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Ep 69: Building, Scaling and Selling a Short-Term Rental Business, with Brittany Blackman artwork

Ep 69: Building, Scaling and Selling a Short-Term Rental Business, with Brittany Blackman

Superhosts Down Under with Silvia and Ray

October 18, 2026

Brittany Blackman spent 14 years in vacation rental property management in Destin, Florida. She helped grow one company from 42 properties to 115, then started Breathe Easy Rentals from scratch, built it to 30 properties in four years and sold it in 2024.

Speakers Ray Yee, Brittany Blackman, Silvia

TopicsEntrepreneurshipBusiness

Ray Yee (0:00)

Great, welcome to this week's episode of Superhosts Down Under. This week, we have Brittany joining our show. Welcome to the show, Brittany.

Brittany Blackman (0:07)

Hello.

Silvia (0:10)

Welcome, Brittany.

Ray Yee (0:13)

Before we get into your story, let's talk about our weekly topic. Silvia, what is our topic for this week?

Silvia (0:20)

Well, I thought we could unpack the process of claiming money from guests for extra cleaning or property damage. In particular, how to navigate the scenarios where the guest denies responsibility and refuses to pay.

I've never had a problem with requesting money. It doesn't happen very often for me, but I'll give you an example which was only a couple of weeks ago, when one of my guests was out celebrating her birthday, and she came back and obviously, she had too much to drink.

Well, that's what she tells me. It was because she had too much to drink. I wasn't being judgy about that. She vomited in the bedroom and it soiled the top sheet, the fitted sheet, and it went through to the mattress protector. I was very glad I had a mattress protector. Anyway, she had put all the sheets in the washing machine, so I didn't have to touch it, and she said, look, I'll pay for whatever.

I put it through a wash. The stains were still there. So then I had to use a bleach spray and wash them all again, like just on the marks. I used a bleach spray, and that worked. So it was two sets of washing and fiddling around. And so I put in a claim with request for money from the guest.

It was after she had left because she did it on the morning that she was leaving. And she paid within minutes. Like I immediately got the email back saying that she had paid. So that was quite a simple scenario in the sense of claiming money. She accepted responsibility. But then a friend of mine, a host, she had a situation. Now, it was the entire home, three bedroom home. There were, I think, three families staying with children. And there was, when the cleaner came in, there was additional cleaning. Some of the toys had been damaged. What else did she tell me? Oh, yeah, that's right, the bean bag. There was a bean bag and all the beans had come out and they were everywhere throughout the house. So she put in a claim via what her cleaner had told her. And, but the guest refused to pay. He said he didn't agree with the assessment from the cleaner that, because the cleaner said she had to go through and wash all the pots and pans all over again because they weren't clean enough. And he said they were. And so he refused. And then it was a process of taking it through to then being assessed by Airbnb. And so that's, that's another process because with that, what I sort of found out, and Ray, you've told me that you've had experiences with this, so we can hear about your experiences, but you then need to provide receipts. So the cleaner had provided a receipt for, sorry, an invoice for extra cleaning. So you have to supply those, you have to supply photos before and after, time stamped, and all of that. And then it gets assessed. What I found really interesting because I always thought, okay, so if the guest doesn't pay, AirCover will pay, and that's all about it.

It does get a little bit more involved than that in the vaccines, which I read up about that if the guest refuses to pay, then as we said, you need to give all documentation, Airbnb will assess it. If they agree with you, and all this has to be done within two weeks, 14 days. If Airbnb agrees with you, then they pay the host, or agrees with the host, and then they chase up the money from the guest. If they disagree, then obviously, you won't get paid and they look at the age of the item. If you're complaining, it's being destroyed or damaged.

It was all very interesting when I looked into that. Ray, I know you've had experiences.

Ray Yee (5:05)

Yes, and my place is an entire space. It's a unit, and so I don't get to, I don't talk to the guests during their stay because I also use a co-host. And so there's a few layers of separation from being able to sort things out in the moment of things happening. And so, which is challenging actually, both for feedback and meeting their needs, but also when things break, I have to go between my co-host and the guest. And I think those disagreements happen more often because the guests experienced it by themselves in the home without anyone seeing. And we don't have a relationship as closely as when you're interacting with them in the unit.

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