One Country Away From Seeing Them All: Q&A With Roaming Entrepreneur Chris Guillebeau

Monday, February 25, 2013


Still in his early thirties, Chris Guillebeau is one country away from completing a tour of every country on earth — all 193 of them — all while never having a “real job.” In his fight for eradicating conventional beliefs, he proves time and time again that “The Art of Non-Conformity” is not just a concept that works for him, but one that can work for anyone.

Ever since his first business, followed by four enriching years of volunteering for a medical charity in West Africa, Chris has never stopped traveling. He has given keynote speeches to presidents, spent time with indigenous populations and inspired people to become entrepreneurs. In doing so, he focused on three major topics: personal development and life planning, entrepreneurship and international travel.

For his latest book, The $100 Startup, Chris identified 1,500 individuals who have built businesses earning $50,000 or more from a modest investment (even from $100 or less). From that group, he’s chosen to focus on the 50 most inspiring case studies. In most cases, people with no special skills discovered that their passions could be monetized, and took the plunge in restructuring their lives towards greater freedom and professional fulfillment.

As he writes in his book, “You don’t need an MBA, a business plan or even employees. All you need is a product or service that springs from what you love to do anyway, people willing to pay, and a way to get paid.”

The Expeditioner: What was your first business idea and how did you come up with it?

Chris Guillebeau: Nearly 15 years ago, I learned how to buy and sell coffee. I loved the idea of earning my own income without depending on a traditional employer, so I kept trying different projects. Those that were successful, I put more effort into, and I haven’t had a job since.

How many days on average a year/month are you traveling?

About 150 days, I think. I’m usually away for two weeks at a time, then home for a while to work on books and other projects, then gone again.

You are one country away from completing your quest to see the entire world of 193 countries. How does that make you feel? What’s next?

It makes me feel both happy and sad. It’s been a 10-year journey, and in some ways I’m not ready for it to end. As for what’s next, well, I write, travel and connect with people. I don’t expect that will ever change . . . at least I hope it won’t.


What are some of your favorite countries? Favorite continent?

South Africa, Macedonia, Liberia, Hong Kong, Laos . . . I could go on. I’m not sure I have a favorite continent, but I do love Australia — which of course is considered both a country and a continent in the U.S. system of geography.

You’re an expert in saving airfare costs, and so far you must have flown on thousands of flights. What’s your favorite airline and why?

A few favorites: Cathay Pacific, Singapore Airline, Royal Jordanian and Etihad. I’ll choose Cathay as number one since I’ve been with them dozens, if not hundreds, of times. I love passing through Hong Kong and the Cathay in-flight experience is great in all classes.

What was your worst flying experience?

More than once I’ve thought we’re going to crash, which is somewhat undesirable. Probably more common, though, isn’t the terrible flights but the sense of being stuck somewhere. I was stranded in Kiribati when the inbound flight had to return to Fiji for a mechanical issue. Waiting out the uncertainty of being stuck for an unknown amount of time was much worse than any bad flight.

What is your least favorite country (or countries), in which the local regulations greatly interfered with your travel plans?

There have been plenty of countries where I’ve run into trouble with regulations, but that doesn’t mean they are my least favorite. Sometimes, in fact, those countries are more interesting. I had trouble getting into Pakistan, for example, but once I made it I had a good experience.

What would be your first choice of living anywhere on the globe, if you had to move out of your home base of Portland, Oregon?

Sydney, Australia. It’s my favorite global city.


How was the process of choosing the 50 most significant case studies out of 1,500 entrepreneurs that contacted you for your latest book The $100 Startup? Could you name one that truly inspired you to make some changes to your own businesses?

It was a lot of work and a lot of fun. I was inspired many times over as I saw how so many ordinary people had been able to start businesses that earned at least USD$50,000 a year, and often much more. One of my favorite stories was Gary Leff, who started a six-figure (part-time!) business helping people book award tickets. He had constructed this business in a way that allowed him to continue working his day job, which he enjoyed. But he also had a fallback plan in case the day job stopped being meaningful.

Is one born an entrepreneur or does one discipline in becoming one?

I don’t think people are born with an inclination toward a certain career. At some point, one sees an opportunity and decides whether to pursue it or not. An entrepreneur will pursue it.

A start-up is a mountain to be climbed towards its peak. What would you say is the must-have “equipment” to reach the top?

Curiosity and the willingness to start something.


Quotes from The $100 Startup:

“The secret to a meaningful new career is directly related to making people feel good about themselves.”

“People will pay for information about travel, if packaged properly.”

“In the battle between planning and action, action wins.”

“Don’t think innovation, think usefulness.”

“Business opportunities are like buses; there’s always another one coming.” Richard Branson

“Good things happen to those who hustle.” Anais Nin

“Business is not a popularity contest.”

By Monica Suma



Romanian by birth, but New Yorker at heart, there is nothing Monica enjoys more than traveling and exploring other cultures. Her 20-something relentless quests stem from a long bucket-list, always accompanied by her camera. Follow her adventures around the world on her blog or on Twitter @MonicaSuma.

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