BIGGEST RISK with Brent Kesler episode artwork

EPISODE · Nov 25, 2025 · 5 MIN

BIGGEST RISK with Brent Kesler

from Commercial Real Estate Pro Network · host J Darrin Gross

J Darrin Gross And so if you're willing, I'd like to ask you. Brent Kesler, what is the biggest risk?   Brent Kessler Yeah, well, let me answer it a couple different ways on there. But so as far as a risk, okay, as far as in our business, and what we do when you have this type of policy, I tell people all the time, there is no risk at all, because nobody's ever lost money in a whole life insurance policy. But then I stop, and I say, wait a minute, there is one risk. The risk is you, the risk is you the client and how you use the policy. So you're the only one that can screw this up. You are the only one that can screw this up. The insurance company is not going to screw it up. So who do you know better than you. So you're the risk factor now, as far as a risk also when I because, again, I invest in in properties. I have short term rentals, long term rentals, Airbnbs, vrbos. I have raw land. And I do a lot of private lending in the real estate world. I lend to individuals for houses, even to cars. And I also lend into big property developments and to big communities, to real estate developers where I'm providing a portion of their financing to build these big developments, like we got one right now going in Covington, Georgia, another one in Fort Collins, Colorado, where these are big housing projects, right? Well, look, I've been doing this quite a long time, and I've learned a lot as I've gone through this, and the one thing I've done to really lower the risk, because anytime you invest money, you invest money, you are assuming some sort of a risk, okay? So that's why the insurance policy that I talk about is not, is, is just not an investment, because you can't lose money. See an investment, it can go up or it could go down, right? So there's a risk involved. But I would say to avoid risk, that's your greatest at right, just as far as, especially as far as in the real estate world, is to be in first position in everything that you do, be in first position. How do I know that? Well, I've been in second position. Did it always work out? No, as a matter of fact, and I guess if I would have known you were going to ask me this question, I would have wore this shirt that I have, and it says, if you're not first, you're last. That's what my T shirt says. If you're not first, you're last. So I protect myself by being in first position. And I want the collateral on any money that I'm loaning. I want that collateral to be, I want that collateral to be at least equal to, if not greater than, the loan amount that I'm actually loaning. Now I might have to spend some time and energy going out and chasing down and trying to get that or get the collateral, which is going to be a pain in the butt, but you would much rather have the collateral than not have it. One more thing I want to point out from my own personal experience. A couple years ago, we experienced hurricane Ian. Part of my portfolio of rental property is in Captiva Island, Florida, North Captiva Florida. I own a property. If you go out and you take a look at it, just for a rental it's called Captiva Beach, sunset.com beautiful property sits right on the Gulf of Mexico, and it sleeps 18 people. It's all short term rental. It gets about 350,000 a year in the annual rental. I pay back in 21 I paid 1,760,000 for the property. I'm about to sell it. I'm about to sell it for a very discounted rate, because I'm selling it to my son, who is a property manager, and he's buying it for $2.4 million in January, he's getting a great discounted rate, even though I paid one, seven, selling it for two, four, I did okay. Got all the rental income on top of that when Hurricane Ian came through. So I had insurance on the property. It didn't flood, but it had wind damage. And let me just tell you, if you live in Florida, you guys know you probably don't even want to buy flood insurance because it's so expensive. And if it and it does, and it's a lot of limitations of what it covers, but I had wind insurance on that property. It took me a while, but I almost got a million dollars on my insurance claim from the damage on that property. Now, a lot of people think, Wow, a million dollars. You got a million dollars from the property. Well, that property was shut down for about two years, which means it couldn't be rented. I had to do all the renovations. Had to pay for that, had to pay for that all out of pocket, because it took a while for the insurance company to pay on that property. So did I really make money? No, I didn't make money. I did okay, but I didn't make money because I lost all that rental income. But, but I but, but, but I do think my lucky stars that I had insurance on that property, because if not, I would have taken all of that hit. https://themoneymultiplier.com/ https://themoneymultiplier.com/brent-kesler  

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This episode was published on November 25, 2025.

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J Darrin Gross And so if you're willing, I'd like to ask you. Brent Kesler, what is the biggest risk?   Brent Kessler Yeah, well, let me answer it a couple different ways on there. But so as far as a risk, okay, as far as in our business, and what...

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