Greg Hartle is re-learning the hard way what it means to be an entrepreneur. A successful small businessman with a decade of experience, he set out this past winter to visit all 50 states, to interview 501 entrepreneurs from across the country and, at the same time,to  reinvent his life from scratch. On January 5th, he left a friend’s home in Seattle, having given away his home, cars, and possessions and with just a laptop, $10 in cash and a backpack with a few changes of clothing. His goal was to build a new life – one introduction, one small business opportunity, and one person at a time; by using the skills he had learned in his ‘old’ life, he would start a new one and see where opportunity took him next. Greg blogs about his experiences and posts the interviews he is conducting with entrepreneurs on his own site, “10 Dollars and a Laptop.”

I met Greg when he visited Chicago last month and was blown away by his judgement, his courage, and his perseverance. Greg was making his own opportunities as he was moving across the country, leveraging the people he met, developing new skills as he traveled, gathering assets which he could use, and defining for himself the next step almost minute-by-minute. As I thought about Greg and his journey, I realized that those are the core elements of what makes an entrepreneur and, in many ways, it is the mix of those elements that can determine success or failure for so many of us.

I asked Greg if he would mind sharing some thoughts on his own adventure with us and sent him some questions which he kindly answered in an email from Long Island this past week.

Whatever led you to start this “venture?” How did the idea come about?
Over the last three years many people who are going through a significant personal and economic transition in their life have come to me asking advice on how I was able to rebuild my life after overcoming a devastating illness that caused the loss of my business, home, and life savings. Rather than simply tell them how I did it, I thought I would show them how I would do it now. In November of 2010 the idea popped into my head and the idea was offically born. Over the next two months I donated everything I owned, flew to Seattle, and launched the experiment on January 5, 2011.

How will you define success?
I define success of the project in two forms. For me: traveling through all 50 states, interviewing 501 entrepreneurs, and launching at least one successful business. For the world: Inspiring as many aspiring entrepreneurs as possible to act on their idea(s).

What are the top three skills you need to execute successfully?
1) Creative Adaptation. The ability to be open to learning something new every day and NOT pulling forward my beliefs about what is or isn’t possible from my previous life experiences.
2) Social Integration. The ability to communicate both online & offline with people and quickly move those conversations to either platform.
3) Inspired Action. The ability to inspire others to move from inspired into action.
How do you find people to meet or network with?
Social networks such as Twitter, Craigslist, Couchsurfing, and Meetup. I also go to every in-person business/entrepreneur/technology networking event I can attend. I now have a network of over 350 people that I’ve directly interacted with since I began this experiment.

Describe a typical ’10 Dollars and a Laptop’ day.
Because I have very few resources (money, vehicle, internet access) to my name right now my day is largely dictated by the people I meet and how we can benefit each other. A few things that I focus upon daily regardless of where I’m at are meditation in the morning, exercise, doing one thing embarrassing to get past judgement and fear, writing in my gratitude journal in the evening, and meeting at least three new people.

How do you decide where to go next?
So far, I’ve gone wherever I can get based on the few dollars I have and where someone will host me. The intention is to earn a living, accumulate access to resources, and be able to choose where I go next. I haven’t reached this point, but I feel I’m close.

How has this journey affected your personal and family life?
To date, I have not seen a single friend or family member in person. That obviously takes a toll of some sort on each of those relationships. I do, however, talk (via phone and skype video) with my friends and family regularly. I’m certain I will lose some friendships over this experience. It’s part of the process.

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