From Behind Bars to Business Owners: How 3 Former Inmates Became Entrepreneurs

UPDATED: April 1, 2024
PUBLISHED: March 29, 2024
claudia shivers coffee life after prison success stories

For many returned citizens who have served prison sentences, entrepreneurship presents a viable route to support themselves and their families. Being able to make a living also helps them avoid the staggering rates of recidivism among returned citizens in the United States. Nonprofit Inmates to Entrepreneurs teaches business basics to incarcerated individuals and to those who have completed their prison sentences. 

The following trio of business owners graduated from the program’s eight-week course and have since become both instructors and board members for the nationwide organization based in North Carolina. They are just a sample of the organization’s life after prison success stories.

Claudia Shivers

Queen Coffee Bean, High Point, North Carolina

Claudia Shivers was working three jobs to support family as a single mother when the promise of good money enticed her to accept a fourth job preparing taxes. It quickly turned into a full-time job that supported her five children and left her summers free to spend with them. Her entrepreneurial pursuits, however, took a turn, and she was sentenced to 21 months in prison for filing false tax returns. 

While waiting to serve her sentence, she worked a shift job at Starbucks that inspired her post-incarceration direction. “I’m a numbers person and an entrepreneur at heart,” she says. “We made about $50,000 a week [at the Starbucks]. I thought, even if I made five then that’s great. To me, I’m filthy rich if I make $5,000 a week.” While in prison, she wrote her business plan for her coffee roastery named after her grandmother, Queen Esther. 

After her release, she found Inmates to Entrepreneurs on social media and figured it would be a place to “hang out until I figured out what I was going to do next,” she recalls. “But then, most of the teachers had the same background. And there were 100 other people on the Zoom call there for the same reason.” The workshops became a safe space not only to develop her business, but also to connect with others who shared her experiences. The camaraderie and support helped her move beyond the debilitating depression she felt upon her release.  

Pyramid of Success offer

Instructors encouraged her to “dream big but start small.” So, instead of trying to get funding for a $20,000 top-of-the-line roaster, she started burning through $130 popcorn poppers in her home kitchen in attempts to practice roasting coffee beans. Even those poppers were a stretch for her post-incarceration budget; however, she kept building the business by buying and reselling a few pounds of flavored beans and drinks at a time. “I learned the value of starting small. It’s so you’re able to control your growth. You’re able to control the direction of the business while you’re learning,” she says. 

Queen Coffee Bean has since outgrown Shivers’s home kitchen, and she has opened a coffee shop to accompany her commercial roasting space. Along the way, she overcame comments from naysayers. “You say, ‘I’m gonna make something out of nothing,’ but they can’t see what you’re talking about. You have to convince people—and you’ve gotta be pretty convincing,” she says.

Josh Nowack

Breaking Free Industries, Santa Ana, California

After serving a sentence for felony fraud by embezzlement, Josh Nowack knew it was unlikely he’d be able to return to his career in the corporate world. “Finding a job post-incarceration is incredibly hard, especially if you want to do something other than menial tasks. I have an MBA. I was a CPA. Now I’m trying to find a job at the supermarket, and they look at me like, ‘Why the hell are you here?’” he says. “The only way to go forward was to kind of do my own thing. It was almost by necessity.” 

Supporting his family—and doing so legally—motivated him. “I’ll get a second chance with my kids. I won’t get the third. Full stop,” he recalls. Post-incarceration, he says he also faced the health challenges of a life-threatening heart condition and rehabilitation after the surgery that saved his life.

Although he didn’t have a background in printing T-shirts, he saw that the industry required less startup capital than others and took a chance. He founded Breaking Free Industries in February 2020 using $400 gifted from a member of his synagogue. Doing so required him to humble himself and ask for help, since his professional networks and bankability had crumbled after incarceration. “I’m a felon. I made a mistake. What can I do about this to change my own personal narrative?” he asked at the time. 

He made second chances core to his business, not only for himself, but also for the other returned citizens he hires and pays well above living wage. “Most people want to create a second chance for somebody who’s been incarcerated,” he says.

Even with an MBA from Duke University, Nowack learned important lessons when he became an Inmates to Entrepreneurs participant. He explains, “The number one thing is that the basics are looked over. How do you attract your customers? What’s your vision for your business? Are you doing the basic things to generate revenue?”

Nowack believes returned citizens are well suited for entrepreneurship. When he took the Inmates to Entrepreneurs course, he had the opportunity to listen to former Illinois governor Rod Blagojevich, who served an eight-year sentence for public corruption. Nowack recalls Blagojevich said, “‘If you can handle incarceration, entrepreneurship is a cakewalk. People will tell you that entrepreneurship is hard. I’ll tell you what’s hard: Go to the yard in federal prison. That’s hard.’” 

Nowack says returned citizens also often have transferable skills. They’ve just gone from hustling on the streets to hustling legally. However, they often need help with business lessons and mindset. 

Inmates to Entrepreneurs teaches more than business basics. It helps returned citizens build confidence. “Coming out of incarceration, there’s just a huge condemnation and self-judgment that happens,” he says. “We’ve all made mistakes. Sometimes we’ve been incarcerated for it… but, on a personal level, it’s like, now what are you going to do about it?”

Scott Jennings

ServiceRX, Raleigh/Durham, North Carolina

Scott Jennings says his entrepreneurship journey started with reselling drugstore candy on the elementary school playground. However, when he was 15 or 16 years old, he began devoting his enterprising ways to selling drugs to support his habit. The trend continued into his 30s, when he was caught and served prison time. 

When he was released, he took what work he could and found himself doing landscaping in punishing 100-degree North Carolina summer heat. “I was 37 years old and making $9.50 an hour. It was really, really hard. Unnecessarily,” he recalls. “I was paying the second sentence. We’ve done our penance, but yet we still pay the price [after release].”

He jumped at the chance to take an indoor job repairing fitness equipment, even though he didn’t have any knowledge of the field. He saw the opportunity to start his own business and launched his company in 2011 with “an ’86 Toyota pickup [to drive to service calls], a bag of tools, $75 in my pocket, and a lot of desperation.” He keeps a photo of the German cockroach–infested trailer he lived in at the time on his desktop as a reminder of how far he’s come.

“There were times when my canoe almost completely tipped over. It’s been scary,” he says. “You can start a business with $0 and your intelligence, but you got to do the work.” Now rebranded as ServiceRX, his company has expanded into four states; he has two franchisees and is in talks with a third. 

He graduated from Inmates to Entrepreneurs’ eight-week course while in prison and has stayed involved with the organization since his release—including representing the organization and fellow returned citizen entrepreneurs at a White House event. 

Jennings says even if the participants don’t go on to start businesses, he believes they’ll be better employees thanks to the course’s lessons. “If you had to get back to being an employee, you understand what the person who’s in charge is going through. I was a terrible employee. I always had a notion in my head that I could do it better. ‘Why don’t we do it like this?’ A lot of employers don’t like you to ask questions,” he says. 

While the organization can be transformative, he says the true work begins with the person. “I had a lesson from a prior roommate, and it hit home when I was incarcerated. He said, ‘You know, Scott, you are always the common denominator in your life.’ Most people don’t understand they are the common denominators. If something is constantly going wrong, they need to look at themselves and stop blaming everybody else and making excuses,” he says. Inmates to Entrepreneurs is there for people willing to take advantage of their second chances. “That’s the power of what we are: that possibility of hope for the people who are really seeking and are really prepared to go do the work.”

Photo courtesy of Claudia Shivers.