A Lot Has Gone Wrong With His Rentals…But He Still Thinks Real Estate Is Worth It With Ari Rubin (Ep 573)

Rental Income Podcast With Dan Lane

Rental Income Podcast

Business, Investing, Entrepreneurship

4.8 • 836 Ratings

🗓️ 12 May 2026

⏱️ 23 minutes

🔗️ Recording | iTunes | RSS

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Summary

Ari Rubin has been investing in rental properties long enough to know that eventually, something is going to go wrong. Really wrong. But despite dealing with nightmare situations that would make a lot of investors quit, Ari says it’s all been worth it.

On this episode, Ari shares some of the craziest situations he’s dealt with as a landlord and investor. He talks about a contractor he didn’t hire who broke into one of his properties, demolished the kitchen, and planned to move into the house himself. He also shares the story of a “professional tenant” who moved in and never paid rent, and a property where he spent $60,000 on renovations only to discover a major foundation issue that caused the entire house to shift just six months later.

We also talk about a property Ari almost bought that had a dangerously unsafe deck built by the tenant, so bad that contractors didn’t even want to tear it down.

Ari shares another unbelievable tenant story involving someone who turned the backyard into a giant litter box.

Throughout the episode, Ari explains how he handled these situations, what he learned from them, and why he still believes rental properties are one of the best ways to build wealth despite all the challenges.

https://rentalincomepodcast.com/episode573

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Transcript

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0:00.0	inspiring interviews with today's top landlords this is the rental income podcast and now
0:08.4	dan lane when you own rental properties it's just a matter of time before something really bad
0:14.2	happens that's going to cause you headaches or cost you money and are you've been in a lot of these situations.
0:22.5	I mean, we totally have, Dan, and at the end of the day, it's still worth it.
0:26.7	It's a great, if you've got the will and you've got a long-term investment horizon and you've
0:33.8	got the skill, you know, it's definitely worth the hassle.
0:38.0	On the podcast today, Ari's going to share some details about some of the horrible tenants he's
0:43.0	had and some of the difficult situations he's been through.
0:46.8	And what I think is great is that none of these stories end with him selling all of his
0:52.2	properties and getting out of the business. He's worked his way
0:55.9	through every situation. And on the show today, we're going to see what happened and how Ari survived.
1:02.3	Joining us on the show today from San Francisco is Ari Rubin. We'll take a quick break to thank
1:08.0	our sponsors. We'll come right back and we'll talk to Ari.
1:11.5	It's a lot of work to find a really good rental property. And when you actually find that
1:15.7	property, you want to make sure you're working with a lender that can get that loan closed.
1:20.3	The lender that I recommend is Chaley Ridge from Ridge Lending Group. She's a nationwide lender
1:26.3	and her specialty is helping investors finance rental properties.
1:30.7	She has a ton of loan programs, and she can find something customized to you for your situation.
1:36.4	If you want to find out more or you're ready to get started today, just go to RidgeLendinggroup.com.
1:42.0	That's R-I-D-G-E lending group.com. NMLS 42056. If you're a real
1:49.3	estate investor, you already know deals don't wait. That perfect property hits the market.
1:55.2	A contractor gives you a short window or a big repair shows up at the worst possible time, the investors that move fast
	...

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