Inmates to Entrepreneurs: A Tech Winner Focuses on Turning Around Lives

Last year, Brian Hamilton, 56, sold his North Carolina-based fintech company Sageworks to Accel-KKR, a private equity firm based in Silicon Valley. It’s unclear how much Hamilton actually netted, though he told one publication that “I’m confident it’s one of the largest transactions in the Raleigh area and North Carolina in the last couple of years.”

Almost exactly a year ago, he launched the Brian Hamilton Foundation, a good example of an individual donor moving on from business to new interests later in life—including leaving a philanthropic legacy. However, Hamilton’s journey into giving began long before he sold Sageworks, and indeed, before he even founded it. I recently spoke with Hamilton to find out more about how he gives, and about his longstanding work empowering entrepreneurs, which has intertwined with his own personal story of his rise through business.

Raised in a working-class neighborhood in Connecticut, Hamilton graduated from Sacred Heart University, and later earned his MBA from Duke University. All along the way, Hamilton was starting businesses, beginning in middle school and later high school. He was drawn to the power of entrepreneurship, which allowed him to pay for his education. “My biggest success came from Sageworks, the largest provider of software to U.S. banks, but even before then, I was always an entrepreneur. I started a landscaping company to pay my way through college,” he tells me.

Hamilton’s interest in social issues also goes back decades. After he finished at Duke, he connected with a local pastor, Reverend Robert J. Harris, who was doing ministry work at local prisons in the Raleigh-Durham area. The two developed a strong friendship, and Hamilton learned about the challenges facing the formerly incarcerated. Some 650,000 people leave prison annually, and many face a tough road to reentry. Formerly incarcerated individuals are half as likely to be hired, and therefore face unemployment rates five times the national average. Partly as a result, nearly two-thirds of this population find themselves back in prison in just three years.

Make Your Own Job

Inside Philanthropy has reported often on foundation-backed efforts to ease reentry, including through job training and placement initiatives. But Hamilton had a different idea.

“This one guy came up to us in minimum security prison. He said he was going to get a job when he got out, but I thought that would be really hard to do with a record.” Hamilton started to wonder if instead of trying to get a job, why not make one? “There’s a lot more attention on trying to help the formerly incarcerated get jobs, which is great, but the recidivism problem is very stubborn,” he explains.

On the heels of this experience, Hamilton and Reverend Harris, who also had a business background, started showing up at prisons and teaching three-hour classes on starting a business. Hamilton did this for years, all the while running his own businesses. “It was like that for a long time… very ad hoc.”

Over time, this work began to take shape, and in 2008, was formalized in an organization, Inmates to Entrepreneurs (I2E), whose mission is to assist people with criminal backgrounds to start their own businesses by providing resources and mentorship. I2E hosts a year-round, in-person course across North Carolina for anyone with a criminal background who has started or is interested in starting their own small business. It also continues to teach currently incarcerated individuals the basics of building a business.

Graduates have gone into home cleaning, car detailing, T-shirt screening, landscaping and barbering, among other businesses. A Durham man named Chuck Manning took a plea deal in 2015 to dismiss his attempted murder charge, but it remained on his record, making it difficult for him to secure employment. He enrolled in the eight-week I2E program, and ended up cooking for over 700 people at an event brokered by his uncle. He later used the money he earned to start his own cooking business.

While Hamilton found success from a humble background, he knows other family members who did not, including his cousin, who was incarcerated on more than one occasion. His cousin also battled addiction and was enrolled in a drug-treatment program, only to relapse. One day in 2005, Hamilton got a call from his mother, who told him that his cousin had hanged himself with a pair of socks in his jail cell. “I’m not typically emotional, I’m just not, but I’m floored, because he’s getting his life straightened out, and he’s got two kids,” Hamilton said, adding that, “Danny fits the perfect profile of a prisoner… a high-school dropout, someone who gets off to a bad start and never recovers.”

A Full-Time Philanthropist

The Brian Hamilton Foundation is a natural outgrowth of his deeply personal work with Inmates and Entrepreneurs. “With the sale of my company, I’m now doing this full time. Selling Sageworks has given me the opportunity to broaden it out and focus on other groups, primarily at-risk populations—in middle schools, high schools, veterans—all around the idea of helping them sort of take part in our economic prosperity as a country, all around entrepreneurship,” Hamilton says.

He’s particularly jazzed about a new online course through the foundation called Starter U, which was launched as a collaboration of about 25 entrepreneurs. After only three months and no marketing, 1,000 people are taking the course, Hamilton tells me. “There’s really nothing on the market that’s practical. What do you actually need to do to launch a business? Technology allows scalability, which is crucial, and this is my background. I’m really pleased with it, and think it helps a lot,” he says.

Hamilton steers his foundation with a staff of about a dozen people, and the new capacity has allowed the team to deepen their inmates program and also visit some 100 middle schools and high schools. The foundation has partnered with the North Carolina State Corrections Bureau and plans on partnering with other bureaus down the line. The foundation’s work now formally touches four areas: Criminal Background, Youth, Military, and Main Street.

Helping Veterans, Too

The foundation recently partnered with local HBCU Fayetteville State University to help veterans become entrepreneurs. And Hamilton finds his work with youth also vital: “As adults, we can change, but in reaching kids, the cement isn’t quite as dry, and they’re a lot more moldable. Capital comes in a lot of different forms, but to me, the most powerful is in the form of ideas.”

It’s worth noting that while the Brian Hamilton Foundation did do some check writing in 2018, this isn’t the end goal. Instead the foundation runs its programs itself. Away from his foundation, Hamilton has done a lot of work with his alma mater Sacred Heart University, where he was on the board for a time. Still, his heart is with his foundation. “This is where I put my energy, and where I can make the most impact, I think. There’s lot of discrimination against people who’ve been in prison… but I’m optimistic that our vehicle is the best vehicle to move the needle,” he says.