What it’s like to be an entrepreneur and a serious traveler at the same time.

Being both an entrepreneur and a travel addict has never been easy. There is really no excuse to be tied to a desk anymore like ‘back in the day’ (which really wasn’t that long ago). Just look at digital nomads, the rising number of people who use technology to work remotely and live a free-spirited lifestyle. It’s the rise of what is being called the “traveling entrepreneur” – people who are making their businesses location independent and manageable from anywhere in the world, whether it’s the beach or an internet cafe.

Let me just touch on the subject of the word ‘entrepreneur’ for a moment, only because it seems like everyone is one these days. In my opinion, you are only a ‘true entrepreneur’ if you have failed many times, because its only then that you really learn what you did wrong, and how to make it right. For example when I was building a business in London, I pulled the plug at the last minute because the financial crisis hit and I knew it was about to get much worse. I honestly didn’t have the funds to sustain it anymore, and was way too stubborn to share the risk with a partner. I literally lost every penny I had, so much so that I had to call my mother and she had to buy me a ticket back home. Once back in Miami I had to regroup, pull my head from out of the sand and try it all over again. So unless you have stories similar to that, please use another term for yourself. I have seen the worse times a lot more than I have seen the good times, BUT, I wouldn’t have it any other way. I am addicted to creating ‘something’ out of ‘nothing.’

I would call myself one of the original digital nomads. In 1999, I went overseas with an open mind of whatever would happen, just would. So I set out to build a life that wouldn’t ever leave me feeling stagnant in one place again. It was a lot different back then, as there weren’t many of us on the frontlines of the digital age. I would say I had to stick my neck out a lot more and take some bigger risks to succeed.  But I’m happy I did it, because living and building businesses in many different countries taught me how to follow my gut instinct. I always had to have a vision, and know exactly how I was going to see it through. Otherwise, I would’ve just fell flat on my face.

I think that being part of that vanguard period was ultimately a good thing. These days, a lot of people are setting out to become digital nomads. But the truth is, while they accomplish a free-spirited lifestyle, they end up losing sight of long-term goals and end up floating around. That’s why being an entrepreneur and a traveler isn’t really two separate entities but rather single, distinct characteristic of achieving success.

Let me give you an example. When I travel to a new country, I’m not interested in tourist attractions. I’m interested in people. I’m combing through Twitter to find out the entrepreneurial landscape: finding out who are the big wigs, who are the dreamers behind new startups, who’s influential on social media. Okay, so how can I meet them as quickly as possible? I’m looking to make contacts, serious contacts, as they are really the starting point of a much bigger picture: the beauty of a digital world is… anything is possible.

That’s the big difference between a digital nomad and a real, serious traveling entrepreneur. I’m not stowed away on a beach somewhere, disconnected and only talking to people through e-mail. I’m making real, tangible connections. If I really like the beach, I’m going to find a way to be there more often: that starts with networking and creating opportunities both online and offline.

The best (and most recent) example I can give you is what’s happening in Portugal where I recently moved. Through just a few tweets I made some very important business connections in my new (short-term) home of Lisbon. Not to mention these guys are now also my good friends. Read that blog “It all started with a single tweet” here.

One of my favorite sayings is this ‘Traveling is like gasoline for entrepreneurs.’ I really believe that is true, the friends that you make, the new cultures you experience, it all feeds (in a big way) into your creativity and mindset.

Travel is gasoline quote image

But I’m interested to hear what you have to say. Is it enough to be a digital nomad, or should there always be an endgame to the lifestyle? What do you think it means to be a traveling entrepreneur?