Afraid of starting a business? Don't tell that to Kenneth Jennings.
Jennings, 54, (not to be confused with Jeopardy! champ Ken Jennings) has started 40 businesses in 35 years. An impressive streak -- until he admits that most of the businesses failed.
"But that's what entrepreneurship is about," he said. "We do what others won't do so that later on we have the freedom to do what others can't do."
After 22 years of "dabbling" in his startup ideas -- everything from selling exercise equipment and office supplies to running an auto service station -- Jennings hit on his most successful one in 1995.
It was a residential locksmith service called Mr. Rekey, which he launched out of the trunk of his mom's car when he was 35. It took a decade for the business to reach its first million in sales. Today, the Austin-based firm generates annual revenue of almost $8 million, employs 100 people and is a national franchise.
"I like taking educated risks and seeing something grow out of it," he said.
He got a taste of this after launching his first startup at 13. It was a door-to-door seed-selling venture that he pursued out of necessity.
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"My dad was an alcoholic who couldn't hold a job and drank up the family money," said Jennings. "If I wanted toys and cool clothes, and later on a car, I realized that I had to make it happen for myself."
He made $400 in the first year and $1,500 the next year. "I couldn't keep up with demand," he said.
But that early startup experience taught him basic fundamentals about entrepreneurship.
"At 14, the important lesson I learned was that it's a lot about relationships," he said.