From Lost to Leading: Dariel Pena on Identity, Justice, and Starting Over, episode 89

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.

In this episode of the Inside Circle Podcast, host Eldra Jackson III sits down with chef, restaurateur, and Inside Circle facilitator Ari Rosen. Ari shares his journey from growing up in Northern California with loving parents, to navigating bullying, building successful restaurants, and ultimately finding himself burned out and disconnected from his emotions. A pivotal moment came in 2017, when Ari entered New Folsom Prison for an Inside Circle weekend intensive—an experience that cracked open years of numbness and showed him the beauty and raw humanity that exists even within prison walls. Today, Ari continues to bring that same work back inside prisons and into his own life as a father, husband, and community leader. With honesty and humility, he speaks about the costs of always "handling everything," the lessons learned from his children, and the transformative power of stepping into vulnerability. This conversation is an invitation to all who long for connection, safety, and freedom to feel. Learn more about Inside Circle's work—or make a donation to support their mission at insidecircle.org  

In this episode, host Eldra Jackson III sits down with entrepreneur, author, and former inmate Rick Culleton to explore what it really means to change from the inside out. Rick shares how he moved from addiction and anxiety to building a thriving business and a mindful life—one rooted in peace, clarity, and discipline. Together, they unpack what it takes to transform habits, embrace ADHD as a superpower, and discover that true success isn't about chasing more, but about finding calm within. Listen in for powerful reflections on healing, daily practices for "waking up happy," and why personal change ripples out into our communities. Visit MyMorningStack.com to access Rick's newsletter, videos, and a free copy of his book Messed Up Like You. For more episodes, visit insidecircle.org.

In this episode of The Inside Circle Podcast, Eldra sits down with social activist and founder of The CUT Project, Aaron Johnson, about the need for holistic, platonic touch in the lives of Black and BIPOC men. Drawing from personal experience and his work, Aaron explores how unaddressed trauma and chronic under-touching affect nervous systems, relationships, and communities — and how healing practices rooted in intention and connection can bring transformation. Aaron introduces his short documentary Dark and Tender, which follows 10 Black men on retreat as they navigate grief, touch, and connection. He reflects on dismantling the "Black brute" stereotype, building personal touch plans, and creating spaces grounded in consent, connection to the earth, and care. Whether you're raising a young Black man, working in healing spaces, or seeking deeper connection in your own life, this episode is an invitation to listen, reflect, and begin again. Learn more: https://cutproject.org More episodes and info: https://insidecircle.org/podcast