Thirteen Years in the System, and What Came After

Craig A. Waleed hosts Prison to Promise, a podcast about the road out of incarceration and what people build once they are on it. Episode 136, released 27 August 2026, is Jamie Leibert's.

They covered the parts most interviews skip. Thirteen years in the system, starting in group homes at twelve and ending in federal prison. Four years inside, sent to solitary again and again across the sentence. Completing RDAP. A meth addiction that did not end when the sentence did, and still gets managed every single day.

And then the part that is harder to explain: what you do with the years after.

The Story They Told

Jamie Leibert is a professional adventure athlete and filmmaker. He climbs into remote places and flies out by wingsuit, across more than 80 countries. That is not the redemption arc it sounds like from outside. It is a daily practice, and it is the same practice he built inside.

Battling Monsters is the movement that came out of it, run by his 501(c)(3) nonprofit Just Care More. Not a program with a finish line. A framework for the days that keep arriving.

The mantra, which he says on the episode: Show up. Struggle. Suck less. Repeat.

The Obstacle That Doesn't Make the Highlight Reel

Getting out was not the finish line. Jamie built a national touring business from nothing after his release, and for a while it worked. Money, a marriage, all of it. Then it came apart. He relapsed. The marriage did not survive it. He walked away from the business he had built and started over, broke, before Just Care More or Sandra existed.

The camps that became the seed of Just Care More started because Jamie went looking for real numbers on youth suicide, paying researchers to pull data most people never bother to find, because he wanted to know if the camps he was running for foster kids were actually helping anyone. That refusal to settle for what sounds good over what actually works is still how the nonprofit operates.

None of it is the redemption story. It's the daily fight, twice.

Episode Highlights

The episode runs 35 minutes. Here is what it actually covers, in order, based on the real conversation rather than the auto-generated chapter titles Spotify slaps on every episode.

• The open: Craig frames the episode around facing your monsters and introduces Jamie's path from a hard youth to entrepreneur, athlete, and nonprofit founder.
• The turning point inside: after time alone with nothing to do but stare at the walls, Jamie asked for help for the first time. A prison counselor taught him to focus his mind in one-minute increments, a practice he built on for the rest of his sentence.
• Why the sentence mattered: a judge gave him the maximum available, five years. Jamie says that hard stop is what finally interrupted a path he could not have interrupted on his own.
• After release: building Just Care More, running camps for foster youth, and the personal struggles, including a failed marriage and a business he walked away from, that came even after he thought he had it figured out.
• The daily tool: how climbing and wingsuiting became a daily practice for managing PTSD, not a cure for it.
• The mantra: Show up. Struggle. Suck less. Repeat.
• Community: what Battling Monsters has become and why he built it as a framework, not a finish line.

Frequently Asked Questions

What is the Prison to Promise episode with Jamie Leibert about?
Episode 136 of Prison to Promise, hosted by Craig A. Waleed and released August 27, 2026, is a conversation with Jamie Leibert about thirteen years in the system, the prison sentence that became the turning point of his life, and how he built the Battling Monsters movement afterward.

Why does Jamie Leibert say he manages PTSD instead of saying he overcame it?
Jamie's framing, on this episode and everywhere else, is that PTSD does not go away. He calls it his monster and says he faces it daily rather than claiming he beat it. Extreme adventure sports, climbing and flying in more than 80 countries, are the tool he uses to manage it, not a cure.

What is Battling Monsters?
Battling Monsters is the movement Jamie built out of his own daily fight, run through his 501(c)(3) nonprofit Just Care More. It is not a finished program. It is a framework for managing OCD, PTSD, addiction, and a criminal mindset one day at a time, built around the mantra: Show up. Struggle. Suck less. Repeat.

What turning point does Jamie describe from his time in prison?
Jamie describes asking to see a prison counselor for the first time and being taught to focus his mind in short daily increments, a practice that became the foundation for how he manages his thinking today. He also says the sentence itself interrupted a path he says he could not have interrupted on his own.

Did Jamie's life go smoothly after he got out of prison?
No. On the episode, Jamie talks about relapsing and going through a divorce after building a business that was working, before he ever started Just Care More. He is open that the fight did not end with his release, it just changed shape. That is the whole point of managing the monster rather than claiming to have beaten it.