‘It’s funny how life works’: Entrepreneur teaches former convicts about creating a business

APEX, N.C. — The American Dream is anything but for some after leaving prison.

2010 report from the Bureau of Justice Statistics showed that of nearly 75,000 people released from federal prison, up to a third didn’t find a job in the following four years.


What You Need To Know

  • Brian Hamilton is a philanthropist and entrepreneur
  • Hamilton has founded multiple companies, including LiveSwitch
  • His Inmates to Entrepreneurs initiative pairs him with current and former prisoners to coach them on entrepreneurship
  • Rob Teasley connected with Brian Hamilton on the TV show ‘Free Enterprise’

One multimillionaire is helping former convicts create the jobs the world won’t give them.

Brian Hamilton lives on a quaint farm in Apex with enough ducks, goats and dogs to keep him company.

“It’s like Noah’s ark,” said Hamilton, 60. “Am I a regular guy? Just a guy from Milford, Connecticut, right?”

But his hometown is only the beginning. The self-made entrepreneur is a first-generation college graduate from a working-class family who has an ABC television show called “Free Enterprise.”

The show was modeled after his other initiative called Inmates to Entrepreneurs, where he coaches incarcerated and formerly incarcerated people.

“I think it’s funny how life works, you know,” Hamilton said.

Rob Teasley has been one of his benefactors of entrepreneurship.

Teasley isn’t the first person who served hard time that Hamilton has mentored.

“It was life-changing. It was huge,” Teasley said.

Hamilton’s philanthropy has drawn inspiration from a conversation he shared with a prisoner in the early 1990s. Hamilton said the conversation centered on the prisoner’s plans upon being released: finding a job.

“I remember thinking like it was yesterday, ‘Wow, that might be hard to do’. And that was the lightbulb moment for Inmates to Entrepreneurs,” Hamilton said.

His nonprofit organization, Inmates to Entrepreneurs, formed the foundation for “Free Enterprise,” where Hamilton and Teasley met.

Teasley said he learned about the show by looking all over.

“The ad literally said, ‘Were you incarcerated and need to start your own business?’ I was like, yeah, that’s me. So I applied.”

And Teasley was accepted.

Teasley now works for Hamilton’s latest company, LiveSwitch, a software technology provider. The 49-year-old said that after four years of prison, there were major doubts about his next steps in life.

“I went to probably five or six interviews when I got out. All of them loved me up until the point they found out I had a felony,” Teasley said.

That’s a common reaction, Hamilton says.

“People who are judicially involved don’t really have advocates in the system,” he said.

But answering a Craigslist advertisement led to a second chance for Teasley, and Hamilton is glad he did.

“If we can do something small on our journey, then hopefully, things get better for people,” Hamilton said.

Teasley says he now has one freedom again after his time behind bars: the right to vote.​

Inmates to Entrepreneurs hosts in-person correctional facility boot camps in North Carolina to teach convicts the basics of building a business.

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