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“I’m consistently blown away by how generous people are – they don’t even think twice about sharing their favorite spots.”

Andrew Cross was tired of conventional trips and wanted to experience life the local way. Not typical walking tours, but real, memorable experiences that only locals knew about. This desire for something more led him to create Tripzaar, a marketplace for experiences planned by locals. Founded in 2013, Tripzaar has already had thousands of dollars in bookings and have received positive reviews from press, travelers and locals alike.


BusinessInterviews.com: Can you expand on how living in South America as part of the Start-Up Chile program last year served as one of the key inspirations for launching Tripzaar?

Andrew: When I arrived in Santiago last year, I wanted to see and experience everything I could. I researched everything that I should go and see, but, to be honest, I was a little disappointed. Most of the recommendations centered around historical museums, like visiting Pablo Neruda’s house. Many people would enjoy that, but when I travel, I prefer to get a more authentic feel for a place, going where the locals go, doing what the locals do. With the information that was available online, it was incredibly difficult to find these authentic experiences. It was only once I’d been living there for a few months and had met several locals that I began to find all these incredible things to do. For example, I was taking Spanish lessons and ended up becoming friends with my tutor, hanging out beyond the classroom – trying some really authentic locals foods from the local market, etc. I also ended up going paintballing in the Andes, an experience I’ll never forget.

Never before had the comparison of the “tourist” experience and the “local” experience been so clear for me, and I wanted that wherever I went. Hence the motivation behind Tripzaar – to find those things the locals do that would make a trip extra-special.

BusinessInterviews.com: Can you talk about the development process from having the initial concept for Tripzaar to actually creating a business around it? What were some of the early challenges that you faced and how did you overcome them?

Andrew: Starting out, we weren’t sure what we wanted to build – just what problem we wanted to solve. Our first idea was to create a recommendation engine for each destination (e.g. when going to Santiago, be sure to try X,Y & Z), but while that would add some value, it wasn’t that different than Gogobot or what Trippy used to be (they’ve since pivoted) and didn’t seem to excite many people we talked to. Additionally, we discovered that finding these experiences is only one part of the equation – the other part is actually connecting with locals and feeling like you’ve had an exclusive activity. That’s what led us to our model today, where you can book directly with locals and receive a high quality, authentic experience.

Once we decided on what to build, the next big problem that we faced was actually finding the local activities to bring onto our site. Because the majority of the tours that are currently out there are very touristy, we have had to work a lot harder to find great content. What we ended up finding was that we could get in touch with boutique hotels and promote them in exchange for connections to amazing local people. It’s a bit of a roundabout way to find these experiences, but the results have been worth it.

BusinessInterviews.com: Let’s say that I want to use Tripzaar for an upcoming trip. Can you talk me through how the process works?

Andrew: The first thing you would do is browse around our site, looking at experiences sorted by destination or popularity. No one books a trip without looking at several options, so we actually encourage this. It helps you dial in on what the ballpark prices are for a destination and what is available for your interests.

Once you’ve found an experience that you like, you book it directly on our site. Locals have 24 hours to confirm a booking, and only when it’s confirmed will we process the payment. We also have a full guarantee for your trip, so if anything goes wrong, we’ll do what it takes to resolve it, whether that’s footing the bill for a different hotel or processing a refund. A big part of what we’re selling is safety, so we take that aspect of our business very seriously.

Finally, after your trip, we’ll follow up with you to see how it all went, if there’s anything that can be improved with the experience and get a review posted.

BusinessInterviews.com: What are some of the features of Tripzaar that you’re most proud of or excited about?

Andrew: One feature that I’m especially excited about is our upcoming Destination Guides by Locals. The first one we’re launching is for Costa Rica, as that has been one of our better performing locations. The logic behind this is that we’ve noticed there are several questions that keep popping up – for example which company to rent a car with and what to watch out for. We have a phenomenal resource with our locals to answer these questions, so we’re building out destination guides that lean heavily on their experience & knowledge. Most of the other travel guides out there are very politically correct, whereas we have an opportunity to give a no-holds-barred take on what to do and what to watch out for.

Another feature that I really like is our experience customization widget. It sounds like a trivial feature, but the traditional customization method is to have an extensive email trail where you have to add up all the “deltas” to figure out the final agreement. To simplify this, we built a widget for our locals to offer customized experiences without this back and forth. It’s one of those features that just makes a lot of sense and simplifies the whole process for both parties.

BusinessInterviews.com: How did you get locals to give away the secrets to their favorite local spots? Did anyone express disappointment that you wanted to attract tourists to their favorite places or were they happy to share?

Andrew: To be honest, I was a little concerned about this when we started out too, but I didn’t need to be. I’m consistently blown away by how generous people are – they don’t even think twice about sharing their favorite spots. If anything, they get excited about it. I think one of the big reasons for this is that they are personally sharing it with others. They get to see the joy they bring, and that’s really fulfilling for a lot of people. If it was just being posted online and they didn’t get the feedback from people that enjoyed it, it might be a different story, but the way our site works avoids this issue.

This is one of the unintended benefits of our model – we aren’t just providing blanket recommendations for people, we’re creating inter-personal connections and really providing value for both the travellers and the locals.

I think one of the best examples of this is our first booking to Costa Rica. One of our locals, Crystal, hooked the travelers up with a hidden waterfall behind a friend’s farm. While she wouldn’t post that online for everyone to see, she was more than happy to make their experience special and give them a real, authentic Costa Rican experience.

BusinessInterviews.com: What’s the most exciting thing on the horizon for you personally or professionally?

Andrew: One of the things I’m most excited about is travelling again. This past year has involved a lot of time in the office, coding away on the site. It needed to be done & I have no regrets, but as we expend and grow our offerings, I’ll likely need to hit the road a little more, which is something I’m itching to do. At the end of the month, I’m actually heading to Spain for La Tomatina (the annual tomato fight) and to meet a few of our locals in the area, so I’m also pretty excited for that as well.

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