The first time I heard of Chris Guillebeau was from the Meet, Plan, Go! event this past fall in New York City. His latest book $100 Startup was one of the giveaways. I didn’t win it, but the next day I ordered it from Amazon. I read it and decided to get in touch with him personally. Some of the entrepreneurial ventures described in the book had really spoken to me, and I wanted to thank him. We started talking on Twitter and despite his crazy schedule, he gladly agreed to an interview.
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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.
“In the battle between planning and action, action wins.”
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.
“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.”
MS: What was your first business idea and how did you come up with it?
CG: 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.
“People will pay for information about travel, if packaged properly.”
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 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.
For more, read the rest of the interview on The Expeditioner.
If you’re passionate about travel and entrepreneurship, then I highly recommend his book.
