CLEAN SLATE: AFTER SELLING HIS 20-YEAR-OLD TECHNOLOGY COMPANY TO PRIVATE EQUITY SAGEWORKS CO-FOUNDER BRIAN HAMILTON HELPS EX-CONS KICK-START THEIR OWN VENTURES.

• Author: Martin, Edward
• Position: NC TREND: Entrepreneurs

In the 1990s, Brian Hamilton, with an undergraduate degree from Connecticut's Sacred Heart University and a Duke University MBA, accompanied a pastor friend to an Orange County prison camp. "One of the inmates walked up to me, and I said, 'What are you going to do when you get out of prison.7' The inmate said, 'Oh, I'll just go out and get a job.' I thought, wow, that's a heavy order."

Hamilton, 55, went on in 1998 to create Sageworks Inc., which grew into a 400-employee enterprise that provides financial-risk software to more than 1,200 banks, accounting firms and other companies worldwide. But the inmate's tough prospects--finding a job with his criminal record--stuck in his mind.

So a decade later, Hamilton formed Inmates to Entrepreneurs, which teaches prisoners how to start their own businesses. In May, he sold Sageworks to Menlo Park, Calif.-based Accel-KKR--terms of the deal weren't disclosed--in order to work full time helping ex-cons stay out of prison by making their own opportunities.

"We got the model down in Raleigh, just opened an office in Charlotte and we'll be nationwide within 24 months," he says. Inmates to Entrepreneurs recently expanded to Wilmington, opening a regional office in April. When the nonprofit advertised for the position of director, about 80 applications poured in, Hamilton says.

Durham's Lawrence Carpenter is one of Hamilton's success stories. Carpenter was 17 when arrested for dealing drugs and sentenced to six years in prison. "I grew up poor," he says. "I'd been dealing drugs since I was 11. It was all I knew." Upon leaving prison, Carpenter's chance of landing a job was near zero, and he faced a reality that haunts small-business startups, prison record or not: No one wanted to lend him money, though he says he did not want to borrow any.

"It puts unwanted pressure on you," he says. "If I'd been thinking of making monthly payments, considering how slow things were to start, I probably would have made some horrible decisions."

So Carpenter started by cleaning homes and apartments. He scraped together $400 and formed what has grown into SuperClean Professional Janitorial Services. The Durham-based business employs more than 50 people, not counting subcontractors, with commercial and construction clients in the Carolinas and Virginia.

Seventeen years after starting his own business, Carpenter, 44, volunteers as a role model, teacher and mentor for Inmates to Entrepreneurs. The program has been taught in...