Prison to Promise

In this thoughtful and timely conversation, Dr. Craig Waleed sits down with Taryn VanderPyl and Kyle Black to explore the human realities too often hidden beneath systems of punishment, control, and social marginalization. Together, they reflect on what it means to center the voices of people most directly impacted by harm, and why dignity, listening, and lived experience must be at the heart of any serious conversation about justice.

The discussion moves through the overlapping issues of juvenile justice, reentry, race, disability, and the ways institutions often fail the people who need care and support the most. Taryn and Kyle offer insight into what vulnerable young people and adults truly need in order to heal, rebuild, and move forward, while challenging the narrow ways systems often define worth, safety, and accountability.

This episode is ultimately a conversation about humanity — about who gets pushed to the margins, who gets heard, and what becomes possible when we choose to see people more fully. Honest, compassionate, and deeply reflective, this is a powerful exchange for anyone concerned with justice, healing, and human dignity.

On this episode of Prison to Promise, Dr. Craig Waleed sits down with Waymon Daniels of Rochester, New York, for a conversation about transformation, healing, and the power of finding your voice. Waymon shares insights on overcoming pain, rebuilding from the inside out, and what it means to turn lived experience into purpose, leadership, and service to others.

In this powerful episode of Prison to Promise, Dr. Craig Waleed sits down with Edward “Scottso” Scott, a formerly incarcerated man who served nearly 30 years before coming home in 2019. Scottso shares his journey from Brooklyn and North Carolina to prison, to transformation, to faith, to family, and to reentry work. He speaks openly about the emotional and psychological weight many people carry after incarceration, including what he and Dr. Waleed discuss as post-incarceration stress disorder, or PISD. Through his work with Wounded Healers, Scottso is helping create safe spaces, curriculum, and support for returning citizens to heal, rebuild relationships, and truly live after incarceration.

In this episode of Prison to Promise, Dr. Craig Waleed speaks with Richie Desersa, currently incarcerated in the South Dakota prison system, about life in prison, his musical journey, and the work of personal change. Their conversation explores mindset, avoiding violence, lessons from solitary confinement, self-belief, legal knowledge, and the struggle to be seen as more than a label.

In this episode of Prison to Promise, Craig Waleed sits down with Nicholas Tsiamis for a powerful conversation about recovery, reentry, education, and personal transformation. Nicholas reflects on the impact of recovery programs, recovery housing, mental health awareness, and the role of lived experience in helping people rebuild stability after incarceration. Together, they explore desistance, age-related change, the importance of persistence, and how education and community can become a foundation for long-term success.

The conversation also highlights Nicholas’s current outpatient work, educational pursuits, future advocacy goals, and his upcoming documentary, “The Struggle Is Real,” which uses real stories to influence policy, challenge stigma, and encourage others to keep pushing toward change.

In this episode of the Prison to Promise Podcast, Dr. Craig Waleed speaks with Gregory Winbush about rebuilding life after incarceration. Gregory shares how family support, mentorship, and personal determination helped him move forward after prison and eventually receive a pardon that restored opportunities and rights. The conversation explores the challenges of reentry, the importance of pro-social support systems, and Gregory’s current work helping others clear their records and find hope beyond their past mistakes.

What does it really take to rebuild a life after prison?

In this powerful episode of the Prison to Promise Podcast, host Craig Waleed sits down with Charlotte-based community leader and reentry advocate Shaheedah Ross.

After spending years incarcerated, Shaheedah Ross emerged determined to transform her experience into purpose. Today, she works to create pathways for justice-impacted individuals seeking opportunity, dignity, and a second chance.

In this conversation, Dr. Waleed and Shaheedah discuss:

• The reality of rebuilding life after incarceration

This episode is a powerful reminder that people are more than the worst moment of their lives—and that leadership can rise from places society often overlooks.

If you believe in second chances, redemption, and community transformation, this conversation is for you.

In this episode of the Prison to Promise Podcast, host Dr. Craig Waleed sits down with prison reform advocate and Justice Ambassador Jesse Crosson for a powerful conversation about transformation, accountability, and the long road from incarceration to purpose.

Jesse shares his deeply personal story of entering the criminal legal system as a young man and spending years behind bars before experiencing a profound shift in how he understood responsibility, harm, and redemption. Through education, faith, and mentorship, Jesse began rebuilding his life from the inside out.

Today, Jesse works to advance criminal justice reform and restorative justice practices across the country. In this conversation, he reflects on the importance of human dignity, the challenges of reentry, and why people closest to the problem are often closest to the solution.

This episode explores what it means to confront the past honestly while working to build a future rooted in accountability, healing, and community transformation.