Hey.

Thought a voice note would be easier. So our summer trip. What's the plan? Do we hide a car there? How much is that? Who's minding the dog with Stella line.

Booking your summer holiday doesn't need to be this whole big thing. Just drive on with everything you need. Packed in with restaurants, bars, kids zones and pet friendly cabins. The holiday starts on board.

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Conan O'Brien needs a fan. Want to talk to Conan? Visit teamco.com. call Conan. Okay, let's get started.

Hello.

Hi, Caleb. Welcome to Conan O'Brien.

Needs a fan. Hey, Caleb, how are you? Good to see you.

I'm well, thanks.

How are you doing? Great. It's very nice to chat with you. I have a few questions. Trying to orient myself in time and space. Caleb, where are you right now?

I'm in Halifax, Canada, so east coast of Canada.

Nova Scotia.

Nova Scotia, exactly.

Okay. All right. Are you on the water? Are you close to the water?

I'm as close as I could afford to be. So probably about a half hour from. From the ocean, but beautiful little neighborhood. We got a couple acres in the woods, so we're very happy.

That's very nice. And also, I got to say, the tides are rising. I think you made the right call. You know, all those rich assholes on the water are going to pay for it, you know?

Absolutely. Is it windy there?

My hair is a little cuckoo. You know what happens when I put headphones on? My hair gets knocked all askew. I'm trying to adapt to the changing media environment and never had to wear headphones until I got into this gig. And it's a curse. It's a pox. It's a pox on my hair. On my crazy red pompadour. Sir, I have a lot to talk to you about. First of all, tell us about yourself so I may get to know you better.

Yeah. So I'm semi retired is what I like to say, because it sounds better than unemployed. But I did a 20 year career split between the army, the special forces, and the Royal Canadian Mounted Police. Those are the dudes with the big hats, red coats on horseback.

We all know about the Mounties, we call them. They're very impressive. That's very cool. But you know what? You just said it kind of under your breath. Special forces. You were in special forces?

I was, yeah, for four years.

And can you tell us anything about it? What are you allowed to talk about?

I'm an open book. I'll tell you whatever you want to know, except for a couple things I'm legally not allowed to let you know. I'm going to take a lot of heat for it. There's this long running joke that Navy Seals can't get to the gym and get home without writing a book about killing bin Laden. I'm going to take a lot of heat for this. But it's all right. I'm an open book.

I take it you were one of the only seals that didn't kill bin Laden, is that right?

Yeah, I was in a different country.

Yeah, apparently, there were 900 seals there. He was shot 10,000 times.

Yeah, I killed him.

Yeah. You were there, too.

Well done.

Yeah, I was there. I did it.

Yeah. You baked him something.

I don't even know exactly where to go with that.

We don't know how to react.

Is your baking particularly bad?

It's not good.

I don't want to bake for Osama bin Laden.

Well, you didn't know it was for him. You made some cookies and he was like, oh, these look good. And then he was gone. But listen, back to listen. The spotlight needs to be on Caleb, not on your terrible, terrible cooking. And trust me, I've talked to tack. He's in misery. Caleb. So, special forces for a couple of years, did you do the special forces training, the intense, you know, insane training that they put you through?

So I was what we call a supporter. So, in Canada, at least, there's sort of three tiers. There's operators, door kickers who go through hell week selection, all that stuff. Then there's close supporters. And supporters, so close supporters are medics, engineers, people who have to be right at the front to support exactly what's happening as they're kicking doors. And I was a supporter, so I was a logistics operations officer. So basically a fixer. So we're going to set up a mission in, we'll say, niger. Because I went there a bunch of times and I go first and then I establish all the logistics pieces. So where we're going to live, how we're going to live. I show up with three or €400,000 backpack, and I got my gun tucked away in case someone tries to take my giant backpack full of cash.

Wait, are you dressed like a civilian? So this is like undercover stuff? Oh, you're the coolest man that ever lived.

Well, hold on.

Yes.

No, no, I'm here. Caleb.

You are the coolest man that ever lived, Caleb.

So you go in, you're dressed as a civilian. Are you going under your name, Caleb, or are you going under a fake name?

So, I go as Caleb McDonald and I fly Air Canada, Air France. And they give me a ton of shit about having €400,000 in my backpack. Because we're Canada, right. We're small, we don't have much money. So I fly coach all the way to Niger.

Tell me you at least dress in a hawaiian shirt and aviator sunglasses.

Oh, of course.

Okay, good.

Magnum PI was my inspiration for all my undercover.

Okay, well, I'm sorry, the Nova Scotia version of Magnum PI. So, you show up in a country, you've got $400,000 in your backpack, and how do you know? You start spending that money to set up the operation. Is that right?

Absolutely, yeah.

Did you have to keep good records? Did you. Would you ever go and drop $51,000 in a strip club and go like, oh, shit. Well, anyway, they're not going to miss it.

Yeah, yeah.

You just write it off as a reconnaissance.

Reconnaissance?

Reconnaissance? That's what you call foreplay.

Yeah.

Yeah. €400,000 in West Africa becomes like 180 million francs. And so your accounting becomes a lot of zeros, a lot of decimals, very difficult to keep track of.

But are you setting up contacts? You paying people to get information? Are you planting bugs? All that kind of stuff?

More or less all those things. I would also say that we rely heavily on our american partners, which is always very nice. So I meet them in country and they help us out with whatever we're up to. But traveling with that much cash, very stressful, especially when it's what we call, OPM, other people's money. And so if it gets taken, I'm still on the hook. And that's why we're always strapped in civilian clothes. The problem becomes, I'm a white, fit, short haired, bearded guy in Niger, and I'm the only white dude in 1000 miles. So I'm undercover, but with a big, fat asterisk. They know who I am. They know what I'm doing.

Yeah.

And you have a bank more or less strapped to your back, and you're walking around saying, oh, I'm up for a public school teacher. I'm just here from Nova Scotia to kind of look around and buy a t shirt or two.

And they can have euros because they're really big denominations. But I traveled with USD to Jordan once, and I had 300,000 american. And your biggest denomination is 100. So I basically had like a, like a duffel, like a hockey bag on my back full of. Full of cash.

Yeah. Remind me to rob you sometime.

Well, I don't have anybody now. I'm retired.

I'm broke, man. I think you stashed a few backpacks around here and there. I think if you took a little walk in the woods, there's an old hollowed out tree. A couple of passports. Exactly. You've got nine passports. Do you know how to fight like Jason Bourne? That kind of sloppy fighting? You know, the fighting where they kind of slap each other?

We didn't cover slappy fighting. When I went through the training, more in the lines of sort of a brazilian jiu jitsu grappling style. Then you add in knives and rifles and pistols as accessible. You know, all that stuff with an asterisk. Again, like as an operations logistics guy, that was part of the training, but it wasn't the focus of the training.

What's the hardest thing you had to go through in the training? Was there some, you know, is there something where they did something crazy to you? Like, held you underwater for a week or something and you just had to get through it?

Something like that. So we did this course called TCCC, which is tactical critical combat care. So it's basically first aid in a wartime setting, because you can't just be like, oh, I'm going to come over and do CPR on you because you got shot in the middle of the street. It's about winning the firefight, establishing dominance, and then extracting the casualties to a safe place and then doing the treatment.

Right.

And we added in. So regular first aid is all the normal stuff. We add in explosive needle decompression. So for tension pneumothorax, when you get, you know, a sucking chest wound, if you've ever watched three kings, when Mark Wahlberg gets that little pin in his chest. Yeah. So we learn that, and we learn what's called, I can't remember the name, nasal genic tubing or something, but basically you shove a silicone tube through your nose, down into your throat, so that if you're a unconscious or a lot of, there's a lot of trauma to your face and throat, you can still get an airway into the lungs. We practice that for real. So I'm. I'm a casualty in this scenario. I'm on my back, I'm covered in fake blood, I'm unconscious. The guy coming over to me is doing his first aid. He does all the right stuff, puts the tube in which, you know, you're like gagging, sneezing, coughing.

You had no anesthesia that went straight in. Because I've had that done with anesthesia and it was crazy.

But, well, there's a hint of lube when they put it in there.

I always ask for a hint of lube. Just a hint. Things go much dollop of lube. Little dollop.

The problem with the tube going in is during this course, it's live fire, so there's bullets, there's explosions, because you're meant to be simulating a combat environment. And so when buddy was done the first aid and I was ready to go, I just opened my eyes and saw this big hand coming down and he just gripped it and ripped it like he was starting a lawnmower. And I felt my soul just, oh.

You know what, I'm sorry, I really want to serve in the special forces in Canada, but that's a. I can't cross that line. I can't have a tube shoved up my nose and then ripped out.

Not ideal.

That's. Well, I'm not even going to say not ideal. I'm going to say absolutely terrible.

Yeah, it's a deal breaker.

Yeah, there you go.

But up until that point, you thought, hey, I could do what he did.

Well, I'm good at slap fighting and.

I sticks out in Nijon.

And I regularly travel with hundreds of thousands of dollars in every denomination. Of course, just cause I am obsessively, compulsively going to ATM machines. But I never spend the money. I just use my credit.

Cardinal.

Hey.

Thought a voice note would be easier. So, our summer trip, what's the plan? Do we hire a car there? How much is that? Who's minding the dog with Stella line?

Booking your summer holiday doesn't need to be this whole big thing. Just drive on with everything you need. Packed in with restaurants, bars, kids zones and pet friendly cabins. The holiday starts on board.

What about the ferry? Bring our car over with Steneline.

With 14 daily sailings. Wherever you're going in Britain, enjoy getting there with Steneline. Book now from only 165 euro car and driver one way at Steneline, ie.

That seemed intense that you did all that. And were you in, I'm guessing you were in some war zones or adjacent to war zones.

Yeah. So I deployed to Afghanistan in zero nine during the war, and then I was in Mauritania, Libya, Jordan, Niger and a few other spots throughout my time it was. You get to see a lot of places that you wouldn't normally see. So the travel is. Is kind of cool. Who else gets to go see Afghanistan? Who else gets to go and see Libya in these days? Right. So it's pretty cool from that perspective. On the other hand, getting shot at while you're sightseeing is not ideal. Were you shot at Florida?

Oh, yeah. Were you shot at?

Oh, yeah.

And what does that feel like? What does it feel like when someone's. It's not meaning, I know there's training where they're probably shooting above you, but you had people that were actually actively trying to shoot you.

Yeah. So it was pretty uncommon, admittedly, for me, because as a logistics dude. But with Afghanistan, the way it was structured was we had fobs all over the place. And so in between these fobs is bandit country, for lack of a better.

Is that a forward operating base?

Exactly. Yeah. So, as you're driving around, look at this guy.

Very nicely done, Matt. It's also something that attaches to a pocket watch. Okay, so it could have been either one. I assumed it was the latter.

It's also someone who's fresh off the boat. That's what we use fob for. I'm sorry, am I the only one?

It's also for someone who's full of bullshit, so I think we've just taken care of the two of you. Caleb, you've got some. So you're saying you were in situations where people were firing at you. That's got to get your attention.

Well, yeah, but, I mean, before you even go out, you have your whole plan, your whole brief and everything sort of determined on. If this happens, we do x. If that happens, we do y. So your training takes over in a lot of ways. I would also say your arsenal puckers up like a snare drum when that happens, too. It's quite the experience.

You know, everything you've described is what we go through before every podcast. That's true. If Ted Danson says this, we'll go to X. If says that, we'll go to Y, and then our assholes pucker up. So it's pretty much the same thing. We're kind of under live fire here when we're just improvising in.

Well, Sona and I are.

That's true. Yeah, from you. Hey, you've got some cool stuff behind you. Do you mind telling us what's behind you? I see a framed knife that looks like a really cool knife.

Well, that's actually. You're a history guy. I think so. This was actually a gift when I left the special forces. That's a v 42 fighting knife. And it was designed by the commanding officer of the first joint american Canadian Special Forces unit and only joint unit that's ever existed during world War two. Yeah. So that's a replica. So as we leave, and if we leave on good terms, and not everybody does, then you get a nice frame knife on the way out.

That's very nice. And what's over your other shoulder right there? It looks like you've got a. What is that?

This?

Yeah.

So this is. It's called an oosic. So it's a fossilized walrus penis that the indigenous peoples of the northwest, you know, Alaska, BC, would use as clubs. So they would wrap leather or something around the handle and then they would brain each other with it when they were having beef.

Wait, so if they're fighting with each other, they. They grab a walrus dick and go at it?

I mean, that's what I'd grab.

And.

Just a little bit of lube.

Just a little.

We covered this in sloppy fighting.

So that's a weapon, the fossil? It's fossilized, yeah.

It's quite old. I got it at a.

Doesn't look big to me right now, so. Huh.

It doesn't.

Yeah.

Oh.

Doesn't look that hard either. I apologize. Oh, God, Caleb, I lost my mind for a second. And I blame you because you've taken us down some dark paths. Sorry. You can handle yourself in a fight.

I'm guessing, right, I think, against a regular, untrained person. Absolutely. Against someone with equal training, maybe against somebody with more training. Yeah. Not a chance, but most people have none, so.

Okay, I'm going to be honest with you, Caleb. I have no training. Okay. What if I came at you? What would your strategy be? I'm six four, about 205 pounds.

Are you in the slap fighting?

No, I'm just coming at them and I'm. Yeah, what would you do? And keep in mind you're a tall guy. Keep in mind you're a fan.

Oh, you want him to go easy.

No, no, no, be serious. What would you do? A guy my size comes at you.

So you're a pretty tall guy. So, I mean, you want to use that against you because everyone's the same height on the ground. So I want to get you down, get you low, and then take advantage of my training in grappling.

Is.

It looks easy, but anyone with some training in grappling is leagues ahead of anyone with no training in grappling.

What's better to know how to grapple.

Or box grappling, for sure.

Yeah. A grappler beats a boxer nine times out of ten, right?

I would say so in my experience, for sure. Because every fight ends on the ground, and so boxing has no value on the ground. So if you can't win it in one punch or two punches, then it's kind of over for you.

What if I have a walrus dick and you didn't know it?

Okay.

No, in my back pocket.

That evils things.

You'd be really easy to beat in a fight. Cause all you have to do is say something that'll hurt your feelings and you'll just cower and scream.

Read me a lukewarm review. And I'm on the floor curled up. Why didn't the Wall Street Journal like what I did? They should know comedy. They know finance. They should know comedy. Caleb, you seem like a cool guy. It's been a pleasure talking to you. And even though I usually say thank you for your service to people that are in the United States forces, but I'm going to say it to you, too, because we're allies. And I appreciate your work. I really do. I appreciate what you did for us all and for the cause of freedom.

Comedy goes a long way when you're in those situations, too, to making them easier to bear. So appreciate it.

Well, you didn't specifically say you liked my comedy. You just said comedy.

That's good.

I think he said enough.

No, no. He was like, you know, I really admire what you did on Seinfeld. And I'm like, what? What do you say?

Instead of a big pistol, shrimps, radio and mall walking guy for a couple podcasts of mine.

Caleb, you listen to that in your forward operations base?

Well, that was before. That was 15 years ago.

Yeah. Yeah.

That was more bulletproof legs and Walker. Yeah, Walker lever. That was back in. That was what I grew up on.

Well, my show, I think, was probably the best tool in the fight for freedom. Oh, boy.

Agree.

I think I'm having a small stroke. Caleb, thank you very much for everything. It was very nice talking to you. And the next time I'm in Nova Scotia, I might look you up. Is that cool?

Yeah, absolutely.

But, I mean, I'm going to attack you. When you fight, I'm going to attack you. That's what I would do. I would attack you. And we'll see how. Because I think you're underestimating me. Yes, you could use my size against me, but I have a. I don't know. I have a I'll have to answer.

The door with my usyk now. Every time.

Yes.

When someone comes knocking, just in case, yes.

Your walrus dick.

Anyone just tuning in should know that Caleb has a fossil. That's it. And that's all the time we have. Bye, Caleb.

Thank you.

Conan O'Brien needs a friend with Conan O'Brien, Sona Mosesian and Matt Gorley produced by me Matt Gorley executive produced by Adam Sachs, Nick Liao and Jeff Ross at Team Coco and Colin Anderson and Cody Fisher at Yearwolf theme song by the White Stripes incidental music by Jimmy Vivino take it away, Jimmy. Our supervising producer is Aaron Blair and our associate talent producer is Jennifer samples. Engineering by Eduardo Perez additional production support by Mars Melnick talent booking by Paula Davis, Gina Bautista, and Britt Kahn. You can rate and review this show on Apple Podcasts, and you might find your review read on a future episode. Got a question for Conan? Call the team Coco hotline at 669-587-2847 and leave a message. It too could be featured on a future episode. And if you haven't already, please subscribe to Conan O'Brien needs a friend wherever fine podcasts are downloaded. This has been a Team Coco production in association with Earwolf.