The “Captive Insurance” for Landlords That Pays You to Protect Your Property
Real Estate Investing for Cash Flow with Kevin Bupp
Kevin Bupp
4.8 • 679 Ratings
🗓️ 25 May 2026
⏱️ 33 minutes
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| 0:00.0 | The litmus test is if you're pissed off of writing an insurance check every year and not getting a return. |
| 0:04.7 | That's a good sign. |
| 0:05.6 | Everyone raises their hand, right? |
| 0:07.0 | Everybody knows how to play blackjack. |
| 0:08.6 | You show up to the casino. |
| 0:11.2 | You get a 21 at the table. |
| 0:13.7 | And the dealer takes your money and says, sorry, you did awesome. |
| 0:17.2 | You were perfect, but you lost. |
| 0:20.3 | Has this been an evolutionary process where things have |
| 0:23.0 | just continually gotten worse, you know, with the traditional model, or has it just always been |
| 0:28.2 | this way? I mean, I can only go back as far as, you know, I've been dealing with it as an adult, |
| 0:33.0 | but I mean, is this a systemic problem that's been going for decades and decades? |
| 0:40.8 | It's a process that, I say, has devolved over time, right? |
| 0:45.0 | When you go back to the history of insurance, why it was created for property insurance, |
| 0:50.8 | at least, it was really back in London in the 1600s when people lived in wooden frame homes and fires would essentially break out and burn down entire community. |
| 0:55.2 | So people, |
| 1:00.1 | what they did is they got together and said, hey guys, in order for us not to have to restart from scratch every time one of our homes burns down, let's put our money together in a fund. And in |
| 1:04.9 | the event that something goes wrong, we can essentially access that fund to rebuild our homes |
| 1:09.4 | together. Right. There was never a third party carrier involved that would come in and say, hey, if no one's home burned down, we're going to take all the money that's left in the bank account, give it to our shareholders, and reset from zero every year. Right? It was always, hey, if no one's home burned down, the money's there, great. We don't have to keep contributing to it, and we still have that safety blanket in the event that something goes wrong. |
| 1:30.7 | So what we're doing is essentially going back to how insurance was done before, where we're not resetting the bank account to zero every time. |
| 1:38.2 | We're not taking the money out, distributing it to third-party shareholders. |
| 1:41.6 | We're really going back to just essentially, right, pooling |
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