Interview with Chris Guillebeau - Live Work Travel USA|Live Work Travel USA

Interview with Chris Guillebeau

Chris GuillebeauI’ve interviewed only expats from countries other than the U.S. so far in my blog. Time to switch it up a little and do an interview with an American for a change. Someone who has lots of experience with other cultures and can compare it to America first hand. I believe there’s no better choice than Chris Guillebeau for this interview, because he has literally seen every single country on this earth. Chris is a best-selling author, speaker, entrepreneur and travel hacker, who I’ve mentioned before in “How to Become a Frequent Flyer Millionaire“. I had the opportunity to ask Chris a few questions:

Chris, back in 2006 you’ve set your personal goal to visit all 192 countries before you turn 35. How long did you usually spend in each country and were you still able to enjoy your travels with this self-made pressure upon you?

The spent in each country varied quite a bit—anywhere from 1-2 years to 1-3 days. Yes, I enjoyed it. The pressure was good. The pressure helped, not hindered. I think if I had made the goal “see a bunch of countries” or “see every country sometime in my life,” it wouldn’t have been nearly as motivating.

Chris Guillebeau with tiger

Expats often complain that the U.S. has very strict immigration laws. Have you had any immigration issues to enter other countries? If yes, please share a few examples.

Yes, it’s unfortunate that the U.S. doesn’t let in more responsible travelers and visitors. I wish they would. However, lots of other countries have pretty strict immigration laws too. I had trouble in at least a dozen countries, most notably Saudi Arabia, Pakistan, and Eritrea. For the first two countries, I managed to talk my way into a visa upon arrival even though such a thing didn’t formally exist. When it came to Eritrea, I was actually deported to Cairo in the middle of the night!

As most travelers know, when you head off the beaten path, things don’t always go as planned.

I personally have learned a lot from your blog and eBook about Travel Hacking and I’m applying it to my own travels now. Have you met people in other countries who have similar success with travel hacking? What are the usual challenges compared to travel hacking in the U.S.?

Travel hacking is fully worldwide! Fortunately, travelers from every country can benefit from many of the deals offered by U.S. carriers, which tend to have the most generous programs and deals. Pretty much the only major part of travel hacking that *isn’t* available worldwide is the lucrative sign-up bonuses on U.S. credit cards. Unfortunately you need a social security number for those. However, mistake fares, round-the-world plane tickets, loyalty programs at hotels, and many other aspects of travel hacking are open to everyone regardless of citizenship or residence.

Chris, for your book “The $100 Startup” you’ve been researching over 1,500 small businesses that started as a side gig or passion and became successful. Have any of these business owners been expats?

The $100 StartupAs with travel hacking, the phenomenon of The $100 Startup is fully worldwide. About half of the businesses we looked at were outside of North America, and maybe 15% of so were fully nomadic. Many of your readers are probably well aware of the possibilities of living and working anywhere you choose. I’m very glad that this practice is becoming more and more common, instead of just something that sounds like a pipe dream.

Imagine you would have to leave the U.S. and move to a country of your choice, which country would it be? Would you even settle down or go nomad?

I love traveling for travel’s sake. Whenever I don’t go somewhere for a while, I start to feel anxious. If I had to move somewhere, I think I’d have a few different bases—perhaps Sydney and somewhere in East Asia—but I’d still continue to travel frequently.

People often save it for retirement to explore the world. You’re in your thirties and have already seen every country. What is next for Chris Guillebeau?

Chris speakingFortunately I love what I do every day. As much fun as travel is, it’s even better to bridge it with people and relationships. These days I have a global community, and much of my work involves connecting with them from city to city. The specific approach and kind of work may change, but no matter what I plan to keep writing, traveling, producing events, and supporting solopreneurs for many years to come.

Thank you so much for your time, Chris!


If you would like to learn more about Chris Guillebeau, head on over to his blog or check out his books The Art of Non-Conformity or The $100 Startup on Amazon. Chris also created some Unconventional Guides about entrepreneurship, writing and travel. I personally bought his Frequent Flyer Master guide and learned a ton about Travel Hacking.

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