Scaling Without Sacrificing Quality with Lindsey Pleasant artwork

Scaling Without Sacrificing Quality with Lindsey Pleasant

The Short Term Show

July 15, 2026

Avery is joined by Lindsey Pleasant, founder of Hostie Vacation Rentals, to discuss how she built one of the largest short term rental management companies in rural Texas by focusing on exceptional hospitality and operational excellence.
Speakers: Avery Carl, Lindsey Pleasant

Topics: Investing, Business, Education, How To

**SPEAKER_2** (0:05)
Welcome to The Short Term Show, the show about short term rentals and long term wealth, with real property owners hosting real properties who are crushing it in the vacation and short term rental space. And here's your host, Avery Carl.

**Avery Carl** (0:29)
Hey, y'all, welcome back to another episode of The Short Term Show. Ignore my sunburn if you're watching this on YouTube.
Struggle bus this week.
We have a really, really cool guest today. Her name is Lindsey Pleasant. She is a short term rental property manager and investor in Round Top, Texas, which we have not talked about yet in the five years and hundreds of episodes that we've done here on The Short Term Show. So really excited to talk to her. And guys, just want to remind you real quick, for those of you out there in the world listening to us, that The Short Term Shop, we are a team of real estate agents, the top team of real estate agents actually, in the short term rental space. So if you want to buy a short term rental in any of the 20 markets that we work in, we would be super happy to help you do that. Just reminding you because somebody came up to me in the parking lot of Buc-E's and said how much they love the podcast and that they had just bought a house with a different agent in a market that we're in. So I want to just make sure you guys know, we're here for you, we're happy to help. Anyway, it's not about me today, it's about Lindsey. How's it going, Lindsey?

**Lindsey Pleasant** (1:29)
Good, how are you?

**Avery Carl** (1:31)
I am doing awesome. So guys, I met Lindsey because I did a few YouTube episodes last year where I walked through people's short term rentals and talked about the different things that were cool about them. And I walked through, I put a, I think I've made a post on Instagram and said, I'm gonna be in Texas, I need some short term rentals to walk through. And she had one in Wimberley, which is probably, I would say my favorite place in Texas. Number two would be Austin, but Austin of 2006, not Austin today.
And anyway, this house was so nice. Actually, Lindsey, if that seller, that person ever decides to sell, please let me know, because I will buy it.

**Lindsey Pleasant** (2:11)
Okay. It was so great.

**Avery Carl** (2:13)
And one of the things that I noticed when I'm walking around properties that are managed by property managers, at least down here, some of the bigger ones, it's like, man, these are beat up, these are dirty. And this house was immaculate. It just looked like somebody's vacation home that nobody ever stayed in. So I'm really curious to talk to Lindsey today because how do you do that? That seems to be the code that property managers can't crack to make it feel like a vacation home and not just like a turn and burn property.

**Lindsey Pleasant** (2:45)
Right.

**Avery Carl** (2:46)
Yeah.

**Lindsey Pleasant** (2:48)
So I think that when I started Hostie, I knew that we had to be a portfolio of homes that were just very high-end. You're going to attract a different type of client.
They're going to take care of the home.
But also having the standards for your operations. I think a lot of property managers try and scale, scale, scale. And then they have like 500 homes with lack of operations on the cleaning side, on just the overall management. And so I think as we have scaled from zero to now 80 properties, every single home we take on, we make sure that it fits all the criteria. We have to make sure that the owners are under the impression that when they come stay at their property, if they come even for a day, that it's essentially like a hotel. So every time you leave, regardless of how long you're staying, if it's just for a day, you have to make sure that those properties are prepared and ready for the next guest. Because I think we run such a professional operation that a lot of property managers that I've seen in the past don't really take things as seriously as we do. And it's such an interesting industry and division of business that a lot of people wouldn't take serious. And so anyway, just for us having those standards upfront of how we're gonna run the business, every single property and every property owner have to understand that we do things a little over the top.
Because a lot of our homeowners have second homes in Aspen or Florida. And so they have property managers. So they've dealt with them in the past. And so every single time an owner comes to us after having a property manager somewhere else, they're like, wow, you guys really do things differently. I'm like, well, I think that should be the standard. I think vacation rentals nowadays have such a bad rap just because especially with property managers, people don't pick up the phone, they don't do what they say they're going to do. And cleanliness, I think, is one of the top priorities. So we've really been able to hone in on that and perfect that as we scale.

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