The Breezeway CEO Has Seen 350,000 Airbnbs. This Is the Mistake He Sees Everywhere | Jeremy Gall
Short Term Rental Secrets Podcast
October 12, 2026
How do you grow a short term rental or Airbnb management business without losing the human touch that makes guests book in the first place?
Speakers Jeremy Gall, Mike Reilly, Michael Sjogren
TopicsInvestingBusinessEntrepreneurship
Jeremy Gall (0:00)
Service is black and white, and hospitality is in color. Service is just like, that's the baseline. That is like the baseline. That is getting everything right, that's doing what's expected, that's showing up to a clean unit, that's well maintained, it's stocked, it's safe, it's ready to go, and people are gonna have a great experience. Hospitality is what comes above that baseline. You don't actually think you had a hospitality experience, unless something extra has happened, and you feel like extra human effort, not machine effort, but extra human effort has been devoted to something that happened in your experience. A connection you had with a server in a restaurant, something nice somebody said to you, walking in and out of a hotel, a note that was left for you, etc.
It doesn't feel special if it's automated, and if you know it's just totally automated, it does feel like you got some attention, but it doesn't feel special. I think that's the trick, and that's going to be the delicate, deliberate balance in our industry, which is how do you automate a bunch of the admin, the scheduling, and get deeper and deeper into automating and controlling the stuff that really can be a time sock so that you're freeing your team up so that they can do more. But what I'm afraid of is that exactly what you said, Mike.
Mike Reilly (1:23)
All right, Jeremy, welcome back to the STR Secrets Podcast. Good to have you back.
Jeremy Gall (1:28)
Thanks, Mike. It's great to be here.
Mike Reilly (1:30)
So from your viewpoint, you run one of the largest software companies in this industry and you focus a lot on, you talked about it offline. The people are actually doing the work, right? The people that are actually in the field and being more efficient and how we can use AI to bridge the folks in the field to be more efficient and provide that unreasonable hospitality.
What's your top priority right now at Breezeway to bridge that gap?
Jeremy Gall (1:59)
Yeah, I think the top priority from us is how we approach, and we talked a little bit about this at the top of the program too, but how we approach the balance between automation and the human capital that's necessary to really deliver hospitality. And for Breezeway, I think that means we kind of approach it from two different sides at the same time. And I think about it as like a top down.
How do we help with additional automation at the top so we can remove administrative work that just increases as your portfolio increases and as owner demands and guest demands increase and expectations rise. Coordinating that administrative work becomes harder and harder. And so how can we eliminate more of that through automation? And then from the bottom kind of up as I think about like the tech stack down to the human element, what can we do to help the people in the field meet expectations more efficiently, understand what work they need to do, find better jobs, get rated and get credit for the great work that they do. And I think focusing on both helps sort of like drive more value across like that whole operational workflow.
Mike Reilly (3:28)
Yeah, I've got 36 listings. We're not on Breezeway right now. But one of the things I'm always working to get better at is getting feedback from them on what does it actually look like on the inspection? What does it actually look like for each turnover?
What does it actually look like to provide and get that five-star on the ground? Because I'm not seeing it very much. I'm kind of, you know, we got a great team and lots of people on the team. We have seven people on the team just for 36 listings. But how do you get feedback from the cleaners, the inspectors, you know, even feedback from guests as well? I know you guys have the messaging as well. But how do you look at that feedback and collect that data to make decisions on what you should develop at Breezeway?
Jeremy Gall (4:16)
Well, we've got this state of work report that we have coming out in October where we just did a survey of about 5,000 operators trying to understand how they get their work done, what's changed for them. And what we hear is that like people really lean into the relationship that they have, right? Like, it's the relationship you have with the people who are working in the field. That ties back to this world like hospitality operator mentality, which I'll keep coming back to, which is like, if you actually run a hospitality business and you wanted to deliver hospitality to your guests, you have to think not just about how you communicate and treat your guests with hospitality, but how you do that with the people who work internally in your company as well. Because if you don't develop that kind of mentality with those people who are in the field, with those seven people you have, you're going to have a hard time helping them understand what it's like to drive that hospitality and care about what you're trying to do for the guests and the owners that you serve. And so I think some of that feedback loop, like some of that's driven through technology. But I think it's like such an interesting business, like vacation rentals and like, with everything that's happened over the last year in software and through Claude and AI, we are understandably very fixated on how we can become more, the whole industry is fixated on how we can become more efficient, what can we automate, and how can we do this. And it's all very important. But I think like getting the feedback from people in the field and having that connection with them is what drives your business. That's the connection and the relationship that ends up driving your business. So like, yes, you can get it through the tools and through Breezeway as well, through ratings, we help you collect ratings on the test in the field.
33 more minutes of transcript below
Thousands of transcripts fetched by people building searchable podcast archives
Fetch the whole transcript
The demo key returns a sample episode in full, no card needed:
curl -H "x-api-key: pt_demo" \
https://spoken.md/transcripts/1000651996090Markdown with the speakers named, for your notes, your knowledge base, or anything that makes HTTP calls.
From $0.10 per transcript. No subscription. Credits never expire. Prices exclude VAT, added at checkout for EU customers. Not what you expected? Email us within 14 days with 20 or fewer credits used and we refund the pack in full.
Using your own key:
curl -H "x-api-key: YOUR_KEY" \
https://spoken.md/transcripts/1000795921780