Interview with Trippy.com’s Founder, J.R. Johnson

Since its debut it has undergone an evolution, referred to internally as “Project Delightful”, which launched Trippy’s new photo-based visual-browsing experience.

I’ve been talking to Trippy’s Founder and CEO, J.R. Johnson (known simply as “JR”), who is something of a travel start-up veteran having previously launched VirtualTourist, which was acquired by Expedia in 2008.

JR, what was the original idea behind Trippy, and why did you pivot to a new model?

The original idea is still exactly what Trippy is about today – collecting travel ideas with your friends.

Our beta launch included the ability to let your friends help you plan your trip, and our app lets you take your itinerary (and your friends!) along for the trip. Now, we’re complimenting that feature set with an inspiration experience, based on a ton of feedback that people wanted even more ways to browse and get inspired on Trippy. So we launched visual inspiration boards with great travel photos so you can follow friends and experts to discover what they are doing… and even just dreaming about doing. Trippy then puts all of your travel dreams on a map so you can see where your travel ideas are landing. When you’re ready to make those travel dreams a reality, your friends can help plan the trip with our original trip planning features.

So Trippy’s evolved to take you from dreaming to doing – and people are loving it!

How is the new site going so far, and what sort of user activity levels are you seeing?

It’s doing really well. We’ve seen an exponential increase in engagement on the site since launching our discovery and inspiration features.

Why should someone use Trippy over a much larger and almost-identical-looking site with a larger userbase like, say, Pinterest?

Trippy’s focused specifically on travel, which lets us do some really unique things that build on the idea of a visual browsing experience. For starters, all of the photos on our site are mapped — so you know where those amazing photos are actually located. We also let you see your travel boards in map view, which gets really fun especially when looking at a larger region of the world.

Also, there’s a valuable reason to save all of these great images — you can turn them into a real trip (plotted on a map), get your friends to weigh in and share tips as you create your itinerary, then have the app with you to follow your itinerary and share photos back with your friends while you’re on the go. Trippy is a full-circle trip planning experience.

How do you feel that the tourism industry is evolving in the wake of social media, and where do you see it going in the immediate future?

Social is a game changer, to be sure. It’s been an exciting time, especially as we’ve come back into the field after selling our last travel site (VirtualTourist) to Expedia in 2008. As the non-compete from that acquisition lifted and we took a look at the landscape it was clear there’s still massive opportunity to make the social graph of real value in the travel context.

We’ve had the Webby Awards this month. Kayak won the Best Travel Website award, but I believe you were nominated despite being such a relative newcomer, along with some big hitters like Hipmunk and TripAdvisor?

Yes, we were pretty excited about our nomination. It seems we are the first social travel site to ever be nominated and we were the youngest site in the mix, so it was a very cool honor.

What do you think? Is Trippy the next big thing? Or is it too similar to Pinterest? Let us know what you think!