Prison reform is a pressing issue that continues to spark debate across the nation. To shed light on this critical topic, we spoke to three individuals with unique backgrounds and firsthand experiences in the federal prison system. Their insights highlight the challenges, the need for change, and the power of resilience and transformation.
Keyon Dooling: Former NBA Player and Assistant Coach
Being High Profile in Prison
“Being high profile while incarcerated is a double-edged sword. Everyone is watching what you do and how you handle yourself. Some see you as a ‘come up,’ but most see you as an asset,” said Dooling.
His time in federal prison came with unique challenges. “I had to go to the SHU upon arrival and had my room shaken down several times by oKicers. But from the inmates, I was able to cross racial lines and extract the positives from all cultures.”
On Reform and Mental Health
Dooling advocates for addressing systemic flaws, including sentencing disparities. “Some people get harsher sentences than others for the same oKenses,” he noted. He also emphasized the importance of mental health support, stating, “The resources and lack of staK don’t allow for appropriately addressing trauma, anxiety, or other mental health issues.”
Advice for Others
To high-profile individuals facing incarceration, he advises, “Stay solid at all times. Learn the rules of the environment, treat people with respect, and stand on business.” He encourages sharing stories, which he believes can inspire and humanize the struggles of inmates.
“Sports play a pivotal role while locked up,” he added. “The teamwork, physical fitness, and competition bring some of the best moments in that setting.”
Matthew Delmore: Marketing Savant and Former Professional European Basketball Player
Marketing Skills Behind Bars
Delmore utilized his expertise to help fellow inmates. “I spent my time helping others plan for their release, turning ideas into revenue and filing paperwork for things they were entitled to.”
He believes that marketing and communication skills should be emphasized in rehabilitation programs. “Felons already have a ‘mark’ on them. If programs focused on
marketing, they’d provide an alternative for incarcerated individuals to build tangible, legal businesses.”
Rewriting the Narrative
Delmore stressed the importance of personal branding. “We need to rewrite our stories. No one wants their last action to define them. We’re coming out to do better and be better.”
Vision for Reform
“Rehabilitation comes from those who’ve been rehabilitated,” he said. Delmore believes storytelling and marketing campaigns featuring formerly incarcerated individuals can oKer hope and relatability to current and future inmates.
Nathan Richard: Former Drug Dealer Turned Activist and Entrepreneur
A Path to Transformation
Richard credits his transformation to faith and self-development. “I read heavily while incarcerated. Books like The 7 Habits of Highly EKective People were life-changing,” he shared.
He realized entrepreneurship was his way out. “Selling drugs took skill, so I decided to use those same skills to make money legitimately.”
Breaking the Cycle
Richard pointed out the systemic flaws that perpetuate incarceration, particularly for drug-related oKenses. “The main cause of recidivism is the lack of business skills. Without someone to open their minds to entrepreneurship, it doesn’t seem achievable.”
Entrepreneurship as a Solution
“It’s exactly like the streets—the fast life, the hustle. Success becomes addictive, and one hero in the ghetto can elevate an entire generation.”
Shared Perspectives on Reform
On the Federal Prison System
All three agreed that the system lacks foundational support for reentry. “There isn’t enough preparation for release,” Richards said, with Dooling and Delmore echoing similar sentiments.
Role of Society
They called for societal involvement, including housing assistance and advocacy for formerly incarcerated individuals. “Housing is the biggest obstacle upon release,” said Richards.
Message to Policymakers
Dooling’s plea was simple yet profound: “See the person behind the mistakes. Some of the most innovative, creative, and talented people I’ve ever met were in custody. If we serve our time, we should still have a chance at the American Dream.”
A Vision for the Future
From addressing mental health to providing housing and business skills, these three individuals underscore the urgent need for reform. Their stories are a testament to resilience and a call to action for change in the prison system—proof that with the right support, transformation is possible.
These stories of resilience, transformation, and advocacy from Keyon Dooling, Matthew Delmore, and Nathan Richard oKer a rare glimpse into the realities of life behind bars and the urgent need for systemic change. Their unique perspectives challenge us to rethink what rehabilitation truly means and how we, as a society, can support those reentering the world after incarceration.
The message is clear: every person deserves the chance to rewrite their story, rebuild their life, and chase the American Dream. Prison reform is not just about changing policies—it’s about recognizing the humanity, potential, and value in everyone.
You can reach out to these advocates via Instagram for any opportunities. It was a pleasure speaking with them and we plan to keep covering their stories.
Keyon Dooling – @keyondooling
Matthew Delmore – @mattdelmore1of1
Nathan Richard – @felon_entrepreneur