Jarett Sitter

Chris Guillebeau begins his latest book, The $100 Startup, with a simple thought exercise: “Imagine a life where all your time is spent on the things you want do.”

While the imagining may be easy, making it happen is considerably harder. But Guillebeau wants readers to visualize this kind of life as the starting point for turning it into reality, because he knows it can be done. The Portland, Oregon-based author has been self-employed his entire adult life, doing everything from coffee-importing to publishing. And anyone else who dreams of being their own boss, he says, can do the same, even if they have little money, few specialized skills and limited business experience.

Guillebeau met many such people on tour for his previous book, The Art of Nonconformity. They inspired The $100 Startup, 50 stories of “solopreneurs” who’ve succeeded doing everything from helping people make the best use of their frequent flyer miles to developing an iPhone app

“I kept meeting these unexpected entrepreneurs,” he says, “and they all started these little businesses, and I thought: ‘I want to tell their stories.’ And I want to tell their stories in a way that is very specific and actionable and practical, and I want to create a whole narrative and a blueprint around this idea of creating your own freedom through a small business.”

The desire for freedom motivated some of the solopreneurs in question, but for others it was just another word for little — or at least nothing — left to lose. Michael Hanna, a Portland sales professional who’d recently lost his job, was searching in vain for a new one when a friend approached him about selling a truckload of surplus mattresses. Hanna was a little skeptical initially, but he accepted the offer and went on to build a profitable mattress-selling business. Two years later, he tells Guillebeau in the book, he’s “never been happier.” It’s the kind of story the author heard often.

“Most people were actually just ordinary people,” he says. “They weren’t highly educated or affluent or incredibly intelligent, they were just ordinary people who kind of pursued something and that’s how their project came to be.”

Although Hanna’s business was unusual in some ways, such as being the first ever mattress store to offer delivery by bicycle, he didn’t reinvent the wheel. As Guillebeau notes, many of the people featured in The $100 Startup have made a surprising amount of money offering relatively simple services. Indian solopreneur Purna Duggirala, for instance, earns a six-figure income running a business that, in his own words, provides training to “help people become awesome at Microsoft Excel.”

“Most of these were not necessarily brilliant ideas,” says Guillebeau of the featured businesses. “They weren’t highly innovative ideas. It’s not Steve Jobs making the next iPhone. [It’s] making something that’s useful and interesting and helpful to people.”

Maybe so, but doesn’t establishing your own business require strength and fortitude some people just don’t have? Guillebeau disagrees. You don’t, he maintains, need to be a Type A personality to succeed in this area — there’s no such thing as a born entrepreneur.

“Part of what I hope to do with the book is to remove the excuses,” he says. “Remove the obstacles and say ‘look at all these different people.’”

He adds: “I just want to provide like this barrage of examples, of case studies that say ‘yes you can, you can do it.’”