Inmates to Entrepreneurs: A nationwide movement

Inmates to Entrepreneurs Inc.’s free online “Starter U” video course is being used in all 50 states and on Edovo tablets in prisons and jails in 30+ states. Founder Brian Hamilton, who started this program 27 years ago, still goes into prisons to teach what he knows best – how to start, run, and grow businesses.


Message from RCM: We are very excited to kick off the New Year with our reentry partner, Inmates to Entrepreneurs, Inc. If you haven’t heard of this organization, boy are you in for a treat! Our magazine teamed up with Inmates to Entrepreneurs National Director of PR & Partnerships, Michelle Fishburne, to share with you the organizations humble beginnings and available reentry resources. We look forward to hosting the monthly Inmates to Entrepreneur column in our magazine to share best practices as it relates to reentry and entrepreneurship. We hope that you find additional reentry tools in their article helpful with your transition back into your communities around the U.S. Enjoy the article.

Inmates to Entrepreneurs Inc., the 27-year-old program started by tech entrepreneur Brian Hamilton, started with a simple question and a simple answer. Hamilton, who had just graduated from MBA school, had accompanied his friend, a pastor, to a local correctional facility as part of an outreach ministry program. Towards the end of the visit, Hamilton asked one of the prisoners what he planned do when he got out. “Get a job” was the answer.

That answer bothered Hamilton. A lot. The year was 1992, the war on drugs was in full swing,  and there was no national dialogue about “second chances.” Getting a job if you had a criminal record was extremely hard for many and impossible for some. Starting one’s own business seemed like a good alternative, and Hamilton knew a lot about how to do that.

Hamilton grew up in a rough, low-income area of Connecticut. As a kid, he started finding ways to make money when he was about eight years old. He focused on service businesses – doing tasks others didn’t want to do and they were willing to pay him to do. His lawn-mowing business took off and by high school he had so many lawns to mow and landscaping jobs to do that he hired some of his classmates.

He was much more interested in his business and football in high school than in his schoolwork, and his low grades showed that. Hamilton pushed forward, though, and used the revenue from his landscaping business to attend nearby Sacred Heart University. He was the first in his family to go to college. Upon graduation, he sold his business to pay for business school at Duke University. Unlike most MBA students, he went pass-fail. Hamilton was there solely to learn whatever it was that an MBA program is supposed to teach you about being an entrepreneur.

After graduating from Duke in 1990, Brian was the minority business consultant for the SBA in the state of North Carolina. While there, he met his friend, Reverend Robert J. Harris (aka “Rev”). Two years later, he went into that first prison with Rev, who had been doing prison ministry work for a long time.

When the simple “What are you going to do when you get out?” question was met with the simple “Get a job” answer, Hamilton started thinking. Employment discrimination against people with criminal records was widespread at the time, as it is today. When a person could not find a job to pay for their food, clothing, and shelter, they still had to find a way to support themselves. For many, that meant reoffending. In 1992, 68 percent of people released from prison were rearrested within three years.

To Hamilton, the solution seemed obvious. If a person cannot get a job working for others, they can create their own job by starting a business. As an SBA contractor, Hamilton was already teaching people outside the walls how to start businesses, so he decided to go into prisons and teach people as a volunteer. He knew that not everyone he taught was going to be an entrepreneur, but he figured that some of them might need those lessons to support themselves, even as a temporary measure, when they got out. And, at a minimum, he would be giving them some insights into business, which would help them understand how future employers approach topics like customer service and marketing.

Hamilton teamed up with Reverend Harris to start Inmates to Entrepreneurs and began teaching in prisons. At the same time, Hamilton continued his own entrepreneurial endeavors. He saw a need for safe, clean, well-lit laundromats, so he purchased and rehabbed what grew to be a chain of laundromats. Never one to settle, when the winning idea for a software program that could help small businesses finally occurred to him, he sold the laundromats and launched Sageworks, which was to become one of the country’s first financial technology companies.

As Sageworks grew and went through inevitable growing pains, Hamilton was still going into prisons and teaching entrepreneurship. What he learned is that people who have served time in prison often are well-suited to be entrepreneurs because they already have an entrepreneurial mindset and know how to persevere when setbacks occur.

“Because of various adverse circumstances in and outside of jail, many people who end up in prison have had to think outside the box from a very young age. That’s an incredible asset for them,” noted Hamilton.  Looked at from this perspective, the people in his classes began to see themselves, and their potential, differently. Inmates to Entrepreneurs grew as people began hearing of his work.

Lawrence Carpenter, who had been in prison twice before launching a multimillion-dollar commercial cleaning business, approached Hamilton about helping out. Carpenter, who now is the Chairman of Inmates to Entrepreneurs and recently was featured in Black Enterprise’s “Success Beyond Bars” series, started off small.  He began his cleaning business by collecting the apartment guides he found in the grocery store and then faxing a letter to each apartment complex, offering his services.  When Carpenter included this story in his Inmates to Entrepreneurs classes, the reaction was immediate – he had given students an example of how it could be done.

Scott Jennings,  who also spent time in prison and started his business small, with just $75 and a pick-up truck, joined Inmates to Entrepreneurs as an instructor and board member as well. Jennings first realized that he was an entrepreneur when he was in prison and attended one of Hamilton’s classes.

“I always had the entrepreneurial spirit,” explained Jennings, “However, I never had any guidance or mentoring. While incarcerated, I was asking a lot of questions about life. Brian showed up when I was the most pliable. Listening and asking questions for a few hours changed my approach.”

After 20 years of running Sageworks and leading Inmates to Entrepreneurs, Hamilton sold Sageworks in 2018 to a private equity firm. The sale enabled Hamilton to expand Inmates to Entrepreneurs and start a foundation, the Brian Hamilton Foundation, dedicated to providing free entrepreneurship education. The foundation’s slogan, “Entrepreneurship for all,” underscores Hamilton’s message that owning your own business is not something reserved for people with money and advanced degrees.

Inmates to Entrepreneurs’ programs have now expanded beyond the live in-prison classes that Brian and others, like Carpenter and Jennings, have been leading for years. Inmates to Entrepreneurs now has outside-the-walls eight-week courses in communities all over North Carolina. The courses’ graduation rate is 77 percent and 65 percent of students already have their first customers by the time they graduate. Students have launched a wide array of businesses, including landscaping, cleaning services, auto detailing, and catering, to name just a few.

One of the 2018 graduates, Don Brown, recently won the NC Rural Center’s “2019 NC Rural Entrepreneur of the Year” award for opening a community gym in his hometown. Brown’s mentor was none other than Hamilton’s student, Scott Jennings, who started his own successful fitness equipment service and repair company. Brown, like Jennings, wants to help those who also are seeking a second chance through entrepreneurship. “Now that I have started my own company, it gives me the opportunity for lifting others when they return to society,” Brown explained.

The success of Inmates to Entrepreneurs’ North Carolina programs motivated Hamilton to create a free online “how to start, run, and grow a business” video course that would be available to people no matter where they lived. The result, STARTER U, is now being used by people throughout the country, in all 50 states. The problem, though, was that  it was not available to people in prisons and jails because most detention facilities do not give prisoners access to the Internet.

In September 2019, Hamilton teamed up with Edovo CEO Brian Hill to provide STARTER U on Edovo tablets, which currently are in prisons and jails in more than 30 states. As Edovo tablets enter new facilities, so will STARTER U. In its first two and half months in prisons, STARTER U was taken by more than 4,200 people. Inmates to Entrepreneurs now regularly receives letters from people who are incarcerated about the course.

In 1992 when Hamilton first started teaching in prisons, the idea of teaching people with criminal records how to start their own businesses was very unusual. Fortunately, in the past ten years similar organizations throughout the country have sprung up, teaching entrepreneurship in prisons and upon reentry.  “Second chance entrepreneurship” has become such a movement that now even the U.S. Congress is considering bipartisan legislation to provide business training inside prisons and in reentry programs.

The NEW START Act legislation, in the Senate, would provide for $100,000 to $500,000 grants to reentry organizations that provide entrepreneurship training, as well as supporting program resources. The Prison to Proprietorship Act bills, in the House of Representatives, would provide for entrepreneurship training inside federal prisons, as well as entrepreneurship training and support services upon reentry.

Inmates to Entrepreneurs board member Scott Jennings spoke at the press conference where Congresswoman Velazquez and Congressman Jeffries announced the Prison to Proprietorship Act. He noted, with hope, that “there will be thousands and thousands of success stories like mine” because of the legislation and programs like Inmates to Entrepreneurs.

“I know the profound impact entrepreneurship classes and mentoring can have,” explained Jennings, “It is hard for people with records to get jobs. If people cannot earn a living to support themselves, they will often end up back in prison. We can teach them how to be their own boss. And we should start while they are in prison, with time to start preparing for their return.”

Jennings’ expressions of concern, and determination, are justified. While the national recidivism rate within three years of release still remains stubbornly high at 68 percent, the rate is dramatically lower for those who obtain employment within the first six months.

With this national movement for second chance entrepreneurship, there is hope that those who cannot find employment working for others will start businesses for themselves and move forward, living full lives outside the walls.

To learn more about Inmates to Entrepreneurs, go to:

To start taking STARTER U, go to:


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