Calvin Hawkes, Cofounder of TripHappy


Who are you?

I am Calvin Hawkes, co-founder of TripHappy, a location intelligence company using data to make travel better for both travelers and tourism businesses. We analyze millions of data points in cities around the world to provide insights into the different areas and help users answer the question, “what is the best area for me to stay in?”.

Can you tell us the story of your business from idea to where you are now?

We have quite a different story from other startups as we’ve been traveling and building TripHappy for the last 18 months. We started out in Asia in 2015, spent 6 months in Africa, finished 2016 in Mexico and now live in Santiago, Chile as part of the Start-Up Chile accelerator program. It’s been quite a journey, and we’ve definitely learned a ton about building a company while living abroad. In terms of the business idea, our current model is pretty different from where we started and we are now moving primarily into the B2B space with our data tools.

What has been your biggest failure or struggle?

Our biggest failure was something that most first time founders struggle with – shooting for the moon and building out the product before validating it. We built a travel tool that we thought fit a niche, and that a lot of users really liked and continue to like, but unfortunately the travel planning market is packed with tons of great tools and we found it hard to stand out in a crowded pack. Instead of trying to be a full itinerary planner we’ve rebuilt our business to focus on our strengths, which are applying our data and tools in the accommodation booking process.

And what has been your biggest achievement or success?

I think we’ve had two pretty big achievements so far. The first was being named one of Travel + Leisure Magazine’s Top Travel Tools of 2017. That was a pretty big validation for us that our new focus is going to be successful. The second accomplishment was being accepted from over 2000 applicants to participate in Start-Up Chile. We are now living and working in Santiago, and the financial and operational support we’ve received has really helped us to develop our business.

What’s your must read business book?

It sounds a little cheesy, but the 4 Hour Work Week by Tim Ferriss was the one book that really kicked off this whole adventure. While we are certainly working (a lot) more than 4 hours per week, the ideas in that book are pretty life-changing and I don’t think we would be here today without it.

Who’s your most inspirational CEO or founder?

Elon Musk to me really embodies the ideal of a great startup founder. He is someone who is truly a contrarian and has continuously trusted his own instinct even when others are calling for his head. I really admire his model of ethical capitalism and pushing for beneficial earth-moving changes in the face of opposition from the outdated incumbents. I also look up to David Heinemeier Hansson and Matt Mullenweg for examples of how to run great companies.

And can you tell us something weird or interesting about yourself?

One time I bungee jumped on fire into a pool at a night club in Indonesia. Check that one off the bucket list.