Brian Hamilton teaches inmates to be 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?’ 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 more than 40 state prisons, reaching some 2,000 inmates and former prisoners. It recently launched eight-week courses for those who’ve been released, averaging about 30 participants per course.

Lakia Young, a single mother of three who had her first child at age 15, pled guilty to Medicaid fraud about 10 years ago. Young, now 40, avoided active prison time with a plea bargain, probation and restitution of more than $10,000. After mentoring and other help from Inmates to Entrepreneurs, she’s founding an online plus-sized lingerie and undergarment boutique.

The Durham resident earned a business degree from N.C. Wesleyan College in Rocky Mount but realized she needed more practical business knowledge. “Entrepreneurship can be scary at times, and that’s what mentors expressed to us. I had pretty much textbook smarts, but Inmates to Entrepreneurs gives me a real-life sense you don’t get in school.”

If starting a business with a criminal record is hard, studies show it’s worth the effort, for both the individual and society. More than one in 10 North Carolinians has a criminal record, according to the nonprofit N.C. Second Chance Alliance, and about 40,000 are in prison now. After release, 40% will be back in prison in three years.

Convictions can haunt criminals forever, even those who commit crimes as teens. Hamilton describes a 25-year-old woman unable to find work. “When she was 16 she shoplifted, stole some underwear from Target or wherever. She didn’t go to prison, but Google her, and that’s the first thing that pops up.”

Though Hamilton found success with Sageworks, Inmates to Entrepreneurs doesn’t sugar-coat the rigors of entrepreneurship. “You’re going to be doing things people don’t want to do for themselves,” such as lawn service, maintenance, painting and other sweat jobs that can be started with little capital, Hamilton tells inmates.

After initially teaching inmates that “anybody can do it,” Carpenter came to a realization. “Not everybody is cut out to be an entrepreneur,” he says. “We can’t all be bosses.” Nor does Inmates to Entrepreneurs teach participants to raise money. Young says she hopes to get help from LaunchRaleigh, a nonprofit that offers entrepreneurship training and micro-loans of as little as $500. But most, like Carpenter, will have to scrape together their own launch money.

“We teach people to start a business with $500 or less,” Hamilton adds. “Nobody is going to loan them money to start a business. Instead, we teach things like, how do you get your first customer? You work two or three weeks, earn a few dollars and go from there.”

Paradoxically, Young, Hamilton and others in the Inmates to Entrepreneurs program say those with criminal records have untapped strengths. They’ve known hard times, they’re not timid. Prison has taught them to spot cons. “He knows the score, and you’re not going to run any [BS] by him,” Hamilton says.

Now that he no longer heads Sageworks, Hamilton has ambitious plans to open branches in 50 major metro areas in the next two years. “This is something needed all over the country,” he says. “We’re going to make it happen.”