From inmate to entrepreneur: How a successful ex-con is helping others start businesses

3 min read · 8 years ago


There aren’t many people as qualified as AJ Ware is to teach entrepreneurship to convicts.

After serving a four-year sentence for committing robbery with a dangerous weapon at age 25, Ware was on food stamps when he started a house painting company with $25. He grew it to 18 employees generating close to $3 million in annual revenues, and sold it. Now, at 43, he’s the owner-operator of a racetrack in North Carolina with “a nice home, a car, a wife, kids, the whole nine yards,” he says.

For the past year, he’s also been Executive Director of Inmates to Entrepreneurs. The nonprofit organization was founded in 2008 as the community outreach arm of Raleigh, NC, financial information company Sageworks, and is now a separate organization that Sageworks employees continue to support with time and resources.

With a mission to reduce recidivism and support small business in the region, Inmates to Entrepreneurs offers business seminars and one-to-one mentoring at state prisons. Ware says, the program teaches inmates—many of whom got caught running illegal businesses—how to run a legal one. “We teach them about business acumen and P&Ls, insurance, workers’ comp, the marketing side and the customer service side. We teach from beginning to end what to do and how to maintain their business.”

Today, there are 17 North Carolina small businesses that got their start through Inmates to Entrepreneurs. They account for at least 28 employees and have paid more than $200,000 in state and federal taxes, Ware says.

In a TEDx lecture last November, he shared the stats that keep him going back to the penitentiaries that most ex-cons would prefer to avoid: 95 percent of the 2 million people presently incarcerated in the U.S. will be released in their projected lifetime. “Who wants to employ a felon?” Ware asked, and, perhaps more troubling, “What kind of work are they going to do?”

That week in Raleigh, for instance, local newspapers reported that 20 inmates who had been in jail since the mid 1970s would soon be released. When they went to prison, Ware pointed out, “Apple and Blackberry were only fruits,” gas was .36 cents a gallon, and people dimmed their car headlights with a floorboard switch. “What are the chances of these people getting a job? Realistically?” he asked. Yet, without jobs, the chance they will commit crimes again is high. Sixty-seven percent of ex-offenders wind up back in prison, Ware says, and 34 percent go back a third time.

Hoping to spare society the additional crimes and expense, Ware and his colleagues encourage their students to start a low-capital businesses within days of their re-entry to society. “Something service based, so that they can walk out this door and start working and making money,” Ware says. “They have to eat tomorrow.”

Among the success stories he cites is James, who had no parents or spouse to go to for support after prison. With loaner equipment, he started power-washing cars, then homes. Two years out of jail, he has an employee “and is doing well for himself,” Ware says. “He comes back and gets guidance, and we talk about saving money to prepare for the winter.”

Ware also points to Brenda, who, 18-months out of prison has a silk-wedding-flower arrangement business; David, who has two employees in a lawn care service; Craig whose business enabled him to pay back $50,000 in child support and win custody of his children three years out of prison; and Melissa, who made $13,000 in one day catering a Super Bowl party last January and recently closed a deal on a piece of property to make her dream of owning a restaurant a reality.

Sure, Ware acknowledges, many of his students don’t start businesses. “They find it too complicated. But there are people with MBAs who don’t start their own businesses either,” he says.