The life of the 'serial entrepreneur'

Michael Villa starts every morning at a table at the West Tampa Sandwich Shop. With a cup of coffee and a cigar, he spends at least 30 minutes just thinking, waiting for his next vision and planning what to do with it.

"Either you're selling somebody on why it needs to happen or they're selling you on why it doesn't need to happen," he explained.

Villa is an entrepreneur who has launched a half-dozen different companies over the past 25 years. He says he's passionate about his ideas and they don't stop. When I accused him of being a "serial entrepreneur," he owned up to it.

The Bright Idea

Villa's current endeavor is called Dealer Wizard, a software program now used by more than 200 new car dealers in North America. It helps them track inventories and mine their customer data bases for clients who might be ready for a trade-in.

Over the years, his ventures have ranged from men's fashion to direct mail. He says he can't remember the last time he wanted to work for anyone but himself.

"It's great that I've been blessed with good income," said Villa, a 50-something family man who lives in South Tampa. "But, at the end of the day, I chased my dream, and I worked really hard to do it right."

Risk and Reward

Most of his businesses have been successful, but a few were not. Like other serial entrepreneurs, he's willing to risk failure to achieve success. And, in the 2000's, a changing business landscape has leveled the field.

"We don't need to form AT&T anymore," said Brent Britton, an attorney with Gray/Robinson in Tampa, who specializes in emerging business and technology law. "You can be an entrepreneur just by turning on your computer and writing some software, or finding someone who can write it for you."

Work, Work, Work

Britton partnered with Villa on Dealer Wizard. Villa says other partners included a former new car sales manager and a software expert. They worked on the project for more than a year.

Both Britton and Villa say people who don't want to work hard shouldn't try entrepreneurship.

"Which means if the garbage needs taken out, they're not calling janitorial, they're taking out the garbage," added Britton.

LINK: Brent Britton's blog: http://www.brentbritton.com/