Mike Drop

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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Ryan Kuperus is a retired Marine Gunnery Sergeant with 17+ years in infantry, recon, and Force Recon. Medically retired after multiple combat deployments and enough kinetic stories to fill a book. From leading teams in Now Zad to pulling his own guys out of multiple IED strikes, this one gets raw fast. We talk leadership failures in combat, hunting, ibogaine, and why the system chews up warriors.

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Former SAS operator Phil Singleton reflects on life after the Regiment. He shares his candid thoughts on the Falklands War, his decision to leave the SAS, and the remarkable journey that followed — from bodyguard work in Saudi Arabia to becoming a U.S. citizen, training American law enforcement with Heckler & Koch, and building his own international tactical training company. Now in his 70s, Phil offers unfiltered perspectives on geopolitics, Britain’s direction, America’s strengths, and the simple “Rastafarian lifestyle” he lives today. This episode closes with honest wisdom, humor, and hard-earned life lessons from a true warrior and veteran.
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