040: How to Turn STR Guests Into Loyal Customers | Matthew Orley
episodePreviously titled “How to Turn STR Guests Into Loyal Customers | Matthew Orley” — renamed by the publisher on Aug 3, 2026
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Why is owning the guest relationship more valuable than scaling unit count?
Everyone in short-term rentals is trying to scale their business. More units, more markets, more automation. But if the real advantage is not owning more homes, but owning the guest relationship. In this episode, I'm joined by Matthew Orley, CEO of Red Cottage, to talk about brand, loyalty, membership, direct bookings, and why human communication may become the strongest mode. In a world full of AI and automation. And if this conversation makes you rethink your own guest strategy, you can book a consultation with me through the link in the description. SGR Global Unlocked is supported by Breezeway. As guest expectations rise, standards tighten, and operational execution has become a key differentiator in short-term rentals, Breezeway provides technology designed to help professional operators.
providers deliver consistent property care. Safety and quality at scale. Thank you to Breezeway for supporting the professional evolution of our industry. Welcome back to STR Global Unlock. I'm Simon Lehman, and today Matt Orley, CEO of Red Cottage, a curated brand of unique stays across the US Northeast. What's different is the order he did it in. Guest first, owner second. We're talking about why brand and owning the guest might be the most underrated moat in this industry, what everyone gets wrong about loyalty and what it takes to stop renting your guests and start owning them. Matt, it's great to have you on the show.
Thanks, Simon. It's great to be here.
Before we kick this off, we do a quick rapid fire together.
Are you up for it? Give us short answers.
Let's do it.
Brand or scale?
Brand.
Always direct book direct booking or OTA? Direct booking, of course. More units or higher repeat rate? Higher repeat rate. Buy a brand or build one.
Could go either way. The one the one number you'd never let anyone else own. That I would never let anyone else own in in my business or Yeah. A number that is so important to you. I would say uh
Recurring revenue, ancillary revenue, everything that is, you know, extra that is not specifically related to the booking itself.
Yeah, that's great. That's already a great segue. I'm sure we'll talk about that as well because that's what people forget. Well, margin are compressing. We need to think about what other products can give us m additional margin contribution and therefore uh bottom line profitability. Uh before we get there, I want to talk to you about the operator context. So you you fell for the product before you ever owned it. Can you take me back and what did you see as a guest of Red Cottage that made you think I want to own this?
Well, I think the truth would be that I fell for the space before I was in it. which might be a a a m more true way o of saying that. I owned a s a a portfolio of homes that I had been self managing and this was years ago. Really felt that there was a lot of momentum in this space, especially as we came through COVID and and and coming out of COVID. Um my exploration, you know. Uh showed that m showed me that there was a lot of new software that was being built for this space, a lot of businesses that were transacting, and it felt very opportunistic. And I personally, after having built a, you know, this portfolio of uh of self-managed rentals, ended up looking for a business to buy in this space that would widen my own moat and and take me uh further in it.
I had been a guest of Red Cottage, that is true. Uh it was not the first business that I went and sought out, but it was the first business that I ended up purchasing in this space. And even as a guest of the business, I always really felt that this was An incredible brand. that had built an enormous amount of goodwill in the region that it was operating and brand awareness. And the homes. They were Completely unique, all of them. Which I think which largely was a function of just building a portfolio outside of New York City where you benefit from. a ton of uh new builds and unique construction and the original Red Cottage business was able to benefit from from that out of the gate.
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Chapters
6 chapters
1
Why is owning the guest relationship more valuable than scaling unit count?
0:00–7:38
2
How did Matthew’s experience as a Red Cottage guest shape his decision to buy the brand?
7:38–17:25
3
What makes Red Cottage’s brand and design‑driven homes stand out to travelers?
17:25–27:25
4
Why do most STR operators fail at loyalty programs and how does Red Cottage succeed?
27:25–37:14
5
What are the essential components of a successful membership program for short‑term rentals?
37:14–50:06
6
How does Red Cottage balance AI automation with high‑touch human communication?
50:06–1:00:30
Speakers
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