Personal Guarantees Change Everything
Guarantees can override carefully built asset protection.
Real Estate Development: Land to Legacy
Aug 29, 2026 · 48 min · 12 segments
The time to protect a project is before a claim arrives. Attorney and Certified Financial Planner™ practitioner Matthew Meredith joins Eugene Gershman to explain how real estate owners can reduce…
Matthew MeredithGuest
Eugene GershmanHost
Yeah, I'm also seeing a lot of folks in the last couple of years been talking about sub-2 transactions.

So it's a, they are buying property subject to the, so sub-2 is subject to, subject to the original debt assignment.

Then they are acquiring their property by... assigning the mortgage payments to their new entity and then you know making an investment that way so in the future then they would sell it and then capture the difference and since now interest rates are much higher than they were a few years ago they could you know make a lot of money on that arbitrage Well, the trick here is that they are trying to transfer it into a trust to make it hidden from the lender that they're in reality changing the owners.

And then through that trust, they're creating this structure to circumvent it and Some are successful, but some are falling victims of that flaw in the structure, because if somehow the lender finds out, maybe the original owner got upset, maybe somebody else got upset and told them, maybe they audited something, and then all of a sudden they have to pay off that mortgage in a very short period of time.

You just gave me the most beautiful idea, and I probably shouldn't say it on a podcast.

But that would be how you get out of it, would it not be? Hey, word on the street, lender, is that somebody put this company, that might break the deal for you.

How long is this person going to live for? What happens if they destroy the house and how bad does it get? Because now they're no longer owners, they're renters.

I'm fascinated by all the different types of loans they have and all these things that are coming out now.

Where you just, you get the loan based off of what your rent's going to be.

Now they're telling me we're able to loan based off of the equity in your other rental properties.

And you sit back and you start saying that real estate is such a fascinating thing.

Yeah, I'm also seeing a lot of folks in the last couple of years been talking about sub-2 transactions.

So it's a, they are buying property subject to the, so sub-2 is subject to, subject to the original debt assignment.

Then they are acquiring their property by... assigning the mortgage payments to their new entity and then you know making an investment that way so in the future then they would sell it and then capture the difference and since now interest rates are much higher than they were a few years ago they could you know make a lot of money on that arbitrage Well, the trick here is that they are trying to transfer it into a trust to make it hidden from the lender that they're in reality changing the owners.

And then through that trust, they're creating this structure to circumvent it and Some are successful, but some are falling victims of that flaw in the structure, because if somehow the lender finds out, maybe the original owner got upset, maybe somebody else got upset and told them, maybe they audited something, and then all of a sudden they have to pay off that mortgage in a very short period of time.

You just gave me the most beautiful idea, and I probably shouldn't say it on a podcast.

But that would be how you get out of it, would it not be? Hey, word on the street, lender, is that somebody put this company, that might break the deal for you.

How long is this person going to live for? What happens if they destroy the house and how bad does it get? Because now they're no longer owners, they're renters.

I'm fascinated by all the different types of loans they have and all these things that are coming out now.

Where you just, you get the loan based off of what your rent's going to be.

Now they're telling me we're able to loan based off of the equity in your other rental properties.

And you sit back and you start saying that real estate is such a fascinating thing.
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3 of 8
Personal Guarantees Change Everything
Guarantees can override carefully built asset protection.
When Death Freezes a Business
Death can freeze businesses without succession planning.
The Lawsuit That Comes Too Late
Protection starts before the first lawsuit arrives.
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