In his childhood, Mark Sheehan enjoyed all the trappings of a privileged Long Island, N.Y., lifestyle: a yacht, private schools, expensive cars and exclusive summer camps. But when Sheehan was 13, his father—the family breadwinner—died at age 42. Things changed abruptly for the family, prodding Sheehan to realize he had a special gift as an entrepreneur and for making money.

In his new book, The Scent of a Dollar: How I Turn Every Day Into a Business Opportunity, Sheehan describes his riches-to-rags-to-riches story, and how he’s applied the lessons he’s learned to a variety of different startups and projects.

He talked about his endeavors and his new book from his home in Sydney, Australia.
 

Q: You can spot an opportunity quickly and move to capitalize on it even more quickly. Are entrepreneurs born with this ability or can they develop it over time?

A: I’ve had pretty good success with being able to smell the crisp greenback, but it’s not innate. It’s just a skill I developed out of necessity. But it’s not an anxiety-driven enterprise. For me it was a game. I’d go to the calendar and staring at me was all of these holidays: Father’s Day is coming up. Who isn’t fretting about what he should get for the old man? I would think, “How do I capitalize on that? How can I turn that into an opportunity?” My old man told me early on that 50 percent of a great business is so much better than 100 percent of nothing.

Q: How do you find your opportunities?

A: Opportunities present themselves in the strangest of ways. Once you’re committed to a project, you make yourself an expert in the field. Ask the experts how to become an expert. Many of them may be quite keen to come along for your ride. I meet some of the greatest folks in all kinds of different places. I met one of my key business partners while standing on the sidelines of my kid’s soccer game.

Q: What embodies the “entrepreneurial spirit”?

A: There’s an extremely close dividing line between success and failure. An entrepreneur is basically someone who’s got the guts to make it happen. I was blessed with a short attention span. I like running in front of the train while others are more interested in having a legacy piece. We all learn that we all have an Achilles’ heel.

Q: How do you turn your Achilles’ heel into something positive?

A: Try to fix any shortfalls in your makeup by dealing with them early on. If you’re not a good public speaker, enroll in a public speaking class. Surround yourself with good people. My best ideas come from others. Don’t worry if you haven’t had the idea for the light bulb yet. I haven’t had it, but I’ve been able to form relationships to make a project happen. Someone may have a good idea but doesn’t have access to cash flow. You can all work together. I recently helped [airline and media tycoon] Richard Branson launch his latest airline. This guy can launch anything. He’s not inventing his own light bulbs. His concerns are traditional but he goes into places and takes a completely different point of view.

Q: What advice do you have for small-business owners right now, especially considering the sluggish economy?

A: I’ve been trying to enlighten entrepreneurs about something I call “victory garden economics.” During World War I and World War II, the government was having great difficulties feeding two different populations by sending food to the trenches while also [supplying food] at home. The American government suggested to citizens that we could help our sons and daughters fighting for our country by growing food and feeding ourselves from our own backyard. These gardens popped up all over America… grassroots campaigns took the pressure off the government to feed everyone at home. It uplifted an entire nation to stand tall. We need to do that again. We’ve lost track of our pioneering entrepreneurial spirit. There are a lot of things that you can do for yourself and your community.

Q: You’re working on a new book. What’s it about?

A: My next book is called Plandome Road and it recalls my memories growing up very happy in Manhasset, Long Island. Recently, I was back in New York and had a reunion with friends in Manhasset, and we were sharing vignettes. They had no idea that my family was living on “Millionaire’s Row” below the poverty line. What people saw was my family’s entrepreneurial spirit. If I had to punch a clock I might as well be incarcerated. I couldn’t have someone tell me what to do in a set period of time. To others this is their security, but the real entrepreneur never wants to breathe this air if he or she can avoid it.

Sharon McLoone is a journalist specializing in small-business, technology, telecommunications and policy issues. She is a frequent contributor to The New York Times, The Washington Post and CNNMoney.com.

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