Today’s interview is with Chris Guillebeau. Chris set an ambitious goal for himself: visit every country in the world by 2013. He achieved this goal just a few months ago. In the meantime, he also wrote the hugely popular book The $100 Startup and hosts the World Domination Summit every year in Portland. Whew! Busy guy. 

Going from grad student to international traveler to best-selling author and startup inspiration sounds like a dream come true, right? And yet, there’s so much negativity surrounding the people who actually take the first steps towards making their dreams into reality. One of the most positive people I know is Chris Guillebeau: this guy has enthusiasm and positivity oozing from his pores.

That’s why I wanted to ask him a few questions about negativity. Sure, it’s easy to let negative comments roll off your back once you’ve made it big, but what about your first few years as a fledgling entrepreneur? What tips does he have for people who are finding that their family and friends aren’t quite on board with their big plans? Here’s what Chris had to say.

You’ve been very successful in writing about your love of travel and living independently. What do you say to people who claim that:…

You’re “selling out” by writing a book and charging for a conference?

I have a great life. I feel very fortunate to be able to write and travel. I do at least 80% of my work for free, and everything on my blog is free. If people feel like they’ll be helped by something else I offer them for sale, it’s available. If not, there is more than one way to support my work for those who enjoy it. I’m just as grateful to those who spread the word as I am to customers who buy something.

So in short: this is the business model I’ve used for five years now, and it’s working very well. If it means I’m selling out, I guess I’m selling out.

Working for yourself is selfish when you have a family to support, and encouraging people to leave their day job is irresponsible.

If you want to support a family, why can’t you do that through a small business? Most wealth is created through entrepreneurship, not by saving 5% of your salary for 40 years and hoping for the best.

As for leaving a day job, I’d never encourage anyone to do anything “irresponsible”. But I would encourage everyone to think about what security really is. Are you really better off entrusting your well-being and livelihood to someone else?

Don’t you need a well-outlined backup plan, and a lot of money in the bank, before you can start your own business? You make it sound so easy…

It’s not easy in the sense that it doesn’t require hard work. It takes a lot of hard work, actually. But as for money, most of the people we studied in The $100 Startup began their business with $1,000 or less. This then turned into a reliable income of $50,000 a year, $100,000 a year, and in some cases, a lot more.

Digital products are dead, no one is buying ebooks or access to webinars anymore.

I’m not sure who would say that. There are more people buying ebooks than ever before. There are more people coming online for the first time all over the world than ever before. Learning has certainly changed, but this doesn’t mean digital products are done. Quite the contrary.

Not everyone can just decide to become an entrepreneur, and not everyone can be the boss. We need people to hold down day jobs!

Well, not everyone wants to be an entrepreneur, and that’s fine. But to return to the question of security, I’ve found that most people do want to create their own security one way or another. Even if you remain in a day job, wouldn’t it be great if at least some of your income came from a different source? Wouldn’t it be great if you had a little extra?

Photo credit: Kıvanç Niş