Inmates to Entrepreneurs Offers Resources to Help Returned Citizens Start Businesses

Lawrence Carpenter says he grew up poor and dreaming of a better life. By age 12, he was following the only example he saw in his North Carolina neighborhood of how to achieve this dream: selling drugs. By age 17, he was incarcerated. After serving six years in prison, he was back on the streets inspired to be an even better dealer.

He eventually attained the life he had hoped for, complete with a house and a car—albeit through illegal means. “I had a taste of how it could be,” he says. However, seven years later, his dream came crashing down around him, and he went back to prison. “I realized I’m an entrepreneur. I was just trying to do it the wrong way,” he recalls.

Determined to take control of his own destiny

Upon his second release, Carpenter decided to use his skills within the bounds of the law. Given his record, he was unlikely to find high-paying work. “I knew I was probably going to have some low-end job. But my mentality was that just because I made mistakes doesn’t mean that I should live in poverty for the rest of my life,” he says. “I felt like if I start a business, I will control my own destiny.”

With $400, a green Geo Metro and supplies from the dollar store, he founded SuperClean Professional Janitorial Service. More than two decades later, his residential cleaning business has evolved into a commercial operation with contracts in three different states, 80 subcontractors and 64 employees.

He has also become a serial entrepreneur, adding trucking and real estate businesses to his growing empire. Real estate, he says, was a fluke. As someone with a felony record, he couldn’t qualify for most rental properties and has always had to buy. “I could show them a bank statement with a million dollars, but they didn’t care,” he says.

Wishing to give back to individuals like himself, Carpenter began volunteering with Inmates to Entrepreneurs, a nonprofit that teaches incarcerated individuals and returned citizens business basics. The longest running program of its kind, Inmates to Entrepreneurs offers returned citizens an alternate path to support themselves and one that, by extension, may decrease the likelihood of them recidivating.

Although Carpenter serves as a facilitator and board chairperson for the program and has never been a participant, his success story is one the organization hopes its graduates realize.

The origin story of Inmates to Entrepreneurs

Brian Hamilton, philanthropist and co-founder of one of the U.S.’s first fintech companies, founded Inmates to Entrepreneurs in 1992. While visiting a North Carolina prison with his friend the Reverend Robert Harris, he struck up a conversation with one of the incarcerated individuals. “I said, ‘What are you going to do when you get out?’ He said, ‘I’m going to get a job,’” Hamilton recalls. “It struck me… that might be hard for him to do with his judicial background. That was the lightbulb moment for me.”

While other people might have seen a problem, but may not have been motivated to solve it, Hamilton says his entrepreneurial nature prevailed. “A big part of my attraction was, ‘Hey, here’s a problem, and I’ve got a solution,’” he says. He also saw it as an injustice that people who had been released decades ago still struggled to get jobs because of their judicial involvement. “All people make mistakes, and it seems to me that they should have a second chance,” he says.

Hamilton’s workshops grew organically, and today Inmates to Entrepreneurs has served more than 10,000 individuals. Its programs are available in 2,400 correctional facilities and online to returned citizens across the U.S., thanks to the organization’s digital pivot during the pandemic.

The program has attracted guest speakers such as Matthew McCarthy, former CEO of Ben & Jerry’s; Sarah Paiji Yoo, CEO and co-founder of Blueland; and Mandy Bowman, founder and CEO of Official Black Wall Street. Its offerings—and the romanticism of second chances—also inspired the ABC TV series “Free Enterprise” that aired for two seasons, with Hamilton delivering business insights to returned citizens starting businesses.

Grit and desire make the best entrepreneurs

To be eligible for Inmates to Entrepreneurs’ free programs, an individual only needs to self-identify as being judicially impacted. Inmates to Entrepreneurs representatives feel returned citizens shouldn’t just turn to starting businesses out of a practical necessity due to dismal job prospects—they should do it because their experiences prime them for entrepreneurship. “If you go to prison, you’ve hit rock bottom. So, you’re willing to take more risks. Once you’ve hit rock bottom, why not take a chance?” Hamilton says.

“The individuals we see come through our program are just some of the most enterprising and cunning individuals,” says executive director Alli Thomas. “They really have that grit and that desire, and they want to make their lives better. They have this innate ability to take everything that they’ve worked through and channel it into their business.”

Courses and programs that set inmates and returned citizens up for success

Inmates to Entrepreneurs’s tentpole is an eight-week course that covers business basics. It starts with “making sure we’re all on the same playing field, like what does it take to be an entrepreneur? What are the skills you need? What are the attitude and mindset needed?” Thomas says. Then the course progresses to topics such as customer service, marketing and human resources.

Additionally, Inmates to Entrepreneurs offers in-person correctional facility boot camps, several-hours-long workshops within North Carolina prisons aimed at getting incarcerated individuals to consider entrepreneurship, virtual two-hour workshops broadcast into prisons and Starter U, an entrepreneurship course preloaded onto correctional facility tablets.

Hamilton says that one of the biggest questions workshop leaders get—and one of the biggest hurdles returned citizens face in starting businesses—is how to overcome the internet’s ubiquity. “The biggest challenge we have right now is literally Google. If you get a DUI, there’s your mug shot right on the internet,” Hamilton says. This can present challenges in everything from gaining customers to getting startup funding.

Inmates to Entrepreneurs says many of their participants start service-based businesses, such as cleaning services and lawn care, that don’t rely as heavily on consumer background searches. Additionally, to bypass the need for getting a loan or other funding, it advocates that returned citizens start small, with the financial resources available to them at the time—whether that’s self-funding or borrowing from family and friends.

Inmates to Entrepreneurs teaches personal and professional skills that last a lifetime

Half of Inmates to Entrepreneurs’ instructors are returned citizens who are business owners themselves. Carpenter says this approach lends the program credibility. He and the other instructors speak to their current successes and their failures. “It allows other people to see that you’re human just like them. Yeah, I made mistakes just like you. But I got myself up, dusted myself off and started working hard toward becoming something greater. If I did it, you can as well,” he says.

Tracking how many Inmates to Entrepreneurs graduates start businesses, let alone recidivate, is challenging due to the program’s scale, the transient nature of returned citizens and because graduates could take months, years, or decades to apply the lessons. However, Hamilton estimates that for every 10 people who sign up for the eight-week program, seven finish the course, and of those, half start businesses.

Regardless of how many participants become entrepreneurs, they gain valuable skills that will serve them well as they reacclimate to society. Thomas says, in 2023, 88% of the program’s graduates said they’d gained more insights into strategic thinking. Two-thirds also reported they’d gained communication and time management skills. “Not every graduate or not every participant is going to start a business. But if we can help people become better with strategic thinking, communication or time management, that’s not only going to help them if they decide to start a business, but those skills can transfer to daily use and every aspect of life,” Thomas says.

There’s one other intangible item Carpenter feels returned citizens gain from the program: hope.

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