This week on Liberty Risk, we sit down with Jonathan Wayne Freeman for one of the most raw, hilarious, and unexpectedly heavy conversations we’ve ever recorded. What starts as jokes and side quests quickly turns into a no-shit, no-filter breakdown of a life built on big swings, spectacular failures, and a late-stage redemption nobody saw coming.

Jonathan opens up about stories he’s buried for over 25 years — from washing out of Navy boot camp after a steroid-induced psychotic break, to flaming out of law enforcement and firefighting careers, to spiraling through mental health crashes that nearly ended everything. He talks honestly about ego, shame, psych wards, and the pressure of trying to be “the guy” before he knew who he actually was.

But this isn’t a sob story. It’s a comeback arc. Jonathan walks us through becoming a paramedic, hitting absolute rock bottom as a night janitor, and then accidentally finding his lane through comedy and social media. From running viral pages like Kook of the Day to working with brands like Bug-A-Salt and Pit Viper, he explains how being unapologetically himself finally unlocked everything he’d been chasing his whole life.

Along the way, the stories are insane — psychotic breaks, humiliating street fights, paramedic calls you can’t unhear, getting “banished” from Kauai, and the most aggressively wrong understanding of oral sex we’ve ever heard. Somehow it’s laugh-out-loud funny and deeply human at the same time.

At its core, this episode is about failure, timing, mental health, marriage, and why life sometimes doesn’t make sense until way later than you planned. Jonathan’s proof that trying, failing, and surviving still counts — and that your best chapter might not show up until you’re 40.

This is Liberty Risk at its most honest. If you’ve ever felt behind, broken, or like you missed your shot, this one’s for you.