Keilen Crenshaw learned early that the world responded to force. Taken from his mother at 10, cycling through foster care, carrying unchecked anger that eventually led to a four-and-a-half-year federal sentence — survival was the only thing he knew. What he didn't know was where that anger came from. Or what it had cost him. In this episode, Keilen traces the full arc: from a school hallway in DC to the Middle Fork of the American River, where getting thrown from a raft and coming up gasping taught him something prison never could — respect. Now a recovery support counselor at Jubilee Housing in Washington D.C., he brings that hard-won wisdom directly to the men who need it most. This is a conversation about the difference between surviving and living. Learn more about Inside Circle at insidecircle.org/podcast

When Aaron Burris walks into the dining room of the Inside Circle Healing Home, he feels two things at once — joy and grief. Joy because a dream that was born in prison circles, in chapel chairs, in hushed conversations about what if we built something — is now real. Grief because some of the men who dreamed it with him didn't make it out to see it. In this conversation, Aaron sits down with Eldra Jackson III to talk about what it really takes to come home after incarceration — not just physically, but as a person. He talks about Butch, a man who knew how to navigate every system inside prison walls and couldn't survive the one outside them. About the near-misses in his own decade of freedom. About the question that has become the center of his healing work: Who am I without prison? The Inside Circle Healing Home isn't a halfway house. It's not a program. It's a place where men coming out of incarceration can learn to iron a shirt, balance a budget, ride public transit safely, and — more importantly — figure out who they are when nobody's watching. This is the story of how it got built, who it's built for, and what it means to plant a seed for a tree you may never sit under.

How do you find self-love after 15 years in prison? In this episode, Edwin Lee joins host Eldra Jackson III to share his raw journey from a lonely childhood in San Francisco's Chinatown to finding his humanity behind bars. Edwin discusses the "Tiger Parenting" that fueled his early resentment, his transition from gang life to becoming a certified counselor, and the "culture shock" of leaving prison for a world that moves faster than ever. It is a powerful conversation about the pressure to succeed, the complexities of modern reentry, and why healing is a lifelong process. Support the Work: Learn more about our mission to heal systemic trauma at InsideCircle.org.  

Fresh home after years of incarceration, Dariel Pena joins The Inside Circle Podcast to share a story shaped by loss, belonging, and hard-won transformation. Raised in Paterson, New Jersey, Dariel reflects on how a lack of connection at home and the pull of belonging in the streets drew him into violence and a lengthy sentence. While inside, something shifted: through reading, taking on leadership roles, and a deepening commitment to juvenile justice reform, a new sense of purpose began to take shape. He speaks to the stark contrast between youth facilities and adult prison, and how advocacy and community support led to an unexpected commutation and early release. Now back home, Dariel talks candidly about the challenges of reentry, the discipline of patience, and why mental health can't be an afterthought. This is a conversation about what it really takes to confront your past, reclaim your identity, and start over.

Dr. Samuel Arroyo joins the Inside Circle Podcast to share the journey from Spanish Harlem street life to a 40-year New York State sentence — and the slow, deliberate work of real transformation. After becoming involved in organized drug activity and serving nearly 15 years in prison, he began confronting what he calls his "violence problem," using education and deep self-examination to break patterns rooted in intergenerational trauma. In this conversation, Dr. Arroyo speaks candidly about reentry pressures, nearly returning to crime, the decision to stop "throwing a brick," and how fatherhood reshaped his commitment to change. Today, he works nationally with justice-impacted communities, helping others interrupt the same cycles he once lived inside. https://insidecircle.org/

In this episode, Eldra sits down with Kentric Devone McKoy for a powerful conversation about prison, emotional healing, faith, and freedom. Kendrick shares his journey from a childhood marked by abuse and suppressed emotion, through decades in the California prison system, to life after release as a truck driver, minister, and mentor. He speaks candidly about how unresolved anger followed him wherever he went and how prison became the place where he first learned to name, understand, and feel his emotions.  

In the first episode of 2026, Eldra sits down with Justin Smith for a candid conversation about negative emotion, honesty, and spiritual growth without performance. Justin shares how his childhood—marked by poverty, a status-driven community, and his father's struggle with manic depression—shaped his lifelong interest in helping people face emotional pain more honestly. Together, they explore why so many self-help and spiritual approaches fall short, and why honesty, community, and shared experience may be the most powerful tools we have. Justin also introduces This Life, an experimental app designed to help people confront negative emotion through reflection and connection—without pressure, polish, or pretending.

As we close out the year, Eldra Jackson III returns to a theme that has surfaced again and again—in his own life, in Inside Circle's work, and across the communities we've sat with: fear, and the choices we make when it shows up. In this reflective year-end episode, Eldra looks back at conversations with guests like Ari Rosen, Felix Mickens, and Ian Manuel—three powerful stories of courage, accountability, and transformation. Their journeys offer living examples of what it means to move toward healing, community, and purpose even when uncertainty or danger looms large. Through their experiences and his own, Eldra invites listeners into a simple but essential inquiry: In the face of fear… how do you show up? Join us for a grounded, heartfelt close to the year—and a call to step into 2026 with intention, openness, and hope. Learn more at insidecircle.org

In this episode of the Inside Circle Podcast, host Eldra Jackson III speaks with Nick Jonsson, global keynote speaker and bestselling author of Executive Loneliness, about the hidden cost of success and the healing power of vulnerability. After reaching the top of his corporate career, Nick's life began to unravel—leading him through isolation, addiction, and loss before discovering the courage to speak his truth. Through that journey, he learned that real strength isn't found in status or control, but in honest connection and community. Together, Eldra and Nick explore how breaking silence, sharing our stories, and showing up authentically can transform not just individuals, but entire systems of leadership. It's a conversation that embodies Inside Circle's mission: turning pain into purpose and isolation into connection. Connect with Nick Jonsson: nickjonsson.com Learn more about Inside Circle: insidecircle.org

This month's Inside Circle Podcast takes a different turn. Host Eldra Jackson III shares a personal milestone: just last summer, he learned to swim for the first time—side by side with kids half a century younger. That experience sparked today's conversation with Cori Myka, founder of Calm Within Adult Swim, who specializes in helping adults face their fear of water. Together, Eldra and Cori explore how learning to swim is about more than strokes and breathing. It's about panic and calm, trust and mistrust, and the lifelong journey from fear to freedom. Tune in for a vulnerable and inspiring conversation that reminds us it's never too late to learn—whether in the pool, in life, or in love.