Understanding How To Thrive As A Digital Nomad

Way back when, being defined by a single word seemed commonplace. You were a “doctor” or a “teacher” or a “lawyer.” Fortunately, it’s a practice that’s antiquated as all hell. Think about at, at a party do you feel comfortable defining yourself with one word? You’re not just a secretary, student, or debtor. It’s 2016, there’s more to the story than one word and we now realize that. You can be a model and a championship squirrel suit jumper, or a barista manager and a world record holder. Hell, you can be a therapist and a travel writer or a graphic designer and a soldier for positive self affirmation.

This week on the Mad Ones we talked to one of the founders of, Ben Granas, who operates a team that can’t be defined with just one word. They’re businessmen, sure, but they’re wanderlust-laden travel aficionados, kiln salesman, and the owners and operators of a very useful travel website. Granas found the time to talk with us while in Mexico, setting aside his modern-day-nomad-operation for just a moment to answer our questions about how it’s all possible.

So, you guys just started a business while traveling. Is that the broad stroke definition of it?

Yeah, we [Granas and his business partner] were working in New York. We each had corporate jobs and we each decided that after years of doing that, it wasn’t necessarily for us. We were looking at different ways of starting our own business. When we’d come up with the idea of TripHappy we realized that we probably didn’t need to stay in New York because what we were doing was going to be all online. We could essentially do it from anywhere. We’re all pretty involved in travel anyway. We thought the most logical and most fun step would be to take it on the road.

We’ve been doing this now for about a year. We started out in Asia, moved to Africa at the beginning of the year. Now we’re in Mexico. In the beginning of 2017, we’re going to be going down to South America.

Have you ever not been able to work when your supposed to be working because of spotty Wifi on the road?

It definitely goes out. It was interesting when we were in China. Not sure if you know, but China bans access to Google. Because our site is map-based and we use Google maps, we potentially couldn’t use our own site in China. We had to figure out ways to get around that, which was interesting. We lived in Morocco for almost three months. When we were there, yeah, the internet was really not great. Actually, in our apartment in Marrakesh, we only got signal on the roof. A lot of times we had to go sit on the roof to work, which was interesting. It’s at the end of the world. Everything was ten times slower than it should be.

Yeah. I mean, that’s part of the adventure, though, right?

Yeah. We are all sort of interested in doing non-traditional travel. That’s kind of the philosophy we’ve put into Trip Happy as well, that anyone can see where everybody has gone. We are actively choosing to go to the places that fewer people have gone, I guess. There is a community of people who work from the road, like what we’re doing. There is a lot of very established cities that they live in, Shanghai and Chang Mai, which we were at for a bit. Berlin is another and there’s a few more, but we certainly go to places that I wouldn’t consider hot spots for this type of work.

Yeah. I guess that’s ultimately how it makes sense because you’re going to places where … You can save a couple bucks, but it also adds to your story, the adventure of it all.

We chose to leave New York for a reason. Part of it was monetary, obviously. Part of it has also been that we wanted to explore the world. This is the perfect opportunity to do that while we can. I don’t think that I would have ever spent three months in Morocco or a month in China if it wasn’t for this company.

How does this work out with taxes?

We’re a US incorporated company and all of our money does flow into a US bank account. We do pay US taxes. We’re totally legit there. We don’t actually earn any income in the countries that we’re in. We’re pretty safe on that front.

That’s a pretty hot topic for the 1099-generation.

There is a rule that we heard about through the grapevine. None of us has tried it yet, but if you spend over 11 months of the year overseas, you don’t pay US federal income tax. You might still pay state, since we’re based in New York, our company will still be paying 20% in US state taxes, but you won’t have to pay the 13 or 15% federal income tax. We haven’t actually tried that out.

Yeah, that’s kind of a risky move without reading the fine print. Uncle Sam might not be too excited about that one.

The visas are especially tricky. We are kind of running a business, we are kind of traveling. Maybe we should have technically applied for business visas in the countries we’re working in. If you have your business visas, it’s possible we should be paying corporation taxes.

That makes sense.

I bet the countries would want tax revenues, so they might disagree, but what we’re doing is definitely standard practice for half the world. It’s one of the gray areas.

I have friends who live in Baja and work in San Diego. They’re making dollars and spending pesos. Their mentality is, “Why would the Mexican government ever have any problem with this?”


What was the learning curve getting into this? Since you picked up and moved were there some failed trials or did it just work out?

I think we’re still in the process of figuring it out. The tension has been one-sided. Everywhere we go, we have to balance with learning an entire new culture, a new language, figuring out how to move around in the environment, the neighborhood that we live in. The business side of it has been every day, we’re learning something new and figuring it out on the fly. I think it’s part of the fun. It’s easier here than living in New York. We do work for probably 12 or 14 hours a day. It’s not all glamorous, but every day is totally different. We’re seeing a new place. We’re discovering a new country, a new culture. Just getting out of that environment has been such a cool thing.

Also, by virtue of being in another country and by seeing a different culture you’re learning new things that you can integrate into your business.

Yeah. That freedom. It’s nice to wake up and say, “I’m going to work on the things that I want to work on today.” That freedom is the best and not have somebody saying, “No, that’s not what you’re going to be doing today.”

Yeah, yeah. Are you making enough from Trip Happy to stay on the road indefinitely?

We actually have a couple different businesses that we run. Trip Happy is our full-time main focus and our other one sort of runs by itself on the side. Between the two, we essentially have enough to cover our monthly costs.

What’s the other company?

It’s an e-commerce company. It’s US based. We have a US based customer service person that handles most of the work. We set that up before we set up Trip Happy and it kind of just runs by itself now.

What does it do?

We sell kilns.

The ovens that harden clay bowls?

Yeah, that’s our e-commerce brand. They’re like $1200 a pop. We get those sales coming in, one every two days or something. That definitely supports our cost of living, which is nice.

Did you guys work with pottery before this? Or did it just fall into place?

We were thinking of ideas of what to sell, and it just seemed like a good idea.


It’s kind of fun because we don’t know too much about pottery and we certainly don’t know about these new, expensive, edgy practices, but we know about travel. That’s what got us to a point where we’re able to talk to you right now.