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Caleb Gilbert

Caleb Gilbert

Founder & CEO of White Glove Protection Group with 25+ years protecting Fortune 200 executives, celebrities, and UHNW families globally.

Aug 14, 2026

20:15
Mm.
20:15
And when we started White Glove, literally I left Salesforce, corporate America, you know, Fortune 200 company, um, and literally had no safety net.
20:26
Literally put everything on the line, invested absolutely everything, all of my real estate, leveraged it fully, uh, all of 401k, you know, all that.
20:36
And I, I can't necessarily say that I would recommend that to, to, to an entrepreneur to put it all on the line, but the reason I put everything on the line w- was, was because two main things.
20:51
A, I believed in the product.
20:52
I knew that the market needed what we were bringing to market because I'd, you know, worked in this on the corporate side of things as the end user for decades, right? So I knew that the market needed it.
21:04
I also knew that the companies that were, were servicing the market were under-delivering to the capacity that we could deliver.

10 MINS LATER

30:48
Mm-hmm.
50:10
So what was the, so what was one of the, if you're allowed to talk about like one of the crazy experience, like on the job experiences?
50:18
Oh boy, I have a 20 year rule on most things.
50:20
So we're, we're, we're coming up to the expiration date on some of them, but, um, you know, it's more of the surreal aspects of being part of historical gatherings, historical signings, things that changed the course of history from the private sector side that have really like are special in my mind type of deal.
50:44
But I mean, you think of any large event in corporate America over the last 20 years, whether it's you know public companies going public you know most valuable companies in the world you know things like that that we get to be a part of like it's wild you know that that and then my nine years is with celebrities you're you're in the middle of the headlines all the time you know it's like oh xyz is getting married in this location there you know and it's like you see me peeking over the castle wall you know like you see my shoe you know hold the door open like it's it's fun from that perspective but it's completely different in hollywood as a celebrity protection agent than in silicon valley and i didn't even realize that you know in my transition because i transitioned because i wanted more stability where being a full-time employee of of the family offices and corporations um But again, it's like you look at major events like World Economic Forum in Davos.
51:41
Every year, most powerful people in the government and private sector gather.
51:47
I know that place like the back of my hand because me and my teams have been there for well over a decade and a half.
51:54
And just the things that go on there and the conversations that take place, just incredible.

26 MINS LATER

78:19
What would you tell them?

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