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How to Make Money While Travelling: TripHappy

Nomad Interviews: 18th Edition

· Nomad Interviews

Welcome to the 18th edition of “How to Make Money While Travelling” which features successful nomadic teams and interviews with location independent entrepreneurs.

This week I interviewed Ben Granas, Calvin Hawkes, and Carl Grafmuller, the founders of TripHappy; a new data driven travel planning startup.

TripHappy helps you plan better trips by seeing exactly where other travelers have gone before you, so you can choose to hit the popular sights or get off the beaten path.

How to Make Money While Travelling: TripHappy

Q1: So, how do you make money while travelling?

We currently make money from both TripHappy as well as our e-commerce business (, which is mostly passive. TripHappy is our main focus and we’re currently spending all our energy trying to build it into a successful company.

Q2: What were you doing before TripHappy?

All 3 of us had corporate jobs in New York City working in finance, consulting, and insurance at some of the biggest organizations in the world. We were all making good money but felt unsatisfied working for such large companies.

Q3: What are your reasons for becoming location independent?

We are all pretty experienced travelers and one of the main reasons for starting TripHappy was to build a company that allowed us to live wherever we want and not be tied down to any physical location. Since we are bootstrapping our company with our own funds, we’ve also been able to save a ton of money by leaving NYC and living in areas with a lower cost of living. So far we’ve lived in Asia, Africa, and Central America, with South America coming up in 2017.

How to Make Money While Travelling: TripHappy

Q4: What challenges do you face in your career while both working and travelling?

So far, most of our challenges have been technical and timezone related. Our site is built on top of a lot of Google APIs, so when we lived in China we had a lot of difficulty just loading our own site. Internet has also been spotty in some of the places we’ve lived, like Marrakech and Cape Town.

We also run an e-commerce business ( that requires daily customer service. Because we spent the first 6 months in Asia, we could not communicate with our customers and had to hire a full time employee. That has turned out to be a blessing though as it’s freed up a lot of our time to focus on TripHappy.

As TripHappy grows we will certainly run into issues like hiring and fundraising that other US-based startups can do much easier.

Q5: What is the biggest lesson you have learnt from becoming location independent?

That being a digital nomad still means hard work and dedication. I think a lot of people have the misconception that digital nomads don’t work as much as regular office workers. In our case, being location independent - and being our own bosses - has meant significantly more hours worked than in our corporate jobs. Our standard workweek is 7 days, 12 - 16 hours per day, with some nights or afternoons off here and there to explore the city we are in. We know we need to outwork our competitors to be successful, and that’s true whether we’re in the US or abroad.

How to Make Money While Travelling: TripHappy

Q6: How do you find work while travelling?

We get nearly all of our users through content marketing, SEO, and social media, which is probably similar for nearly every startup.

Q7: Do you think businesses should offer more remote working opportunities? If so, why?

One of our biggest complaints we had with our corporate jobs in the US was the focus on facetime, or presence in the office. Even if there was no work to be done, we were expected to remain in the office until it was an acceptable time to leave. We found it was much easier to get distracted by our co-workers too. Remote working allows employees to focus on their tasks and work on their own time, which is a much more efficient way to get stuff done. Companies seem to be recognizing this and are trending to more flexible working schedules, but it’s likely to be a very long time before offices get phased out.

Remote working obviously has its drawbacks, and we’ve experienced a loss in productivity when the 3 of us are separated for long periods of time. Collaboration becomes much harder, and it’s difficult to keep tabs on other employees. But overall the benefits outweigh the costs.

How to Make Money While Travelling: TripHappy

Q8: What would your advice be to someone who wants to quit their desk job to become location independent?

Make sure you have at least 6 months of savings and ideally much more. The last thing you want to do is worry about running out of money immediately after you leave your job. Though I would also add that if you make a budget and stick to it, you can live for much cheaper than you would expect without sacrificing much. We average about $600-800 per month in expenses each, and our quality of life is much higher than it ever was in NYC. Just be smart about where you live and stay there for 1-2 months at a time. And don’t fall into the typical traveler traps of spending your entire budget every night out partying.

Q9: What is your favourite travel quote?

“Twenty Years From Now You Will Be More Disappointed By The Things You Didn’t Do Than By The Ones You Did Do”. Mark Twain​

Thanks, TripHappy!

How to Make Money While Travelling: TripHappy
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