Chris Guillebeau is the New York Times bestselling author of The $100 Startup. During a lifetime of self-employment, he visited every country in the world (193 in total) before his 35th birthday. Every summer in Portland, Oregon he hosts the World Domination Summit, a gathering of creative, remarkable people. Connect with Chris on his blog, or at your choice of worldwide airline lounge.
Thank you! It's a big honor for me too.
I'm a writer, traveler, and entrepreneur. From 2002-2013 I visited every country in the world, often thanks to travel hacking. I wrote The $100 Startup and have also traveled to meet readers in every state, every Canadian province, and many other countries.
Much of my life has been oriented around travel, as well as creating a livelihood that makes travel sustainable for me.
I began much of the adventure from a four-year volunteer commitment in West Africa. I lived on a hospital ship deployed to Sierra Leone and Liberia, and as part of the work I had to travel a lot in the region in advance of the ship's arrival. After I moved back to the U.S., I kept traveling as much as possible, picking up the pace after I became a full-time writer in 2008.
–You’re one of the most well-known and successful ‘travel blogger turn entrepreneur’ on the web today... Please, if you would, talk a little about how you got to where you are now. What was the catalyst that helped you become successful?
Again, thank you.
“How I got to where I am now” – well, first let me say that I have a long ways to go. There are a lot of things I don't do very well, and I hope to improve. But to answer the question more directly, I have always worked for myself since the age of 20. I never wanted to have a job or answer to someone else.
After I started writing online, I focused as much as possible on building direct relationships with readers. I know that whatever I hoped to achieve, whether writing books, touring, producing events, or building online businesses, would all rely on the support of readers.
After I published my first book I went to all 50 states and every province to meet many of these readers, and that helped a lot. Along the way I kept hearing lots of interesting stories, and I learned much more about the community. It was out of that experience that I wrote the next book and began focusing more on helping people with travel and self-employment in specific ways.
–You have dedicated most of your work to helping others. You’re even quite well known for saying “Freely you have received, freely give.” And you’ve done just that – inspiring hundreds of thousands of people worldwide. So, I’m sure that most of my readers will be interested to hear more about your work... What are some general tips for those individuals who wish to become online business owners? Do you suggest that starting a blog is an important beginning step? If not, why?
A blog was a great step for me. It gave me the chance to connect with readers directly, without relying on a third party. In the early days of writing posts and emailing back and forth with people, I realized I needed to go further than just saying, hey, here is my travel goal, I'm going to a bunch of countries, etc. That was fine for success as a traveler, but I found more sustainable success when I focused much more on how I could help people.
Finding the convergence between what you are passionate about and what others also care about is key. I talk about this a lot in The $100 Startup and everywhere I go.
Whether it's through blogging or some other format, you have to make sure you're providing solutions to problems or otherwise meeting a need.
–Without a doubt, your book “The $100 Startup” has inspired and helped so many people around the world. You move seamlessly through basic and intermediate guidelines and tips, as well as business structures and ideas, then you back up everything with interesting case studies and thoughtful examples... How has the response been thus far? Is there anything you wish to add to the book in the future? Anything else you can add for my readers – a sort of insider tip that may not be present in the book yet?
The response has been great! We've sold more than 200,000 copies worldwide thus far, with versions in 15 languages. That makes me happy, but what's most important is that people are acting on it. I regularly hear stories of new businesses being started by readers, as well as big improvements being made to existing businesses as a result of the case studies and examples in the book.
One thing I didn't understand earlier was that a lot of people are very worried about failure. On book tour it was the #1 question: “But what about new business owners who fail?”
The thing is, most people who start online businesses will start more than one in the course of their lifetimes. They also usually do so without investing capital or otherwise taking on a lot of risk. In other words, things can certainly go wrong, but I actually believe that starting a micro-business is one of the safest and best things you can do to create freedom and security for yourself.
–You’ve traveled every country in the world now, it’s taken you ten years, so it’s safe to say that you’re a very experienced traveler. Do you always travel alone? How do you find time to work abroad? How did you find the confidence in knowing that you would visit every country in the world – as you had originally promised on your website, by giving yourself a deadline date?
I usually travel alone, yes. As for work, I take my work everywhere. I work wherever I am for at least half the day. If I'm in a new place or a fun place, I try to be efficient and get as much done in the morning as possible, so I can go out and explore in the afternoons.
The deadline to the overall travel goal was a help, not a hindrance. Knowing that I simply had to finish on time didn't allow me an “out” or an excuse to fail. Without the deadline I'm not sure it would have ever happened.
–Chris, what’s your most favorite and least favorite place – and why?
As for favorites, well, I tend to believe that travel experiences are highly contextual. My favorite city is Sydney, Australia. My favorite countries include Laos, Ghana, Macedonia, South Africa, and probably several more.
Normally I wouldn't pick a least favorite, because I don't want to offend anyone. But your audience seems intelligent enough to understand that not everywhere in the world is beautiful or amazing. When I went to Eritrea, I had a rough experience and was eventually deported on an Egypt Air flight to Cairo. The Eritrean people are probably wonderful, but the government, not so much.
–You have several projects besides that of your book and your blog. Could you talk a little about each of them and why my readers might be interested in learning more?
Sure. A quick rundown of a few current things:
Travel Hacking Cartel: a membership site to help users earn hundreds of thousands of Frequent Flyer Miles without getting on a plane
Unconventional Guides: the original business side of AONC (specific guides to help people with travel and self-employment)
World Domination Summit: our annual gathering of creative, awesome people (2,800 attendees this year)
Adventure Capital: a year-long course to help business owners create better offers and reach more customers
–Chris, thank you so much for taking your time to speak with me and answer some questions for Eye & Pen... If you would, leave us with some inspirational thoughts or ingenious thought-provocation?
I like this quote from Alan Keightley, which is in my email signature:
"Once in a while it really hits people that they don't have to experience the world in the way they have been told to."
I hope it will “hit” your readers that they can pursue a dream of their own while also making the world a better place. That's what much of my work is about, and I'm very fortunate to be able to connect with great people all over the world who are doing similar things.