Chris Guillebeau and The $100 Startup

by Nate St. Pierre on May 17, 2012

It’s always great to run into Chris Guillebeau, especially when it’s in my own hometown, and not some far-flung (for me) location. Last time I saw Chris in Milwaukee, I was sitting in the main terminal of the Mitchell International Airport, waiting for someone to arrive. This random guy slowly shuffled into my field of view, alternately looking at his boarding pass and the terminal letters. He stopped literally right in front of me, and as he turned around I recognized him.*



It was a fun little chat in passing, but I’m excited today because he’ll be here in Milwaukee for real on Monday evening, hanging out with us on his $100 Startup book tour. I can count the number of business books I’ve bought on one hand, guys, and I was first in line to pick up a copy of this thing.

No, it’s not an affiliate link. No, he did not ask me to write a recommendation or a blog post. I asked him, that’s how good this book is. If you have any kind of inkling at all that you’d like to earn a side income or create a new career for yourself, this is the book for you. Story after story of exactly what people (just like you) did, how they did it, what worked, what didn’t, and how much they earned. It’s not a get-rich-quick blueprint; it’s a hard work, hustle, and a willingness to see opportunities around you blueprint.

It’s one of the best business books you’ll ever read. It will inspire you, but better than that, it’ll make you think about what you can do in your life right now to accomplish your goals.

Take a look.

Since I was already going to write about the book, I thought I’d ask Chris a few questions too. Enjoy!

As you know, I’m really big on making a difference for others, and we’ve seen that you are as well. In your experience, what has been one of the most effective ways to enrich the lives of those you meet, even as you go about your own business?

Always focus on the question of empowerment or value. These words are often used without an examination of what they really mean, but I think it’s fairly simple: at its core, value means helping people.

You can help people by providing answers, education, or even inspiration. You can choose to be encouraging. You can go out of your way to look out for someone. You can regularly check in with people and say, “Hey, how’s it going? Is there anything I can do for you?” Jonathan Fields, a good friend of mine, is especially good at this. I’ve learned to follow a similar model.

This is your second book and tour. What did you learn the hard way last time around (about either process) that you’re doing differently this time?

Good question. The tour is just beginning, so check back for lessons on that later in the year. As for book writing, I learned to be more specific. My first book was well-received, but bookstores had a hard time categorizing it and comparing it to other books. I generally hate comparisons, but in publishing it’s important to be specific. With The $100 Startup, there’s a clear message: if you want to create freedom for yourself or start a small business, the skills you already have are all you need. Here’s how other people did it, and here’s a blueprint for you to follow yourself.

If you could recommend one person for us to check out, someone who’s had a big influence on the way you do things, who would it be and why?

Many of the people I can think of that fit that category aren’t online much. They are aid workers who live in West Africa or elsewhere. But I also think of people like Barbara Sher, who was a pioneer in the whole field of alternative work and life planning. If you haven’t read it, definitely check out the book Wishcraft. It made a big impact on me back in the day.

You’re on another big multi-state tour right now. I love to drive around the country – give me a couple out-of-the-way places that would be worth my time to see. (For instance, I enjoy North Platte, Nebraska. No kidding.)

Well, I’m not sure it’s out of the way, but on the last book tour I had a great stop in Portland, Maine. I live in Portland, Oregon and it was nice to see the place my hometown is named after.

A bit more off the grid, I also had an interesting time in West Virginia. There was a Rush cover band that played over my whole talk at the coffee shop. I finally stopped fighting it and we all listened along. By “we all” I mean myself and the four people who showed up. As I said, it was interesting.

You always have something cooking – do you know yet what your next big project will be?

With just eight countries left, I’m finishing up my quest to visit every country in the world. That will take another year, and I’ll be writing the next book about it. But one thing at a time; for now it’s all $100 Startup, all the time.

Why is Milwaukee such a cool place to roll through?

Great people, great beer, great cheese—better known universally as “the trifecta.” Also, the last time I was there was in December… so a stop in May sounds even better.

*It’s amazing that I recognized him at all, since I have a mild case of face blindness.

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