Learn From Unconventional Entrepreneurs: Help Others And Do What You Love

Chris Guillebeau’s new book, “The $100 Startup,” traces the stories of successful entrepreneurs around the world who grew their businesses with no business background. The keys to making it are simpler than you think.

Learn From Unconventional Entrepreneurs: Help Others And Do What You Love

Some of us enjoy taking our cues from a boss in an office. Others like Chris Guillebeau, author of The $100 Startup: Reinvent the Way You Make a Living, Do What You Love, and Create a New Future, published on May 8th, favor a different approach. The 34-year-old high school drop out–he did manage to squeeze out a master’s in International Studies–just wasn’t a great employee.


“I wanted to keep my own schedule and set my own rules,” says Guillebeau. So after selling coffee on eBay and doing other odd jobs around the turn of the millennium, Guillebeau got serious. By 2010 he’d launched the Empire Building Kit, an online business course that inspired his current book. The idea involved “capturing lessons from unconventional entrepreneurs and extracting the secrets of their success.”

The $100 Startup features “unexpected entrepreneurs,” like Selena Cuffe whose Heritage Link Brands helps support black-owned vineyards in South Africa and Mr. Rhet, a Cambodian tuk-tuk driver who earns $50 a day–10 times the usual amount. As for Guillebeau, he’ll be doing his own tuk-tuking around the globe soon to reach his goal of visiting all of the world’s 185 countries by his 35th birthday next April. Guillebeau spoke to us from his home base in Portland about the importance of following your passion and helping others.

Co.Exist: Why is now the time to create a microbusiness?

Guillebeau: People have been creating microbusinesses for a long time. So, in some ways, that’s not new. But one thing that’s changed is the dramatic accessibility and instantaneous nature of these enterprises allowing you to get results right away–like being able to connect with people all over the world. The barriers just keep coming down. Plus, in this time of economic uncertainty and high unemployment many people have started reassessing their lives and careers thinking maybe they should do something for themselves.

Your book features all these “ordinary” individuals who got started accidentally–often without a formal business plan. But do average people really end up making six figures a year by accident?

When I say ordinary people, I’m really referring to non-traditional business people. They’re not natural-born entrepreneurs; they never went to business schools and many of them never had an idea or expectation they were gonna end up running the business that they did. They’re obviously intelligent, determined, and resourceful individuals but the accidental thing just came along. We talked to 1,500 people originally and then narrowed them down to 70 people for the book. Obviously, you have a range of stories and there are some who might’ve been a bit more determined. But there’s also a number who just stumbled into it. Like Gary Leff, the guy who does make six figures as a side business helping people book their frequent flyer tickets. He had no idea that people would actually pay him to help them do something they could do themselves for free.


You favor action over planning. Why the bias away from business plans and the like?

Most business plans are ineffective. And that’s because they’re written, not with the goal of operating the business, but with getting funding. There’s nothing wrong with planning but I think people often get stuck on planning the perfect thing, whereas, a more action-oriented approach does the planning after things work. Then if the idea isn’t successful, well, you haven’t invested much. You’ve reduced the risk.

So tell us about your “not-so-secret” formula for microbiz alchemy?

First there’s “convergence” which centers around this concept of “follow your passion” or “follow your passion to the bank.” But it’s really a double-edged sword because, on the one hand, lots of my interviewees really were able to follow their passion and earn a great living. On the other hand, you can’t just pursue anything you’re passionate about and expect to get paid. For example, when I was younger I was really into playing Halo on X-box, but no one was ever gonna pay me to do that. So the whole point of convergence is to find this balance, this overlapping circle between what you’re excited about and skilled at and then what the marketplace values. I always encourage people to make a list of a number of things besides passions and skills. You also have this source of knowledge which people are always asking you about because they perceive you as an expert. How can we create convergence around that?

And “skill transformation?”

The whole point is that if you’re good at one thing, which everyone is, you’re probably good at something else as well. For example, my wife was a high school teacher so she’s not only a good instructor but she’s also good at crowd control, lesson planning, and discipline. The challenge for some people learning to be entrepreneurs, whether they want to use that word or not, is how to turn their skills into something that’s valuable. There’s this guy Nev Lapwood from Whistler, British Columbia, who was a snowboarding instructor. He was doing okay and just paying the bills, but then he found a way to make snowboarding instructional DVDs that grew and grew. Last I heard, it was a $300,000-a-year business. He’s following his passion and using his skill, but he’s also found a way to connect that to the marketplace.


One of the book’s overrunning themes relates to “helping others.” Why is this so important?

That’s something I try to instill in all of my work, thanks to my experience working in West Africa. After 9/11, I was depressed just like everyone else was and trying to figure out how I could contribute. So my wife Jolie and I went to Africa for four years to do volunteer work for a medical charity. We had a great experience, but it was also very transformative. In fact, out of that I formed the whole Art of Non Conformity worldview, which turned into a book. The idea is that you don’t have to live your life the way others expect you to. You can do good things for yourself and others at the same time. It’s not a false choice. Legacy is very important to me and your $100 startup can be part of it. Not only can you make a good income, you can also find a way to better the world.

Back in 2010, Fast Company ran an article with the following quote: “In the future, marketing will be like sex: Only the losers pay for it.” So did it come true?

In some ways it is or at least on its way to becoming true. The whole point is that the best advertising is word-of-mouth. And maybe that’s always been the case. But now, word-of-mouth is so much more powerful and reaches so many more people. In the book, I talk about an experiment I did with the travel hacking cartel. I devoted $10,000 to advertising and I devoted something like 10 hours of hustling time and compared the results. The hustling time returned results far greater than the financial expenditure. Especially when you’re starting up, connecting with people, and inspiring them to join your cause is now much more effective than traditional advertising.