Building Careers Inside Prison with April Bosworth and Michelle Cirocco

April Bosworth is a graduate of The Last Mile program and now a Website Specialist at Televerde, where she previously served as a teaching assistant inside of prison helping other incarcerated women learn coding. Michelle Cirocco is the Chief Social Responsibility Officer at Televerde and the Executive Director of the Televerde Foundation, organizations that for nearly 30 years have pioneered employment and reentry models for incarcerated women. Under their leadership, Televerde has grown into a global B2B sales and marketing firm whose clients include Microsoft, Adobe, Dell, and SAP, offering incarcerated women the opportunity to build careers that lead to long-term success after release. Their work has supported thousands of women, resulting in a 95% post-release employment rate and less than 2% recidivism.

In this conversation, April shares how she discovered coding through The Last Mile, overcame self-doubt, and built confidence by learning problem-solving and resourcefulness—skills that carried her into a corporate role while still incarcerated. Michelle reflects on her own journey through prison and describes how programs like Televerde and The Last Mile provide not just training but also financial independence, dignity, and a bridge to meaningful careers after release. Together they explore critical issues such as imposter syndrome, the stigma of incarceration, and the transformative power of being able to earn a fair wage behind bars. For those interested in criminal justice reform, this episode offers a compelling look at scalable models that reduce recidivism, break generational cycles of poverty, and prove that second chances create value for individuals, families, and businesses alike—making it essential listening for advocates, employers, and policymakers.

Episode Outline:

(00:00:00) Introduction and Guest Backgrounds

(00:01:20) April’s Journey from The Last Mile to Televerde

(00:03:20) Learning Resourcefulness and Problem-Solving in Coding

(00:06:00) Building Confidence Through Asking Questions and Making Mistakes

(00:07:00) Michelle on the Power of Safe Learning Environments in Prison

(00:09:00) The Origins and Growth of the Televerde Model

(00:11:30) Proven Success: Employment, Salaries, and Reduced Recidivism

(00:13:00) Bridging the Gap Between Incarceration and Reentry

(00:14:30) The Role of Loyalty, Gratitude, and Overcoming Imposter Syndrome

(00:16:30) Televerde’s Culture of Belonging and Encouragement

(00:17:30) Messages to People Still Incarcerated – Using Time to Transform

(00:20:00) Michelle’s Personal Story and Life-Changing Advice from Prison

(00:23:00) Explaining Televerde’s Business Model and Client Partnerships

(00:26:00) Televerde Foundation, Employment Rates, and Low Recidivism

(00:28:00) April on Financial Independence While Incarcerated and Beyond

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