In this interview, Shelley shares her extraordinary journey from growing up in a home shaped by addiction to battling her own struggles with substance abuse, incarceration, and federal charges before finding sobriety and purpose. She recounts the turning point of discovering she was pregnant while incarcerated, her persistence in seeking treatment despite systemic barriers, and the faith-driven mindset shift that became the foundation of her recovery. Shelley details the challenges of reentry, including her fight against discrimination during Microsoft’s hiring process and the pivotal role of San Francisco’s Fair Chance Ordinance in securing her first job in tech.

Episode Outline:

(00:00:00) Introduction and Shelley’s Early Life in a Home Shaped by Addiction
(00:04:00) Bartending in North Dakota and Returning to Drug Use
(00:06:00) Entering the Drug Trade and Federal Investigation
(00:09:00) Sting Operation, Surveillance, and Arrest
(00:14:00) Jail Time, Detox, and Facing Withdrawal
(00:16:00) Pregnancy, Sobriety, and Turning Toward Treatment
(00:19:00) Fighting for Admission into a Faith-Based Program
(00:21:00) Surrender, Mindset Shift, and Beginning Recovery
(00:24:00) Transition to Reentry and Dreams of Working in Tech
(00:25:00) Microsoft Job Application and Background Check Challenge
(00:28:00) Invoking the San Francisco Fair Chance Ordinance
(00:31:00) Securing the Job and Excelling at Microsoft
(00:33:00) Rising to Top Sales Rep and Winning Microsoft’s Gold Club Award
(00:35:00) Microsoft Changes Hiring Policies and Launches LEAP Program
(00:37:00) Advocacy for Fair Chance Hiring and Broadening Opportunities
(00:41:00) Founding Winner’s Circle: Mindset, Literacy, and Sales Training
(00:44:00) Message to Incarcerated Listeners: Hope, Programs, and Change
(00:45:00) Expanding Winner’s Circle to 25 Prisons Nationwide
(00:46:00) Closing Reflections on the Power of Stories and Programs

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

Dr. James JC Cavitt is the Executive Director of Project Rebound at CSU Fullerton, a transformative program supporting justice-impacted students as they reenter academic life and broader society. He was previously a founding student of The Last Mile’s inaugural class at San Quentin State Prison, where he began his remarkable journey from incarceration to academia. Today, Dr. Cavitt holds a Doctorate in Marriage and Family Therapy, an accomplished spoken word poet, and a nationally recognized advocate for criminal justice reform. His scholarly work centers on the impacts of incarceration on emotional intimacy post-release—a subject deeply informed by his own life experience.

In this episode, Dr. Cavitt shares an intimate and powerful narrative that begins with a life sentence at age 17 and culminates in crossing the stage as “Dr. Cavitt” decades later. He speaks candidly about the emotional weight of having his dream of becoming a pediatrician denied due to a felony conviction, and how mentorship, community, and programs like The Last Mile helped him reimagine that dream through the lens of healing and mental health. Particularly compelling is his concept of the “trauma equation,” which underscores the importance of understanding the path that leads to incarceration—not just the outcome. For those passionate about systemic solutions, Dr. Cavitt’s reflections on confronting trauma, reclaiming identity, and pursuing education inside prison walls offer a profound blueprint for reform

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org

This week, Tara visits Homeboy Industries, an organization that helps gang members and formerly incarcerated people transition into productive, independent lives. Hear her captivating conversation with former CEO of Homeboy, Tom Vozzo.

The Last Mile Radio is a production of The Last Mile and Sirius XM Radio. The show's executive producers are Chris Redlitz and Beverly Parenti at TLM and Liz Aiello at Sirius XM. The show is produced by Robert Roche and Ana Sessions at TLM, with technical production by Greg Sahakian, James Bilodeau at Sirius XM. Original music by Maserati-E. For more, visit www.thelastmileradio.org