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Nightmare Success In and Out
brent cassity
202 episodes
3 days ago
What happens if your worst fear becomes your reality? Brent Cassity was a successful CEO working in a family business that grew to a national company that was recognized by the media of being the pioneers in their industry. Brent had it all and lost it all. He found himself standing at the gates of Leavenworth Prison to serve a 5 year sentence. Brent's podcast explores the stories of inmates who were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad. often funny, but always interesting.
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Self-Improvement
Education
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What happens if your worst fear becomes your reality? Brent Cassity was a successful CEO working in a family business that grew to a national company that was recognized by the media of being the pioneers in their industry. Brent had it all and lost it all. He found himself standing at the gates of Leavenworth Prison to serve a 5 year sentence. Brent's podcast explores the stories of inmates who were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad. often funny, but always interesting.
Show more...
Self-Improvement
Education
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From Time Served to Voice Heard: Eddie Ellis
Nightmare Success In and Out
1 hour 47 minutes 34 seconds
1 month ago
From Time Served to Voice Heard: Eddie Ellis

In this powerful episode of Nightmare Success In and Out, host Brent Cassity sits down with Eddie B. Ellis Jr., returning citizen, author, and advocate to unpack his personal journey from teenage conviction to lifelong activism. Arrested at age 16 and sentenced to decades in the criminal legal system, Eddie reflects on the transformative path of reentry, the perseverance it took to reclaim his voice, and the ways language and labeling shape not only identity, but opportunity. He shares firsthand what it means to rebuild, the gaps in the system he’s worked to repair—especially around solitary confinement, sentencing of youth, and supports for people coming home—and the hope he holds for social change. Listeners will walk away not just inspired by Eddie’s survival, but challenged to rethink how we see “success,” justice, and redemption.

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Nightmare Success In and Out
What happens if your worst fear becomes your reality? Brent Cassity was a successful CEO working in a family business that grew to a national company that was recognized by the media of being the pioneers in their industry. Brent had it all and lost it all. He found himself standing at the gates of Leavenworth Prison to serve a 5 year sentence. Brent's podcast explores the stories of inmates who were in and now out of prison. What was life like before they went in, life inside prison, and life now that they are back home. These conversations are deep, sad. often funny, but always interesting.