Creating your own $100 Startup: An interview with Chris Guillebeau

I'm (nearly peeing my pants) delighted to bring you an interview with Chris Guillebeau, the author/ entrepreneur/world traveler behind the just-launched book, The $100 S tartup.

Guillebeau, a fellow Portlander, has never earned a regular paycheck nor held down a traditional job. Instead, he has mastered the art (and, frankly, science) of turning ideas into income and adventure.

If you're considering (or dreaming about) opting out of a traditional corporate job to create something meaningful and adventurous? You absolutely must own this book.

(I'm giving away a copy-- read on!)

In The $100 Star tup, Guillebeau tells the stories of 50 regular people who launched a variety of "microbusinesses," each with an initial investment of $100 or less. These businesses today earn at least $50K in annual revenue. Many of them? Generate much more.

(As in, you don't need to have a pile of cash on hand to launch a business, folks. You just don't. I certainly did not!)

The book isn't just an inspiring read. It provides a clear plan of action for anyone itching to try self-employment as a career option.

I caught up with Chris this week, as he's traveling the country on his $100 Startup book tour. Here's the advice he offered JobJenny.com readers:

JF: In your travels/interviews, what have you found to be the most common roadblock people struggle with when contemplating a transition from "day job" to entrepreneurship?

CG: In order to finally walk away from a full-time job, people usually want a real sense of direction and the confidence that they'll be able to make their new businesses work. Without definitive next steps and a clear action plan, it's hard to blame anyone for being afraid to go all-in. My goal for The $100 Startup was to provide exactly that: clear steps and an actionable plan.

JF: I often counsel people with kids, spouses, mortgages, etc. Many feel like, "Oh, if only I'd done X, Y or Z BEFORE I had a family and all these obligations. But now I'm trapped." How do you encourage this person that entrepreneurship is still entirely doable?

CG: More than anything, people don't want to feel like they're alone or doing something for the first time. I always point people who feel burdened by obligation to stories of other people in similar situations who have found a way to get started. All of us are busy and have obligation, but the truth is that we make time for the things that are truly important to us.

JF: You talk about people who have a clear-cut monetizable passion in the book. What about those who know they aren't cut out for Corporate America, but don't necessarily have a definitive, monetizable passion? Can they still find a spot as entrepreneurs? And, if so, how can they get started?

CG: One of the stories in the book is about a guy who actually has people pay him to redeem their frequent flier miles for them. In other words, he gets paid to do something that these people could do themselves for free, and this side business brings in more than $100,000 a year. Finding something that's monetizable is all about skill transformation. Everyone's an expert as something; you just have to find something you're good at that people will pay you for.

JF: I talk with people regularly who are struggling with long-term employment. They're so frustrated and scared. I typically counsel them to make a job if they can't find one, but to some this can seem daunting. What can you suggest that might make this option seem less scary?

CG: It's all a matter of perspective. Personally, I find the idea of getting a job scary. I think what really frightens all people is redefining their paradigms and assessing real security and risk. It can be scary to think, "I've lived according to these sets of rules for so long; what if I walk away from them?" However, for many of us, creative self-employment truly is the safe-conservative choice.

JF: Do you recommend quitting the day job, or keeping the day job going while you try out a microbusiness?

CG: There isn't any more glamour or glory in doing it one way or the other. If you have real obligations and responsibilities, there's no need to quit right away -- but there's also no reason to wait forever to being your project. Start on the side. Put two of your weeknights and half the weekend to use building your project. Again, we all make time for what's important to us. Many people in the book decided that freedom was important enough to spend time pursuing.

JF: Any "most profound" stories about a person or people who had been just mired in a high-pressure, highly unsatisfactory day job and just said, "What the hell. I'm going for it!" ?

CG: We talked with 1,500 people and 50 of those stories made the book. Flip to any random page in The $100 Startup and you'll find exactly that. No one went to business school. No one went begging for money at the bank. They all found that convergence point between passion and usefulness. Then they go paid, and then they created a new future for themselves.

Win the book!

Chris and his publishers have very graciously provided me with an extra copy of The $100 Sta rtup.

Wanna win it? Just post a comment below -- Tell me why you must own this book immediately - What's your idea? What are you dreaming about? I'll draw one person from here and send you your own lovely, brand-spanking-new hardcover.

You have a dream? Let's get cracking already.