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


Great Q&A with Chris here, Ophelie.

Man…some of those questions sounded awfully whiny. Did you feel bad asking them? lol

I understand where the people asking them are coming from, though. Starting your own business “feels” like a big risk and can be a scary prospect. It’s definitely not for everybody…which is why encouraging some people to do it won’t ruin it for everyone, no matter how many people join in.

I’ve heard the argument, “If everyone is off selling stuff online, how is this sustainable?” before. The truth is…I’m doing it…and I have no problem spending my money with those that are doing it too. We can still buy products/services from each other…that doesn’t go away.

It’s crab mentality – if I can’t have it, neither can you.
I have heard so much of it from family, friends, strangers that I don’t care anymore.

People tend to focus on what they may loose, and hugely overstate this “something”. If someone want to move forward, they need to focus on worst case scenario which in reality is usually pretty manageable in compare with the potential reward.

For the vast majority of people, the idea of forging your own path and doing something different is frightening. How do most people react to something that scares them or is an unknown? They hate on it, recoil and run away. And because humans crave validation of their own actions, they want you to do the same. So when they see you ignoring the fear and making your own way, many of them will try to scare you. Just thank them for their concern and politely ask them to mind their own business. Trying to convince them you are doing what’s right for you is pointless, like arguing politics. Live the life you want and ignore the cowards, no matter how well-intentioned they are.

The best counter to Naysayers is success, You just have to keep doing what you believe in and over time they will be wrong.

I felt *awful* asking these questions, but each one of these is a real question that was asked of myself or of an entrepreneur I know.

When you’re on this side of things — when you’re well-connected to other people who are living life on their own terms, it’s easy to forget just how strong the urge to fit in can be. My life isn’t all that unconventional, and yet I still get hostile comments about where I live and the work I do. It’s tough out there, for no good reason really.

Whiny is exactly how I’d describe those questions.

It’s interesting to ask naysayers exactly what they think is at stake. Financial stability, social status, reputation? You’re right to say that the worst case scenario usually isn’t all that bad (within reason, of course…).

Some people are in love with security, but they don’t see that working for an employer that doesn’t really care about them or their future is also very risky. I was about to download the audio book of Chris when I saw this post on Facebook.

I like the “Tall Poppy” analogy. In the Philippines, they call it “Crab Mentality”. Put a bunch of live crabs in a pot of hot water and they won’t let the others climb out…they’ll consistently claw them back down. 🙂

I’ve noticed that people with entrepreneurial mindsets are rarely naysayers. Its the conformists who “save 5% for 40 years” who will speak negatively about a venture or ‘out of the box’ thinking. It seems obvious to me that the thought of you or I making a success from creative means would challenge their own life course. Deep inside (or maybe closer to the surface) these people despise your success because of the way it makes them feel.

Great article on a ‘close to home’ subject for all of us.

I’ve worked for an employer and worked for myself. I feel like I have much more security working for myself, as it gives me more control over my life. Not everyone wants to work for themselves though, and that’s ok. Each to his own.

Hi Ophelie,

I don’t know where those comments came from, but those Nah Sayers are nuts. I know it takes a lot of courage to start your own business and to become an entrepreneur, but with the right kind of help, hard work upfront and dedication to keep going, the rewards are limitless. You get your financial freedom, you are your own boss, which means you set your own working time and you can afford to achieve all your dreams and live the life you want. I am looking at ways to start my own business and as Chris Guillebeau says, you don’t need a lot of start up capital, $100 or even less will do and you can build it into a multi-million Dollar business.

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