Need creative ideas to fuck with someone who owes me money

I made a $25K private hard money loan to a guy in Jackson MS. He had an investment property he said needed a roof, and we set up the loan to be paid back in 1 year. I had some history with the guy prior to this, he had done a few really kind favors for me at different points. He had a good reputation and I trusted him.

For the last few months when I asked him how it was going he was slow to respond. Not the loan is delinquent and he said he was sick, then him mom was sick on close to death. He said is trying to sell the property.

The property is not listed for sale anywhere, and I had photos taken and its occupied. So I'm guessing the guy is rent skimming, collecting rent and then not paying on the mortgage. Similar to the Big Short. He doesn't know that I know this yet.

I can foreclose, and I will. But I feel like this guy needs to be taught a lesson. He's been around the Jackson MS real estate investing scene for decades. He has a big network, and I have the map of that network. He also has a real estate investing group with several hundred people in, which I was able to scrape the list of.

So what's my next move? My goal is not to optimize my financial return or how fast I get paid. My goal is to maximize how much I can fuck with this guy until he pays. Let's get creative here. Money is not an object and anything is on the table.

Have a 40 yard dumpster dropped off in the driveway and send him an email that the roof is coming off next week if he doesnt restart payment.

Semmes expensive for a roof got mine done for 13k six years ago and that included new wood. I hope you have something in writing. Put him in collections. Maybe an attorney would take it on contingency. Mechanics lien

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Originally Posted by Pablo

Have a 40 yard dumpster dropped off in the driveway and send him an email that the roof is coming off next week if he doesnt restart payment.

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That shits gonna cost like 700

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Originally Posted by FRANKRIZZO

Semmes expensive for a roof got mine done for 13k six years ago and that included new wood. I hope you have something in writing. Put him in collections. Maybe an attorney would take it on contingency. Mechanics lien

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everything construction related is up 50 percent in the last 6 years.

You had good timing getting your roof done when you did.

It would cost you at least 20k today. Unless you find some mexicans to do it.

They did a really good job tore and replaced in 2 days I am sure much higher today especially with new wood. I had bathroom remodeled recently cost 18k did nice job but yes things are going way way up. Doing kitchen next expecting 40 thousand. Attorney with contingency best route I can see for op worst case has to pay fees best gets paid in full. Actually it was way more then six years ago way way more

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Originally Posted by Pablo

Have a 40 yard dumpster dropped off in the driveway and send him an email that the roof is coming off next week if he doesnt restart payment.

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Not a bad idea. But I don't really want to mess with the renters. Ideally if he's rent skimming they could just send the rent to me to start paying me back. I hired someone from Craiglist to deliver a letter tomorrow letting the renters know their landlord isn't paying the mortgage and there is going to be a foreclosure and they'll get tossed. Hopefully that lights a fire.

Or maybe order some cheap dirt / rocks / landscaping stuff and have it dumped on the lawn of his house?

A roof shouldn't cost $25K. I think he was supposed to be doing some other work too, can't remember.

I wouldn't do nothing crazy, times are hard and you don't wanna pick up charges or a lawsuit.

Sounds like a job for Tankazoo

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Originally Posted by Orko

I wouldn't do nothing crazy, times are hard and you don't wanna pick up charges or a lawsuit.

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I'm not going to go crazy and put myself at risk. I want the guy to regret being a scumbag, and have some funny stories to discourage future borrowers from trying something like this.

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Originally Posted by Orko

I wouldn't do nothing crazy, times are hard and you don't wanna pick up charges or a lawsuit.

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:lol2

or catch a bullet in head

Put a Lien on the property for the amount of the roof if/when sold, you'll get your money

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Originally Posted by Buck Nasty

I made a $25K private hard money loan to a guy in Jackson MS. He had an investment property he said needed a roof, and we set up the loan to be paid back in 1 year. I had some history with the guy prior to this, he had done a few really kind favors for me at different points. He had a good reputation and I trusted him.

For the last few months when I asked him how it was going he was slow to respond. Not the loan is delinquent and he said he was sick, then him mom was sick on close to death. He said is trying to sell the property.

The property is not listed for sale anywhere, and I had photos taken and its occupied. So I'm guessing the guy is rent skimming, collecting rent and then not paying on the mortgage. Similar to the Big Short. He doesn't know that I know this yet.

I can foreclose, and I will. But I feel like this guy needs to be taught a lesson. He's been around the Jackson MS real estate investing scene for decades. He has a big network, and I have the map of that network. He also has a real estate investing group with several hundred people in, which I was able to scrape the list of.

So what's my next move? My goal is not to optimize my financial return or how fast I get paid. My goal is to maximize how much I can fuck with this guy until he pays. Let's get creative here. Money is not an object and anything is on the table.

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Are you 100% sure he really owns the property?

Many scammers pretend to own income property or other businesses, solicit loans for "improvements", and then spend the money on other things.

There are also semi-scams where the self-identified landlord is actually really the owner, but in reality is also in tremendous financial distress, and is on the verge of losing the property. The loan for "improvements" is often just buying time to prevent foreclosure.

Most people don't scam for fun. Anyone taking a loan like $25k and dodging payback is obviously broke, and if he could solve this by simply refinancing, he probably would.

I would first verify that he's really the owner. Then you might want to look into whether this guy actually replaced the roof, and if the $25k was entirely spent on the roof even if it was replaced.