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Caleb
Okay, I got the red smoke.
Host (possibly a podcaster or interviewer named Michael)
Sun runs north or south. West of the smoke.
Caleb
West of the smoke.
Host (possibly a podcaster or interviewer named Michael)
Okay, copy. West of the smoke. I'm looking at danger close now. Come on with it, baby.
Caleb
Give it to me.
Host (possibly a podcaster or interviewer named Michael)
I need it. You're clean, hot, can't be cleared hot. What do they generally want? I mean, we'll get into what you do, but I'm curious, what for a. Call it a high net worth person, what do they want when they call?
Caleb
95% of what I do now is educational, to be perfectly honest. Like. Like either. Either something's gone wrong.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
Or I need to explain something to them.
Host (possibly a podcaster or interviewer named Michael)
Okay.
Caleb
Because, you know, my role has changed, you know, in the last three years. And so moving into being a vendor from being, you know, an end user security director, my role changed drastically. So it used to be they called me for everything, you know, hey, I'm going in front of the Senate, let's talk this through, you know, like wild stuff. Hey, you know, I'm going to Columbia. What do we need to. What do we need to do? What are we looking like? So it'd be real time, you know, updates, things like that. Yeah. Now I have a director in charge of every client, so all their, all their, you know, kind of tactical things like the day to day operations is handled by the director. I'm just there as oversight and you know, if they want to reach out and, and talk to me, then that I'm there. And yeah, a lot of the times it's like, hey, your team's doing amazing. You know, we just had that last week you was. Which is really cool. So.
Host (possibly a podcaster or interviewer named Michael)
Yeah, well, it's better than the other call.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
I don't. What is the relationship you have with the woman who first reached out? Does she work for you? She a booking agent?
Caleb
No, just booking agent. Okay.
Host (possibly a podcaster or interviewer named Michael)
Yeah, I don't, I don't mean it negatively in any way. I just didn't know how to refer to her professionally. So when she first reached out, it was about a week after Charlie Kirk was assassinated. And it took us a little bit to sit down together, but here we are.
Caleb
Here we are.
Host (possibly a podcaster or interviewer named Michael)
I. So what I don't ever want to do is ever Monday money, morning, quarterback, anybody. But that situation was a nightmare. And I wanted to open with, if you're good with it, just talking about the absolute complexities of protection in an environment like that, especially when you don't have law enforcement authorities.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
Michael, pull up this picture because I think people need to understand the complexities of what is involved with that. Because people will say, how did that happen? How could it possibly happen?
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
And I don't ever want to give anybody ideas, but I have some, which I will keep to myself. So. Okay, where do we have here? Let me orient myself. It's been a while since I've looked at the location issue. Okay, so we're going. The shooter was in the viewer's right, looking down to the left. As somebody who. And we'll get into your background, obviously, but let's just say you're very steeped in the personal protection world. How are you looking at this? Where do you. As a civilian again? And obviously they had law enforcement that was there. How do you guys start breaking this down? How do you even get to a place where you are approximating a level of comfort for somebody like Charlie who was. Depending on the lens that you're looking at? Some people would say he was. I'd actually. I don't know what they would say. He was polarizing.
Caleb
Absolutely. Yeah.
Host (possibly a podcaster or interviewer named Michael)
We can. We can leave it at that. He was polarizing. How do you. How do you start this?
Caleb
I mean, obviously, the prep starts weeks in advance. Doing your. Your digital advance of the site, understanding the topo, understanding ingress, egress, all of those things that you can work on well ahead of time can be done so that when your advanced team actually hits the ground, you're able to understand what has changed since the pictures that you. You. You reviewed it. Now, as far as day of. There always going to be those changes because of how they set up the venue, how they set up things. But keep in mind, we're talking about an individual here. That's. That's. This isn't a large stadium, you know. Yeah, we're talking about a.
Host (possibly a podcaster or interviewer named Michael)
It's actually really tiny. I mean, obviously every picture is from above, so things will look smaller. But the POV, the camera POVs. It makes it look like it was, you know, Petco Stadium in San Diego and it wasn't.
Caleb
Right. Yeah, exactly. The reality of the situation is, is you have an individual who had an escalated level of risk by their own admission. But at the end of the day, we're still talking about somebody who goes and talks on college campuses. Right. There's no legal way for someone in the private sector to cover all the bases of risk that you're looking at in that picture. It's just, there's. There's no legal way you look at typical assets, let's say, for a POTUS movement or something like that.
Host (possibly a podcaster or interviewer named Michael)
Oh, God.
Caleb
The assets that are required to pull something like that in this venue are literally illegal for the private sector. So what we have to do is we have to look at it from a place of creativity, not only from the adversary's perspective, but take a look at that and say, all right, how can I do the most good? You have to prioritize your resources based on what you have available, but also where you think the risk will most likely come from. And that's what that, that calibration happens every day out in the field. You look at teams that are working, protectees all over the place. Politicians, you know, vast majority of politicians didn't have protection. Now they're starting to have protection. Now they're having one or two agents on coverage. They're going and speaking to crowds that are larger than this.
Host (possibly a podcaster or interviewer named Michael)
That's thin, man.
Caleb
That's very thin. But it's just not practical to say we can mitigate every single risk. So you really have to be creative. You know, when you have an escalated level of risk, then take and increase your security posture where you can they. If they wanted to add CS teams, if they wanted to add redundant layers, they literally couldn't because that was somebody else's jurisdiction. Right? So as someone in the private sector, you really have to be, be prepared to tell the protectee, this is up till this level is where I'm comfortable with. If it gets past this level, it's a no go. You know, we're not going to show up to this venue. We're going to have to figure out something else. And that's something that I think has, has been under discuss is at what point do you tell your client no? Because us telling the client no isn't something we want to do. But oftentimes that's exactly what we need to do to be able to develop a situation that we can actually protect them in.
Host (possibly a podcaster or interviewer named Michael)
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Caleb
Absolutely. And I've heard it. And, and if they say that, then that's fine, you know, and, and there's, there's, there's, there's ways of going about it to social engineer the conversation. That's why relationships with your protectees is so important. So they understand that you are doing everything to make it happen. But at the same time, if you have a risk that's identified, if you have a no go situation and you're saying no go and they want to go, then that's what I call an unsustainable risk level. You know, we talk about risk levels from protective intelligence standpoint and we, we like to allocate risk into categories, try to keep it under five and everything like that. I have a category, category called unsustainable. And that's where you take, and you say this, this is where we throw everything in the kitchen sink out there. Unsustainable is where we, it's like an all call all resources. Everybody we can get any mutual aid, anybody that we can call in a favor. Can we get any resources beyond what is currently allocated? Because you're going into a situation that you can't control, you have to have an unsustainable level of protection in order to sustain their protective posture.
Host (possibly a podcaster or interviewer named Michael)
Given what happened that day, I have to assume that that rippled through your industry.
Caleb
It was insane. It was insane.
Host (possibly a podcaster or interviewer named Michael)
What, what I mean, as that day played itself out, how did it go out in real time? Just. And then what are the, what have the cascades been that you've seen in changes?
Caleb
We've seen an unprecedented number of attacks on principals in the last 18 months. Charlie Kirk was different because people that didn't know Charlie Kirk felt a personal level of vulnerability. Protectees who had never had protection before all of a sudden said, wow, I could be go visiting my daughter on campus. And I Could get popped. I could be going to a campaign event and I could be, you know, assassinated. The level, the personal level of interaction that that protectes felt that resonated through the entire world. You know, people with a protective posture that have been hesitant to add to the team or have someone beyond their, you know, residential coverage, you know, have somebody in the field actually doing close protection, people all of a sudden became aware that wow, my risks have. Have. Are actually real. You know, I like to say that, that both both UHC and, and Charlie Kirk and you know, New York Tower incident, really.
Host (possibly a podcaster or interviewer named Michael)
Uhc.
Caleb
United Healthcare CEO Thompson, did he have.
Host (possibly a podcaster or interviewer named Michael)
A protective detail of any kind or was he solo mission out there, just Jason borning it?
Caleb
He had a protective detail on the books. We know locally, I can't talk about what, what was that day because I wasn't there. Okay. But I do know that there was security certainly inside the venue, you know, from the hotel, security from, from working many that, you know, there's absolutely a level security that's there. It's just weather is focused on on the area, you know, that took place.
Host (possibly a podcaster or interviewer named Michael)
And yeah, if you go outside the bubble.
Caleb
Well, and, and the reality situation is, is you look at, you look at the practical level of protective operations and accounting for human nature is something we have to do all the time in our planning. And, and I'm not saying this by the way, is anyway an influencing factor on the Thompson murder. But you, you take six the morning in New York City on a frigid December night morning, and you have people out there you might have, if it was warmer weather, you might have had an advanced agent ready to, you know, receive your protectee. With a lot of financial events like that, there are advanced agents that will receive. You might have had, you know, somebody from physical security, from the site, you know, site agent that would have been outside for the arrival, you may not have, you know, but, but the chances of somebody going out in the cold and waiting for scheduled or unscheduled arrival from a protectee, that's pretty low. Right.
Host (possibly a podcaster or interviewer named Michael)
And so walking from his hotel to.
Caleb
The venue, that's what I've been told. Okay, yeah, yeah, yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
Because it happened on a public street.
Caleb
Public street. Right, right. I, I've had events there many times with the different corporations I've worked for.
Host (possibly a podcaster or interviewer named Michael)
Yeah, I would say it would be almost statistically anomalous for somebody to sit there and wait like that. That's. I mean crazy people do crazy things, let's be honest.
Caleb
Well, Black Swan event for sure. But when you have an enemy that can choose the time and place. They don't need to know who necessarily. You know, keep in mind, Thompson was a sub CEO. You know, there were, there were other CEOs, other people that were at that same venue who very well, you know, could have. I don't think that there's any indication that anybody else was, and I don't want to, you know, overstate that, but what I'm saying is a nefarious actor has the ability to choose the time and the place. And if they're choosing the time and the place, they don't have to get it right every day like we do every day. When that protectee goes in, out, they're not the president. They can wave off their detail if they want. They can say, hey, you know, I know I'm paying you, but I don't need you here. Right? And then, and then you, you go to whatever appropriate distance is and your options for, for protection are limited. That's the difference between, you know, government details and, and private sector.
Host (possibly a podcaster or interviewer named Michael)
I have heard, and I'll just say this is unconfirmed, but I've heard that Bush Jr. When he would go to Texas, he would get on his bike and dip out on his detail and go into town.
Caleb
Freedom, right? Yeah, freedom.
Host (possibly a podcaster or interviewer named Michael)
I mean, again, I don't know the. I want to believe that story because I think that's awesome. Kind of because nothing happened. I could also see that being a horrible nightmare and also the shift leader going, I'm sorry we can't find our protection, right?
Caleb
Oh, absolutely, absolutely. One of the Hollywood details that I worked early on, when I was in my early 20s, was a 12 year old boy that since he was born, he had had 43 agents assigned to him.
Host (possibly a podcaster or interviewer named Michael)
What?
Caleb
He just kept going through them because they'd get upset and they'd get, you know, ticked off because he'd go jump out a window and go down to the park and play and they wouldn't even know he was gone. You know, feeding the purpose a little bit. Well, it is, it is. And, and I went to it with a little different attitude. I was like, if you're gonna jump out the window, let me know so I can jump at it with you. You know, and at least then I could stay with him. And as we went around the world, all sorts of crazy places, you know, I was his adventure buddy rather than the leash that kept him from doing fun things. You know, so there's a little bit of social engineering that you have to add with the protective posture just to Be able to be allowed in a place. You look at most protectees today, they don't have board mandated programs. You know, they, they don't have somebody saying you're gonna lose your job if you don't have your EPTM on you.
Host (possibly a podcaster or interviewer named Michael)
How common is that where a board was? Is that just for a key personnel or.
Caleb
Very uncommon. I think there's about six in the US that I'm aware of, possibly more, but very few, you know, and, and that is, that is, you know, literally the closest to a POTUS level detail where they say you have to have this in place, you have to, you can't drive, you have to have somebody driving you, you have to have an agent with you 247 if you want to remain employed at the company.
Host (possibly a podcaster or interviewer named Michael)
You know, what was the event you were going to talk about that was before the UnitedHealthcare. I interrupt you and I was asking what UHC meant.
Caleb
Oh yeah. Oh, it was after it, the New York tower incident where the NFL and the nefarious actor walked in with the, into the plaza with the AR15 blasted up the New York tower middle of last year.
Host (possibly a podcaster or interviewer named Michael)
God, how is this not.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Ringing a bell?
Caleb
Yeah, yeah. I mean there's, there's, there's been quite a few. You know, that one, that one resonated only because it hit the financial sector and a lot of unintended victims were actually victims in, in that case.
Host (possibly a podcaster or interviewer named Michael)
345 Park Avenue, Midtown Manhattan, killing at least four people, 6:30pm Striking police officer into a found dead self inflicted wound. God.
Caleb
One of the victims was Blackstone.
Host (possibly a podcaster or interviewer named Michael)
Oh, okay. Yes, I do.
Caleb
Yes. Yeah.
Host (possibly a podcaster or interviewer named Michael)
What you said that there's been an unprecedented increase in attacks on protectees in 18 months. What, what do you think kicked that off? Because that seems pretty precise that you're able to look back and kind of.
Caleb
Pinpoint that it's, it's actually slightly spooky, you know, to, to think back over, over that period of time. But I don't know what has necessarily kicked that off. But I will say that, you know, in the last two and a half, three decades that I've been doing this, I have never seen the thin barrier to violence that we're seeing today. I'd say you can look at the 60s and 70s where, you know, you had people, you know, they go out and shoot up schools, you know, from the clock tower, and, and they would do violence and they didn't have the conscience. Right. That, that barrier to violence just wasn't there for whatever reason. And I don't Know what happened, you know, necessarily to say, you know, this was the cause of it. But we kind of didn't have that. There was a. There was people. You know, there were school shootings and things like that, but they weren't the high numbers of violent activities. And so the really that, that barrier to violence we're seeing now is, is, is razor thin. And that's why, you know, we're seeing an increased cadence of people that it's like you would not think this person would be someone that would go out, get a rifle and shoot at the president, but they did, you know.
Host (possibly a podcaster or interviewer named Michael)
Yeah, I can't make sense of that either. I mean, I mean, it's partly tongue in cheek when I say crazy people do crazy things.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
But yeah, you can't really ignore the, the stats on it either. And, you know, the tinfoil outcry would be. Well, it's fluoride in the water. I'm not sure that it's not. I am not an expert on fluoride or teeth care other than brushing my teeth, but yeah, I, it's something that. I certainly hope the trend, it doesn't continue to increase. I would hope it would go the other direction. But, man, you look at the news on any given day right now and it would indicate that it maybe is accelerating as opposed to decelerating.
Caleb
Absolutely. Because you look at the number of people that have something to lose that, Whether it's polarized political figures, whether it's polarized, you know, workforce, whether it's. Whatever it is, like people's skin in the game is only increasing, you know, and, and you can, you can also point and say, you know, there's much more video games that are, you know, causing, causing people to pull the trigger. A lot more simulated, you know, you can go down that road. I don't know. I don't play video games, so I, I don't understand that. Yeah, but there's, there's absolutely bad people doing bad things. And you know, from what we see from a protective intelligence side of things, a lot more bad people are trying to do bad things, but thankfully are being stopped.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Michael, can you go back to the Utah, the Charlie Kirk event? I'm just curious. I mean, again, no intent whatsoever to Monday morning quarterback. It's always easy to look at this in the rear view mirror. If you could go back with a crystal ball knowing that something like that would have happened, what changes do you think that they could have made that would have been beneficial? We talking like getting a drone up and looking at Rooftops. Even though it seems, I'll be fascinated if they ever release a full investigation on this one. Because there are, it's like this is logical. Logical, really big gap in any evidence or logic. Maybe because it hasn't been released yet. Right. I'm try, I try to, if I'm going to wear a tinfoil hat, I try to keep it only like a beret, not a full suit.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
And then a little bit of logic, logic, large gaps. So maybe those things will fill themselves out. I'm not sure and I'm not even going to hypothesize. But, you know, it seemed as if from the spot that the person was, they may have been able to been seen. But like, what are you thinking about it that they could have done differently? You talking drones put somebody on the roofs. What are your thought?
Caleb
Well, I have the advantage of working in Silicon Valley for the last decade and a half, and one of the things that we leverage very effectively in our protective posture is technology. Yeah. So how can you not.
Host (possibly a podcaster or interviewer named Michael)
It's a force multiplier.
Caleb
Absolutely, absolutely. So, so testing and evaluating different forms of technology. You know, I don't want to go into exactly what should be used, but I will, you know, say that protective, protective agents everywhere have tools at their disposal to be able to use a combination of everything. You just, you just said there's no single tool that would have stopped this incident from happening if it went down exactly like we've, we've been told. Yeah, right. But use a combination of tools, combination of redundancy, combination of taking your advanced planning and combining that with your operations, then you reduce the avenues an attacker can get to you and you increase your ability to get your protecting off the ax. Yeah, right. We saw post incident the, the actions of the protective team were absolutely in line with what you would expect. They were right. They were moving, they were coordinated. You can tell that that team has trained. Right. And I think that, that for other teams out there, I think that, that, you know, we all have to take a look and say, all right, we need to train in more things. We have to be creative about how do we use technology with humans, with communication with the protectee, with understanding that if, if the AIC tells the protectee this is a no go, and the protectee says we're going to, you're stuck. Right. And I know of situations where that's happened in the past that it's, this worked out fine. And I know situations where that's happened in the past and it didn't work. Out. Fine.
Host (possibly a podcaster or interviewer named Michael)
How do you document that? Because I feel like there's a level of liability that passes hands when you say, we are able to protect you to this point, and the person says, did you get my last check? We're going at that. I mean, again, I'm not a lawyer. I got my juris doctorate by watching suits during the pandemic. But I would want to document that somewhere, somehow, because at that point the responsibility has got to pass to the person making the call. In the face of being told by professionals we shouldn't be doing this.
Caleb
It does. But, but keep in mind, you know, when you're talking about providing services for somebody, documentation is good for a lawsuit later on, and that does the protecting no good if, if they're, you know, deceased. Right. So, so documenting it, being able to communicate it is important for the well being of the protector. Right. For me as a protector to be able to tell the protectee, this is my recommendations. This is what we're seeing. This is what intel is telling us. This is what, what we need to do to keep you safe. Client says no. All right. You know, at that point I have to make a decision. Do I want to put my team in harm's way or, or do we do a full stop?
Host (possibly a podcaster or interviewer named Michael)
You know, have you ever heard of a situation where somebody refused to put their team.
Caleb
Oh, absolutely.
Host (possibly a podcaster or interviewer named Michael)
What did the protectee have to say about that?
Caleb
Blazing mad. Blazing mad. And everybody's fired. Absolutely.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
I mean, I don't think my personal thoughts on, and I only have access to the social media stuff. My personal thoughts is he was probably pretty close to dead by the time he hit the ground. I don't think if he had fallen off of that chair into a surgical suite that they would have been able to save him. So it's kind of a moot point. But I'm curious your thoughts as to how come they didn't have an ambulance staged.
Caleb
Most of the time having an ambulance staged is, is too expensive. Okay. For somebody of, of, you know, that.
Host (possibly a podcaster or interviewer named Michael)
Does college, you basically got to pay for their. I'm sure you shift.
Caleb
Absolutely. You're, you're paying $6,000 to have that bus on site.
Host (possibly a podcaster or interviewer named Michael)
You know, and this was the kickoff of his tour to like, like, I think in the high double digits, maybe like 50 of these in a row. Multiply that by six. That's 300 grand and bambooz right there.
Caleb
Yeah, no, absolutely. The other, the other thing is, is, you know, with the majority of my teams, we have, you know, higher level of care than is on most ambulances, if you have a paramedic, you know, bus, then, then that's great. They have the tools there. But you know, most, many of the teams that I've managed, you know, are EMT or above. You know, we have a lot of, you know, PJs and, and individuals with higher levels of care that are already there. And so we integrate that with our planning to have our own resources on site, especially for the ultra high net worth individuals, which makes this was, this.
Host (possibly a podcaster or interviewer named Michael)
Was a wound that was incompatible with life. Like I said, I don't think he, if he fell into. With the highest level of thoracic surgeon. I'm sorry, like in my limited experience. What are you about to hit? These guys are booking. I mean they, this is just. Yeah, they're going to put him in the Suburban.
Caleb
Yep. You see the movement, you see the coordination. You know, like there's not chaos. You look at, there's a.
Host (possibly a podcaster or interviewer named Michael)
Vehicles are staged, ready to go. Yep, yep.
Caleb
Yeah. The vehicles were also staged in that order from what they, you know, they said afterwards to prevent somebody from ramming from behind. Yeah. Which I think somewhat effective. I, you know, you could argue a different formation for that, but you know, again, that's Monday morning quarterbacking.
Host (possibly a podcaster or interviewer named Michael)
Again. Yeah. And that is absolutely not what I want to do. They did the best that they could and again, they were constrained. Again, they're not. I'm sure some of them could carry based off of former or current law enforcement creds, but there's only so much you can do.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
You know, HR 218 is a beautiful thing, but it only gets you so far.
Caleb
Yeah, yeah, no, absolutely. And they were moving. They were coordinated. You look at a lot of other Alps and you don't see that level of coordination. You don't see that level of consistent training. You don't see that level of dedication to the trade craft. Yeah.
Host (possibly a podcaster or interviewer named Michael)
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Caleb
I don't know in that case, most of the time with, with my protectives, it depends if they're celebrity or ultra net worth. If it's a, if it's a company event, then, then we'll, we'll pay anything that we can. Most of the time it's Odo off duty officers. Yeah, that, that will pull in the actual venues for like college campuses. Typically they'll allocate a of, of their officers, you know, towards it, depending on the crowd size, you know. But again, you're talking about reactive officers. You know, there's, there's, there's a different security posture when you're talking about proactive protection versus reactive law enforcement. The law enforcement officers are there to enforce the law. That is what they are focused on. They're, they're, they're there to document, to stop, you know, lock bad people up. They aren't there to proactively look for anyone who would be a nefarious actor. And, and that's why we have to really account for. Yeah, we have those local le resources, but we can't expect them to do something that's out of line with their, with their job. Right.
Host (possibly a podcaster or interviewer named Michael)
What do you think that event will change about a public venue like that? Open air. They were in the low ground. Not that they meant to be. It's just, I mean, that's where they put it. I had heard that he had had conversations about potentially wearing body armor in the future. It wouldn't have made a difference in this anyway. I mean, are you thinking they'll move stuff like this indoors? Do they put up ballistic shields in front of them? I mean, what do you think is going to be the landscape going forward? He's not the only person who does this for a living.
Caleb
No, no. And it's sad, you know, because this depending on how long, heaven forbid, it takes for the next one to happen.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
We see the security life cycle continue on. Right. And bad things happen. You know, I, we saw it in YouTube in, in 2018 when, when that hit, you know, the YouTube headquarters was shot up. We saw everybody in Silicon Valley take. And they wanted to have two guards on every building, two armed officers on every building. So they added all these resources. They're paying insane amounts of money to secure every building in Silicon Valley. Nothing happened for a while. The bean counter started doing their audits. They said, wow, we're spending way too much money. Let's cut, you know, nothing's happened for, for X amount of time. So Then they cut, and literally then it goes back down, you know, to lower levels, and then it doesn't. Doesn't go back up until the next cycle. Right. And the difference between, you know, kind of that era, 2017, 2018, and now is the cadence of attacks on principles has increased in the last 18 months, you know, really, since Butler, that. That is keeping it at the forefront. So you're not seeing budget cut. So. So depending on how long, you know, the teams are able to kind of illustrate their contribution to the overall success of the organization, then I think that there will continue to be funding in place for programs like this. But you look at your average political event outdoors, you know, that's moving indoors. That's. That's already happened.
Host (possibly a podcaster or interviewer named Michael)
I mean, it takes largely not the whole thread away for this type of what happened in Utah. I mean, yeah, you're taking a lot of angles off the table, which helps.
Caleb
Yep, yep. Yeah, yeah, you can control your elevation. You know, you can. You can have someone with the high ground in an indoor space that has, you know, a good visual of. Of the high ground. You can integrate tech with it. You're seeing a massive increase in magnetometers and, you know, crowd control and things like that at all these events. But again, how long does that remain sustainable becomes the question. Right, because. Because that's all based on perceived value. The perceived value of each protectee for what they're paying. And when they're spending, you know, four or five million dollars a year to have a team around them, they really have refined expectations of what they want, you know, that team to provide for them.
Host (possibly a podcaster or interviewer named Michael)
I feel bad for that team, man. You know, those guys were all working as hard as they possibly could.
Caleb
Did a lot of things right.
Host (possibly a podcaster or interviewer named Michael)
They did a lot of things right, but like you said, they have to get everything right every single time.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
The YouTube aftermath of this event, the number of people who. What a sniper, he shot him in the neck. And so I went through sniper school in 2000. I like to claim I'm the Seal sniper with the most confirmed misses, because I can just slap a trigger. Like. No, it's like just, you know, hold your breath until you gray out and then just really lurch with it. And I'm like, guys, I've never been taught to shoot somebody in the neck. Like, this is not Jason Bourne. He was either aiming at the head and jerked it or aiming probably center mass and got lucky. I hate to use that term.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
And then just the debriefs afterwards. And it was an inside job. From the security detail because the guy had sun in his eye. And they're like, that was the moment.
Caleb
I'm like, that was the signal.
Host (possibly a podcaster or interviewer named Michael)
Do we have to do. I mean.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
It's interesting. I've had some conversations with people and I think a lot of it stemmed from they didn't feel like they could do anything. And they felt in some way that involving themselves in that way meant something. And I'm nobody to tell somebody how to live their life. So that makes a little bit of sense. But it also created this environment of what I'll just call utter BS that muddied the water so much that I don't even know if it's possible if an investigation does come out. Let me clarify this. I'm not saying by any stretch I trust our government at all have an investigation. There's plenty of things that our government has done to erode just about every bit of faith and integrity that people have looking at them. So even if an investigation does come out, there is so much BS out there and so many people pointing at things and using the word truth. This is the truth. That is the truth. So now we can't agree upon the truth. So where are we? Even if it does come out, people will say, yeah, but you guys are the deep state.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
And maybe they are right. Depending on what your definition is. Or you're the global cabal.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
On every other Thursday and in your robes with chicken heads in your pockets or whatever it is. So it was so God was horrible to see. The worst thing about that for me is all three of my kids saw that on their social media. Not a single one of them was looking for it.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
So I had to have some very real conversations with my kids. I didn't think I was ever going to.
Caleb
Yeah, it was wild. Yeah. That's a heavy load for a kid. You know, I'm as heavy load for anybody.
Host (possibly a podcaster or interviewer named Michael)
Unavoidable. If you were on an electronic device that day.
Caleb
Absolutely everywhere.
Host (possibly a podcaster or interviewer named Michael)
I mean, I think I saw the first re. Somebody sent it to me directly under. We're talking single digit minutes before.
Caleb
Oh, absolutely.
Host (possibly a podcaster or interviewer named Michael)
My response was, why did you send me this?
Caleb
The same exact response. Why do I want to see this?
Host (possibly a podcaster or interviewer named Michael)
Yes.
Caleb
You know, like, man.
Host (possibly a podcaster or interviewer named Michael)
Seen enough of this in my life. I don't need to see that.
Caleb
Yep. Yeah, exactly. Exactly. I'm. I'm not part of the solution. So don't. Yeah. Bring the problem to me.
Host (possibly a podcaster or interviewer named Michael)
You know, how'd you get into this world?
Caleb
You know, I. As it. As it would happen as A teenager, I had this, this idea. I wanted to actually go into the teams, and I started doing underwater search and recovery diving, volunteering, just preparing, you know, I was 16 years old.
Host (possibly a podcaster or interviewer named Michael)
The team doesn't do a lot of that, by the way.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Really transitioned out of the water.
Caleb
Yeah, yeah, it would seem, it would seem.
Host (possibly a podcaster or interviewer named Michael)
God, you train so much in the water pre 9 11. And they're like, yeah, hang up the scuba tanks. We're going to two largely landlocked countries, get some. Which was honestly appreciated because the water is rough, but, yeah, you might have dodged a bullet on that one.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
No pun intended.
Caleb
It's. It's been wild to see, you know, the full circle, you know, because, you know, what I thought was, was the career I wanted to go led me to executive protection, literally 16 years. Fell in love with the concept or said, you know, carry gun, make money, travel the world, you know, and I had no idea what that meant.
Host (possibly a podcaster or interviewer named Michael)
How'd you get exposed to it?
Caleb
Literally doing, doing PT in a park for. For drive, dive school. Really? And there's three, three corporate agents that just happened to be doing PT at 6, 6am in the same park and then started talking about it. And I was like, wow, this sounds incredible. You know, and so I started pursuing it. I had no way of getting into the industry. You know, there's not a. Especially in the mid-90s, there wasn't a lot of, you know, Eastern Washington and Whitefish, Montana. So if.
Host (possibly a podcaster or interviewer named Michael)
Which by the way, it is wild that you're fifth generation white fish. Which for people who don't know, I record in Kalispell, Montana, which is 15 miles south of Whitefish.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
The fact that we are now reconnecting here, given what you do and where you live, is wild.
Caleb
Yeah, yeah. No, it's. It's insane. My grandma lives literally three minutes away from where we are right now. Like, it's amazing.
Host (possibly a podcaster or interviewer named Michael)
Yeah. I don't remember it being. I wasn't paying attention. I was very front side focused about entering the military. But. But even when I was in the military, I don't remember it even being talked about much. Except for in the movie the Bodyguard. I feel like. Much like the movie Navy seals with Charlie Sheen. That brought some attention.
Caleb
It did. It did. And still maintains the expectations of the vast majority of protectees. And that, my friend, is annoying.
Host (possibly a podcaster or interviewer named Michael)
Expect Kevin Dutton slash.
Caleb
Yep, yep.
Host (possibly a podcaster or interviewer named Michael)
Kevin Costner to show up.
Caleb
Yeah, yeah, no, exactly. What's fun is, is some of my friends work Whitney Houston during that. That period. Stop it. And so, like, literally, like like, my expectations of what, you know, the EP industry should be would be these guys that are working Whitney during that, that period of time, you know, as a, as a young protector, and they continue to be my friends to today. But, but yeah, it's, it's, it's. It's amazing how influential that was in shaping people's expectation of even the type of agents that they want, you know.
Host (possibly a podcaster or interviewer named Michael)
That's wild. You were exposed to it in a random encounter.
Caleb
Yeah, yeah. I mean, I, I grew up a very simple life, you know, no way of accessing anything. You know, EP started working security after I, you know, fell in love with the concept because I was like, you know, we've got to do something, you know, And I actually almost started working for Flathead County Sheriff's Office. My grandpa was lodge buddies with, with one of the guys and, and I went through the whole process and unfortunately I told them I wanted to get into EP so they wouldn't hire me because they're like, you're going to work here for five years and then you to work, go travel, you know, move away on us. And so they, they didn't hire me specifically because of that, but it ended up working out well because then the next year I moved to Hollywood and the rest is history, you know.
Host (possibly a podcaster or interviewer named Michael)
How does it start, though? I mean, I'm assuming you got to get your foot in the door somewhere and probably, if it's anything like the new guy cycle, I'm familiar with not doing the sexiest jobs.
Caleb
Oh, absolutely. So. So I went to ESI, which at the time there were two executive protection schools in the country, ESI in, in Aspen, Colorado at the time, and then EP East Coast.
Host (possibly a podcaster or interviewer named Michael)
How long are those schools?
Caleb
ESI was 30 days. So 30 days of distance education and then 30 days in person to where, you know, when you went. And basically you learn the fundamentals, you become familiar how to talk, how to walk, what is involved. You know, it's an awareness training is how I like to like to categorize it. The competence has to come later because that obviously takes, you know, a lot of time and a lot of refinement over the years. Yeah.
Host (possibly a podcaster or interviewer named Michael)
Okay, so you go to the court. Do you have a job with a company before you do that?
Caleb
No.
Host (possibly a podcaster or interviewer named Michael)
So you're. Oh, so you're self funding?
Caleb
Oh, absolutely. I spent, I spent selling plasma. Well, I started a landscaping business with my brother when I was 11. And so I ended up selling all the equipment from that, which paid the 10 grand for me to go to EP school.
Host (possibly a podcaster or interviewer named Michael)
Okay.
Caleb
I left EP school with 43 bucks to my name, drove to Hollywood and just started knocking on doors and who, who would, who would hire me? Literally started guarding parking lots, you know, is 12 bucks an hour. I think my first couple gigs, you know, were, and just worked my way up, continued to use all my, all my funding to pay for EP schools, shooting schools, you know, every, every kind of school I could do paid and paid my own way through. I think now, I think we have documented just under 500 grand in security specific training since I started. You know, that's specific to the, to, to what I do.
Host (possibly a podcaster or interviewer named Michael)
You know, I have no real familiarity with the ecosystem out there protecting high net worth people. But I have to assume there are categories or layers. Like with your A listers being up top and then guarding the parking lot, we'll call that maybe more towards the bottom. We won't call it the bottom.
Caleb
Well, you know, closer, a few more.
Host (possibly a podcaster or interviewer named Michael)
Rungs down the ladder. I'm sure there's everything in between. How long does it take to go from that parking lot job to getting into those, the, the A list category? I'm assuming that's the. If that's what you went to Hollywood for, that's what you're probably trying to do in the EP world.
Caleb
It was because that's all I knew. I didn't know there was any other categories outside of that, you know. And so it took me nine years, I most of those years for 29 different security agencies picking up odd jobs. You know, work the Academy Awards, work the Oscars. You know, most people don't realize most celebrities don't have full time agents working with them. Especially at the time they didn't. It's becoming more so now because you have more billionaire celebrities. But at the time, most of my protectees didn't have full time agents, especially beyond their residential details.
Host (possibly a podcaster or interviewer named Michael)
You just pick them up at the door, basically.
Caleb
Basically, yeah, yeah. You, you know, either ride right front or, or you know, meet them when they arrive at the Oscars. You, the assignment might be or you know, on the movie sets and then you meet them, you know, when they arrive and, and go from there. And so it took me nine years of grinding, you know, night shifts. I'd work 36 hours straight in Beverly Hills, drive back to Temecula where I was living at the time.
Host (possibly a podcaster or interviewer named Michael)
Beverly Hills. I'm very familiar with Temecula.
Caleb
Exactly.
Host (possibly a podcaster or interviewer named Michael)
All that eastern LA base for those. It is, yeah, not under the Hollywood sign.
Caleb
Yeah, yeah, yeah, exactly. And, and I would drive back and forth because I Couldn't afford, you know, to live anywhere closer, you know, and. And I just kept building the momentum, kept building my training, kept focusing on, you know, taking care of the people around me. I never said no to a job. That was a big thing is I. I never wanted to say no to a job because I knew that if I said no to a job that they would. Wouldn't call me the next time, you know, and so that's where working 36 hours straight. This is before overtime rules kicked in. Yeah, like, you know, it was just the hustle for nine years straight before I got my employee opportunity. Work for a private family office in New York and Philadelphia. And that was my first big chance at the rodeo.
Host (possibly a podcaster or interviewer named Michael)
I think a lot of people, and I probably fall into this category. I've now, I've been fortunate enough to rub elbows with some people that others would consider to be or I would consider to be on the A list tier. And I think it's really easy if you see them on TV a lot, to think that they are not normal people or that they don't have their weird quirks.
Caleb
Right, right.
Host (possibly a podcaster or interviewer named Michael)
And unfortunately, I think most people, if they spent a lot of time around people like that, they would probably be underwhelmed more than anything because they would realize, crap, this guy deals with BS just like I do every single day. Was it kind of like that when you finally got into that A list here? Did you just realize, like, oh, these are just people and whatever, they have a better bone structure or they can emote better in front of a camera, but they're still just people at the end of the day.
Caleb
It was underwhelming. It was absolutely underwhelming. Yeah, because you look at, you know, most of your 80s action here, heroes, you know, were far shorter than I had imagined. They were. Their biceps were far smaller than I had imagined.
Host (possibly a podcaster or interviewer named Michael)
They were about camera angles. Notice that's what I was focusing on before we started.
Caleb
Right. Let's get those right. You know, don't forget lighting. When I moved to Hollywood, I was 116, 160 pounds, you know, 6 foot, 160 pounds. I was not a large person. You know, I was in good shape, but I moved there and I was working an A list celebrity on the residential detail. And the celebrity sister came up to me was like, caleb, I like you, but you're too damn small. And I'm like, all right, I'm working on it. You know, do a quick trip to.
Host (possibly a podcaster or interviewer named Michael)
Tj, get some chicken breasts.
Caleb
I'm on It. I'm on it.
Host (possibly a podcaster or interviewer named Michael)
It.
Caleb
So I, I built, you know, for. For 10 years, got up to 285.
Host (possibly a podcaster or interviewer named Michael)
You know, that's almost on the other side.
Caleb
That. That was on the other side. Then I moved to Silicon Valley and. And we're in. In a major Silicon Valley facility that everybody knows with two people that everybody knows, and they look over me. And Caleb, I like you, but you're scaring the hell out of everybody. And I'm like, I can't win.
Host (possibly a podcaster or interviewer named Michael)
You know, 285 is definitely the other side of the pendulum for once.
Caleb
Unhealthy. Yeah, unhealthy. Took me 10 years to get there.
Host (possibly a podcaster or interviewer named Michael)
But that's about how long it take. You do 100y if you didn't have a myocardial infarction along the way.
Caleb
I can do the dash just fine. I just can't stop.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Yeah. I bet you have a collection of pretty awesome A list stories. What's the. Obviously, leave all names out of it, but what's just the wildest or weirdest thing that you saw when you were doing in that world? In Hollywood, specifically?
Caleb
Yeah, Hollywood. I was absolutely underwhelmed by my time there, you know, because you would watch a. A historic film on the couch of a historic A lister with their kids. Like, it was nothing. And it was just like, yeah, we're doing this, you know, and it's like, all right, that's surreal, you know, but. But it's just normal, right? You just, it's just part of your normal life. There's just another human being interacting with them. And, and then you just go on about your day, you know, or, or, you know, you're driving down the road and there's somebody broken down on the side of the road. And, you know, literally you just had a stalker banging on your window in, in Santa Monica, two weeks. Two. Two blocks before, and they see somebody broken down, they're like, oh, let's help them. I'm like, no, I don't want to help them. You know, let's help them. Let's help them. So you pull over and get out and. And like, they want to push this person down to the next exit. So, like, get out there and push this person down to the next exit to get them off the, off the highway. Like, they're cool people, you know, they're just eccentric. Right.
Host (possibly a podcaster or interviewer named Michael)
Do you find most of them to be kind?
Caleb
Depending on what time of day it is, I think, you know, or the setting they're in.
Host (possibly a podcaster or interviewer named Michael)
I've seen some very interesting Machiavellian shifts from the private to the public Persona. And I have never lived under that level of a microscope or scrutiny or. I. I actually. I think I heard Ben Affleck say it once. He's like, listen, take the money, leave the fame.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
You know.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And if you think about that, it's like, you know, that's probably the move, actually. I'd rather have money and be a gray man than have money and not be able to go. Like, I heard Troy Aikman, as an example, used to have to go clothing shopping in the middle of the night. They, you know, he can't have a normal. When he was the quarterback for the Cowboys, he couldn't have a normal life experience because he was just going to get mobbed.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
That's got to wear a little bit thin, too. So I kind of can get, I guess, a little bit of the Machiavellian where they're in public and they're doing their thing, and then they get home and they're like, I hate everybody. I hate humanity. Leave me alone.
Caleb
Yeah, yeah. Well, and also, Hollywood specifically, you know, thrives on substances. Right. And those substances introduce different challenges, depending on what time of day it is, depending on what groups you're around, depending on what, you know, venue you're in and all that. And so trying to, you know, stay awake for three days straight when. When you, you know, you have. You going on with zero breaks, zero backup, you know, for me, is a matter of slamming Red Bulls until, you know, it's unhealthy for them. You know, it was titrating the solution based on the need, you know. Yeah. And for me, that was a little bit, you know, daunting because I'm sitting here thinking, all right, at what point am I going to have to Narcan? At what point am I going to have to render care?
Host (possibly a podcaster or interviewer named Michael)
I mean, obviously, they're paying you to be there as part of your security. Are you just a fly on the floor wall hoping for the best?
Caleb
Oh, absolutely. And hoping to not be harassed by.
Host (possibly a podcaster or interviewer named Michael)
The Jekyll and Hyde that's getting ready to happen. Depending on what it is they are injecting or snorting or swallowing.
Caleb
Yeah, yeah, yeah. You know, and it's like, you know, I've never been law enforcement, Right. So I'm. I'm a nobody from nowhere. So I. I don't judge anybody for anything that they do or how they do it. Right. I'm just looking out for people's safety. Right. And so when. When you're looking out for individuals who are living an unhealthy lifestyle. While I had to come to a point to where I had to decide, all right, what level is it healthy for me to be here? Because, you know, these constant transitions, these constant ups and downs and, you know, flailing and umbrellas and, you know, everything under the sun, it's like, do you really want this to be part of your world? You know? And that was, thankfully, where I found a lot more stability in the Silicon Valley and the family office founders, and then, of course, corporate.
Host (possibly a podcaster or interviewer named Michael)
Yeah, I was going to ask you about that. I mean, I feel like in Silicon Valley there, in comparison to Hollywood, there's probably a massive wealth difference, but also a massive fame difference. There's people in Silicon Valley. I was born and raised in Santa Cruz, so just over Highway 17, Silicon Valley. And I don't know any of those people, but you'd see the houses they built along the coast between Santa Cruz and Monterey.
Caleb
Yep, yep.
Host (possibly a podcaster or interviewer named Michael)
Like, did somebody just buy 3 oceanfront lots to destroy all the house that was on there and make a really awesome house, but also is kind of destroying history? Like.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
That just happened.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
I don't think that's cheap, but you would never know who the person is. So an immense amount of wealth, but probably a difference going back to that. Take the money but not the fame.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Did you find a difference in those people who perhaps had way more wealth but were not as well known?
Caleb
Oh, 100%. Operationally, it created massive challenges for the industry as a whole, because when I moved to Silicon Valley, we were used to traditional protection methods that you would see with somebody that had, you know, fame, fortune, you know, things like that. But then all of a sudden, you have these people who are worth, you know, 10, $20 billion, who nobody knows who they were other than the fact that they have six knuckle draggers walking around with them.
Host (possibly a podcaster or interviewer named Michael)
Yeah. All of a sudden they have a real tight diamond of guys with dark sunglasses on and stuff out of their.
Caleb
Ears, like, yeah, yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
It could be too much. You can actually draw more attention to yourself than you want. For sure.
Caleb
100. And. And that actually was a. Was a massive transition in my career. You know, up, I had been working my way into management. I've been working my way to become a better professional. But I always had imposter syndrome. Right. Like, I'd wanted to be a seal. I had wanted to be this and that. And for me, you know, I never felt like I had quite made it because all these people around me are incredible human beings. You have, you know, Dev, you have, you know, cag, you have all these just incredible human beings that are working in Silicon Valley, you know, alongside me. And I'm like, who am I? I'm a nobody from Spokane. I quit school at 13, you know, like I should not even be here. And then when it came time when the client said, I like the team, I just don't want a bunch of knuckle draggers everybody sees around me. And Caleb, who had no background, Caleb, who had no preconceived notions of how it should be done, no biases based on, on previous, you know, occupations, Caleb said, I'm going to take and find a solution for this. So I worked with my chief security officer and I proposed creating, you know, 100% covert protection teams where we took and we combined the different styles of protection, we combined medical, we combined intel, we combined technology, we combined counter surveillance, surveillance detection, you know, and then, then they took all the best tactics we could from the clandestine world to be able to create a sustainable style of protection. That had never been done in the private sector at scale before. You know, not full time, full time teams working day in and day out out. And that for me was certainly the biggest challenge of my career because the complexities, you know, are massive. But it was also a, you know, really watershed moment for me because it took and, and my imposter syndrome was no longer there because the innovation that was flowing was based on the context from my, my previous, you know, decades in the industry, working in the field, working night shifts, you know, figuring out what works and doesn't. But then I was able to fuse that together with some of the best human beings who had operated, you know, all around the world, who, who then became part of my teams and then created a new trend in the protection industry.
Host (possibly a podcaster or interviewer named Michael)
So you created that system for yourself or while working for somebody else.
Caleb
So I was working directly for a private family office. Okay, So I was full time employee of the private family office. So I created it directly for the family that, that we were protecting and.
Host (possibly a podcaster or interviewer named Michael)
Then turned it into a business model essentially eventually.
Caleb
No, no, because after that I, I started the program after I left there, I started the program for PayPal, then went on to another family office and then, and then in Salesforce. So I, I, it's not the only style of protection I've done, but it's had ripple effects in the industry. Tons of, of companies took what we started and then have carried it. And then obviously today, you know, my company integrates it for sure. But I didn't start my company until. Until 2020, you know, so it's relatively recent. Yeah, no, absolutely.
Host (possibly a podcaster or interviewer named Michael)
What was the impetus behind that? Going working for other people to just saying, screw it. Yeah, you all work for me.
Caleb
Well, I never wanted to start my own company. You know, I owned a lawn service when I was 11 and my dad was an entrepreneur and tried so many different things that I had this kind of negative, negative vibe in my head about it. And I wanted to be a, you know, corporate executive, you know, and so that's the route that I pursued literally my entire life. Plan from. From, you know, know, this time I was 30 on was to pursue my education based on my goal to be a chief security officer of a Fortune 50 company by the time I was 50. So I wanted to give myself 20 years to be able to take and prepare. And so that. That's why I followed the educational path. I went through Stanford and Johns Hopkins and all those to be able to prepare, to go in that direction. Well, I ended up.
Host (possibly a podcaster or interviewer named Michael)
What kind of courses were you taking at those universities? I'm curious what they.
Caleb
Yeah, so.
Host (possibly a podcaster or interviewer named Michael)
Well, actually, so a chief security officer, I'm assuming their role is largely in the ties vital. Are they responsible for physical security of the infrastructure as well as. And making sure that key personnel have private security as well. Basically anything that touches the security world. That's what a CSO does.
Caleb
Yep, yep. Some companies, especially Fortune 50 companies, will separate out. So you have your CISO, your technology side of things.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
And then, then physical security, your intelligence teams, your executive protection, you know, all your site work, you know, alarms, things like that will typically follow, follow under the chief security office officer.
Host (possibly a podcaster or interviewer named Michael)
So what were you taking at Stanford and John Hopkins? I don't know a lot about college, but I recognize those two names.
Caleb
Yeah. Yeah. So Stanford has their international security graduate program, which is incredible program. Just basically, you know, from an engineering perspective, looking at risk as it relates to the global market. You know, so we. We would take and do war games. We would take and look at security as it affected different portions of the world. And then if. If action was taking, seeing what the secondary and tertia responses were to that they didn't have a full master's program at Stanford. And so I applied to Johns Hopkins because, again, I quit school at 13, so because I hated. Hated education, like, I hated school. By the time I was 30, my client had inspired me to go to school. And so I was like, all right, I'm gonna try the best schools. And then if I don't get accepted, then I'll move on to the second best, you know. And thankfully, both schools accepted me in. Hopkins has a full. Full, you know, master's program in global security studies and intelligence and fascinating program. About 92% of the cohort is from the intelligence community.
Host (possibly a podcaster or interviewer named Michael)
I was going to ask you, who teaches these courses? Like, what's the pedigree of the people who are up there at the lectern with, I would imagine, like a monocle on?
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
Jacket with one of those watches.
Caleb
You're not wrong. You're not wrong. Yeah. It's primarily intelligence community. Some of the psych, psychological side is other people. But yeah, no, the campus is in D.C. it's. It's very much intended for the intelligence community. But it was amazing for me because I wrote my master's thesis on the modernization of executive protection. What is the modern art of ep? Because everybody else is looking at from, you know, government's perspective of security in the world and, you know, what are the effects of water on, you know, security and all those things. And I was looking at it from an executive protection standpoint of how do we protect protectees who are going into these emerging markets, who are. Who are going into these markets where they have risk. How can we look ahead and use our protective intel assets to be able to plot a path for us, for that company's growth so we can keep them safe at each stage rather than trying to come up with it on the fly?
Host (possibly a podcaster or interviewer named Michael)
Do you have a class that stood out during that time in education that was your favorite?
Caleb
Honestly? My favorite was. Was at Stanford, and it was where. Where Dr. Perry, the former Secretary F under Clinton, was talking about the history of nuclear proliferation.
Host (possibly a podcaster or interviewer named Michael)
He taught a whole class on that.
Caleb
Yeah, yeah, it was incredible. Had had guest speakers from Russia who were his counterparts.
Host (possibly a podcaster or interviewer named Michael)
Just a course.
Caleb
Fascinating. We have brown bag lunches, and nobody'd show up at these lunches because they were optional, you know, so it'd be like three of us, you know, four of us sitting here, you know, eating and just asking questions. And by far my. My biggest, you know, treasured memory from that entire period.
Host (possibly a podcaster or interviewer named Michael)
What a fascinating course. It is wild how nobody would show up to the extracurricular and just sit there.
Caleb
They didn't have to but, like, pick.
Host (possibly a podcaster or interviewer named Michael)
The brains of a former sec. Def I. Come on.
Caleb
Yeah. And he's so open with information, just. Just truly wanting to share, you know, you can see his passions, you know, but also it's fun for him to sit. Sit back with his buddies and Talk about, you know. Oh, yeah. Remember when, you know, and you're talking, you know, the end of the Cold War, like, you know, you're talking about some serious buttons.
Host (possibly a podcaster or interviewer named Michael)
I love how they brought in or were able to link up the US versus whatever axis they were going against that. To me, that's fascinating.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
To come full circle for them to be in an educational environment, talking back and forth.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Each lens and what they saw.
Caleb
Oh, absolutely.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Go to the. Go to the brown bag lunch.
Caleb
Well, and the thing, the thing that stood out to me was these are just people. You know, we look at it in history, we look at these, you know, mutually assured destruction. And like, every, Everything that you see in the history books, like, it's people against people. And, and, you know, like, wow, let's. Let's quit fighting for Christmas. All right. You know, that's humans, right? Like, like, that's really what it did for me. You know, my, My, my grandpa, you know, worked for the railroad here in Montana. Pow. For. For three years. You know, and like the human factor during that era, in my mind, for my perception, hearing his stories, it wasn't humans, you know, it was more like a ro. To fear, you know, and hearing Dr. Perry and his counterparts talking about it. It was humans talking to humans. And, you know, they both had their side, they both had their priorities, they both had their allegiance, but both of them, you know, absolutely, at the end of the day, were humans and just wanted to go have a beer with the other one.
Host (possibly a podcaster or interviewer named Michael)
It's wild. What, what was it that got you over the hurdle of deciding to start your own business? Business?
Caleb
So I was a salesforce and had an incredible security. Yeah, yeah. I was director of protective services for, For Salesforce Global Safety insecurity over there. And amazing team. You know, we had, we had a lot of good things happening. It was in the middle of the. The Silicon Valley drawdown about four years ago to where a lot of, A lot of politics was going on. And I, I was surfed right through the politics and got paid, picked up, got hit by somebody else's politics, basically, is the easiest way to say it. And so I found myself unexpectedly, you know, like my, My boss didn't want to let me go, but, you know, it was the end of the crunch and it really boiled down to what do I want to do next? You know, I'd experienced corporate. I built, you know, two, two corporate programs from scratch. I. I'd built, you know, six programs in the industry. And I was like, my biggest frustration as the end User. You know, this is the director of security for, you know, whatever client or corporation has been my vendors. And so I was talking with Jerry Jacobs, one of my buddies who, you know, has had ran the California governor's details for quite a few governors. And we started talking about, well, hey, there's a, there's a better way to do it. You know, why vendors?
Host (possibly a podcaster or interviewer named Michael)
Do you mean the people who. Providing the security personnel?
Caleb
Yeah, security company. Okay, the security company. You know, because like every detail, I would start, you would hire X amount of agents and you needed a security company for them to work for. And then I, I would pay as a family officer corporation. I would pay the, the security company a fee and they would pay the agents. Right. And so I was like, well, why don't we just create a better security company that isn't focused on shareholders? Because the majority of, of security companies right now are owned by venture capitalists and shareholders who they have to make their profits in order to be able to sustain the things. Why don't we take and create a new way of doing it to where we say our employees are our shareholders and we're going to take and we're going to build everything around developing them, so we're going to develop the next generation of practitioners. And that was the foundation for what we started through accountability, through training, through coaching, that's mandatory for every single agent on the team to become better week by week, month, month by month. But it's not a line item that the client has to pay for. That's what white glove pays for, for. And so that's, you know, we call it the white glove difference. But basically we hold people accountable on our teams and then we give them profit sharing based on their ability to contribute to the protection efforts of the client.
Host (possibly a podcaster or interviewer named Michael)
Was it easier or harder to build and scale your company than you thought it would be?
Caleb
You know, I didn't really have expectations. What's been harder for me is to understand human nature. Nature. Because.
Host (possibly a podcaster or interviewer named Michael)
Let me know when you got that.
Caleb
Oh, my goodness. Like I, I was used to for the last couple decades being a security director for XYZ Corporation. Everybody knew who I was. They associated me with the protectees and, you know, corporations and all that. It's like, oh, yeah, that's the, you know, PayPal guy or Salesforce guy or whatever. And then, and then I started my security company and all of a sudden they weren't taking my calls. You know, all of a sudden I'd start getting ignored and it was like, oh, that's kind of Weird. Like I've been having lunch once a month with them for the last 15 years, you know, so it was, it was a different phase in life, you know, just kind of understanding that I had crossed over into the, the vendor side, you know, and it was at that point I said, I'm never going to try to sell something. I'm going to share the vision, you know, I'm going to, I'm going to share solutions, but I'm never going to try to sell something because that's not me. You know, nobody needs to sell what I have to pedal. I'm pedaling the same thing that I've pedaled for the protectees, you know, for the last couple of decades. And we know it works, you know, because of the top teams in the, in the world have been created based on these principles, you know, because, because I had the privilege of being there working alongside some incredible human beings. So that was really the biggest surprise for me.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Finding the right people, I feel like, is a challenge. This episode is brought to you by Brunt. How many people out there need a good set of boots? Maybe not, not professionally, even though there's a huge market out there for that. But personally, if you live in a place like I do, this type of footwear is, I'm not going to say mandatory, but it's helpful for about six months out of the year. And most people think that you have to choose between like this crazy durability and functionality and comfort. And that is probably what I like the most about these particular set of boots, at least the ones that I have. They sent me a set of the Omen boots, which is the first slip on like Chelsea type boot that I've ever had. Of course I'm not wearing them today, otherwise I'd be able to show it to the camera. But I ran out of the house this morning when it was still dark, getting my son to work. I thought there was gonna be a break in period because that was my history with other pairs of boots that I have ordered and there wasn't. Right out of the box, true to size, super comfortable. And they've been my kick around town boot for the past three months since we've transitioned into winter. Maybe you've already got a good set of boots, you're not in the market for it. That's okay. Brunt is a lot more than just just work boots. They offer a full range of high performance gear built for tough jobs. From heavy duty work pants to weather resistant jackets. Brunt designs durable, reliable workwear to keep you protective and productive in any condition. If this sounds like something that could benefit your life. If a Brunt product, whether it be outerwear or boot wear, is something that you're in the market for, my suggestion would be head over to bruntworkwear.com and if you use the code cleared hot, you're going to get $10 off your first order. That is brunt work. Workwear.com using the code cleared hot, you're going to get 10 bucks off. Surf through the site, check out some stuff. What I will say about the boots is they are comfortable and true to size right out of the box. So you don't have to worry about a crazy break in period, which has been my experience with most other boots that I have had. Bruntworkwear.com using the code cleared hot, back to the show. Other than human nature, what kind of. I don't want to say selection course because that not it. I think you know what I'm getting at though. How do you know you have the right person?
Caleb
Yeah, yeah. The majority of the people that we hire have been working full time in the industry for at least five years.
Host (possibly a podcaster or interviewer named Michael)
Okay. So slightly vetted at least by somebody else.
Caleb
Absolutely, absolutely. One of the, one of, I spent about 30% of my time volunteering. So, you know, the world's largest security organization, ASIS, that's 35,000 members. I'm the, the chair of the executive protection community and then the largest executive protection specific organization. I'm the treasurer on the, and on the board of director directors, ipsb, those organizations. I spend a ton of time volunteering. What that does for me is it allows me to get to know more people in the industry. It really allows me to know who's working where, how they're doing and watch people's trajectory. And so what has been incredibly gratifying for me since I started White Glove has been seeing the people that we've pulled in, especially our management roles. Them, me having watched them for the last 10, 15 years, them come in and start thriving in their roles where they had been, you know, previously, either stagnant or uninspired. We'll say, you know, so, so really my volunteering is, is I would say a secret weapon because it allows me to get to know people outside of the context of a job interview.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
And have that extended interaction watching them, staying in contact with them, you know, from a networking perspective, certainly. But you know, just to see if they have the same vision, the same culture, the same drive, you know, day in and day out. Out as they do when they're applying for the position that they really want.
Host (possibly a podcaster or interviewer named Michael)
How's it been scaling your company?
Caleb
Incredible. So grateful. We spent the first 14 months with zero profit and.
Host (possibly a podcaster or interviewer named Michael)
Sounds fun.
Caleb
I'm familiar. We were very strategic about what we wanted to focus on because most security companies go out there and they want to do everything for everybody, which is a great way to make money, but there's nothing different about that. And so we wanted to bring a paradigm shift. And so with White Glove we only focus on embedded protection, full time agents, full time protectees. Because having full time agents is the only way that I can truly develop the next generation of practitioners. We put everybody through a three year training plan, right?
Host (possibly a podcaster or interviewer named Michael)
Three years.
Caleb
Three years. Because if we're investing three years into them, we're putting a bet that their culture, their drive, their alignment and their skills that we're helping them develop will be a long term investment in, then they will eventually return on White Glove, you know.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
And so that structured plan, again, that training is also tied to the profit sharing that, that each agent is eligible for after a year with the company. And so we're not only paying them to go train, but we're rewarding them on their ability to learn. One of the things that I'm, I'm sure you've seen throughout your career, but people either grow on the vine or they die on the vine for sure. Right. Human nature is human nature. And, and we typically in Silicon Valley see people last maybe three years, statistically speaking, three years in a position and then they move on. Right. We did a little bit better on my teams. You know, we got five, five and a half years. But really identifying what is it that keeps people inspired? You know, it's not executive protection specific, but people in general, human beings need to be inspired in order for them to grow and develop and continue as a professional. And so we said we want to do something different. And so we created what we call the Executive Protection Excellence Cycle. It's, it's, it's our way of saying we're going to take, we're going to train, we're going to coach, we're going to develop, we're going to put it into a structured process to where every single quarter, from 0 to 100%, every single employee knows this is how I did, this is how I stacked up this quarter. And then based on that score of 0 to 100%, then that agent gets, gets compensation based on how much money the company's made during that quarter. So it's our Kind of carrot and our stick. Right. Because if somebody gets 23% percent eligibility, that might be good for them. But we're also going to highlight. All right, this is where you can improve in. Our goal is to help you get to 100%. That's our way of helping people grow. Because as you continue your, your voyage in life. Right. What is success?
Host (possibly a podcaster or interviewer named Michael)
Depends on who you're talking to.
Caleb
Exactly. Success for me has changed at different iterations throughout my life. And so, and so we try to say, all right, how can we take and capture, Capture success, but on a sliding scale as it develops. My clients, you know, through the years have given me incredibly generous bonuses, you know, annual bonuses, and I'm ashamed to admit it, but I would go out and I would spend that bonus and I would think to myself, maybe three months later, when's the next one coming? You know, you'd forget about it.
Host (possibly a podcaster or interviewer named Michael)
Well, at the end of the year, traditionally.
Caleb
But realistically, basically, they just gave me what used to be a full year salary for me as a thank you. And not even within a couple months. I'm sitting here thinking, oh, when can, when can I get the next tractor? When can I get the next, you know, whatever, you know.
Host (possibly a podcaster or interviewer named Michael)
Wild how your Optica money shifts over time.
Caleb
Exactly, exactly. And so that's why I said we want to do this in the three month cycle, because you get it, you get inspired. All right, this is, this is where I'm, where I'm at. This is my, you know, kind of bump. Yeah. But also you have your marching orders from there. You, you know that. All right, in the next quarter, if I want to get a higher level of compensation, then I can work in these areas. Maybe it's getting your emt, maybe it's increasing your proficiency with, you know, firearms, working on your soft skills, whatever it might be. We have the three year training plan. So it's like an academy to where people can go through and become a better version of themselves, but we're compensating them to do it. But if they don't do it, then we're also identifying if somebody's not growing on the vine. And that's our way of finding, figuring out early if somebody turns into a bad apple.
Host (possibly a podcaster or interviewer named Michael)
It's good to have that objective metric, because in the world that we live in, without that and this subjectivity, easy way to say it is we live in a very litigious world.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
Yeah. You better have your ducks in a row when you're getting ready.
Caleb
Especially Silicon Valley.
Host (possibly a podcaster or interviewer named Michael)
Oh, man, I can't even fathom there's. There's just.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
For people who've never been over there, I haven't spent an immense amount of time. But again, growing up that close before the dot com boom and then just seeing what was happening, it was a little wild.
Caleb
Yeah. Yeah.
Host (possibly a podcaster or interviewer named Michael)
You know, most people will never. Probably a combination of two things. One will never probably get to a place in their life where they feel like they need EP of any kind. Or two, probably wouldn't be able to afford it. It's not cheap. I don't know the exact cost of this stuff, but I mean you can. It's expensive.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
For what you're paying for, especially what you're talking about full time agents, emphasis on the S at the end of that. So not singular but most multiple. Unless you want to burn somebody down to their bones.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
What. So for the vast majority of people though, one of the things that I. And I don't live in this world professionally, and I'm not saying it's the phone's fault, but one of my favorite. Saw it again recently. It's an artist who takes pictures and they photoshop the phones out of people's hands and so everybody's posture is just down. Situational awareness is low.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And I think a lot of people don't even recognize the risk that they are sometimes inadvertently exposing themselves to where and for me, I like practical things that can have an impact for somebody who works in this world. And again, the challenges for an everyday person. Yes.
Caleb
My God.
Host (possibly a podcaster or interviewer named Michael)
Click on a couple. Oh, do the wedding one, Michael. Or yeah, the bed one's a great too.
Caleb
Yeah, yeah. So true.
Host (possibly a podcaster or interviewer named Michael)
It's so true. And once you see it like this, like that's just a picture of a hand. Once you start seeing these though, it is so ridiculous from an outside perspective to look at that. And yeah, there you go. That's just getting married. No big deal. Y And it looks so creepy without the phone, huh?
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Distractoring. That's probably in motion too. Yes. Sharing family time together. What is the. What do we got here? Eric? Pickersgill.com removed for people who want. Go back to the main screen, Michael. Just scroll the other direction. Obviously. My goodness. Scrolling to the top of the page. Thank you, Michael.
Caleb
Speaking of finding good help.
Host (possibly a podcaster or interviewer named Michael)
Yeah, man. Ah, there's less than I. Less than I. I thought. Situational awareness to me is the beginning of. And I don't. Before I say anything else, I'm not. I don't think people need to walk around pretending like they're Conducting espionage or be tuned up to a 10 all the time either, because that will actually fry you to the bone as well.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
But being ignorant to the world that is around us and the threats that are around us is all. Well, it's ignorant, irresponsible, Perhaps we'll use another I word. What, what do you, you. Where would you start? We'll just call it your everyday mom and pop. Joe and Jane, what is your recommendation to people to actually increase their own security?
Caleb
Don't overcomplicate it, but be aware of it. You look at the majority of threats that people are actually facing today, and I would say probably in, in the next 10 years from the average person that doesn't live in a high crime area. Area is actually digital, so.
Host (possibly a podcaster or interviewer named Michael)
Oh, well, let me tell you about my dad. How much time we have on that SIM card, Michael, Because I understand now, my dad turned 79 last week. Oh, I understand why the digital world is so dangerous for them because I am not joking. I could fill up half of that 2 terabyte SSD drive with this just happened. And this just, just happened from putting credit card information online, which is a different type of threat. Right. Which people say that's not really physical. Well, it becomes physical when you no longer can pay for your mortgage or get food or put gas in your car. That's a real physical complication. It is sophisticated and his generation is probably the most susceptible. Mine's right around the corner though too.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
So I'm talking about myself in a little bit. Yeah, yeah, man, it's wild west out there.
Caleb
Yeah, yeah. And the amount of data that each product owner has on each user is mind boggling. You know, I won't go into the numbers, but, but you know, every one of the Facebook account has literally hundreds of three ring binders worth of data about each user. And the average person that thinks, oh, it's kind of funny that I was talking about blenders today for the first time in 10 years and all of a sudden that popped up on my feed in Instagram and Google and everywhere else.
Host (possibly a podcaster or interviewer named Michael)
Probably just random.
Caleb
Probably just random. Right. But the secondary consequences of that that we don't typically think about is that data goes somewhere and that data being somewhere is somewhere that is open to being compromised. And that data that, that is now 24 hours a day. Everything we're talking about, everything we're doing, that data now is being held somewhere where somebody wants to get it. And so they're no longer actively pursuing your dad. They're actively pursuing the benign Data don't even know it's necessarily him. They get lucky, they get into a crack in a door, through an emergency exit of the data center and get that data, and then all of a sudden that is. That is compromised. Or more sophisticated. More sophisticated ways of going about it. Either way, that danger, you know, is all out there. And that's something we're not really talking about now on the physical side of things, I like to simplify that as well. Right. I've had the benefit of attending lots of tradecraft training that isn't publicly available and, you know, spent six months in, you know, behavioral science training in understanding micro expressions and ticks and how the human nature works.
Host (possibly a podcaster or interviewer named Michael)
Where did you that course?
Caleb
Through instructors that we specifically brought in through our training. It's not an open market course.
Host (possibly a podcaster or interviewer named Michael)
Are they basically just telling you how to observe the small, subtle things in people?
Caleb
Basically? It's not that. It's not that simple, but yes, absolutely. Every. Everything from the shape of a person's head, right? Oh, absolutely. Like a lot of snipers go through the training, you look at the shape of a person's head, shape of a person's eyes, shape of their jaw, shape of their ears, all of those things. And then understanding how to correlate micro expressions with the progressions, with the patterns that they have when you're interacting with them, understanding what their natural, you know, reaction is, whether it's top right, top left, you know, for their eyes, whatever it is, each of those things is as a data point that you can take and you can form your general impression based on all of those. What I've done is I've taken and said, all right, the average human being isn't going to go through behavioral analysis training or any of that.
Host (possibly a podcaster or interviewer named Michael)
That.
Caleb
But they do have something called intuition. Right. And my wife is incredibly good at this. She was a flight attendant, and when there was a creeper on the plane.
Host (possibly a podcaster or interviewer named Michael)
Talk about snap judgment.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
You don't think you're getting snap Judge, if you come onto the plane and take a right, the second they can see you, it's like, who is this guy gonna be? Or gal.
Caleb
Yeah, no, exactly, exactly. And I'll never forget the day that, you know, she had a passenger on her plane that tried to take one of those, you know, disposable cameras and snap a picture up her skirt, and she grabbed that camera out of his hand before he was able. And it was based on her ability to see that he had, you know, bad intent. Right. She didn't have any special training. She Just, you know, understood that there was somebody with bad intent. Thankfully, you know, he got arrested and never got a picture, and, you know, it all worked out. But that same level of. Of understanding is something that we can all put into play. Doesn't matter if it's a secretary. Doesn't matter if it's cp. CEO. Right. You walk into a bar, there's baseline in that bar. Right. Just like with a polygraph. Right. And you got to get your baseline right. So you look around that bar. That's thumbs up. Right. People sitting there, people throwing darts, people, you know, playing slots. Whatever it is, that's your baseline. That's. That's thumbs up in my world. Then if you look over in the corner and there's somebody that. There's something a little different about them, it might be just who they are. Might be something a little off.
Host (possibly a podcaster or interviewer named Michael)
Show your face, Michael. You look over, you look over, you look over. You're like, who cut this guy's hair? Why does he have a half beard but a full stash? You're like, we have to go. Because clearly on America's Most Wanted Top.
Caleb
10, that's where you recognize. We call that a thumb sideways. So him.
Host (possibly a podcaster or interviewer named Michael)
I have three quarters.
Caleb
Yeah. You're almost. Almost dipping. Almost dipping. Like somebody that raises the index of suspicion.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
Just because something's off. Right. It could be the way they look. It could be. You know, it could be something. Could be nothing.
Host (possibly a podcaster or interviewer named Michael)
Wild in this era because a lot of a big message not pushed by everybody is you have to accept everybody for who they are. Their expression.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
Is their identity. So it's almost because I agree with what you're saying, and I tell my kids this. If something doesn't feel right, you don't have to ring, like a five alarm bell.
Caleb
No.
Host (possibly a podcaster or interviewer named Michael)
But also, don't push that aside. It's a data point, like.
Caleb
Yes, exactly.
Host (possibly a podcaster or interviewer named Michael)
And you'll hear people.
Caleb
Well, you're.
Host (possibly a podcaster or interviewer named Michael)
You're judging that person. Yes, to a degree. Agree. Are you. Are you profiling them?
Caleb
Like, I don't.
Host (possibly a podcaster or interviewer named Michael)
I mean, like, we don't have to get crazy with these magic words that are always associated with negativity.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
I'm paying attention. What I saw makes me feel a certain way. Does that mean that I'm right? No.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Does that mean that I should ignore how I feel? No. Let's find a middle ground.
Caleb
Yeah, yeah. Exactly like you said.
Host (possibly a podcaster or interviewer named Michael)
It's like we're no longer at the thumbs up, the dials coming a little bit the other direction.
Caleb
Yeah. Yeah. And the difference between thumbs up and thumbs sideways could, could just be everybody else in the room is wearing a T shirt and they're wearing, wearing a coat. Right. So you're not saying that this person. Yeah, yeah. Or just the fact that they're wearing the coat, you know, because this person isn't. There's nothing necessarily wrong with them. It's just we have to give a little more attention and let our index of suspicion raise a little bit. So there's thumb sideways and, and people can go from thumb sideways. You look at them, it's like, oh, yeah, well they're thumb sideways because of, you know, whatever qualifying factor. And then, then they can go back to thumbs up or it's like, I'm going to pay a little extra attention to this individual. And then halfway through the night, you know, you see somebody that has something egregious, that something that, you know, a gun or, or whatever it might be, then that's thumbs down. Right? That means create time and distance between you and whatever the thumbs down is. Right. So we don't have to have this int. Incredibly complex progression to be able to say, how do we apply, you know, clandestine level behavioral analysis to everyday life. We can say, is this, is this environment thumbs up, is this thumb sideways or is it a thumbs down? Because if you take and you're able to make that transition as a regular civilian, as a regular secretary or CEO and just have that awareness to say, all right, that thumbs sideways went to thumbs down, I'm going to go. That's the difference. Creating time and distance is often the distance difference in these bad situations between somebody being close to an event and being part of, of an event.
Host (possibly a podcaster or interviewer named Michael)
God, that time and distance is so important. And I don't think it's talked about my. I'll tell a story my daughter won't.
Caleb
Appreciate, but it's okay. She doesn't listen.
Host (possibly a podcaster or interviewer named Michael)
But this goes into people maybe absentmindedly, drastically involving themselves in something. They can get risky, risky at a very non linear rate where everything is fine. But, and this is what I tell people, everything is fine until it's not. If you can really flatten that curve between everything being fine until everything not being fine. Yeah, you have, you have time and distance, right? It's when you smash everything being fine with everything not being fine right up on top of it. It's. What are you going to do? So, Michael, what, what words would you use to describe my daughter's level of sass? Oh, we're going 1 to 10.
Caleb
It's like 11 or 12 yeah.
Host (possibly a podcaster or interviewer named Michael)
Okay. So Michael and I are aligned very infrequently. But on this one we agree. She's amazing. Love her to death. She's the best. And are you a parent?
Caleb
Yes.
Host (possibly a podcaster or interviewer named Michael)
Okay. So you understand.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
It's impossible to describe with current vocabulary how much you can equally love. Be worried about the same thing and then sometimes so utterly frustrated and wonder why you made the life choices that you did.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
Yeah. So I get a phone call. She's crying, dad, I don't know what to do. Dad, I don't want to do. I'm being chased by this guy. She. It was here in Kalispell.
Caleb
She in her car.
Host (possibly a podcaster or interviewer named Michael)
I'm not even in the same state at this point, which she knew. So she called him. Like, listen, what's going on? I couldn't even necessarily understand at that point. It was happening so fast that her ability to kind of tell me what was leading up to the event was tough. I was like, listen, actually that doesn't matter right now. How close are you to the police station, which is actually just on the other side of this building.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
Like go drive and go drive. Start driving towards the police station station. And worst case scenario, you're going to park in front of that and call 911. Didn't get to that point. Later on, the real story comes out. She was critiquing somebody else's driving through, shall we call it sign language? And this is another thing I try to tell my kids too, and this is good advice for everybody. You don't know what somebody else is dealing with in their life, in their. That moment. You don't know if just a quick little. Your number one is going to be the straw that breaks the metaphorical camel's back. Are they in the middle of a contentious divorce and they just got news that they couldn't barely, barely hang it on and that snaps them? Or are they having the best day of their life and they're going to laugh at you because you realize you're a 17 year old girl.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
So I also think she might have cut this person off.
Caleb
This whole story, the rest of the.
Host (possibly a podcaster or interviewer named Michael)
Story, this entire story, story likely is based on her driving ability, which if we were to again rate that Michael, on a 1 to 10, 10 being good, she might be closer to a 3.
Caleb
Send her O'.
Host (possibly a podcaster or interviewer named Michael)
Neal. She's mathematically, she's at 100% ding or damage rate of every vehicle. We'll just leave it at that. And then she'll tell me, but those weren't my fault. I'm like, really? Is the telephone pole you hit that just was like, it juked you, it was snowing. Like never cut somebody off, flips them off. And this then becomes this person driving behind her, super crazy, cutting other people off to get up next to her. She has a young female friend in the car with her. They're in tears, trying to figure out what to do. Now they're trying to get away. So she's starting to drive erratically and recklessly. So it's just like this whole risk matrix went from everything is fine, space, time, distance, to right up there. And eventually, as she got close to the police station, the guy peeled off and left. And I got home the day after and I sat down and you know, we've all made mistakes in life of which I don't have the time to even go alphabetically. But what I do with my kids specifically, I try to be honest about my mistakes and I try to talk to them about what I did to correct for that behavior. And more than anything that I am at least trying to not always successfully not repeat the mistakes, mistakes I have in my past. Let's talk about what happened, the error chain. Where did this start? Well, he was being a total asshole, I agree. But I said, where did this start?
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
Well, I probably, you know, I probably couldn't have flipped him off.
Caleb
Okay, let's go back.
Host (possibly a podcaster or interviewer named Michael)
Where did this start? Well, I probably couldn't, you know, maybe not cut him off. I'm like, okay. By doing that, you expose yourself to a level of risk that you weren't ready for. So let's think about that and let's. And it's so hard with anybody that age to try to forward, think into the risk that they may be exposing themselves.
Caleb
Right?
Host (possibly a podcaster or interviewer named Michael)
And the conversation ended up being great and we, we ended up laughing about it. But it's still something that I bring up. I'll still talk to her from time to time, like manage again that space and distance. You don't have to do those things that increase your risk threshold. And there's some things you can control and there's some things you can't. I mean, I have another example from Montana. We're driving home one night with my wife and again, I don't know what's going on in people's world. And we're on a road that is two lane traffic, one going in each direction. We're in the truck and this guy pulls up next to me like hauling ass, and I'm driving the speed limit. He passes in a Non passing area cuts right in front of me. Break checks. And at this point the first thing I'm doing is as I'm like slowing back, staying away. We get to a roundabout, he stops at the roundabout even though there's nobody else there. So at this point I stopped like a hundred yards back and throw my blight my brights on.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And my wife is like, what are you doing? I am managing our exposure because I don't know what this person is.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
Now having said that, there's also tools that were being prepared.
Caleb
Nothing wrong with being prepared.
Host (possibly a podcaster or interviewer named Michael)
There's nothing wrong with being prepared. No. Have no desire what to use whatsoever. But I'm already like, okay, I'm going to move laterally. We're going go to couple. Like the first thing I was going to do is separate my wife from the threat.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
But again that starts with recognizing as early as possible where a threat could come from. And I try to give myself as much distance as possible and the tactical advantage by turning the brights on. So if somebody pops out of the car, I can see them and they can't see me.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
My wife's just like, what is going on? Like nothing. Then they have taken off and then you have a choice. Do you want to chase them?
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
Do you want to turn this into Michael's laughing. So you, you would have put in his glove box. He has a Batman mask. He would have put that on. He would have put that on and turned all of his lights off and gone whisper mode after this guy go Comic Con after. How many people would do that though? Right. They're like that person wronged me.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
I'm on. And then that's how you end up out of a car. And in Montana just about everybody has a gun.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
That's how a firearm or tool gets introduced into something. And the next thing you know you go from having a normal night night to a funeral.
Caleb
Yep, yep.
Host (possibly a podcaster or interviewer named Michael)
Why manage your risk people?
Caleb
Yeah, yeah. No, it's, it's, it's mind blowing.
Host (possibly a podcaster or interviewer named Michael)
I mean I just had time and distance, man. Yeah, it's huge.
Caleb
Yeah, yeah. No, I just had an incident. Somebody tried to rob us two weeks ago and what? Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
State.
Caleb
Washington. Washington. Right on the Idaho border.
Host (possibly a podcaster or interviewer named Michael)
And it was a Washingtonian or an Idaho.
Caleb
I don't know if that's how you say it was. It was a fit. Two 50 time felons. Recent weapons. Yeah, yeah, weapons. Weapons charges and from recent weapons charge, illegal possession. Obviously. I didn't know that at the time. Yeah. Just knew the Wife saw some suspicious people, you know.
Host (possibly a podcaster or interviewer named Michael)
How did they approach you to fill me in?
Caleb
No, no, they drove onto, onto our property and we have, we have storage units that we built. Like that's, that's on the lower part of our property.
Host (possibly a podcaster or interviewer named Michael)
Maybe they just wanted to inventory what you had.
Caleb
Absolutely. They, they were doing a very systematic job of in invent pop the law helping you out. That's right, that's right. That's right. And yeah, four. Well, three minutes, three minutes into it, it was very, very apparent that, you know, they were relieving us of some things.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
And so I, I went down and, and got between them and the exit and thankfully didn't have to use the staccato. Yeah. But was very, very. The, the interesting thing, you know, for me doing, doing, you know, post incident myself in, in motion is I'm not in law enforcement, you know, so everything that I do in a situation like that where, where, where it is full on, you have two, you know, obvious felons who have bad intent. Who knows what they have, you know, inside their tender vehicle. I'm not trying to enforce the law at that point, right. Like, like it's a life or death situation and I'm systematically trying to eliminate risk, you know. And I remember clearly in my head, you know, because I only a couple weeks ago, like in my head thinking, you know, all right, the risk if they get out on that side is going to be more if they get out on this side because I don't have a clear visual. I'm going to have to engage through the windshield, which means that the round is going to rise. Like, like systematically going through this in real time. And then I remember thinking, wow, this site on this staccato is incredible. Like mid incident, right. Thankfully both got them both proned out law enforcement came, you know, and they look like, like they're going to be, you know, serving some good time for that.
Host (possibly a podcaster or interviewer named Michael)
Why didn't they serve time for the other 50 felonies?
Caleb
Welcome to Washington State.
Host (possibly a podcaster or interviewer named Michael)
Is it really that bad? I mean, I know that there's different counties inside of Washington, but there are some horror stories coming out of there.
Caleb
Yeah, yeah, it's, it's, it's sobering. You know, like I've split my time between Washington and Montana. You know, my dad is from, from Washington. My mom's from, from Whitefish.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
And so we've literally come back and forth my entire life and, and Washington is, is, you know, just, just continues to go downhill. And you know, I'm not, I'M not, not real political about things, but, you know, people are making decisions that have consequences. Those consequences are, are, you know, coming to light. And I think that that's a lot of what you see. We're, we're out of the country, so we typically don't see, you know, the instances like, like, you know, we saw here. It's typically very safe, you know, but it's, it's definitely, definitely a lot more wild than it was in the, the past.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Time and distance. That's a good T shirt. We should make that one. Michael. I had another good suggestion today, actually, based off the episode we released. It was called. It was just says Navy SEAL fatigue. People just exhausted. I saw that. I was like, I'll make that. I will wear that on a show, because that's awesome.
Caleb
You know, it used to be that you never heard about teams, guys talking to anyone about anything other than the little circle.
Host (possibly a podcaster or interviewer named Michael)
I agree. But it also used to be like I was. I would say I was late to the social media world, but it wasn't even an option before. And you know, I ask myself this. If the people, let's say the Vietnam Air seals of which you hear almost nothing about, or the UDT before that, people don't even recognize that the underwater demolition teams were the precursor to the SEAL teams. Both existed simultaneously for a while, and then the SEAL teams absorbed the udt. Would we have heard about them and heard from them if they had the same tools available that the modern era does? I think so.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
I do.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And, and I don't think it's a bad thing. I was inspired to go down the path that I was through a direct connection. My father was not a seal, but it worked adjacently to them. But you never know. And I know guys I served with who read a book and it inspired, inspired them. And I know many people now who have either heard a podcast or seen content of some kind, and that inspires them. So there is actually a lot of net positive that comes from it. And I think the volume of communication. If you're not using Ironclad for contracts, you could be leaving millions on the table without knowing it. Every contract holds renewal dates, pricing terms, and obligations you can't afford to miss. But good luck finding them when it matters. Ironclad's AI instantly surfaces what matters so you can act before opportunities slow slip away. That's why they're trusted by OpenAI, L' Oreal and Salesforce. Find the savings hiding in your contracts@ironcladapp.com podcast, that's ironcladapp.com podcast is directly related, probably. Well, to a degree, I'm not going to say the whole way, but directly related to the efficiency of the tools that are available now. And quite frankly, frankly, perhaps something that didn't exist, exist back then, but is 100% real, is you can get rewarded from having that kind of background.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And my theory is this. People's experiences are theirs to do with what they want. I'm not here to tell people what to make or how to make it. My only ask is, you tell the truth. That's it. And as long as people are doing that, I may not personally agree with the Navy SEAL Cookbook, of which I'm not aware that there is one, but I'm sure that there is, if not several. I wouldn't do that. But you know what? You earned your Trident. You do whatever you want to do. Yeah, but it's like anything else. I think it'd be, you know, if you drink too much water, it's going to kill you too.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
So I do actually think, though, just knowing the community of absolute chuckleheads that I worked with, and I say that in the most loving manner, craziest, and also most sane people that I've ever worked with and are the most hilarious with, like, the best and also worst interpersonal communication skills, I think if the tools existed back then, I think you.
Caleb
Would have heard from him.
Host (possibly a podcaster or interviewer named Michael)
I really do.
Caleb
Yeah, that makes sense.
Host (possibly a podcaster or interviewer named Michael)
Yeah, it's. But then it can also be taken too far. There is legitimately Special Forces or, well, Special Forces, Green Beret specific. I meant to say Special operations, which is the umbrella for everything. There's a little bit of hero worship around that that I don't think should exist. And a lot of that, I think, has to do with the 20 years of the global war on terror. And I think that is fading a little bit because I think people, it's. It's too much. It's too overexposed. And again, but that goes back to who you are and how you present yourself. If that's all you ever talk about and all you do, that might have one type of result. And if it's something that you can pay respect to and it is a part of who you are, but it's not your whole thing. I think that leads down a different path, too. But I'm not anybody to tell anybody anything.
Caleb
Yeah, no, I am. I am certainly not anybody to say anything other than thank you for your service, you know, because at the end of the day, like, you look at. You look at the hero's shoulders that each SEAL is standing upon. Like, there's weight behind that. Right.
Host (possibly a podcaster or interviewer named Michael)
The guys who taught me were guys who never had the chance to see combat. Those people are still absolute legends and heroes in my mind. And people will say, well, but they didn't go to Iraq. Like, they didn't get the chance to.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
I took what they taught me with me. I mean, we evolved it over time.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
We can't forget where we came from either, people.
Caleb
The foundation of the trailer tradecraft. Yeah. Like, yeah, no, it's. It's incredible. It's been one of the amazing privileges of my career to be able to work with, you know, people from different backgrounds. It's so much fun for me because I like to pull people from different backgrounds so that we have what I call constructive conflict. Right? You have your team's guys, you have your, you know, green race, Rangers, CAD.
Host (possibly a podcaster or interviewer named Michael)
Guys, all sorts of stuff.
Caleb
Full gambit, right? And then they come together with the sole mission of protecting people. And I call it construction conflict. It's like, no, we should do high ready. No, we should do low ready. You know, like, we just don't shoot each other. How about, you know, but like that, constructive conflict. I like it from the perspective of somebody in the private sector because we can take and we can, in a professional way, say, this is the way I used to do it. This is the way I used to do it. Combine that together. This is what we do now. This, as a team is what we do now based on our current mission, not the mission of the past. Take those tools and say, all right, what are these tools apply here? Because again, we're not doing direct action every single day. When you're running a protective detail.
Host (possibly a podcaster or interviewer named Michael)
That would be amazing, but one would hope not.
Caleb
Yeah, yeah, well, yeah, no, things have.
Host (possibly a podcaster or interviewer named Michael)
Gone really, really bad.
Caleb
Yeah, yeah, you guys are doing that. Exactly. Certainly not the goal. But improving the tradecraft, improving our ability to use the tools available to us to protect our protectees, that is. Is what I love about that. Constructive conflict. It gets interesting to manage at certain times, you know, because when you have somebody that's been a pipetter. Yeah, absolutely. For that many years, you know, it's. It's wild. But that's why we focus on the cultural side of things. If somebody's culturally aligned with the vision and values and. And, you know, progression of the organization, but also the protectee. Yeah, that's a big part of getting people, you know, to just come in under the same banner and say this is how we're going to protect and we're going to, we're going to, you know, stack this way or run the, the posture this way. That's, that's where we have the innovation in protection. That's how you move the industry forward, find better ways to do it.
Host (possibly a podcaster or interviewer named Michael)
You know, how does your, does White Glove offer the cyber aspect as well? Because I agree with you, I, I am not a tech guy by any stretch but it is so interwoven into the average person's life and air quotes.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And again I, I'll reference my dad who is 79 who has got an iPhone and a laptop and these are his portals to the world. So he, he would say, say he's not. Well, anybody who knows him would say he's not tech savvy and when he does say that he is telling the truth. But it's, you know, it's the world that we live in. How do you guys address that for the average person as well too? Because again they are getting more sophisticated at a rapid rate.
Caleb
Oh absolutely, absolutely. There's several different ways to go around it. You know, education is a big part of it. Just understanding, you know, what info not to enter, you know, things like that.
Host (possibly a podcaster or interviewer named Michael)
But yeah, and I had that talk. Don't ever under any circumstances enter your credit card information nation again.
Caleb
Yeah, yeah, right, exactly. Exactly. Yep. That's called a clue, you know. Yeah. But we have with strategic partners that that's all they focus on. They've been working with the highest levels of the intelligence community, you know, and targeting aspects before they moved in the private sector and then they've created solutions for digital executive protection that are second to none.
Host (possibly a podcaster or interviewer named Michael)
You know, do they address it all if they have children, the risk almost to the protectee via the child's online usage.
Caleb
Oh absolutely.
Host (possibly a podcaster or interviewer named Michael)
So Deliver Fund is just up the road in Whitefish and they are an anti human trafficking organization. Their CEO Nick McKinley was just on. Every once, once every year we have the Andy and Nick sit down and scare the crap out of parents conversation and we were talking pretty heavily about Roblox Roblox this last time. And not only just the games but that seems to be well known and established reality to include by the people who are running Roblox that it is a. I don't want to say a cesspool. It may not be fair. It is a. It is an environment where people who have malicious intent can maneuver pretty openly and they try to though starts with a game and they'll try to off platform, you onto Discord. And I just, just re. Re. Xed or whatever you're supposed to call it now. An episode. Saw it in Fox News. A child is missing because it was a conversation they were having on Roblox and the kid was talked into going in the real world to go meet somebody somewhere else and hopefully this will have a happy ending. Statistically, not the best, but you want to talk about somebody who is savvy and nuanced and wants to play the long game. And you have these families. Right. It's not just the protection. Protectee, because maybe the protectee has great EP executive protection. Where do you start pushing around the edges?
Caleb
Yeah, yeah, no, absolutely. That's, that's why they're especially the last five years, has come to prominence. Last 10 years we've been focusing on it deeply and that is what is the digital footprint of the protectee as well as the secondary and tertiary levels around them, you know, because oftentimes you'll have good digital hygiene when you're talking about the protectee and, you know, Mr. Mrs. Maybe.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
But, you know, the children, they're going to do what they want, you know.
Host (possibly a podcaster or interviewer named Michael)
And talk about leverage on a parent. My goodness.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
There's no vocabulary to describe what you would do.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And the horrendous things you would do to another human being to keep your child safe.
Caleb
No, exactly, exactly. So we include all this in our onboarding with any client going through the process to understand it, but also to understand, you know, when, when Aunt May comes over for, for, you know, Christmas dinner center, it snaps pictures of the family and posts it to her unsecured social media account that is geotagged. That shows, you know, exactly what trajectory, you know, your windows are, what neighbors are in, background to where, you know, a bad actor can come in and literally get your digital, you know, blueprint of your house just through her photo, you know, like most people aren't aware of that, you know, and so doing an assessment and understanding. All right, what's that there now? What can be managed? Because again, not everything can be managed. Publicly available information is stuck there, you know. Yeah. So what can be managed? And then moving forward, what do you need to do about that? Because that, that will fundamentally change somebody's protective posture. If their digital footprint is so intense that they have an unsustainable level of risk, then you have to do something about it. You know, either that or you're going to lock them down in a bunker.
Host (possibly a podcaster or interviewer named Michael)
They'd have to agree to.
Caleb
Yeah, exactly. Which they're never going to agree to.
Host (possibly a podcaster or interviewer named Michael)
What would it take for you to say no to a client? Would it be an un? I don't mean no, like in the moment, but you're. Somebody calls you and they're like, hey, we want you to come take a look at this. And you're looking at it and like, no, what would it take?
Caleb
Well, we have, we have very narrow parameters for who we accept as clients. You know, most of our Clients are Fortune 500 companies or CEOs of Fortune 500 companies, so private family offices of that. So we already have a very narrow, you know, acceptance rating. But it has to be a sustainable level of wealth. It has to have an embedded director.
Host (possibly a podcaster or interviewer named Michael)
You don't want their checks to bounce.
Caleb
Preferably not. Preferably not.
Host (possibly a podcaster or interviewer named Michael)
How dare you, sir.
Caleb
Yeah, you know, it's funny, in the three years since we've existed that our, our highest net worth protectee has been the only one that's been slow to pay. You know, which is, which is hilarious.
Host (possibly a podcaster or interviewer named Michael)
It's hilarious, but it makes sense because there's a difference between being a high net worth person and being liquid.
Caleb
Well, yeah, no, it's not. It's not that. It's the infrastructure in place to. It's. Well, I won't get too far into it, but yes, no, definitely. I mean, we're talking. I mean before, before I started White Glove, we'd never. I'd never. In the last 15 years, I hadn't worked a client that was worth less than $15 billion with a B. Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
I don't. I was having this conversation with somebody today. I don't understand that. I know that that means 15,000, thousand million dollars.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
What?
Caleb
Yeah, no mind officially blown.
Host (possibly a podcaster or interviewer named Michael)
Can you imagine waking up and just thinking every day forever I could do and possess and. Well, probably you can't do anything. Let's be clear about that. But you could, within a phone call, possess anything you want to. One, I think that would ruin you. Likely. Two, I think you would actually get tired of that over time. And the things that you have would probably end up feeling like they have less worth. But I, I'm sorry, I would like to try it for a week.
Caleb
Yeah, yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
I take that back 30 days.
Caleb
I don't.
Host (possibly a podcaster or interviewer named Michael)
And I get to keep the things.
Caleb
Yeah, yeah. I don't ever want to be worth more than $20 million. I. I've been around old money protectees. I've been around new money protectees. I've been.
Host (possibly a podcaster or interviewer named Michael)
What's the difference between the old money.
Caleb
And the New money in behavior, expectations.
Host (possibly a podcaster or interviewer named Michael)
Who has more of them?
Caleb
Old money, especially second and third generations. The expectations are rooted in the understanding that I was born with xyz. And probably one of the most sobering, sobering stories that I can remember from about two decades ago was the, the grandpa who was my primary protector, protectee, went out and bought a brand new vehicle for his 16 year old granddaughter. And I, I went out and got a big bow. It was in the color she wanted. Everything was to the nines, you know, very nice vehicle. And I take and I go deliver it, put it in the front and then she comes walking in. Yep, yep. Oh, that's the wrong shade of the color I don't really like. That was her entire response.
Host (possibly a podcaster or interviewer named Michael)
Like no happiness. It was straight to like, eh, straight 100%.
Caleb
Like I don't even want that because it's the wrong shade of the color that I asked for.
Host (possibly a podcaster or interviewer named Michael)
I think I would immediately light the car on fire.
Caleb
I had.
Host (possibly a podcaster or interviewer named Michael)
Not that I have the money to.
Caleb
Do that, but it's like really?
Host (possibly a podcaster or interviewer named Michael)
Do you like the shade of this burnt?
Caleb
Yeah, yeah, yeah. But the face of grandma and grand grandpa who had hustled, who had started with nothing, developed, everything had that level of net worth. This, the, the, their face probably just.
Host (possibly a podcaster or interviewer named Michael)
Broke him inside a little bit.
Caleb
Yeah, yeah. You know, and, and that was one of the early times when I was like, I don't want to be worth too much, doesn't matter if I win, whatever. Right. Like I want sustainable income so I don't have to worry about paying the bills. Right.
Host (possibly a podcaster or interviewer named Michael)
And you can do what you want with your time.
Caleb
Well, exactly, exactly. Like be able to, to make the world a better place, you know, not focus on paying the bills. Right. But I don't want to be controlled by the excess that's in my account. And I think that's what you see with a lot of the old money is they'll buy vehicles specifically because they're like, oh, I don't want to buy that vehicle because people will think this about me, you know. So it becomes about impression, but it becomes about living the life that you think other people want you to live, you know?
Host (possibly a podcaster or interviewer named Michael)
Well, and then there's always more. I've heard Rogan talking about this a few times. He has. Pretty sure he talks about it through the lens of the friends that he has. So there's the guy with 15 billion and then there's the guy with 150 billion. And in that dynamic, the dude with 15,000 million dollars feels poor because his private jet and Then the guy with the 150 billion, I bet you he knows, knows somebody. He's whatever. He knows Elon Musk. He's like, why don't I have five G650s that are flying around? I. I guess it's ramen again tonight for dinner on my china from the Titanic. You know that I sent a Japanese pearl diver down on a breath hold to get that. Cost me $80,000 a plate. Well, I mean, it's just, it's an escalation to no happiness if, you know.
Caleb
Yeah. Context is everything.
Host (possibly a podcaster or interviewer named Michael)
Also, I still would like to do the 30 day trial. If there's a billionaire out there that would like to fund this. Michael, would you like to attend if we can get a sponsor?
Caleb
Yeah, I, I'd be down.
Host (possibly a podcaster or interviewer named Michael)
Okay. Sweet. Good. So it'll be two of us. Need a few bill.
Caleb
There we go. There we go.
Host (possibly a podcaster or interviewer named Michael)
30 day test. We get to keep. You know, I would have quite a selection of helicopters. Michael would have like some jiu Jitsu gis, and like a new pair of shoes.
Caleb
I'm guessing you're not going with an R44.
Host (possibly a podcaster or interviewer named Michael)
No, no, absolutely not. Those are great helicopters.
Caleb
That's what I did.
Host (possibly a podcaster or interviewer named Michael)
So do you guys do aviation stuff? Stuff at all?
Caleb
We do aviation security. Most of my clients have. Have, you know, previous, you know, to current clients because I can't talk about them. But yeah, for sure. You know, like the old ones have full fleets and. Yeah.
Host (possibly a podcaster or interviewer named Michael)
Of everything.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
They get the rotary to the fixed. Yeah.
Caleb
Oh, yeah, yeah. No client in Philly. We would. We'd fly from Philly to New York, you know, two, three times a week, just back and forth, you know, and then obviously jets on both ends as well, just in case you got to take off.
Host (possibly a podcaster or interviewer named Michael)
Like it gives you a different perspective on time.
Caleb
Absolutely. And managing time, you know, for sure. You know, or what your time is.
Host (possibly a podcaster or interviewer named Michael)
You know, how much your time is. Is worth.
Caleb
Well, and. And you have protect these, you know, in both categories that you mentioned earlier. You know, that, that I've certainly had that. You are driving to the airport, you're driving to the fbo, and they don't know where they want to go. And so planes just sitting there. No, two planes are sitting there.
Host (possibly a podcaster or interviewer named Michael)
What.
Caleb
Because one is ready to go to Antarctica if they want to go to Antarctica. The other is scheduled to go to Tahiti just in case they want to go to Tahiti because they don't know exactly what direction they want to go. Because there's tons of influencing factors. Possibly in the car, possibly out of.
Host (possibly a podcaster or interviewer named Michael)
The car and they can go wherever.
Caleb
They want to go wherever they want. And it creates so many challenges for us. That is fun to guesstimate. Yeah, right. Like where do I send my advance team? Well, obviously you send them to both.
Host (possibly a podcaster or interviewer named Michael)
I mean, you can skip Antarctica, but you're going to be fine. Security risk is low.
Caleb
Yeah. One of my guys there right now, it's. There's definitely some spikes, but.
Host (possibly a podcaster or interviewer named Michael)
Well, that would probably be depending on who the other people that are around. And also, don't go out on the glacier by yourself.
Caleb
Yeah, exactly.
Host (possibly a podcaster or interviewer named Michael)
Crevasse brief that we got when we were there was very real.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
Then they showed the overhead and they're like, this is why this red flag section exists. If you go outside of that. Yeah, don't go outside of that.
Caleb
Yeah, yeah, yeah, yeah, exactly. But that in that entire dynamic is something that you don't even think about until you're working with somebody who's with that, you know, excess.
Host (possibly a podcaster or interviewer named Michael)
We'll say that rolling up to two jets. And again, this is. This is where my mind doesn't understand that level of choice. Because the first thing I think of it's like, God, what's the acquisition cost of that jet? I bet you the insurance. I'm like, wow, how much is it to fill it up? If you got brake pads you got to replace? Where do you hanger that thing? How many pilots do you have? We're not even off the ground yet. You're already in seven figures easily on both it and to not. I can't fathom a headspace where you have so much money where that is not part of your equation.
Caleb
Money is not a limitation. It's access.
Host (possibly a podcaster or interviewer named Michael)
That's a good way to put it.
Caleb
It's. It's been hard for me to wrap my head around it because I used to try to provide value the amount of money that is spent to. To protect these. Right. I want to be able to show the value of what I'm providing.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
But that doesn't really resonate once people are at a certain level of. Of net worth. Right. What resonates is can you get me access to the things or activities or memories that I want? Can you get me to that part of the world that I want to be in at this time of the year, year for this activity? You know, is it physically possible? Because I have my board of directors meeting at 5 o'. Clock. It's going to end at 5 o'. Clock. We can't leave till then. But I want to be to that crazy part of the world by midnight so that I can have this experience. Right. So it no longer becomes part of a, A, you know, value for, for anything. It becomes. Is it physically possible for you to get creative? Because this isn't stuff that normal what people do. Right. Like we can't fathom it as normal humans, you know. Yeah, but can you get it? How, how can you work the logistics to be able to facilitate that? You know what, what makes me light up is the smile on their face when they get there and they make it in that amount of time when you made the impossible happen. And they don't see all the constructive chaos that took place behind the scenes. The hundreds of people that have been calling in every favor government across the world to be able to get a landing permit in an area where you're not allowed to land after 8pm but you need to land at 11:59 to be able to make it there for the midnight deadline. You know, like, like them, it's almost like a challenge seen in their mind. Like, is it possible, you know, do.
Host (possibly a podcaster or interviewer named Michael)
You think they appreciate it? I think like a deep appreciation. Or do you think it's fleeting?
Caleb
I think that it's different with each protectee. You know, value to them is, is absolutely subjective, you know. You know, I had one of my favorite protectees give me an amazing timepiece Rolex several weeks before I was let go for no reason. And that's the reality of this world is transitions happen in their world at a point pace that you either keep up with it or you're irrelevant. Right. And it's not a personal thing. Right. Like none of the protectees that have let me go over the years did so with, you know, for any egregious reason or malice or anything like that. It just, you know, I wasn't relevant to their time and space had run out.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
At least their, their impression. Yeah, exactly, exactly. You know, and so there's no security in the executive protection world. You know, the only job security we have is the people around us. And, and I've been so grateful that for the last two and a half, three decades, I've never been without a job within two weeks of me leaving a previous job, you know, but I moved, you know, my, my wife and I moved 19 times our first 15 years together. That's a lot pursuing different opportunities around the country, you know, because we wanted to have that progression and I wanted to be able to move forward in the industry, you know. And so really it's been my goal to align my value with the needs of the protectee, you know, and so you kind of have to be a chameleon with their culture and figure out what's important to them and, and what environments, you know, do they want to experience and, and then really take and get creative. How do we protect this person in a way that's in, in line with their culture and values and expectations today?
Host (possibly a podcaster or interviewer named Michael)
You know, my first exposure to the difference in the worlds that people live in is I did some charter flying as a Gulfstream pilot. I'm type rated in a G4. Oh, wow. And we were, I'm pretty sure we were in Hawaii. I don't remember the exact island, so I'm not gonna guess. And same thing, fbo, which for people to know is called fixed based operations. If you've never experienced an fbo, I mean, how would you describe it to someone? Somebody. It's a totally different optic on aviation.
Caleb
Oh, for sure.
Host (possibly a podcaster or interviewer named Michael)
And if you're high net worth people rolling up, you're probably going to be rolling to under five miles an hour as the gate opens. Yeah. Pulling up to the vehicle, onto the carpeted stairs, luggage in the back, engine starting, see you later. And somewhere in there you may get your passport checked. Maybe not, maybe your id. Maybe not.
Caleb
Depends what part of the country total. Totally.
Host (possibly a podcaster or interviewer named Michael)
Let's just say it's not like tsa, it's the anti commercial terminal experience.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And so we're sitting there and so the part 135 flying, which is the charter operations, the FAA part 135 uses EPIOS all the time. So we're sitting there and I love Gulfstream products. I love the oval windows.
Caleb
Oh absolutely.
Host (possibly a podcaster or interviewer named Michael)
And this was when the 650s were pretty new. So one lands and rolls up and a car pulls up and a man gets off with a dog and a dog carrier hands the dog to the guy in the car and the car leaves. The guy got back on the plane, the ramp came up and they took off. Now I don't know exactly how much a G650 is to operate per hour, but I know that the G4 was at about 8,000. Just to turn that thing on.
Caleb
Yeah. Bump it up by three.
Host (possibly a podcaster or interviewer named Michael)
So let's say like 11 to 12. That would be a safe bet. That bird came from New York. That man was essentially the dog's babysitter until it could be brought on vacation with the family. And then that 650 came back later on. And I'm sitting there like what?
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
I'm talking like dog. Just like ten pound dog. Well into the six figures. Like you said, money not a limiting factor.
Caleb
We had a massive team deployed in Central America with a protectee. And this is right in the middle of COVID And this protectee was trying to cook things in a certain way and they found out that they needed butter and butter was not available in the middle of the jungle to their liking.
Host (possibly a podcaster or interviewer named Michael)
And so I was like, hey, of net wealth, butter becomes available.
Caleb
So I literally had a, a. We'll just call him a highly skilled guy, fly, pick it up, come back and I think eight and a half hours later, butter was served to the.
Host (possibly a podcaster or interviewer named Michael)
Liking of the protect per ounce cost of that butter. But again, they don't care.
Caleb
It's not about, it's not about the value, right? Like it's about the, the, our ability to deliver access, deliver the experience, you know, deliver things that make their lives better. Right. Because you look at these people, no matter what anybody says, their lives are stressful, you know, and, and I had one protectee that, that I hope to someday be able to, to maintain that level of mental discipline. Because Everybody Day at 4 o', clock, it was like a switch flipped and went from board meeting to him. And I be walking down the beach talking about the Beach Boys, you know, talking about, you know, Johnny Cash, you know, just regular, regular guy, guy talk type video, you know, and literally minutes before that you're talking highest levels of, of, of corporate America, right? And the ability to just switch it off as, and then just be able to kind of come down from that high level of attention to detail that you have to have is something that, that I try and do, you know.
Host (possibly a podcaster or interviewer named Michael)
Because I think I struggle in those transitions too. I know exactly what you're talking about. It's the ability to transition from those head spaces. It's tough. You can get caught without that. You, you're stuck at a 10. But you need to, you gotta have some time at a two.
Caleb
Yeah, yeah, exactly. Yeah.
Host (possibly a podcaster or interviewer named Michael)
Candle burning at both ends. Let me tell you how that works.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Candles burned out.
Caleb
It doesn't. Yeah. And, and I've crashed three times in my career. Like to burnout. Once was in Israel. I remember laying on flat on my back at the King David Hotel. They were feeding me water. My team was feeding me water through a, a straw because my throat was so swollen. Just pure exhaustion. Gone three months without sleeping more than an hour night. Like we're traveling on tour with a client. And that was just life, you know. And it happened two other times since then and it got progressively worse each time, you know, know probably because it wasn't any younger. But also, you know, you, you worked 80, 90 hour work weeks for, for decades and as it's, it's toll on you, you know, but being able to find, find that, you know, whatever, whatever it hobby it is or whatever it is to be able to, to scale back I think is super important.
Host (possibly a podcaster or interviewer named Michael)
What do you like to do outside of the protection world?
Caleb
I'm trying to figure that out right now, being perfectly honest because it's been, been literally so much of my life. I'm thankfully, I've, you know, small kids right now, so being able to spend time with my wife and them is, has been incredible.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
But, but I don't have, you know, traditional hobbies. I used to golf, but I haven't golfed in 25 years. You know, I used to love sports, you know, but I haven't had time to, you know, follow anything consistently, you know, because I literally lived my clients lives for the last several decades. You know, whatever, whatever music they wanted live to listen to, that's what I listen to, you know.
Host (possibly a podcaster or interviewer named Michael)
Are there any business sectors that interest you that you would want to get in outside of the EP world?
Caleb
We've dabbled some with the commercial real estate. We have about 25,000 square feet of indoor storage space which has been, which has been great. But, but really I, I'm really more focused on the, the volunteering side of things. You know, um, once, once I turned 40, I was at a point to where I didn't have to worry about my kids being able to eat if I didn't work. Right. Worked non stop my entire life, you know, doing this. And once I got to that point I was like, all right, there's got to be more than, than just, you know, chasing a buck because that had been my motivation for so long. And, and, and my, my old chief security officer at PayPal said, Caleb, if you, if you chase a paycheck, you're never going to be happy. He said, you need to chase your passion, you know, because the paycheck will follow.
Host (possibly a podcaster or interviewer named Michael)
I think it's usually a blend. I know a lot of people who are passionate about some really weird stuff.
Caleb
Absolutely.
Host (possibly a podcaster or interviewer named Michael)
And I want people to be able to chase their passion. The advice I give them is this. Make sure you can pay your bills.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Devote your off time to your passion and then you can probably build an off ramp. It is irresponsible to only chase your passion because your mortgage payment doesn't care about your passion.
Caleb
For sure, for sure.
Host (possibly a podcaster or interviewer named Michael)
Car payment. It's like oh, you're passionate about this? Well, we're passionate about getting paid.
Caleb
Right, right, right. Yeah. And contextualizing. That is amazing. I'm so, so glad you did that. Like, the context of his conversation with me was, you know, about two workaholics that have worked their entire careers, you know, to where it's like, all right, I'm going to try to get another 100,000 raise this year. That was the progression in corporate America. You're trying to follow that. Right. And being able to take a step back and say, all right, I'm a highly competent professional. I'm gonna, I'm gonna take and focus on some other things, you know, so I started focused on the, the volunteering aspects. Volunteering, giving back to the industry, which, you know, became my passion. For the last 10 years. I've served in volunteer, you know, capacity on different leadership boards and mentoring and, and things like that. And then, then that passion turned into white glove and that's, you know, turning into the, the, you know, profit producing entity. Yeah, so absolutely. Good advice. Make sure you're, you know, not chasing rainbows and butterflies.
Host (possibly a podcaster or interviewer named Michael)
Money for groceries. Especially if other people relying on you.
Caleb
For sure.
Host (possibly a podcaster or interviewer named Michael)
I just don't want to be on my deathbed with regrets.
Caleb
Yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
And, you know, you hear people say it all the time, hey, you're not buried with the money that you make. Which is a very true statement. Statement. But it's also money does make the world go round. If you want to do things, it's going to come at a cost. If you want to have thing I like, and don't be wrong, I like money and nice things just like everybody else, of course. But I just can't fathom how bad it would be to be on your deathbed with a feeling of regret for things you wish you had done.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
And sometimes to do that, I have found in my life at least, I have to say no to opportunities that may produce a little bit more income.
Caleb
Income.
Host (possibly a podcaster or interviewer named Michael)
But I'd rather take the experience, especially with my wife and kids, than a 1% increase in net worth that I'm probably gonna blow on something stupid anyway.
Caleb
You know, another Hilo.
Host (possibly a podcaster or interviewer named Michael)
Don't tease me. I'm gonna get targeted by an Instagram ad and be like, I do need 17 storage bits for the garage made out of titanium. That's sink down.
Caleb
I'm like, there's what with my flamethrower.
Host (possibly a podcaster or interviewer named Michael)
Harder than you have it. And then it sits in a garage and you never use it.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
That's one of my favorite Exercises. You go into the garage and you look at your things, you're like, what that cost? How many times have I used it? What's the cost per use on that? What that cost? And just really remind myself of how much an idiot I could be.
Caleb
It.
Host (possibly a podcaster or interviewer named Michael)
It has helped, though. I used to. And I've been in phases in my life where I had to say yes to everything because I didn't know I was going to pay the mortgage.
Caleb
Yeah. I didn't enjoy that.
Host (possibly a podcaster or interviewer named Michael)
God, I felt ragged and just pull, like the amount of stress, stress in that. And it's. I just want to be the master of my own time.
Caleb
Well, and, and being able to do the things that inspire you, not worry about the finances, that to me is, is that healthy balance.
Host (possibly a podcaster or interviewer named Michael)
You know, I, I think that's being rich.
Caleb
100. I mean, how do you define success, right, in. In like contextualizing success at different phases of life? To me, success right now is spending time with my wife and my kids. Right. That wouldn't have been the priority 20 years ago, 15 years ago. You know, like, priorities change, priorities shift. You know, like, and being able to thrive at each stage in life. How do you do that? Right. How do you, how do you find things that align with your priorities as well as your pocketbook? All I know is, is, is there was one year that I. That I made more money than I ever made and still have made to date. And, and that year was the most miserable year of my life. And I was like, there's gotta be more than this. There is gotta be more than this, you know?
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
Literally flying 300,000 miles over the course of that year, you know, all over the place. I'm just like, it's not all about money, you know? And so that, in my mind, made a fundamental shift in my priorities, you know, My priorities, obviously, you know, I grew up. I grew up, experience extremely poor. Right. My dad made five bucks an hour until I'm. Until I moved out. Right. And we, we lived perfect, perfectly fine life, you know, paid 150 bucks a month in rent. And I didn't know what it was like to be anything different. You know, we. We didn't have a car that my parents spent more than 300 bucks on for my entire childhood. And so I know what it's like to live below the poverty line. Right. And being a kid, I didn't care about it. It was like, whatever, you know, I'm going to make the best of it. Right? Right. And as, as I've achieved different milestones in My life, I want to maintain that same level of like cognitive awareness, you know, that it's not all about money, it's not all about the experience. It's not certainly, it's not about status, you know, it's about the people around you. Like if you can take the people. One of, one of, one of the most amazing things of starting White Glove is being able to bring in people that have, that have supported me, that have helped me progress in my career over the last couple decade, decades into, into positions to where they're able to thrive in their roles, you know, to where they're able to be the best version of themselves, impact the industry in a positive way. You know, that for me is, is the people I'm around is what's making this experience so enjoyable, Right? Yeah, that's different for every person. But you know, what is success? And, and I think that taking a cold hard look at that for, for anybody out there is absolutely, you know, time well spent.
Host (possibly a podcaster or interviewer named Michael)
Yeah. How do you, how do the team stay sharp? Are there schools that you guys can go to? I mean, I'm assuming there's shooting schools, but EP skills, soft skills, driving skills. Do they just allocate time to train outside of their shifts? Do you guys train internally? How do you guys run it?
Caleb
Yeah, yeah. So we're, we're fundamentally changing the way that that's done. Traditionally you'll go to like a five day EP school.
Host (possibly a podcaster or interviewer named Michael)
Totally.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
It's probably part and parcel. It's like a buffet menu. Right. Like this week is this and then this and then this.
Caleb
Exactly. The problem is, is most teams don't have time to be able to send agents consistently. And if they have time, they don't have the budget. If they have the budget, they don't have the time. You know, so it's. Yeah, exactly. So a lot of training gets compromised. So that's why we developed our three year training plan, you know, again, with the intention of developing the next generation of practitioners. So three years, you're number one. Every agent focuses on the skills to be able to need to be at the highest level of proficiency for their position. So if they're residential, if they're a detail leader, if they're, you know, close on the close protection team, whatever their specific position is, has a different set of requirements but also different levels of training. So they might have, you know, TCCC training for medical, they might have, you know, level one and two firearms training for their, for their firearms. We, we do our best to immerse all the schools in all the training in real world operations, because I like bringing the instructor to the students rather than sending students out to different instructors. Because the quality of instructors in the executive protection industry varies greatly. I'm going to put that delicately.
Host (possibly a podcaster or interviewer named Michael)
I think that's true in every sector, to be honest. Yeah, there are legends and then there are people who have the same title and not the same skill and ability.
Caleb
Right, right, exactly. And nobody can be great at everything. And so somebody that's trying to teach a five day EP school might be strong at advances, but they might not be as good at, you know, motorcades or whatever it might be. And so instead of looking at and saying, we want to send people to these traditional schools, we've taken a new perspective and said, all right, we're going to, we're going to have instructors teach our agents where they are in their home ao and take that area of operation and teach them. Where are your local choke points? Where are your, you know, hard points? Where, where in your world do you want to, you know, improve and grow and develop? What medical training is most salient to your client? Like what's relevant to your client client? Because if you're focusing on, on heart attack stuff and you, you primarily covering down on kids, then, oh, let's, let's maybe focus on some things that are more relevant to, you know, treating your kids. I used to send all my agents to EMT school. Just that was part of our standard every year. You know, first year you go to EMT school. Now I've changed to say, I want everybody to be a first responder so that they're under medical direction. But I want them to have training that's specific to their protectee.
Host (possibly a podcaster or interviewer named Michael)
Again, that only makes sense like if you're, again, like you're watching, watching a kid. I don't know. People think about this like not all tourniquets are created equal.
Caleb
Exactly. How many people know the difference? Right. You know, your Pete's kid, they would.
Host (possibly a podcaster or interviewer named Michael)
Wait until they were opening up the. And they're like, wow, I really can't get this to bite. It's like, yeah, that's an adult tourniquet.
Caleb
Exactly.
Host (possibly a podcaster or interviewer named Michael)
You bought a tourniquet, which. Awesome. You should have several.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
But if you're tasked with protecting a child.
Caleb
Yeah, dude, yeah.
Host (possibly a podcaster or interviewer named Michael)
Pack the right stuff.
Caleb
Yeah, exactly. Same thing. You drive a motorcade operations and you're doing the drop off at school. Do you need to drive your typical stack in order to keep them safe? Or can we get creative?
Host (possibly a podcaster or interviewer named Michael)
All the Honda Odysseys out of the way.
Caleb
Yeah, exactly, exactly. Right, but, but you know, we teach in the schools. There's one way for things, for things to be done. And guess what? That's why Butler happened. Because there's one way for things to be done and when circumstances fall outside of that one way way, stuff falls through the cracks. Yeah, right. So unless we take a holistic look at protection and say we need to accommodate to the lifestyles preferences risks of each individual protectee, then we're falling behind the threat curve. Bad guys are getting better day by day. Bad guys are out there saying, hey, you know, I can, I can take this. You look at the, you know, Wisconsin killer that killed the politicians in Wisconsin. He went online, he looked up their information online from the publicly available data databases, had a whole list based on what he found online. He went there and he started, you know, following his delirious intent. Right. Like how do we prevent that? Well, let's do something about your digital footprint, right. Like let's take proactive steps. That stuff that anybody can do at home, that stuff that anybody can, you can go online and delete them yourself if you want. Right?
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
It just takes awareness. It just takes, you know, trying to take and you know, maintain that level, level of focus. You know, we use 360 Privacy for any of that digital deletion end of things just because I found them to be the best for, for me and my protectees. Right. But at the end of the day doing something is better than doing nothing.
Host (possibly a podcaster or interviewer named Michael)
I agree. And there will be people say, well I, I can't get rid of these apps. This is a part of what I do. And to them I say, okay, if that's the premise, then you need to be more aware of what it is you're putting out there. You and you know, simple things like don't post where you're going to be before you go there. If you want to post a picture, post it the day after you were there. You know what I mean? So you can make the content that you want to make, but if you just the awareness aspect of the, hey, see everybody at, you know, 1234 Fifth Avenue tomorrow at the bar at 5:00pm yeah. Versus you post after you have left. I'm sorry, there's a, a different risk, risk profile right there. That's the awareness piece. So you can live in that world too. And I wouldn't recommend posting pictures of your kids. So again, where you live, the internal of your house, I mean there's so many different, like you can go on Zillow and figure out the internal of most people's house. Not that I want to give anybody ideas.
Caleb
Right, right. But yeah, the digital footprints out there, before you get there.
Host (possibly a podcaster or interviewer named Michael)
Insane. So, yeah, if you have to have it, think more about how you use it. Because I do get the argument, like, my kids are super interconnected with their friends. They're using. I'm like, okay, just please, for a, I don't even know, a fraction of a second, think before you go brain hit. Like, that's all I ask.
Caleb
Yeah, yeah, exactly. Simple things, you know, take a screenshot of the photo before you post it. You know, at least do some things to create a barrier so you make it harder for the bad actors, you know, to. To be able to take and do bad things, you know, doesn't take a rocket scientist. Just takes awareness.
Host (possibly a podcaster or interviewer named Michael)
So what do you think it looks like if you were to forecast if the last 18 months have been this uptick, what do you think the next 18 are going to be?
Caleb
That's a hard question. All the, all the intel, forecasting trends, everything we're seeing, you know, shows increased level of, you know, not only online chatter, but, you know, propensity for violence. You know, um, we're seeing increased rhetoric both from the left, from the right. You know, you have elections coming up, which always spikes in the risk index. You know, so there's gonna be a lot of need for people to use, use their objective head in, in the next two years.
Host (possibly a podcaster or interviewer named Michael)
You know, it's a lost skill for some.
Caleb
Absolutely. And it's sad, right?
Host (possibly a podcaster or interviewer named Michael)
It can be found, though. That's one of those things you can find, Find your objective head.
Caleb
Yeah. And at the end of the day, if we just remember we're all humans, right? We all have preferences, we, we all have, you know, beliefs. We all have, you know, things that are important to us and things that aren't important to us. You know, I, I think we just need a reality check, right? As a nation, what is our priority? You know, is our priority really polarizing ourselves from everybody else, or is our priority just, you know, enjoying the American dream that so many people are living the American dream that so many people have fought and died for? The American dream that, you know, my grandfather was a POW for three and a half years for. Right. Like that American dream is alive and well and we're not even looking at it because we're so busy looking on our phones.
Host (possibly a podcaster or interviewer named Michael)
I get to the place where I wonder if there are people driving us to not look at it, trying to drive us apart, trying to Drive the conflict. Right. And again, I'm not going in three piece tinfoil suit. You can't mean again you're talking about. A lot of that comes from their electronic devices. The usage, which we do have a heavy hand in and it's. A buddy of mine came in and we decided to take a look at our screen time and post it. Not the most fun or justify related. Like what does that number say? I don't remember being on there that much. Almost as if it's designed to be addictive.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
And we're trying to get it under an hour. Last week I was one hour and one minute was my average. I'm gonna destroy him this week. Cause I'm gonna like hide my phone from myself. But God, I feel healthier. I have, shockingly enough, my battery in my phone is more charged throughout the day.
Caleb
Amazing.
Host (possibly a podcaster or interviewer named Michael)
I don't feel a lot less disconnected. I have missed some things. Like one of the things I honestly didn't see because I wasn't on social media, not that I want to see this anymore, is the most recent shooting in Minneapolis where the guy had the gun taken from him and then he was shot by the ICE officers. I'm still trying to wrap my head around that one.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
But I can see a world where nation state actors would love to manipulate American society and get us pitted towards each other. I don't think. I think a more realistic argument is it's not the deep state. It's just people. People who hate who we are because they have a different alignment as a nation and they are crushing us by getting us to fight each other.
Caleb
Well, and a lot of that isn't even hearsay. Or, or it's well publicized.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
In the, in the intel community specifically. That the vast majority of trending data on social media is being put pushed by somebody. Right. And you look at the number of, you know, employees specifically focused on that. With Iran and Russia and China specifically focused on disinformation. There's absolutely a massive effort, you know, that if we don't realize that, you know, we start to think that, that it's a, you know, a real thing, if you will.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
That there's so much. But I mean, look, look, the shooting happened what, yesterday? Day before yesterday.
Host (possibly a podcaster or interviewer named Michael)
I think it was in the last 72 hours.
Caleb
Yeah. And any of your social media you try to look at, you know, is dominated by that. Who's pushing that? You know, is it the algorithm because so many people are clicking on it, or is it somebody that is using a approach that's been well documented since 2004 that, you know, we're talking MySpace days. Yeah.
Host (possibly a podcaster or interviewer named Michael)
Or both.
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
Combination of the two.
Caleb
Exactly. You know, so like, like I, I think that there is technology out there that is pushing a narrative and I think that people's desire to consume the, the, you know, things that are entertaining is, is also pushing a lot of things, but it's each of our responsibilities. Say, does this make sense?
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
Right. Like, like, you know, in my mind, you know, there, there are things where with United Healthcare, with Charlie Kirk, with Butler, they just don't make sense. It doesn't mean that I'm saying that I have a tin hat.
Host (possibly a podcaster or interviewer named Michael)
Yeah.
Caleb
I can acknowledge this just doesn't make sense from a reasonable perspective as a human being taking a step back and saying, why wasn't this happening? Right.
Host (possibly a podcaster or interviewer named Michael)
Maybe it's because at the time, like you're saying the investigation about around Charlie Kirk, it may not make sense now because there's a missing information gap. Maybe it'll be filled in and maybe it won't.
Caleb
Yep.
Host (possibly a podcaster or interviewer named Michael)
What I'm not trying to do and what I advocate for people to not try to do is don't rush to try to fill that gap.
Caleb
Exactly.
Host (possibly a podcaster or interviewer named Michael)
I don't know. Is an incredibly acceptable answer. Somebody pointing out there saying, I know the truth and this is all that it is that again, live your life however you want to. But when a hundred people are saying that no one will ever agree on the truth.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
Because how do you separate the wheat from the chest?
Caleb
Have. Yeah, yeah, yeah.
Host (possibly a podcaster or interviewer named Michael)
There's a lot of things that don't make sense to me. And I try to remind myself, maybe it's because I don't have all the information. Another one with the social media stuff. I constantly remind myself because depending, you know, what you click on the rabbit hole you go down, you can, man. And this has happened to me, you can really warp your sense of the world around you. And I will ask myself, is what I'm seeing right now reflective at all of what I'm seeing in my day to day interactions in real life?
Caleb
Right.
Host (possibly a podcaster or interviewer named Michael)
I have yet to come to a place where it's like, yes, it is. It's, to this point has always been no.
Caleb
Yeah.
Host (possibly a podcaster or interviewer named Michael)
It's not reflective of my real life. And that's actually the answer that I get from everybody that I ask as well too, which is very important to remember.
Caleb
I agree wholeheartedly. Yeah, we're, I mean, talk about polarized society. Right. You have, you know, far left. Far right, far, far, whatever. Like, you know, People are more polarized than ever. I would, you know, in my lifetime, at least. For sure. Yeah, absolutely. And. And why is that? You know, you can say there's a lot of different, you know, reasons why it is, you know, me, I try to focus on what I can understand, right. Because in my finite brain, I know that I can't understand everything. You know, I know that. That I have a ton of weapons available to me in my life in. In. In my. My job. My favorite weapon is truth. Right. And identifying the truth, at least pursuing that, the pursuit of truth, that is unbiased truth as well. Because I think that, you know, biased truth is just as dangerous. But. But that pursuit of truth in my mind is what protects me from the rabbit trails. Right. Because if I'm pursuing a narrative, if I'm pursuing a bias, then I'm. I'm following the rabbit trail.
Host (possibly a podcaster or interviewer named Michael)
Yeah. If you're looking for confirmation of what you believe, let me tell you what you're going to find.
Caleb
Exactly.
Host (possibly a podcaster or interviewer named Michael)
Confirmation.
Caleb
Yeah, exactly. But if I'm wholeheartedly focusing on the truth, trying to figure out, all right, what is the best way to do this? How do you improve this, you know, what did happen? You know, then. Then that pursuit in and of itself is kind of a distillation process for me that allows me to dig through the layers and really, you know, see what makes sense over time. I think if we took that filtered approach to life, I think that it would allow us to have, you know, a lot more measured approach, certainly, to the training tragedies, you know, that we see.
Host (possibly a podcaster or interviewer named Michael)
I think so, too. What do you want to close out with, man? We've been at a couple hours. I want to get you out here if you're going to go see your grandmother. Enjoy your second hometown. Welcome back.
Caleb
Yeah, yeah. Always good to be back. Get grandma's famous spaghetti tonight. So definitely look forward to it.
Host (possibly a podcaster or interviewer named Michael)
I mean, that's not going to suck. Grandmothers traditionally don't make bad spaghetti.
Caleb
Not at all. Not at all. Not at all. She's still rocking it at 91.
Host (possibly a podcaster or interviewer named Michael)
That's awesome. Yeah. What do you. What do you think? Closing thoughts, boy.
Caleb
Honestly, in my mind, I'd just like to thank your audience, like, talk about a. A dense audience of people that have put time, you know, downrange and in the field and doing things that so many of us never had the opportunity, you know, didn't. Didn't put boots on the ground and doing, you know, like, I. I just. Me being here gives me great gratitude, you know, for everybody that Listens to you and watches you and. And, you know, very grateful for you, for your service, you know, but also for your audience and their service. Because I think we, you know, me being a civilian my entire career, you know, Absolutely. You know, wasn't exposed to the same level of. Of things and can't understand.
Host (possibly a podcaster or interviewer named Michael)
Good.
Caleb
Absolutely. Absolutely. You know, but many days I wake.
Host (possibly a podcaster or interviewer named Michael)
Up and I like, you know, life choices.
Caleb
Right, right. But your life choices have facilitated mine. Right.
Host (possibly a podcaster or interviewer named Michael)
And you have to have both, you know, for sure.
Caleb
Absolutely. I'm not discounting one or the other. I'm just saying. Thank you.
Host (possibly a podcaster or interviewer named Michael)
98 of it was my pleasure. 2% of it was. Really sucks.
Caleb
Pure suck.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Before you leave, though, Tactical World, you're from my friends down at Montana Knife Company, I think. Let me see. Flip that box my way. This might be the TF24.
Caleb
All right.
Host (possibly a podcaster or interviewer named Michael)
Yep. All right. That's all you. You can open that up. Don't Dana White yourself and cut your hand open.
Caleb
I love it. Yeah.
Host (possibly a podcaster or interviewer named Michael)
Now right down to Missoula, they make these. Josh Smith is the youngest master bladesmith that there ever was.
Caleb
Very cool.
Host (possibly a podcaster or interviewer named Michael)
And this was based off of. It's a little bit of a bigger knife. Probably not something that you would maybe edc, but if you got some property out in Washington, this thing might have some great utility.
Caleb
So one of the thing that not many people know is every country I go to. Oh, wow. This is incredible. Every country I go to, I try to find a locally made knife.
Host (possibly a podcaster or interviewer named Michael)
Nice.
Caleb
And so in my office, the whole top left section is. Is over 100 knives from all around the world.
Host (possibly a podcaster or interviewer named Michael)
Yeah. Just grab it normally. Yeah. Then you just pop it with your thumb up top. Yep.
Caleb
Sick.
Host (possibly a podcaster or interviewer named Michael)
It's a good blade. Like I said. For me, I'm never been a folder much. There's some utility to it, but. Yeah, that's probably a touch big, maybe a touch heavy for edc, but that thing is. It's sharp.
Caleb
I love it.
Host (possibly a podcaster or interviewer named Michael)
Yeah, that's their TF24.
Caleb
TF24. Well, thank you so much. Thank you. Montana Knife Company. That's going to be front and center in my. My office for sure.
Host (possibly a podcaster or interviewer named Michael)
Don't cut yourself with it. Yeah, I've cut myself with almost every knife I own.
Caleb
Mess around with them we get. Emerson's is a hollow holiday gift. One year and about half the team cut theirselves. And I sliced myself. Well, right.
Host (possibly a podcaster or interviewer named Michael)
And if they didn't do it, then, let me tell you, when they're flipping it around and they're like, exactly. Well, hell, yeah. Thank you for your time, man. And thank you for making the travel up.
Caleb
Oh, thanks for having me. Really appreciate it.
Host (possibly a podcaster or interviewer named Michael)
Marketing is hard, but I'll tell you a little secret. It doesn't have to be. Let me point something out. You're listening to a podcast right now and it's great.
Caleb
You love the host.
Host (possibly a podcaster or interviewer named Michael)
You seek it out and download it. You listen to it while driving, working out, cooking, even going to the bathroom. Podcasts are a pretty close companion. And this is a podcast ad. Did I get your attention? You can reach great listeners like yourself with podcast advertising from Libsyn Ads. Choose from hundreds of top podcasts offering host endorsements, or run a pre produced ad like this one across thousands of shows. To reach your target audience in their favorite podcasts with Libsyn Ads, go to Libsyn ads.com that's L I B S Y N ads.com today.
Date: February 2, 2026
Host: Andy Stumpf
Guest: Caleb Gilbert
Length: Approx. 2 hrs 40 min
This episode features Caleb Gilbert, an executive protection professional with decades of experience, discussing the escalating nature of violence—particularly high-profile attacks and security in the current climate. Host Andy Stumpf and Caleb reflect on recent assassinations, breakdowns in security protocols, how the nature of violence has changed, as well as practical advice on personal and digital security for both high-net-worth individuals and everyday people.
The conversation draws on Caleb's background in Hollywood and Silicon Valley, the transition to entrepreneurship, and his philosophy on risk, personal success, and living a fulfilled life in a dangerous world.
| Timestamp | Speaker | Quote | |-----------|---------|-------| | 04:03 | Caleb | "There's no legal way for someone in the private sector to cover all the bases of risk..." | 15:49 | Caleb | "I've never seen the thin barrier to violence that we're seeing today." | 19:47 | Caleb | "Use a combination of tools... you increase your ability to get your protectee off the X." | 21:57 | Caleb | "Do I want to put my team in harm's way or do we do a full stop?" | 47:38 | Caleb | "...10, 20 billion dollars who nobody knows...other than the fact they have six knuckle draggers walking with them." | 76:35 | Caleb | "But they do have something called intuition...and that same level of understanding is something that we can all put into play." | 80:58 | Andy | "Everything is fine until it's not. If you can really flatten that curve between everything being fine and not being fine...you have time and distance." | 99:08 | Host | "Talk about leverage on a parent. My goodness...there’s no vocabulary to describe what you would do." | 134:51 | Caleb | "At the end of the day, if we just remember we’re all humans...I think we just need a reality check as a nation." | 140:18 | Caleb | "My favorite weapon is truth... that pursuit in and of itself is kind of a distillation process for me." | 104:17 | Caleb | "I don't ever want to be worth more than $20 million..." | 125:47 | Caleb | "As I've achieved different milestones in my life, I want to maintain that cognitive awareness that it's not all about money, it's not all about the experience…it’s about the people around you."
The episode is candid, storytelling-driven, and at times rawly honest. Both speakers use personal anecdotes, dry humor, occasionally gritty language, and a relentlessly practical lens for both professional and everyday security.
Caleb’s closing: Direct gratitude for the audience, veterans, and the reality that those who serve enable both his world and others.
Andy reflects on the shared challenge of living ethically, managing risk, and finding meaning beyond status or money.
For more:
Follow Caleb at White Glove Security and connect with host Andy Stumpf through Cleared Hot.
This summary excludes all advertisements, intros/outros, and only covers substantive content of the podcast.