Episode Transcript
[00:00:01] Speaker A: Skyler, welcome aboard to the show today. So happy to have you.
[00:00:04] Speaker B: Thank you for having me. It's good to be here.
[00:00:07] Speaker A: I gotta ask you, what was going through your mind when you decided to join the Army?
[00:00:12] Speaker B: When I first went in, it was during the 1980s. Ronald Reagan was president. And I had a lot of people in my family that had been in the military. My dad had been in the Marines.
I'd had a couple of brothers in the Air Force.
And so I decided, I'm going to go in the army, went to all the recruiters and decided I wanted to be a paratrooper and go airborne.
[00:00:38] Speaker A: What was that? What was that first, like, adjustment period where you kind of figured out not to quote, I'll quote the song, you're in the army now. What. What changed? What were the things that surprised you, and what was the reality?
[00:00:50] Speaker B: The first two weeks were probably the hardest. Just getting used to the routine, you know, having someone tell you at this time you're going to be here dressed like this, you know, having every minute of every day controlled and not having a lot of free time, that was the most difficult. But once you learn the routine, it's not so bad.
[00:01:17] Speaker A: And relatively quickly, you went into maybe a surprising area. You became a DEA agent as part of the Army. How did that come about?
[00:01:27] Speaker B: Well, it wasn't part of the dea, if this was. That's right at the end of the Cold War.
So a lot of the Marxist groups in Central and South America needed a new way to make money because they weren't getting the support of the Soviets anymore. So they turned to kidnapping and drug production.
Well, the cool guy units, all the special operations people, wanted to go after cocaine.
Nobody really wanted to go after marijuana because that wasn't seen as glamorous, I guess. I don't. I don't know. That's kind of what we. Our conjecture, you know, going to bust Scarface for cocaine is cool. Going to bust Cheech and Chong for marijuana, it's kind of lame. So they put out to just regular units.
Who wants to go do this? They had some quick selection process, and they gave us two weeks of training and sent us out. And so that was. We were operating different areas. Our main job was to assist local law enforcement with collecting evidence for their cases.
So we were primarily just doing in marijuana grows all camouflaged up with cameras. They'd come in to tend their plants.
We'd take video of them, and then when the local cops thought they had enough evidence, they'd arrest them.
And I kind of Got the feeling that's all we were expected to be doing. But the way it worked out, we were split into two groups. There was a northern unit and a southern unit. I was down south, so we were away from leadership, and the local cops wanted us to start doing plainclothes surveillance in town. So we started doing. They got us different cars, so, like, I had three cars that I'd switch off on. So I'd sit on a location watch for who came in, who left.
Some of what we were doing was seeing, like, how they were laundering their money and to build a case. Like, this one guy we were on, he had a fake business, but it had a real location. Well, to prove that he's not making his money, that he's washing through the bank through that business, we had to sit there and document during all business hours who came in. And of course, we're sitting there for weeks, and nobody comes in. So it was a lot of just very boring sitting and watching, but also got to do some cool stuff. But I think the people up north had no idea what we were doing. It's like, you guys are doing what. Yeah, we're doing plainclothes surveillance. We're, you know, following people and, you know, changing clothes, changing hats.
One guy had a hat, and he took a wig and stapled the hair from the wig in the hat so it'd make him look different.
So we had a lot of leeway with what we were doing. It was a lot of fun.
[00:04:44] Speaker A: And. And how do you. And, you know, you progressed, became a platoon leader, then you became an accountant. That. How. How does that work? What. What. What brought. How do you go from, you know, surveillance to accountant?
[00:04:58] Speaker B: I left active duty, and I was in the National Guard in the reserves and went through college, got my degree in economics. And I had a relative who had a commercial property development and management company, and he needed some help in the accounting department. There was somebody that was retiring, and he's like, hey, when you get out of college, I can give you a job.
Okay? And so I did that, and I ended up getting out of The Guard in 95, but then rejoined in 2007.
[00:05:32] Speaker A: We say that you can take, you know, you can take the person out of service. You can't take the service out of the person.
[00:05:36] Speaker B: Yeah, absolutely.
[00:05:39] Speaker A: I maybe, you know, a regular. Let's say, you know, Joe's. Don't understand what that means. What brought you back to service?
[00:05:48] Speaker B: Part of it was I had moved back to Oregon.
You know, my job after college was in Northern California. I Worked there for three years and then left. I was doing some contracting during the dot com boom in San Francisco and then the dot com bust happened around the year 2000 and everything just. I couldn't find work, so ended up moving to Colorado where I had some relatives. My dad lives out there.
Ended up becoming a deputy sheriff out there for a few years.
Didn't. I wasn't a good fit with the department.
Didn't really like the politics. I expected it to be more like the military, and it wasn't.
[00:06:32] Speaker A: So in what way, if I may ask?
[00:06:35] Speaker B: Realizing that working for an elected official means everything you do gets scrutinized under, is this going to hurt the sheriff's chances for reelection?
And this particular sheriff ran his depart. He ran the agency like it was his own private fiefdom. He fired people for stupid reasons. They were happy to say, you work at the pleasure of the sheriff. You can be fired for no reason whatsoever at any time. And he ended up, at the end of his tenure, ended up, a lot of things were coming out that he did. There were bank accounts that the county treasury didn't know about that he said, oh, this was just a bookkeeping error. This was, yeah, okay, there's a million bucks in cash that the county doesn't know about.
And he ended up getting arrested and charged with a number of crimes. But yeah. And then so ended up moving back to Oregon and rejoined the National Guard and within about a year was back in Iraq.
Well, not back unit was back in Iraq. And so, yeah, that was my first deployment with the military.
[00:07:48] Speaker A: In this case, your role was. Was very different. You were in linguistics. Tell us what that means.
[00:07:54] Speaker B: Well, I was managing our linguists. So we had interpreters who would either go out with the patrols or work at the gates anywhere we needed. Because at the time, Victory Base complex outside Baghdad had thousands of local nationals who would come on to the base every day to work.
And so we had to screen their identity.
And so we needed linguists. And so my main job at that point was being the linguist manager.
[00:08:28] Speaker A: And over your career, you know, 12 years in the National Guard, what was the big takeaways? What are the things that you kind of learned and that, that surprised you in some way?
[00:08:39] Speaker B: One was seeing how well the National Guard performed.
And a lot of people who have been and even, you know, around the world, because I've worked with British soldiers and a lot of active duty guys, don't think reserve forces count for much. And I was, well, you get the, you know, in the United States, they Call them weekend warriors. You do one weekend a month, two weeks a year. You don't really do. And so not a lot's expected. And Even in the 70s and early 80s, the National Guard was a drinking party. It was, you show up and you start drinking by noon, and there's not really any training going on. And so that attitude carried over. But Also in the 80s and even early 90s, most National Guard units were using equipment from the 1950s and 60s.
[00:09:39] Speaker A: Oh, wow.
[00:09:40] Speaker B: And so one thing that was discovered during Desert Storm was that the National Guard units couldn't talk to the active army units because their radios were incompatible.
And so that caused at the Pentagon level, people to go, okay, we need to get the National Guard using the same equipment.
And then when things kicked off In Afghanistan in 2001 and Iraq in 2003, there were a lot of National Guard units that were getting the same. They were up there with the frontline active duty units. A lot of people don't realize the Oregon National Guard was actually in Fallujah before the Marine Corps was. And they're doing, you know, 15 month tours.
And so they've got a lot of experience. And one thing that surprised me was I left, you know, with the National Guard, they move units around sometimes. Hey, this unit's gonna go from this town to this town. We're good. So there's some shuffling going on. And I ended up going to, I was in a cab unit and then left to go to an infantry unit. So from went from reconnaissance, surveillance, target acquisition, to just regular infantry. And in that unit, I went to every squad leader had been in a Ranger battalion.
And it's like, okay, there's. So there's a lot of experience there. And that company had a very high standard. So. But another thing that surprised me was it kind of morphed, starting about 2010, 2012, back into a good old boys club where everything seemed to be, we need to promote the careers of the officers. And it became, yeah, there were a lot because, like, there were, like, when I started contracting, I became Persona non grata to my unit. It's like, yeah, you're going overseas, you're going back to Afghanistan as a civilian, but you're not here doing weekend drills, so you're of no use to us.
And they started, they wanted to keep me on the books because they thought I'd only be doing it for a year at most.
Ended up on that contract for a year and a half, came back, and I was preparing to go to do a State Department contract. So I drilled for a couple of months, but what the National Guard was required to do was put me in what's called the inactive ready reserve. And by regulation, they had no choice in the matter, but they just said, no, we're not going to do that and there's nothing you can do.
So that was kind of a disappointment with them. And I ended up retiring out of the Guard because I was contracting and they're like, well, we're going to go spend a year in Jordan.
Or Jordan. No, where was it anyway? Like, they were going to. It was in Europe.
And it's like, you know, I'm in back. At that point I was in Iraq and I was getting ready to go on a different contract.
And so I just retired. I'm like, yeah, I'm done.
[00:13:14] Speaker A: That's a. That's a. Was it a difficult trans transition for you going from army, military, National Guard into civilian life?
[00:13:23] Speaker B: A little bit.
A lot of civilians don't like stateside civilians working in an office building. They focus on things that don't matter.
[00:13:34] Speaker A: I felt, tell me more. What. Give me some.
[00:13:37] Speaker B: Help me understand working for a big company. I guess it was just different values because it was, we want to promote our bottom line. We don't really care about the people.
People are interchangeable.
And there wasn't the camaraderie there.
You know, in the military, you get up, you spend all day working with the same people, and then when you're off duty, you're still with the same people. You know, you live with people seven days a week. And, you know, there's a lot of jobs I've worked where I couldn't tell you the name of any of my co workers.
[00:14:20] Speaker A: You know, there's people of trust that you just can't live, literally live without, and it just doesn't exist.
[00:14:28] Speaker B: Like, I found contracting, you know, you're with people, especially when you start. Like the first contract I was on was, it was a Department of Defense contract. So it was a foot in the door, nothing high speed.
And they Only required like 3 years military experience, no combat time. Just if you had been in the military, you're good. And so we had a lot of people. You know, this was in 2016.
So the movie 13 hours came out like a year before. So there were people that had Benghazi fantasies, like, we're going to go get in gunfights. And it's like, no, that's not what our job is.
Like, our job is we're on guard duty.
That's all we do. Like we're permanent guard duty on a base within a base. You know, we've got several rings of defense around us. We're just one of them.
And so there were a lot of people that came in, they'd work for three months and go, oh, this is all we're doing, and leave. But then I started working for the State Department, so I was doing diplomatic security, and that was a lot better because you're working with people who are professional, intelligent.
And we trained to a standard that most military units never reach when, like, I was in Erbil, Iraq, at the consulate.
And so we also had the Marines there with us. And we trained the Marines.
And I hate to say it, but they were nowhere near up to our standard for building clearances, for react to contact, any. Any of your typical battle drills. It's like we were showing them how to do it. And then I went. Stayed with them for a while, and then went on a different contract where I was working for what they call an oga, which is an other government agency. So all I can say about that is I worked for the US Government, and that was the best contract I was ever on because I was working with people who knew their job, but they were also some of the smartest people I ever worked with. And, yeah, it's.
Sebastian Younger talked about when he went to Afghanistan with a unit and then later on talking to these guys who went through the harshest conditions, and he's like, would you go back? And, like, do you ever miss it? He's like, every day. Because you're working.
[00:17:16] Speaker A: Counterintuitive.
[00:17:17] Speaker B: Yeah.
[00:17:17] Speaker A: Why would. Why is that?
[00:17:19] Speaker B: Well, you're working with people that are at their best, and you're doing a job that matters.
You know, if. And I think that's why I had a hard time in civilian life, was you're doing a job that if you don't do your job, yeah, eventually you'll get fired. But it's like, nobody really cares. And you know that you're doing a job that, especially when you're working for a big company, you're just a cog in the machine.
What you do doesn't matter.
When you're deployed overseas, everything you do matters. There's consequences. And you're working with people that are working at their highest level. And also there's, you know, most civilian companies, nobody cares. Nobody cares about you.
When I was contracting, I was working with people that would give their life for me.
[00:18:13] Speaker A: There's something that I feel like fundamentally changes everything when.
Is both terrifying but also inspiring. It makes you jump out of the bed in the morning when what you do actually matters to the level that it can impact the lives of your friends, family, nation. It just changes your whole perspective of. Of everything you do.
[00:18:37] Speaker B: Yeah. And there was, like, when I was doing the drug enforcement, there was. We were sitting on this guy, and he was one of the. You know, he was the head of this group, and I followed him to a shopping mall and just wandering around the mall, and I'm just hanging back and. But he went to a bank to draw cash out. He goes to the atm.
And I had opened an account at the same bank, and they had a very distinctive red and gold ATM card.
And I saw that he had the same color atmosphere card. So it's not just he's pulling money out from that network, but he has an account with that bank. Okay, put it in my notes. And at the end of the day, we're like, what did you see? You know, like, okay, this vehicle pulled in at this time. And I said, yeah, he went to this bank and he drew cash out with an ATM card from this bank. And they're like, oh, he doesn't bank there.
No, he does.
He has the same ATM card, this red and gold card. And they were like, wait a minute. We didn't know that.
And that little tiny detail, you know, from weeks of sitting on this guy, you know, finding out who he's cheating on his wife with, who his wife's cheating on him with, and just sitting in the sun for hours in a car just watching to see who comes and goes. The most boring surveillance ever.
And got a detail that let them figure out where his. Where he was doing his banking and how he was laundering all his money.
It's like, when you do stuff like that, yeah, it matters, you know, that's.
You know, when you're sitting in an accounts payable department getting invoices and going, do we have authorization to pay this? Do we have authorization?
And you're just doing stuff that if you stop doing it, nobody noticed.
[00:20:47] Speaker A: When you look back and you think about your experience and then youngsters kind of coming into finding their own way nowadays, what. What would you advise them? What are the big takeaways that you've had?
[00:21:00] Speaker B: I'd say with the military, find what interests you? When I went in, I went into the infantry. If I had to do it in again, I probably would have gone in the medics, because that's kind of more where my interests lie. There's a lot of different things you can do. Yeah, Just, you know, and I have had some family members that have come to me going, hey, I'm thinking about going in the military.
What's the good? What's the bad? I'd say if you're thinking about it, look at all of it and go, okay, what's the downside?
You know, okay, you might be like, if you want to make a career, you might make it 12, 15 years, but then your body starts breaking down.
You know, I know one guy who's sitting at about 15 years and he's going, I don't know if I can physically do this anymore because he's been in the infantry the whole time.
And so there's. And part of the downside of the military is there's a lot of units that think, well, if you're no longer useful to us, we're just gonna like, you're done. And so. But there's.
There's good and bad everywhere, but you just need to go into it with your eyes open.
[00:22:19] Speaker A: Absolutely. A little bit of a sharp shift. You're doing two things today. Kind of counterintuitive or very different than you would expect.
Your writing.
[00:22:30] Speaker B: Yes.
[00:22:32] Speaker A: And also advising as an expert witness. Tell us more about that.
[00:22:37] Speaker B: Well, I started doing that that grew out of writing articles because I write for a firearms magazine, Concealed Carry.
And you write about what? You know. So I was writing about firearms, but also with my experience as a deputy sheriff on the legality of use of force in self defense. And I was contacted by an attorney who had a case and he needed an expert opinion on whether or not this was legitimate self defense.
And that was a really good case for me to cut my teeth on. And so the job of the expert witness is. Well, first. First of all, what an expert witness is is somebody who has experience in a field that's beyond the knowledge of a layman. So, like, I can speak about use of force and firearms, police procedure. I can't speak on blood really about like blood spatter psychology, because that's not my field. But on my narrow field, yes, I can speak on this. And the job is really to look at the evidence and then explain things to a jury. So a lot of people think, well, the attacker had a knife and he was 10ft away. That's not really a threat.
Well, no, it is because. And there are studies that have been done that show at 21ft, someone with a knife and someone with a gun, if the person with a knife decides to attack, they'll tie. Which in self defense, a tie is as good As a loss, you know, you shoot your attacker and your attacker stabs you. So.
And also had one case where the attacker, he outweighed the victim by 170 pounds.
[00:24:41] Speaker A: Oh wow.
[00:24:42] Speaker B: He wasn't armed, but he kept trying to grab her around the neck. And so explaining to a jury that even an unarmed person can be a threat where use of force is justified. And I've learned like I won't take a case where I think it's iffy or where it's definitely this is not self defense. I had one where the guy's story is he was just riding around with his friend in a car, he was playing on his phone and his friend just all of a sudden decided to do a drive by at this other guy's house. And when they were leaving, the guy that his friend had shot at shot his friend and then he got out of the car and started shooting. It's like, no, if your friend does a drive by, you shooting at the guy that shot your friend is not self defense. And had a few others like that where somebody went to get a weapon and came back. It's like, no, that's not self defense. That's, you know, that's a homicide at this point. That's murder.
[00:25:58] Speaker A: Skyler, thank you so much for joining our show today. We have only one question that is scripted that we ask everyone and it's a difficult question. Okay, if you had to go back to 20 something year old Skyler, what would be your advice to him?
[00:26:13] Speaker B: I'd say follow what I'm passionate about.
Don't do things because I think other people expect it. It would be do the things you love doing and don't worry about what family thinks, what you think other people expect of you. Follow your passion. And like if I had to do it all over again, I probably never would have gone into accounting.
I probably would have stayed in law enforcement, gone, you know, career military, on active duty, gone into being a paramedic. Something else. But probably, yeah, but you get to a point where accounting pays the bills and you're kind of stuck for a while.
But now I'm with, because I also, I'm an accountant with a small company that I truly love great people and they actually value what I do. So it all worked out in the end.
[00:27:16] Speaker A: Better. Thank you so much for joining the show today and sharing your story. I appreciate you.
[00:27:20] Speaker B: Well, thank you. It's good being here.
