Mike Drop

Retired Army Sergeant Major and Green Beret Terry Wilson closes out a conversation that covers everything from geopolitics to personal redemption. Terry and Mike dig into the Venezuela raid, the consistency problem with U.S. foreign policy, and whether fighting an ideology like Islamic extremism is even winnable. Then it gets personal — Terry reflects on rebuilding his marriage, watching his kids move forward after losing their brother, and how faith, not discipline alone, became the foundation that finally held.

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Retired Army Sergeant Major and Green Beret Terry Wilson returns for Part 2 with some of the rawest conversation yet. From witnessing a Chinook go down in flames in Afghanistan to losing his son in 2020, Terry opens up about the grief he buried for years — and what it finally took to break him open. A brutally honest look at rock bottom, rebuilding, and the unlikely path that brought him back.
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Retired Army Sergeant Major and Green Beret Terry Wilson spent 24 years in uniform with the 7th Special Forces Group, racking up 11 combat deployments and nearly 11 years total downrange. He is now the CEO of Tactical Edge Coaching and Consulting, where he works with high performance men to become better leaders in all aspects of their life.

In this episode we get into the daily troops in contact grind of Helmand Province, watching a Chinook get blown out of the sky a couple hundred meters away, recovering bodies from the crash site through the night, losing a teammate to an IED within days, the brutal reality of the Afghanistan withdrawal, and hitting rock bottom after losing his son before faith and fitness gave him a way back.

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Retired Marine Force Recon Gunnery Sergeant Ryan Kuperus closes out his conversation with Mike Ritland with the kind of honesty that makes people uncomfortable — and that's exactly the point. From a brutally candid take on the "silent professional" myth and what weak leadership actually looks like, to a raw account of his ibogaine experience in Mexico and what it revealed about his relationship with his kids, Kuperus doesn't hold back. He also weighs in on Iran, Israel, the Epstein files, and why he thinks the Monroe Doctrine is the only foreign policy that makes sense. And after nearly losing everything to a court-martial he should never have faced, he found his next mission: The Reason Outdoors, a nonprofit using hunting and the backcountry to pull veterans back from the edge — one hunt at a time.

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Retired Marine Force Recon Gunnery Sergeant Ryan Kuperus returns for part two with some of the most harrowing combat accounts you'll hear. From a near-fatal friendly fire incident involving Cobra attack helicopters, to navigating an IED-saturated district center while rescuing a shattered sniper team, Kuperus pulls no punches on what it actually costs when leadership fails on the ground. He also recounts the operation that quietly identified a Taliban shadow governor in northern Helmand — the kind of mission that rarely gets told. The conversation shifts into a candid reckoning with the military's promotion system, the compounding damage of poor senior leadership, and why the men who fight hardest are often the ones the institution fails most.

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