scholars and experts in different topics for intellectually curious travelers. The people who join our “walking seminars” are generally not tour people. They don’t want to be in a big group, listening to some schmaltzy tour guide, reciting a script. If they’re visiting the Roman Forum they want to do it with an archaeologist from a local university who’s written a book about the topic. Context ensures that they’ll get the most out of that experience and not waste their time.

2) Why do you do what you do?

I hate tours but I love learning about new places. I used to be a journalist and so got in the habit of connecting with local experts (sources) whenever I went somewhere. After a 2-year trip aboard a 38-foot sailboat with Lani, we decided that there were others out there like us who valued local expertise and would pay to engage with an expert during their trip. I also believe that the era of packaged trips will soon end. Who really wants to spend 10 days with 20 other people in a pre-packaged experience? Not me. Everything we do is a la carte. If you want to take a single, 3-hr tour with us during your trip, that’s fine. If you want to take two Context walks every day for a week across several cities. That’s cool too. We’re set up to allow the traveler to shape their cultural learning around their needs and interests.

3) What are you most excited about right now?

I’m always in love with our newest cities. We opened Kyoto and Tokyo this winter, and we have an amazing group of people there doing innovative things like a tour on Japanese aesthetics and a Manga walk. We also just opened Amsterdam and are working on a walk around Dutch social experiments like legalized drug use and prostitution and the proliferation of bicycles. For me, this is the most interesting part of travel: digging deeply into a place and what makes it unique.

4) What’s next for you?

We’re putting together a program in Buenos Aires. We’re also moving into the final phase of an internal quality improvement program that’s taking the level of our walks—already considered by many to be the best in the tour industry—and raising it. This is a quiet, hard-to-perceive change for someone from the outside, but it’s critical. We compete against the rest of the “day tour” industry on quality, and I think we’re setting ourselves up to have a major impact over the next 2-3 years on this metric.

5) What’s a cause you’re passionate about and why?

Context does a lot of work in sustainable travel, and we’re one of the few travel companies that’s also a B Corp. But, that’s work related. For me, personally, I volunteer with Big Brothers, Big Sisters, which is a mentoring program for at-risk youth in urban areas. It’s a cliche to say that kids are our future, but it’s true. I think that many of our social issues in the U.S. can be addressed by targeting kids—teenagers, especially—and opening their minds to different possibilities. The schools aren’t doing it. Hell, in Philadelphia where I live we just closed down half the libraries and cut the music program from all the schools. It’s frightening to think what that means for low-income kids.

If you’re keen to connect with Paul further, you can find his current location on his OHW profileA big thanks to Paul for sharing his motivations and current projects. If you’d like to connect on social media:

Context Travel on Twitter and Facebook

Paul on Twitter

We’ll be featuring a number of other travel entrepreneurs in the coming weeks. If you are an entrepreneur in the travel vertical, and want to be profiled, please sign up for an OHW account and add “travel entrepreneurs” as an interest on your profile — then shoot me an email (drew at ohheyworld).


Drew Meyers

Drew Meyers is the co-founder of Horizon & Oh Hey World. He worked for Zillow from September of 2005 to January of 2010 on the marketing team managing Zillow’s API program and various online partnerships. Founder of Geek Estate Blog, a multi-author blog focused on real estate technology for real estate professionals, and myKRO.org, a blog devoted to exploring the world of microfinance. As passionate as you get about travel.

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