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Wealthy Way

Why Average Short-Term Rentals Fail (and What Actually Wins)

Wealthy Way

Ryan Pineda

Entrepreneurship, Business

4.82.1K Ratings

🗓️ 18 December 2025

⏱️ 9 minutes

🧾️ Download transcript

Summary

Send us a text From long-term rentals to building top-performing short-term properties, this conversation breaks down why “average” no longer works in today’s market. We unpack how super properties outperform, why design and positioning matter more than price, and how treating real estate as a long-term wealth tool not a lifestyle flex... changes everything. Learn how to invest in real estate with the Cashflow 2.0 System! Your business in a box with 1:1 coaching, motivated seller leads,...

Transcript

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0:00.0

So I've been in real estate.

0:01.8

Gosh, I bought my first duplex in Bakersfield in 1996.

0:06.1

I've done commercial.

0:07.2

I've done multifamily.

0:08.0

I built the first gold lead certified building in Nashville back in the day.

0:14.4

But I was literally playing golf and my electrician.

0:17.8

We owned two-bedroom condos doing long-term rents in downtown Nashville. And he shows me, dude, I've been doing this Airbnb thing for like three or four months. And we were getting like $2,000 a month for a two-bedroom long-term back then in 2015. He's like, dude, I just made $7,000. I'm like, bullshit. You didn't make $7,000. And he's bring, next week, we play on Friday afternoons, right? Saturday mornings. He'd bring me the thing. After a couple of months, I'm like, I need to sell that. So my partner, Reg had already bought a place in Estes Park, Colorado, big house that we were vacation running, weren't really Airbnb or short term running. And then bought a condo in Destin. The first one me and my wife bought was in 2015, and we bought it down at the beach in Gulf Shores, Alabama.

0:58.2

So we got out of the long-term rents in Nashville and then moved down to do short-term rentals.

1:03.2

When COVID hit, that's when we accelerated.

1:06.6

So we had two at that time.

1:09.2

And then I flipped 17 properties in Gulf Shores, Alabama, just Gulf Shores. Yeah. Taking a page out of your book, made about $3 million. I think my friend Ricky Cruz out there. Yeah. And then I bought and I've had about 27 properties down there. Then I just started diversifying around the country. And what I learned is, you know, average doesn't work, right? So Pace talked about on him and I did his podcast and he talked about, he learned why he failed when he got into short-term rentals in Atlanta because he bought average $350,000 properties, you know, sub two. Then he would have his people furnish them through IKEA and it doesn't stand out. Yeah, it's just a generic house. So I do something that's called building a super property. A super property is the top performing property in the market. To do that, you've got to invest more money. You've got to do better underwriting. But most importantly, you have to put in the work, right? So you've done how many flips? Thousands. Yeah. Right. It's adding movie

2:03.6

theaters. It's adding saunas. It's doing the stuff that's going to be attractive and creating the

2:08.1

destination, if that makes sense, to where people aren't just coming to Vegas to go to the strip.

2:12.4

They want to come to my short-term rental because I've got pickleball courts and cold plunges

2:16.1

and saunas and all the stuff

2:18.4

that they're looking for into that specific buyer persona. Does that make sense? Yeah. So that's,

2:23.4

by the way, that's what I've heard from pretty much any short or Airbnb guy these days is like,

2:27.8

bro, unless it's just the best, you're going to get crushed. If you, I'll use an old school term, if you're not the Mac Daddy, you know, Airbnb,

2:38.0

you 100% will get crushed.

2:39.3

And that's kind of what I coined the term and trademark super properties.

2:42.3

That's kind of my 10x deal is super properties, wrote the book about it, and that's what me

2:48.1

and my wife have specialized in.

...

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