Chapter 1: What do high net worth individuals typically want from personal protection services?
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?
95% of what I do now is educational to be perfectly honest. Like, like either, either something's gone wrong or I need to explain something to them.
Okay.
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 or 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 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 time it's like hey your team's doing amazing you know we just had that last week you know which was which is really cool yeah well it's better than the other call absolutely um
What is the relationship you have with the woman who first reached out? Does she work for you? Is she a booking agent? No, just booking agent. Okay. Yeah. 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. Yeah.
It took us a little bit to sit down together, but here we are. Here we are. So what I don't ever want to do is ever Monday 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.
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? 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.
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Chapter 2: How has Caleb Gilbert's role in security changed over the years?
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 don't know what they would say. He was polarizing. Absolutely. Yeah, we can leave it at that. He was polarizing. How do you start this?
I mean, obviously the prep starts weeks in advance, doing 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 reviewed it.
Now, as far as day of, there's 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... This isn't a large stadium, you know? Yeah.
We're talking about a... It's actually really tiny. I mean, obviously, this picture is from above, so things will look smaller, but... the POV, the camera POVs, it makes it look like it was Petco Stadium in San Diego, and it wasn't.
Right, yeah, exactly. The reality of the situation 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 no legal way. You look at typical assets, let's say for a POTUS movement or something like that. 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 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 in speaking to crowds that are larger than this.
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Chapter 3: What complexities are involved in protecting public figures in today's environment?
The level, the personal level of interaction that protectees felt, that resonated through the entire world. People with a protective posture that have been hesitant to add to the team or have someone beyond their residential coverage, have somebody in the field actually doing close protection, people all of a sudden became aware that, wow, my risks are actually real. I like to say that
both, both the UHC and, and Charlie Kirk and, you know, New York tower incident. Really UHC?
United healthcare CEO, uh, Thompson. Did he have a protective detail of any kind or was he solo mission out there? Just Jason boarding it.
Uh, he had a protective detail on the books. We know locally, I can't talk about what, what, um, was that day, um, because I wasn't there. Okay. Um, but I do know that there was security, um, certainly inside the venue, you know, from the hotel security, from, uh, From working many events like that, there's absolutely a level of security that's there.
It's just whether it's focused on the area that it took place.
Yeah, if you go outside the bubble.
Well, and the reality of the situation is 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 I'm not saying this, by the way, is in any way an influencing factor on the Thompson murder. But you take 6 o'clock in the morning in New York City on a frigid December morning
And you have people out there. You might have, if it was warmer weather, you might have had an advance 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, a site agent that would have been outside for the arrival.
You may not have, you know, but. The chances of somebody going out in the cold and waiting for a scheduled or unscheduled arrival from a protectee, that's pretty low, right?
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Chapter 4: How can individuals improve their personal security in a digital age?
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 probably center mass and got lucky. I hate to use that term. 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 I'm like,
That was the signal.
Do we have to do that? Yeah. 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 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. 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. And maybe they are, right?
Depending on what your definition is or you're the global cabal that meets on every other Thursday and in your robes with chicken heads in your pockets or whatever it is. So it was so... God, it 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.
So I had to have some very real conversations with my kids I didn't think I was ever going to. It was wild.
Yeah, that's a heavy load for a kid. You know, it's a heavy load for anybody.
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Chapter 5: What does 'thumb sideways' mean in threat assessment?
We call that a thumb sideways. I am, I have three quarters. Yeah, you're almost dipping, almost dipping. Like somebody that raises the index of suspicion just because something's off, right? It could be the way they look, it could be something, it could be nothing.
That's 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 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. No. But also don't push that aside. It's a data point. Exactly.
And you'll hear people, well, you're, you're judging that person. Yes. To a degree. Are you, are you profiling them? Like, I don't, I mean, like we don't have to get crazy with these magic words that are always associated with negativity. I'm paying attention. What I saw makes me feel a certain way. Does that mean that I'm right? No. Yeah. Does that mean that I should ignore how I feel? No.
Let's find a middle ground.
Yeah. Yeah, exactly.
Like you said, it's like we're no longer at the thumbs up, the dial's coming a little bit the other direction.
Yeah, yeah. And the difference between thumbs up and thumbs sideways could just be everybody else in the room is wearing a t-shirt and they're 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, oh, I'm going to pay a little extra attention to this individual. And then halfway through the night, you know, you see somebody that you
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Chapter 6: How can individuals improve their personal security?
has something egregious, something that, you know, a gun 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 incredibly complex relationship 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? Cause if you take and you're able to make that transition as a regular civilian, as a regular secretary or CEO, and, 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 these you know bad situations between somebody being close to an event and being part of an event God that time and distance is so important.
I don't think it's talked about My I'll tell a story my daughter won't appreciate. It's okay. She doesn't listen But this goes into people maybe absentmindedly drastically involving themselves in something that can get risky at a very nonlinear rate. Where everything is fine, 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, you have time and distance. 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 words would you use to describe my daughter's level of sass?
Oh. For going one to 10, it's like 11 or 12.
Yeah. Okay. So Michael and I are aligned very infrequently, but on this one, we agree. She's amazing. Lover to death. She's the best. And are you a parent? Yes. Okay. So you understand. Yeah. 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. Absolutely. 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. It was here in Kalispell. She's in her car. 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. Like go drive and go drive, start driving towards the police station.
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Chapter 7: What are the implications of digital footprints for personal safety?
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 that moment.
You don't know if just a quick little you're 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 hanging on and that snaps them or 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.
Yeah.
So I also think she might have cut this person off this whole story.
The rest of the story.
This entire story likely is based on her. driving ability, which if we were to again rate that, Michael, on a one to 10, 10 being good, she might be closer to a three. Senator O'Neill. 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. I'm like, never mind. Cut somebody off.
flips him 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
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 through my own. 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.
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Chapter 8: How can we balance financial success with personal fulfillment?
And my wife is like, what are you doing? I am managing our exposure because I don't know what this person is doing. Now, having said that, there's also tools that were being prepared.
Nothing wrong with being prepared.
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 to come like, the first thing I was going to do is separate my wife from the threat. Yeah. 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. My wife's just like, what is going on? I'm like, nothing. Then they have taken off. And then you have a choice. Do you want to chase them? Do you want to turn this into Michael's laughing? So you would have put in his glove box, he has a Batman mask.
He would have put that on and turned all of his lights off and gone whisper mode after this guy. Go Comic-Con after him. How many people would do that, though, right? They're like, that person wronged me.
Right.
I'm on. And then that's how you end up out of a car and in Montana, just about everybody has a gun. Yep. That's how a firearm or tool gets introduced into something. And the next thing you know, you go from having a normal night to a funeral.
Yep. Yep. Why?
Why?
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