A CONVERSATION WITH CHRIS GUILLEBEAU
Whipster,
Recently I had the opportunity to interview Chris Guillebeau, author of The $100 Startup.
If you know anything about Chris (and chances are you do!) you know that he’s an entrepreneur, author, philanthropist, and world traveler.
He’s incredibly driven, and he’s a big believer in bootstrapping. And I think every single one of us can learn from him. So read on! Take notes! (And buy his latest book! I love it. And one of my clients Erica Cosminsky is featured in it!
* Chris, you know a little something about bootstrapping. (Hello, understatement of the year!) How did bootstrapping early on in your career impact you and your business?
I've always been a bit of a renegade, so you might say I've been bootstrapping my whole life. I think bootstrapping a business (or any sort of lean startup initiative) is a little bit like Outward Bound. When you're equipped with just your own ideas, skills, and nerve, it's somehow easier to begin to solve problems using those skills rather than looking externally for solutions.
On a personal level that's been incredibly empowering, and from a business perspective I'm likely to trust myself and my own judgment because I've had to figure everything out firsthand. Success really does breed success, and even those small victories at the very beginning can create the kind of momentum indicative of a viable project.
Who are your top three picks for entrepreneurs that you know are gonna be huge? (We’re talking Chris Guillebeau in 2008!)
1. Emily Cavalier: Emily is one of the people we were excited to feature in the trailer for The $100 Startup. She's such a great example of someone who walked away from a high-paying corporate job to create a business around her major passions: food, culture, and community. Her underground supper club Midnight Brunch consistently sells out and now she's begun to use the event to connect brands with each other and their customers. I have no doubt that her work will continue to evolve.
2. Selena and Khary Cuffe: I love what Selena and Khary are doing because they have such an appealing social entrepreneurship angle: they're wine distributors, but they're committed to promoting the relative handful of African wineries with black ownership. They've brought together something everyone loves to get on board with -- wine -- while encouraging economic development in unexpected places. That kind of message (think Tom's Shoes and Warby Parker) resonates with people.
3. Elizabeth King: Elizabeth is an up-and-coming superstar who has a million irons in the fire all based on education, critical thinking, and creativity. Her test prep biz is booked solid (she caters to ass-kicking kids like members of the actual Olympic team), she writes books, and she kicks ass. All she needs is a whip... maybe you can hook her up.
I think one of the biggest challenges my uber-talented Whipsters face is the fear of focus – which is really the fear they might be leaving someone out or leave money on the table. I'm handing the whip to you on this one—what's your advice?
I worry more about leaving money on the table by entertaining unfocused ideas. A dozen unrefined ideas aren't worth nearly as much as one carefully honed concept. I do a lot of different kinds of work, and I offer a number of different products, largely because I have a lot of interests. It's totally fine to have breadth in your areas of knowledge, but if you hope to get someone to pay you for something, that particular thing needs to be somewhat focused and meet that person's need in a specific way.
At the end of the day it's most important to remember that each piece of the puzzle has to be of real quality. By the same token, if you tell someone you don't offer something in particular because it's not your area of expertise, she's going to trust you when you say "Oh, but I do this really well."
Thanks, Chris! I can’t wait to see what you do next!
Kisses + Whippings,

P.S., Now it’s your turn, Whipster. I want you to take a couple of minutes to reflect on what bootstrapping has done for you. Head on over to my Facebook page and share your bootstrapping lessons with us!
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