Michael Masterson is not your typical businessman. An ex Peace Corps volunteer, he never took a class in business, doesn’t read the business press, and doesn’t like to talk business. He spends his spare time writing poetry, collecting fine art, and practicing Brazilian Jiu Jitsu. His neighbors call him a bohemian. But he’s also an entrepreneur. He started his first business when he was 11 years old, and in the 45 years that have elapsed since then, he has started or co-started dozens of successful businesses – public and private ... local and international ... retail, wholesale, and direct mail.

Who is Michael Masterson

Michael Masterson is not your typical businessman. An ex Peace Corps volunteer, he never took a class in business, doesn’t read the business press, and doesn’t like to talk business. He spends his spare time writing poetry, collecting fine art, and practicing Brazilian Jiu Jitsu. His neighbors call him a bohemian. But he’s also an entrepreneur. He started his first business when he was 11 years old, and in the 45 years that have elapsed since then, he has started or co-started dozens of successful businesses – public and private ... local and international ... retail, wholesale, and direct mail.

Notwithstanding clandestine luncheons that erupt into new multimillion-dollar ventures, Michael insists that he has been spending most of his time teaching and writing since he retired, for the second time, when he turned 50. “I have wanted to be a writer since my father complimented me on the first poem I wrote. I was, I think, 12,” he says. “There is nothing I like better than spending three or four hours in the morning writing, and then spending the rest of the day reading, wrestling, and going to museums and art galleries with my wife.”

Michael’s first business was selling his booklet, Excuses for the Amateur, to fellow fifth-grade students when he was 11. In addition to this early entrepreneurial effort, he worked afternoons and evenings as a paper boy and in a car wash, for a sliver polisher, in a warehouse, as a busboy, and as an aluminum-siding salesman. It wasn’t easy growing up with seven brothers and sisters in a working-class neighborhood in New York. His father, a teacher at a private Catholic college, had an annual salary of only $12,000. Besides working in his spare time to contribute to the family’s income, Michael wore hand-me-down clothes and grew up in “the poorest family on Maple Avenue” – which, he says “wasn’t on the other side of the tracks … it was on the tracks.”

Michael doesn’t complain about how difficult his childhood was. On the contrary, he says he was privileged. “It gave me good values, lifelong friends, and the impetus to go out into the world and make some money. How can I complain about that?”
On the other hand, he admits that when he read Frank McCourt’s memoir, Angela’s Ashes, he thought, “So what’s the big deal?”

In college, after working for $6 an hour one summer installing above ground swimming pools, Michael and two friends started their own company, doing the same thing. Working 15 hours a day for $30 an hour, he was suddenly making more money than he could spend. “That was a first for me,” he says. “And I liked it.”

During the winter, when it was too cold to build pools, Michael supplemented his income by tending bar and painting houses. “After that, I never had to rely on a single income,” he says. “It became a habit, one that was hard to break.”

Michael continued to hold jobs and run side businesses throughout college and grad school. And then he quit everything and joined the Peace Corps. As a volunteer in Chad, he published his first book, taught at the university, and spent his spare time learning to speak French and play rugby.

He later landed a job in Washington, D.C., writing and producing newsletters while working on a Ph.D. and teaching. A move to South Florida was next – and an experience he had there while he was editorial director of a financial newsletter-publishing company in the early 1980s changed his life.

It happened at a Dale Carnegie success course, “How to Win Friends and Influence People,” which he wound up in by a twist of fate. He had meant to enroll in a public-speaking course to help with some of his job responsibilities – but there he was. And though he was initially cynical, he started to work the program – beginning by critically examining his life goals ... and then choosing one that would be his primary objective.

After mulling over scores of possibilities, he came to the realization that making “being wealthy” his number-one goal would put the rest of them at his fingertips. He also realized that working for other people was not going to get him there.

After making this decision, which he calls one of the most important he has ever made, Michael put all his efforts into becoming wealthy.

These days, Michael is determined to work as little as possible. “The problem,” he says, “is that I don’t know the difference between work and play. If it makes me happy, I want to do it. Am I crazy?”

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