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Real Estate Investing for Cash Flow with Kevin Bupp

The “Captive Insurance” for Landlords That Pays You to Protect Your Property

Real Estate Investing for Cash Flow with Kevin Bupp

Kevin Bupp

Business, Investing, Education

4.8679 Ratings

🗓️ 25 May 2026

⏱️ 33 minutes

🧾️ Download transcript

Summary

Landlord insurance has slowly become a major cost for many operators. After 2020, insurance prices began to rise rapidly, and making a claim became even harder when disaster struck. For many operators, it feels like throwing tens of thousands, if not hundreds of thousands of dollars, into the furnace every year, for a benefit you’ll rarely use. And who stands to profit from it? Insurance companies. But an overlooked insurance structure is becoming increasingly common among operators, saving them 20% on their premium costs and sometimes even making them a profit on insuring their properties.  Nicolas Lares, CEO of Insur3Tech, worked as an insurance agent for years before ever hearing of "captive insurance” or “risk pooling.” When the small businesses he was tasked with insuring were being priced out so badly they could barely operate, he began building alternative structures, all federally backstopped, but without the middlemen.  Now, Nicolas’s clients are profiting from their insurance investment, getting premiums on average 20% lower, and getting claims paid out in a matter of days, not weeks.  How would your NOI improve if one of your greatest costs became a profit driver? Insights from today’s episode: The “risk pooling” insurance model that drops your insurance cost significantly  How to get paid to pay your premium (the insurance company actually pays Nicolas’s clients) Who can (and should) opt for "captive insurance” instead of the traditional route   The real reason why your landlord insurance premium is so high (it’s making insurance companies billions) How do these alternative providers make money without baking in a profit margin?  — Connect with Nicolas on LinkedIn Insur3Tech Recommended Resources: Accredited Investors, you’re invited to Join the Cash Flow Investor Club to learn how you can partner with Kevin Bupp on current and upcoming opportunities to create passive cash flow and build wealth. Join the Club! If you’re a high-net-worth investor with capital to deploy in the next 12 months and you want to build passive income and wealth with a trusted partner, go to InvestWithKB.com for opportunities to invest in real estate projects alongside Kevin and his team.  Looking for the ultimate guide to passive investing? Grab a copy of my latest book, The Cash Flow Investor at KevinBupp.com.  Tap into a wealth of free information on Commercial Real Estate Investing by listening to past podcast episodes at KevinBupp.com/Podcast. 00:00 Insurance Is Broken in 2026 03:40 They're Making Billions off of Us 06:19 Cutting Out the Middlemen 11:58 The Insurance "Pool" Structure 16:23 Getting Paid to Insure Your Property 19:33 Who Can (and Should) Do This? 26:28 How Do THESE Providers Make Money? 31:15 Work with Nicolas!

Transcript

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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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