From SEAL Platoons to Survivor's Guilt: Chris Osman's Battles On and Off the Battlefield | Ep. 268 | Pt. 2

Mike Drop

Mike Ritland

Society & Culture, Personal Journals, Documentary, Politics, News

4.9 • 6.3K Ratings

🗓️ 4 December 2025

⏱️ 135 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

In this gripping second part of Episode 268 from the Mike Drop podcast, hosted by former Navy SEAL Mike Ritland, guest Chris Osman—a veteran Marine, Navy SEAL, and entrepreneur—delves deep into his extraordinary life story. Listeners will discover raw, unfiltered accounts of Osman's journey from rigorous SEAL training and high-stakes deployments in Afghanistan, including untold real-world missions and the emotional toll of survivor's guilt from helicopter crashes and lost comrades. The episode explores his transition to civilian life, building multimillion-dollar gear companies like Tactical Assault Gear (TAG), and the dark side of success: grappling with "spending dead man's money," family sacrifices, and a descent into alcohol, Adderall, Molly, and cocaine use amid a partying lifestyle. Through candid reflections on professionalism, addiction, and redemption, Osman offers profound insights into the mental battles faced by elite operators, making this a must-listen for anyone interested in military life, personal resilience, and the unvarnished truth behind the SEAL ethos. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Kevin Harlan here. The NBA on Prime Crew is back and the quest for the Emirates NBA Cup is center court once again.
0:08.0	Group play is over. Now the remaining eight teams do battle in the knockout rounds and Prime is your exclusive home for all the action.
0:15.7	It all starts with the quarterfinals. Two consecutive nights of can't miss NBA doubleheaders this Tuesday and
0:22.9	Wednesday night.
0:24.2	If you're not a prime member, sign up for a 30-day free trial to get started today.
0:29.9	Restrictions apply.
0:31.6	See amazon.com slash Amazon Prime for details.
0:35.5	The Emirates NBA Cup quarterfinals, Tuesday and Wednesday night, only on prime.
0:41.4	Yeah, so, but yeah, man, and, you know, the platoon that I was in wasn't the drinking
0:48.4	platoon.
0:49.4	I wasn't introduced to that lifestyle because of the guys in my platoon. In fact, I kept,
0:57.4	I was so nervous about not being professional. And again, like I said, you know, you got that
1:02.2	that guy, Derek Morris, he was, I mean, from a perspective of professionalism, I don't,
1:08.9	I don't think I could literally point to another person
1:11.9	that I've looked up to more as far as someone who was like dedicated to their craft. And so for
1:17.5	me, that was like the first example. And I desperately wanted to be that. I wanted to be respected
1:23.6	for my craft, not for my last name, not for some mission I went on that didn't even get a choice
1:29.4	in or some ribbon or metal I got that, of course, I didn't have a choice in. Some random dude just
1:33.8	was like, hey, bro, on Friday, you're getting a bronze star. You're like, are you? Cool. Great.
1:38.0	Like, it's not a world like that. And so that was it for me, man man. And so we go out to shaws and I see for the
1:46.6	first time real shooting, right? And my new guy shit, we're out there and this is 1999. We're now
1:55.1	at John Shaw shooting school, which is known, which is now the Mid-South Institute of Self-Offense
	...

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