Stories of Redemption & Second Chances
Brent Cassity went from CEO to federal prison. Now he interviews others who hit rock bottom and found their way back. Wrongful convictions. White-collar cases. Addiction. Athletes who lost everything. Entrepreneurs who crashed and rebuilt. Over 200 conversations with people who know what it's like to lose it all and start over. No sugarcoating. No PR spin. Just real stories from people who've been through it.
All Episodes
From Federal Prison to Entrepreneur | Doug Feller’s Comeback Story :Reentry Truth
Doug Feller
From Prisoner to Prison Owner: Kerwin Pittman’s Blueprint for Second Chances
From Prisoner
From Federal Prison to a Piano: Jason Made Turns a Nightmare Into Music | Jason Pears
Jason Pears
All Charges Dismissed: Ryan Bloom’s 18-Month DOJ Nightmare
All Charges Dismissed
Fox & Rob Richardson: 21 Years as an Incarcerated Family | TIME Documentary, Angola Prison, Clemency & Redemption
Fox & Rob Richardson
He Managed Beyoncé & Mariah… Then Stole Millions: Jonathan Schwartz’s Comeback Story
He Managed
Sentenced to Life Without Parole at 19 | How David Carrillo Earned an MBA in Prison & Won Clemency
David Carrillo
Pageant Queen to Drug QueenPin to Purpose — Jennifer Rogers' Fenced In No More
Jennifer Rogers
From Wall Street High to Rock Bottom: Sean Mueller's Redemption Story: Fuel To Change
Fuel To Change
Sentenced at 16, Free at Last: Cheryl Armstrong on 26 Years in Prison & Planting Purpose
Cheryl Armstrong
The Power of One Decision: From Prison to Paychex — Allyssa Baker’s Comeback Story
From Prison to Paychex — Allyssa Baker’s Comeback Story
Wired on Wall Street: Tom Hardin (Tipper X) on Wearing a Wire and Surviving the Sting
Tom Hardin (Tipper X) on Wearing a Wire and Surviving the Sting
Your Host
Brent Cassity
Brent was a CEO who had it all and lost it all when he walked through the gates of Leavenworth Prison to serve a 5-year sentence. Now he interviews others who've been through the system and come out the other side. Deep, sad, funny, and always inspiring.
New
Practical Guides
Federal Sentencing Step-by-Step
A practical breakdown of the federal process from investigation through sentencing and immediate post-sentencing steps.
Family Preparation Before Surrender
A preparation playbook for families managing communication, finances, and logistics before surrender.
First Week in Federal Prison
What to expect during intake and early adjustment, plus practical ways to reduce avoidable first-week stress.
Rebuild Career and Reputation
A staged reentry strategy for rebuilding trust, employment credibility, and digital reputation.
Recovery and Reentry
How to align sobriety planning with reentry realities and reduce relapse risk after release.
White-Collar Triggers and Mistakes
Common escalation patterns in white-collar cases and concrete early-stage discipline to limit damage.
Support a Loved One During Incarceration
A grounded support framework for families balancing emotional care, boundaries, and long-term stability.
Second Chance Playbook
Thirty tactical steps for stabilizing life, rebuilding trust, and creating momentum after crisis.
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