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The Vacation Rental Show, Hosted by Lynell Gordon artwork

Owner Retention Is the Conversation Nobody in Vacation Rentals Is Having with Annie Holcombe of Annie and Company Solutions

The Vacation Rental Show, Hosted by Lynell Gordon · 2026-07-28 · 45 min

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Key moments - from our scoring

Substance score

66 / 100

Five dimensions, 20 points each

Insight Density14 / 20
Originality12 / 20
Guest Caliber16 / 20
Specificity & Evidence11 / 20
Conversational Craft13 / 20

Annie Holcombe, chief strategist at Annie and Company Solutions and newly appointed brand ambassador for Booking.com, addresses the industry's blind spot: owner retention. While everyone focuses on acquiring new property owners, few discuss keeping existing ones satisfied - a critical gap as shorter booking windows and economic uncertainty create margin pressure. Holcombe explains how post-COVID market dynamics shifted the landscape, with new entrants often underprepared and isolated from professional networks, creating friction between legacy operators and the growing "short-term rental" segment now representing 80% of the market. She details her work bridging this divide through her Booking.com ambassador role, including bringing non-users to the company's Click event to provide direct feedback on product and positioning. Holcombe emphasizes that Booking.com's willingness to listen - proven by inviting critical voices and securing CEO Glenn Fogel as VRMA keynote speaker - sets them apart. The conversation highlights systemic issues: owners at the Florida Panhandle who paid $900,000 per square foot now struggle to generate returns; expectation-setting failures threaten operator churn; and legacy providers may be reaching exit points after years of operational strain.

Key takeaways

  • →Owner retention, not acquisition, is the critical gap in vacation rental strategy that will determine 2025 viability as booking windows shorten and owner expectations clash with market reality.
  • →The post-COVID influx created a 80/20 split where newer short-term rental operators lack access to professional networks and knowledge, fueling a divide that generates friction and poor decision-making across the industry.
  • →Booking.com's approach of inviting non-users to strategy conversations and listening to critical feedback positions them differently from other OTAs and opens opportunities for positioning with under-25-property managers who feel abandoned by support systems.
  • →Owners who purchased properties at peak real estate prices (particularly in markets like the Florida Panhandle) now face negative cash flow scenarios that will trigger either portfolio exits or operator churn if revenue expectations aren't reset.
  • →Legacy property management providers are approaching burnout and potential exit points, signaling consolidation and M&A activity that will reshape competitive dynamics in professional vacation rental management.

Guests

Annie Holcombe

Topics in this episode

Booking.comPropertyManagementGrowthOwnerRetentionVacationRentalDistributionStrategyBooking.comForPropertyManagersShortTermRentalIndustryOwner retention strategyVRMA (Vacation Rental Management Association)Airbnb vs. OTA advocacy modelsProperty management software and integrationsGDS integration strategyGoogle SEO for vacation rentalsChannel management and distributionFlorida Panhandle vacation rental marketShort-term rental vs. vacation rental operator segment

Questions this episode answers

What is the biggest challenge property managers will face in vacation rentals this year besides AI?

Owner retention driven by shortened booking windows and unmet revenue expectations, particularly among owners who purchased properties at peak prices during the real estate bubble and now cannot generate sufficient revenue to meet their financial projections.

Why didn't professional vacation rental operators and new short-term rental hosts integrate earlier?

Professional operators initially excluded smaller players from conferences and integrations; this was countered when VRBO and OTA distribution allowed single- and two-property operators to reach global markets, creating the fringe segment that now represents 80% of the industry.

What makes Booking.com different as a brand ambassador relationship?

Unlike traditional OTA partnerships, Booking.com invited non-users to their Click event and engaged in direct feedback conversations to understand why operators weren't using them, demonstrating genuine listening rather than sales-driven positioning.

How did the COVID-19 pandemic reshape vacation rental market dynamics?

New destinations emerged as people sought travel outside cities; markets that were previously flyover towns became destinations; this influx of new operators created a gap in foundational business knowledge and professional networks, especially around financial modeling and operations.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

14 / 20

The episode offers several substantive insights about owner retention, technology stack management, and channel diversification that would be useful to operators, though much of the conversation drifts into relationship-building philosophy and anecdotal tangents. The core actionable ideas (communication cadence, mentor relationships, avoiding shiny-penny tech) are sound but not densely packed, with considerable fluff about the Pope, personal branding philosophy, and podcast guest retrospectives.

owner retention is the conversation nobody's talking about...this year in some markets is not as strong as people thought it would be because of the way the economy's been flowing
if you're thinking you want to grow, get your ducks in a row now because I think there's going to be a lot of opportunity to pick up some

Originality

12 / 20

While Annie makes some fresh observations about the divide between legacy vacation rental operators and newer short-term rental entrants, and about owner retention gaps, most of the strategic advice (mentor relationships, personal communication, channel diversification, tech stack optimization) is well-established industry wisdom. The Booking.com bridge-building narrative is interesting but not particularly counterintuitive or contrarian.

that fringe is now 80% of the industry and their lack of access to knowledge and information has created friction between the two
building an empire on one channel is not in your best interest, regardless of what

Guest Caliber

16 / 20

Annie Holcombe is a highly credible guest with 30+ years in the industry across property management, OTA strategy, owner relations, and technology. She's now a brand ambassador for Booking.com and runs her own consulting firm. She speaks with genuine authority and has worked at scale (managed 1000-1500+ properties). This is a legitimate practitioner, not a career podcast guest or consultant with limited operational experience.

She has a career that spans over 30 years...and she has shaped the industry from nearly every angle. She's been in property management, she's been in owner relations, she's been in OTA strategy
the last company I was with, I mean, you know, we had close to a thousand properties, but I had worked for a company that had 1500 on rentals

Specificity & Evidence

11 / 20

The episode lacks concrete numbers, specific case studies, and quantified metrics. Annie references the Florida Panhandle market and $900,000/square foot real estate prices, mentions a few named individuals and companies (Abode Luxury, various past employers), but provides minimal hard data. Claims about owner expectations, booking windows, and market trends are asserted without evidence. The conversation stays largely abstract and anecdotal.

people bought these homes at $900,000 a square foot and there's just no way to make that kind of revenue in a six week period
a lady...gave a really bad review, and everything about the property was spectacular, but the wind kept her up

Conversational Craft

13 / 20

The host asks solid open-ended questions and does probe deeper on owner retention and technology decisions, but many follow-ups are soft or allow Annie to drift into tangential territory (the Pope, podcast guest anecdotes, chickens). The host misses opportunities to press on specifics - e.g., what exactly should smaller operators do if their direct booking strategy yields 50% occupancy? How do you systematically identify which channels make sense for a given property? The conversation is warm and respectful but lacks edge.

if you were sitting down with a property manager today who wanted to future proof their business, let's say 20 properties, what would your first three recommendations be
What's the single biggest shift that property managers need to pay attention to other than AI?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A66%
  • Speaker C32%
  • Speaker B3%

Most-used words

industry36property22love21help18booking17rental17feel17vacation16everybody15annie14back14rentals13managers13didn13owners12show11

Episode notes

Annie Holcombe has been part of the vacation rental industry since 1992, building a career that spans property management, owner relations, OTA strategy, business development, hospitality technology, and industry leadership. Today, as Founder and Chief STRategist at Annie & Co. Solutions, she helps property managers strengthen owner relationships, improve business development, and build long-term growth strategies, while also serving as Brand Ambassador for Booking.com and co-hosting Alex & Annie: The Real Women of Vacation Rentals . Throughout her career, Annie has become one of the industry's most connected voices, known for bringing people together and helping businesses grow through meaningful relationships. In this episode, Lynell sits down with Annie to reflect on how the vacation rental industry has changed, where it's heading next, and why relationships, not technology alone, will continue to determine who succeeds.

Full transcript

45 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I mean, there's a lot of things. The one thing I think people aren't talking, everybody's talking about owner acquisition. I don't think people are talking about owner retention. I think that people are just making the assumption that they can retain their owners. But let's face it, this year in some markets is not as strong as people thought it would be. Because of the way the economy's been flowing. People are waiting longer to book, so the booking window is shortened and that's going to make a lot of owners very edgy.

Speaker B: Welcome to the Vacation Rental Show. This is your essential playbook to grow and scale your vacation rental business with advice and insights from the best in the biz. I'm your host, Linnell Gordon.

Speaker C: Welcome to the Vacation Rental Show. I'm Linnell Gordon, your host and I am excited today to have Annie Holcomb rejoining us. She's one of my favorite people guys in the industry and she is one of the most connected and trusted voices that we have in vacation rentals. She has a career that spans over 30 years, guys, and she has shaped the industry from nearly every angle. She's been in property management, she's been in owner relations, she's been in OTA strategy, business development and hospitality technology. There are not many people in our industry that have seen business evolve the way that Annie has. And these days. I love this. This is great. As chief str adigist. She's a strategist but she capitalizes short term rentals. I love that. Annie at Annie and Company Solutions and she is the brand ambassador for booking.com. just letting that sit for just a second because we're going to talk about that. She's also helping property managers and suppliers grow smarter and strengthen our relationships and stand out increasingly competitive market, as you guys know. Annie, welcome back to the show.

Speaker A: Flannel. Thank you so much. That was so many flowers coming at me. I don't know what to do with it. But I appreciate that. Uh, and I can say the same for you. I feel like you're one of those people that is look to as like the gold standard for what this industry can be. And so just being on your show, always an honor. But as I said, uh, before we hit record, being with you always fills my cup. So thank you. I appreciate it.

Speaker C: Thank you so much. There's like nobody else that I'd rather see as a Brand Ambassador for Booking.com. that was a very exciting thing for me to hear because I was like, if anybody can bridge a gap here that we Might have. It will be you. So congratulations on this. Excellent. In my opinion. We're going to talk a little bit more about it, but it's an excellent place for you. Because I'm like, yes, at least, you know, I know that, you know, it's one of those if you know, you know, kind of things when it comes to people being appointed as bridges between vacation rentals and anything else, whether it's property management software, whether it's vendors of any sort, you look at that bridge and you're like, oh, that was a bad idea. And we know it. Everybody on the inside knows when it's a bad idea. We had one of those. And I said to someone, I said, that's probably not your best pick, but okay, I'm with you and I will support you in any way I can. But you, on the other hand, that's like a great pick. So let's talk about what you're doing and, um, let's talk about where your passion lies right now and what you're doing.

Speaker A: Yeah. So I think I had an epiphany when I was reading a book recently. Not that I wasn't already kind of convinced, but I think that people walk through their life and like, my passion is. My passion is. My passion is. And in this book is Ryan Holiday. And I cannot remember the name of, to say my life right now, but he talks about people mistaking passion for purpose or purpose for passion. And, like, people will walk through life and go, it's my passion. It's my passion. It's like, but is it a passion or is it your purpose? And so I went back to. When I decided to start Aiding company, I felt like, okay, I'm at the point where I've got 30 plus years of knowledge. Maybe I should listen to the people around me that are saying, why aren't you sharing this with everybody? Because essentially, I was only sharing it with the companies that I was working for. So this is an opportunity to share it with more broadly. But where I noticed right after Covid was the influx of new people coming in the business and love it. I love that we had a spotlight on an industry that you and I have been involved in for so long. And for a long time, it was kind of, you know, standing on the street corner with like, a sandwich board saying, see us. Uh, see us. You know, we're back east rentals. We're here, We've been here. And, like, having people pay attention to us and getting that proverbial seat at the table was so difficult. And so I really wanted to make. Make people feel at home and feel welcomed. Now, what ended up happening was so many people came in so quickly, the money was flying all over the place because basically you couldn't raise your rates high enough in most markets. All of a sudden, markets that weren't markets became markets because people wanted to get out of the cities and they wanted to get to new places. And they decided, like, I've been pent up, I need to see the world. And so they wanted to get out and see. And so places that were just drive through towns, or as they say, like the Midwest flyover, became places, destinations that people were looking to visit. And so like, that allowed people who had maybe a cottage in some little lake town somewhere to put it on rental. But with that came a lack of information to help them set up foundational business practices. And what we started to see on, I would say this is not meant to disparage anybody who's in the business, but the professionalized side, the side that had been around before COVID who already kind of had operations in place, they had processes, they had the technology, they had tools, they also had a of people to work with. These new entrants necessarily didn't have that network. So they were kind of flying by the seat of their pants. They were Googling. And we know how bad you Google your symptoms. You'll be dying by the end of the week or you're going to be fine. It just depends on the answer Google gives you. But they were getting bad information, and not necessarily that it was totally wrong, but it maybe wasn't right for their situation. There were people that were on YouTube and TikTok and saying, like, I've got the one size fits all solution. Mark Simpson, he jokes about it a lot and I always laugh. But there's people that are like, I'm an Airbnb expert and I've been in the business a year and a half and I've only got one property. Well, that doesn't make you an expert at anything. It makes you somebody who has experience but doesn't make you an expert. But then these new entrants were seeing that someone who's claiming to be an expert with this sense of authority, oh, they must know I need to pay them. And they were losing money. They were losing money that they could have done to get with our side of the business, the professional side of business to learn from. So I felt like there was this gap kind of speaking to the booking.com that there's a gap that people that, you know, this divide happened and I. That's where the vacation rental versus short term rental, I feel really, really became the way we spoke about the industry. Short term rental has always been here, but vacation rental became like the legacy operators in these destinations that everybody knew about. In short term rental was like the side of the road guys, maybe in a urban destination that they weren't showing up at VRMA or they weren't members of any of the associations. And so they were kind of on the fringe. But if you look at it, that fringe is now 80% of the industry and their lack of access to knowledge and information has created friction between the two.

Speaker C: And it was intentional.

Speaker A: Yeah, for sure. But I also think that the people that got caught in the crossfire, if you will, it wasn't intentional on their part. They didn't know.

Speaker C: No, no, no. But they were intentionally left out. When they first came up, they were like, who are these fancy pants startups that are coming in? Are we going to write code that's going to allow them to integrate with our large systems? Because they're just one off, two off, maybe six properties, seven properties. And they're only using OTAs. They're like, no, I just remember when they were blackballed from that until. So here's where I think it tells them. You tell me. Um, until VRMA decided not to do their own ota, basically where people were, all the professionals could come in one place. They decided. No, that they would instead integrate with like the airlines.

Speaker A: Oh yeah, with the gds.

Speaker C: Yeah, yeah. They decided to integrate there. When they did that vrbo at the time, you know, before they became vrbo, that was where they got a foothold. And that foothold was good for operators who had single properties or two properties. So at that point it really didn't shift immediately. Of course not. It took about three to four years for the Google SEO strategy, which was so important at that time, which is not as important now. In the same way. It's important, but not in the same way.

Speaker A: Different way.

Speaker C: Yeah, yeah, completely different way. One thing though, that remains the same and I want everybody to hear this, content is still king. It will always be king. Because even with AI, it really became more important. So it went content, then it went paid results, then it went Google local and now it's back to content. But I feel like it really shifted at that point and then it just grew exponentially.

Speaker A: Yeah, well, it also, I think it also, like you said, those smaller operators, the ones who had the ones and twos, they had been alienated. So this was a solution that allowed them to open up to the world.

Speaker C: Like they wouldn't even allow them into some conferences. I mean they literally were not allowed to register for conferences and things. Yeah, and this is funny, this is an example of, to ring true of what you're saying. I have a long term rental and I've been in real estate a long time. I have friends that were managing it, were in real estate and they were like, ah, we'll do yours, we're doing ours. And it was a long term rental. And so I called, I was asking my real estate people, okay, my people are no longer going to be doing property management too hard for them. They really don't want to do it. It really is its own niche. They're going back to just real estate investing and that type of thing. And so I said, I need some ideas of people. So they gave me someone and I called that person and she was like, oh, well, I really don't do long term rentals. I really only do short term rentals and midterm rentals. And I thought, wow, that's crazy that you can talk individual real estate agents who are helping people to manage short term rentals and the term. And they're not even, I mean, I guess they're property managers but it's shifted. Look at our shift. And now you're the brand ambassador for booking.com.

Speaker A: yeah. Crazy, right?

Speaker C: It's good, but crazy.

Speaker A: Yeah, I'm hoping that, I'm hoping that internally their team is going. That was a really good choice. Um, so far it seems like it is.

Speaker C: Of course they are. So talk to me about bridging that gap. Talk to me about what that looks like.

Speaker A: Well, you know, it was interesting when I left property management I went to ota. That was my first foot into otas. So I really understood at that point that there's power in being able to, you know, the eyeballs. There's definitely. The billboard effect is real. Google was costing so much. You're paying, you're competing against everybody for stuff. And it's like, okay, what's the highest and best use of my inventory? And at the time when I was in property management, the last company I was with, I mean, you know, we had close to a thousand properties, but I had worked for a company that had 1500 on rentals. So I was very well aware of you had to have diversity and distribution. So I've always been a proponent of that. So over the years I've seen varied channels and how they treat the property managers and treat hosts and that type of thing. And when Airbnb blew up, I started to see, like, wait a minute. I'm not opposed to them. I don't like the way they necessarily advocate more for the guests than they do for the host. But I think that there's two sides to the coin. I mean, it flips quite frequently.

Speaker C: No, they advocate for the host. They advocate for guests.

Speaker A: Uh, I'm trying to be diplomatic, Lyna.

Speaker C: I'm not. I love them, but let's just spit it out.

Speaker A: They do advocate way more for the guests than they do for the host. That is 100% true. But I went to channel management, and I started to see, like, the ability to turn on a promotion. I'm an ota, and get instant results is, like, super gratifying, because we live in a culture of instant gratification. So I was like, okay, I've seen this work. I know this can work. And so I had been working with booking, and their team was wonderful. I went on sales calls with their acquisition team, and I loved their culture and what they were trying to do. And they weren't coming in with this. We're bigger and better than everybody. They were channel. They really genuinely. They're. Their people want to help people. And so I always just had this, like, affinity for them. And I think my nature of, like, just trying to promote the diversity. I had been talking about them a lot, and so they noticed it and actually approached me at, uh, the army last year and said, hey, we've heard about you. And people say you're always talking nice things about us, like, could we work together? And I was like, well, sure. I don't know what that looks like. So we basically came up with this framework of, like, they don't have an ambassador program, per se. I'm the first person that they've done this with. But it was really trying to get an understanding of what they were doing and why it wasn't resonating and how they could get in front of more people. And so it's been a really great learning lesson, I think, for them and for me as well. Uh, to understand these hosts need help, these smaller managers need help. The larger managers need help, too. But a lot of times they have access to an account rep at these channels, they have access to a account rep at their pms. But a lot of times these people that have less than 25, they're in a support queue, talking to a bot, never getting anywhere, and just feeling left alone. And so it was like, how can we reach them and talk to them and help educate them? So it's been a process of really, um, trying to dispel the myths of what people think booking is and what it actually is and how they have been listening to hosts and changing. And so this year, for the first time ever, they allowed me to invite some people to their in the US event is called Click. And they do that typically for their top partners. So, you know, a small host under 25 is never going to be a top partner. They're never going to generate that kind of revenue to be there. But also the other part of it that I thought was really great on there, to show that they want to learn, is that the hosts that they had that we invited don't use them. So these hosts weren't even using them. And they were like, why aren't you using us? So we were able to have these really deep conversations about this is why we're not using you and what you need to do to make it better. And so I did a post a couple of weeks ago after the event and I was like, people will say they don't listen. They won't, do they? And I was like, they is not booking.com. my experience with them has been anything but. They're not listening, they're not paying attention. They're a large company, they're a publicly traded company. They're not a company based in the US So they have a lot of things that they have to navigate in terms of, like how they speak and what they do and when they move and how they iterate and their technology. And let's face it, I mean, their technology stack is ginormous. I mean, they're dealing with hotels and they're dealing with resorts and they're dealing with vacation rentals. They're dealing with all of the things. And so they don't have one lane to stand in. So it's a kind of precarious position for them to be in when they go out and say things. And so it's really more about helping them understand, like, they have the technology, but how do we explain it and make it work for this segment of the industry? And so I'm excited because through that relationship we were able to get Glenn Fogel, who's going to be keynoting at, uh, VRMA this year, and he's never done that. And so I've never seen the man speak before. So I'm really excited about that. And then just having them be more present in the market, I Think that they have a big name and people know who they are. And if you watch Major League Baseball or NBA or wnba, you see them all over that. And I think it's great on the consumer side, but I think on the property manager side, it's like, you know, is that my guest? Yeah, they are, but maybe you're not seeing it in that realm. So we're trying to figure out, like, what does the language look like? How do we show up? How does this channel show up for these managers and help them to understand that building an empire on one channel is not in your best interest, regardless of what. Um, I mean, if you would never want anybody to be just on booking.com, you need to have multiple channels, and you need to have a direct strategy. I mean, all of it plays together, but they're open and they're wanting to learn and they're wanting to participate. And I have just had opportunity to talk with people from top to bottom. Never, never talked to Glenn, but a lot of their product people, so really, them making assumptions about what people need versus what they actually need. And at the end of the day, what we walked away from some of the conversations was if they were just present, if they just were there and talking more. And so that's one of the things that we're committed, is trying to find ways to connect with people so we can hear what they want and maybe dispel what they think the channel is and really show them the power that it can put to their business.

Speaker C: I think the booking is different. It's a different OTA to me. I kind of. I, too, for some reason, I put it outside the other OTAs. I think of it differently. I use them when I'm in Europe extensively. They've always been very nice people, and they've always been very nice to the VRMA people. Even when we had a VR, we had a VRMA in Amsterdam not too. I think, long ago. So it was long ago, years ago. And they invited people over to their office there to meet and talk. So I think they've always been smart enough to include their people in it. I mean, not just smart enough, but it's like you said, they really care. They do. These are people that actually want to do good for people and help them find somewhere to stay. So I find it, uh, years ago, we used to walk into an office and look at how they did business and say, okay, how can we make this business better? How can we make them more money, make it more profitable, make it easier for them? And I Think that the conversations that you have, you are having or that you can provide to them through property managers don't use them to find out that big why and what they actually need and what would make it better in an industry. That's very powerful, Annie. That's very powerful. That's a powerful conversation and that really could change the way that people use it and the way they think about it in the property management industry. So good luck there. I think it's really an important conversation. It's one I didn't expect right now. So I'm so happy to hear that that's going on because that's the way you change things. You have conversations with people that know what they need with the vendor and they go back and they go, okay, well I think if we had xyz, it would be different. So I mean, that's powerful. Let me ask you this. What's the single biggest shift that property managers need to pay attention to other than AI? I feel like you talk about passion, you talk about purpose. My passion is AI.

Speaker A: Yeah, I love it. It's just, it's so overwhelming right now. I just can't talk about it anymore.

Speaker C: I'm just so happy about it. No, for seriousness, seriously, I presented a problem this morning that we're having that would automate a process to save hours on duplicate emails that we're getting. And I'm like, it'll be ready by this afternoon. It really will be.

Speaker A: Yeah. I mean, that's the great thing about the tool.

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Speaker C: So other than AI, so we'll take that out of the picture, other than AI, what are the biggest? I mean, if we can, what do you think? What do we need to pay attention to this year.

Speaker A: I mean there's a lot of things, I think somebody asked this question this morning, I think on a LinkedIn post and I said like the one thing I think people aren't talking, everybody's talking about owner acquisition. I don't think people are talking about owner retention. I think that people are just making the assumption that they can retain their owners. But let's face it, this year in some markets is not as strong as people thought it would be because of the way the economy's been flowing. People are waiting longer to book so the booking window is shortened and that's going to make a lot of owners very edgy. And so if they don't get the revenue that they expected, which let's face it, sometimes these owners have m really outlandish expectations, especially the ones that bought the last couple of years, they bought at the height of the real estate market. So they're losing money in some of these places. The Florida Panhandle is just ripe with this because people bought these homes at $900,000 a square foot and there's just no way to make that kind of revenue in a six week period. Now is the market doing well? Absolutely. But when you're trying to meet expectations that are way outside the ballpark, that's where it comes into place. I think there's going to be a lot of owners that post. These are going to be looking, but I also think, I feel like people are talking about it, but maybe in a more quiet way is that I feel there's going to be a lot of legacy providers that are going to just at the end of the business they're going to be like, I am done. I am just, I can't do this anymore. I think that for the M and A, I mean, I think we're seeing it already and I don't know that it's not being talked about. I just feel like that's an area that if you're thinking you want to grow, get your ducks in a row now. Because I think there's going to be a lot of opportunity to pick up some. And it doesn't have to be a uh, 200 unit property manager. There's some people out there that got 20 properties that are burnout because once again you go back to when they came in the business and the support that they got and the education and some YouTuber told them it was passive income and they wouldn't have to work and they're taking phone calls at 3 o' clock in the morning and Dealing with the craziest things. You know, I was talking to somebody recently, and they were saying that a lady, she gave a really bad review, and everything about the property was spectacular, but the wind kept her up, and she was mad about that. It was like, okay, now you're dealing in a whole area that none of us can deal with. But I think the guests have gotten. Their expectations are outlandish, and they just complain about anything to get. Save money, get a refund. I, um, mean, again, you follow the money. That's always kind of where it goes. But I do think the biggest thing is, like, the owner retention is just something. I was talking to a group recently in Central America, and we were talking about dealing with owners, and they were like, well, you know, we have owners from all over the world. And I was like, what's your communication cadence? And they were like, what do you mean? Like, they're not communicating. Like, they have a newsletter, but they're not proactively getting out there. And I always think back of a conversation we had with Sarah Bradford, and, I mean, there's so much wisdom out of this woman, but she said, you know, like, make it part of your weekly plan to call an owner. Just. Cause, like, just call them and say, how's the weather? I was thinking of anything. Because owners want to be felt, and they want to be seen and heard, and they want to know that you understand, you know, you can't fix everything for them. But that way, when you do have these hiccups and you do have a down year, they're more likely to say, well, you know what? They've always. They're a friend. They've been here. They care about me. I feel part of the conversation. So I think that people don't put enough attention on that. And then this is the hill I will die on is diversity and distribution. There's been so much conversation about direct booking. Direct booking. Direct, yes, absolutely. Have a direct booking strategy. If you don't set that up from the beginning, that's stupid. But to think that you can have 90% direct booking and you're only running 50% occupancy, then what are you doing? Like, people have got to understand that diversity is okay. Yielding your channels is okay. Like, you have to do it. And so I feel like that's, like, something I could be like the Pied Piper, like, going out there to get people, you know? And it's not just about booking. It's just about the right channels. Like, people are using channels that they have no business being on they're never going to get anything from it. But for whatever reason, that channel talked them into listing. So that channel has the inventory number and now it's time to really look at it and say, like, what makes sense for my inventory? Because it varies by market, it varies by inventory, it varies by season. Like there's so many variables and I think people just, I don't think they dive enough into it. So those are my two things.

Speaker C: No, I love that. I was just going to ask you, believe it or not, what the biggest mistakes were that managers are making with homeowner, uh, communication. So I mean, I think it's really clear that you have to have consistent and personal communication. I love the fact that you brought that up because a lot of the owners that are doing really well, there are lots of, I mean, property managers are doing really well. They do have that strategy to have personal communication with their owners. A lot of them are doing these quick videos too that are just, duh, you know, it's like five seconds and they see your face and you keep that in front of them. And I thought that was a really good. Well, I made the recommendation, so I thought it was really good that it worked. You know, that makes it excellent, excellent. Glad it worked.

Speaker B: Woo hoo.

Speaker C: You know, but these are things that we have been doing for years, you know, that we knew back when it first happened. If you were sitting down with a property manager today who wanted to future proof their business, let's say 20 properties, what would your first three recommendations be for people who are less than a hundred properties? Let's just go there.

Speaker A: I mean, button up your tech stack. First of all, don't be lured in by the shiny pennies. Because it's funny, my husband just started working for Abode Luxury out in Park City a couple of months ago and he'd been out of the industry.

Speaker C: I, um, love them.

Speaker A: Yeah, they're wonderful. And so he'd been working with, um, some property managers here in Panama City Beach. So he was not removed from the industry. But I joked with him, I was like, if you'd listen to my podcast, you would understand this. But he didn't know the proliferation of technology. He was like, do you understand how many pieces of technology? And he was just like, they're crossing over and they're double dipping and they're like just so much because it's like all these people coming at you and AI has made it exponentially worse because now everybody can build. Now in terms of the amount that's, uh, coming at you now, I'm not saying it's not making it better, it's just making it worse in terms of like what you have to vet. Like I get five or six a week that message me like, I've got this new tool and it's AI. And I'll look at their background and the company, like they've been in existence six months, they never touched the vacation rental, short term rental industry. So that to me is like red flags all over the place. But the problem is these smaller people, I don't know that they're necessarily doing that research to like find out where you're coming from. Some are, some aren't. But I think that uh, he just was like, I just don't understand all this technology. So I think that it's really understanding where you want to take your business to know what you actually need. Because if you don't want to be 200 properties in two years, you don't need to have all of these pieces of tech in play. You can have your PMS and maybe one or two other things. You don't need to have all of it. And I just, even starting my business, the amount of technology that I could use to power me, it's like once you start paying all these SaaS fees, it's like you don't have any income because you're paying for all of these components that are out there.

Speaker C: That's not the way to do it.

Speaker A: Yeah. So be mindful of that. And definitely, you know, a setup accounting, that's one thing. I think people just start out like you said to one property and it's two properties and then you have a pms. But you're not thinking about talking to an accountant and having all your contracts done so they're legal and getting the foundational things in place. Like some people, like they find themselves 50 properties in and going, oh crap, like I needed to do this two years ago. So I think there's just talk to others. And my third recommendation, and actually this is probably my number one recommendation, is if you're in this business and you think you want to grow, is find a mentor. Find somebody in your market or even in another market. I mean, one thing that this industry is ripe with is people that want to support and help people succeed. There's nobody that I know of that is visible anymore that wants people to fail. Everybody wants to see success because the better we are individually, we are as a whole. So I think that find a mentor should be your first priority and make sure you know it's somebody that you can go to and you might need one or two, you know, you might need different markets. It could vary. But don't be afraid to ask. And LinkedIn is like, again, we joke, it's the water cooler of the industry. But you could ask a question, you could find somebody within a day to help you navigate whatever it is. So mentorship is absolutely crucial.

Speaker C: That's incredible advice. I will tell you to give you a little. I will tell you that for AI, you shouldn't use AI for the sake of using AI. I'm about to start teaching people how to do things like create AI that will automatically answer your emails and create them in a draft format so that you can go in the morning and just push a button. Everything's already done and you can edit the emails if you want, but it does things like that. AI for the sake of AI is sucky. But being able to teach a property manager how they can actually save time using it, that's one of my passions. It's not just. And I think it has a purpose too. And so I'm going to start just a basic series for property managers to help them. Here's how you do this. Here are things that will help you in your everyday life because they would help any of us in our everyday life to manage our appointments, to manage our emails, to manage our responses, those type of things. People that actually can be learned by AI, that are helpful. So I think with any company buying a new tool, no paying SaaS fees, no my $20 a month. That 20 bucks a month does a whole lot for me that you would not even imagine. But, uh, being able to capitalize on that and teach smaller owners how to use that, I mean, smaller posts, how to use that and how to save time and how to make this easier for them. Someone said to me this past week, who's a host, small host, and she was like, if I get. And she's a friend of mine in real estate, she said, if I get one more airbnb question this week is going to drive me crazy. And I thought, you know what, there's an answer for that. And it's not expensive, it's something that you could do. So since your last appearance with us, you've launched Annie and Co solutions that you talked about. I am, um, so proud of you for that. I mean, you are just a very forward pushing person in the industry and I wonder what inspired you to do this, to take everything that you've learned in these last 30 years and package it into Your own brand. That's huge. And that's a big deal.

Speaker A: I can't point to any one thing, but specifically, like, I'd had people. Steve Trover, he was big chip. Like, just me doing it. He's like, he should be doing this. Amber Hurdle. There was several people that just over time, just kept asking me. And then really, like last spring, my husband was like, why don't you do this? And my husband is, like, very conservative in that way of, like, you know, like, be cautious about things and overthinks it. And so I definitely. Him saying you could do this was, like, all I needed. Like, it was just like, okay, that's what I need is if he supported. I mean, he would support anything I did. Not to say that he wouldn't, but I think that that was the moment when I was like, okay, that time is right. And. And I remember sitting down with Valerie, Genghis and Amber Hurdle, and we did this, like, this one day, like, kind of retreat to go through everything. And Amber does this process where she just, like, puts up a piece of paper on the wall and just writes down all these things and just asks you all these questions. But Valerie said to me, how long have you been in the industry? And I was like, well, I started in 1992, and she was sitting in front of me, but facing the wall, and she turned around, like, leaned over on the couch, on the couch backwards, and she looked at me. She was like, that's your hook right there. Nobody's been doing this like that. And so it just was like, oh, okay. Like, it was a light bulb moment.

Speaker C: My.

Speaker A: You know, like, Alex, I talk about on the podcast, like, the aha, uh, moment that, like, it was like, I do. I have value. And, uh, why can't I do this? And so I've learned a lot about me, and I've learned a lot about doing things. And like I said, I feel like I've forged some really strong relationships and my personal net worth. As people say, your network is your net worth. And I am so rich in that. My network is wonderful and the support that I have. These people are family. I have a core group within the industry that I literally text all day, every day, and sometimes in the middle of the night, you know, so it's just. You just find these people that are supportive of you, and you can do anything with that. And that's where it just all kind of clicked and came together. And I was mulling over names and just Annie and Co just felt like the right thing because my Name is people know me as Annie. There's not a ton of Annie's in the world that you run into. And so I did that, and it was funny because people are like, oh, like Tiffany and co. And so that was kind of how the color scheme sort of came about. But the Annie and company, I wanted to do that because I felt like that way, if I did grow, the CO could be other people. I could bring people within, like, as collaborators for projects and that type of thing. So it didn't sound like it was just only me. I didn't want it to be like, it's Annie's thing. It's me and my network and all these people I work with, and I tap people all the time, and I send people their stuff that comes across to me that I could probably do, but it's not where I'm strongest. So I don't want to give people false hope that I could help them out exactly the way they need it. So I send it to other people, and I've done a lot of that. And I think you and I talked about this before, but I talk about this frequently. I became a big fan of Deepak Chopra years ago, and he had this principle of, everybody's born naturally hospitable creatures for the most part, but we're all born with buckets. And our job is to fill up others buckets. And when we fill up others, that flows back to you. And I have had that principle for 10 years, and I have just focused on it, focused on it, focused on it. And I can say without any doubt that that is a proven principle. It works, because I am starting to see that flow back to me. And it's not in a disingenuous way. It's just the goodness that you put out in the world. You eventually get it back, and it may not be in the form of high value. I haven't won the lottery yet, but, you know, I probably need to play. But it's just I'm very rich in my relationships and my partnerships and my collaborations, and I'm very, very grateful for that.

Speaker C: Your podcast, Alex and Annie, the Real Women of Vacation Rentals. It's a very respected, uh, voice in our industry. I love it. Tell me, what's been one of the most interesting conversations you've had in your podcast or some of your favorite conversations? I'd love to hear about that, because we remember those right.

Speaker A: Yeah, it's interesting because I think one of the things that Alex and I did, we purposely didn't want it to Be. Even though the name is Vacation Rentals, like that's in the name. We didn't want it to be just about vacation rentals. And so we wanted it to be all the things that are kind of tangential to the business, so, like personal branding, marketing, hospitality in general. And so we've had the opportunity to talk to so many different people. But I think some of my favorite ones is when we get some operators that have history and they get together. And so we did an episode last year was with Steve from Inhabit. Steve Karen. So Steve Karen, who's like one of the most fabulous individuals. It was Lino, it was Paul Wolford, and then it was Jim olin. And the four of them riffed off each other for 45 minutes. And Alex and I didn't really have to ask a question because they were just asking each other questions. But they have such long history. And what I love about it is, and it's been a running joke, is that there's something in the Panhandle water that has provided the industry with a lot of technology, with a lot of advancements, with a lot of knowledge. So I say, like, if you cut your teeth in the panhandle, in this industry, you can go anywhere because you know all the things. But you think about, like, Jason Key Data, like, everything that he's done's come from here. Leo's done multiple things. Jim Olin's done multiple things. I mean, not to mention, like Jim's sons, you know, Ryan and with Away Day and Jacoby, like, they've done so, so much has come out of the Panhandle. But just listening to their stories and how it was when they started out 30 years ago, and I always, like, think, like, gosh, they were literally in my yard and I didn't really know them until, like, years later. And it's fascinating to me. So I think just being able to hear the history from some of these operators, it's been a joy because it's almost like capturing moments that just in a different perspective. And then I think another person from the panel, um, Jeannie Daley from Newman Daly here, she's just an icon. I mean, she's just an absolute icon. So I think those conversations and then just having some people outside of the industry that have come on that again, sort of like the tangential industry. We've had Mike Flasky, who's with Marriott International of the timeshare division, he had been with Diamond Resorts and sold them. So just some really fascinating conversations.

Speaker C: Do you remember Derek Kayongo? Who spoke about the global soap project at, uh, Vermont or somewhere.

Speaker A: I have to look him up. I don't know that.

Speaker C: He was amazing. He spoke at one of our conferences. I don't remember. He was a refugee in Kenya before coming and stay at like this hotel in Philadelphia. Saw the barely used soap and was being thrown away. And he created this global soap project. He was on cnn. He's been got all these civil and human rights. Anyway, reason I mentioned him, I thought you would have interviewed him. If not, you should. I'm just saying because he's tangential to the industry and hospitality. He's such a real person. Like when I had him on, I didn't know him from Adams Housecat. I really didn't. But he is such a genuine nice person and he's like this very humble person who's received all these accolades. So that's like I was thinking about who would stand out for you and who would stand out for me. There's lots of people, of course, that stand out for me too. I'm with you. Those icons in the industry to learn from. I mean, Steve, Karen just. He doesn't stop. He just came up with some. Just this amazing new project that he's created. You might have him on to talk about it. It's different than anything that you would think that he would do.

Speaker A: He's so smart. He is so stinking smart. But I love talking to him about his chickens. I mean, I think that that's like the thing as you. His chickens just threw me for a loop. I wasn't expecting that. But there's some incredible people in this business. And I can't say that there's one favorite because I love all of them. I mean, I think that that's the great thing is we get to talk to people and we get to like, ask. And you get to ask them all these burning questions. And I always laugh. It's like none of these people would have taken my phone call five years ago if I'd called them. You know, they would have passed me off to some assistant somebody else and been like, oh, you know, whatever. But it's like now they reach out to us and I'm like, oh, we get to talk to these people. And so it's neat to like finally get to talk to people that you like, admire and stuff.

Speaker C: Uh, so, Yeah, I agree 100%. I think I could have Amber heardle on all the time.

Speaker A: Just.

Speaker C: I could just listen to her talk all the time. She's a fount of information. She's like you, she's got. There are people that are very well spoken. I don't feel like I'm one of those people. Like, I know I'm not. I love talking with people, but she's very well spoken and very well put together in the way that she puts her thoughts together. And it's very easy to follow. And people like that that we've had on are so much fun. So if you could pick anybody in the world to have on your podcast in the next six months, who would you have? The Pope. You know, that's probably doable. Talk to Matt. Matt just texted back and forth with him. I have some contacts if you really want that. Seriously.

Speaker A: I know we talked about that. No, I don't. It's funny because the Pope is always the person I want to invite to dinner. And now that he's an American Pope, like, even more so. Like, that's the person I want to have. But if it was somebody in the industry, it doesn't have to be in the industry. Yeah, I mean, I don't know where you go higher than, like, better than the Pope. For me, I don't know. The Pope is my go to guy.

Speaker C: I love that. But it really could be doable. You think about that. I know they're busy. They keep very busy. Well, what you talk to him about

Speaker A: how we make humanity better. Like, I am not against people doing well, and I'm not against people being wealthy, but I think we're seeing so much grotesqueness within that wealthy. And you see people suffering and it just. And I'm not doing enough. I mean, I know I could be doing more, but you see these things. And so I just feel like the Pope is, to me, always been that person that could bridge all the gaps to bring it all together. And I love to see him going into mosques and I love to see him walking the walk. And all the Popes have done, you know, in my lifetime, have done their various parts of this. And I think just having an American one just feels more relatable because one, he's so accomplished, I mean, speaks what, four languages fluently? It's just incredible. And I think after going to the Vatican and being able to walk through and do the tours and go into St. Peter's and all that, like, it just really drove it home for me, like, the position that the Catholic Church, but the Pope is in, to like, bring everybody together in a more Kumbaya, you know, way that at the root, religions, like everybody's God or whoever they worship is there to help you be grounded and be a better person. And I find that sometimes people are using that in a manipulative way. And I just feel like, here's this pope who's speaking to. He's a U.S. person. He represents, you know, one of the largest religions in the world. And, like, he can be that person to. To help us be more harmonious.

Speaker C: So that's my wish, to bring people together. Because it's about relationships. All of that is. I think that's remarkable. I really do. And, um, my husband said to me. He said something in February. We were working at the Vatican, and he said to who did he say? Probably the head librarian, but somebody there, he said. I remember we were speaking, and he said, you know, if I was the Pope, I would spend all day in my library. And I'm just thinking about what you're saying. You're saying here, you know, no, he's there to have relationships. So I think it's on the perspective that you're in. I think it's a remarkable time in our lives to have that as to have him as pope. So I love that for you. Thank you for sharing that.

Speaker A: I feel like it was meant to be. I feel like it was one of those things that was a counterbalance to other things happening. So I hold out hope for he to be the beacon of change for good. So it's a lot of weight to

Speaker C: put on the Pope.

Speaker A: I don't know that he's prepared for my wish there, but I'm just a small part.

Speaker C: I'm sure that what everybody does has been, um. Will be remarkable. Everything's been remarkable so far, so I'm looking forward to it. Is there any other advice you want to give to property managers or anything you want to say?

Speaker A: I think, again, I think this industry is a relationship business, and the more you foster relationships, the better off you're gonna be when times are bad just as much as when times are good. So you'll have a network there, but we're just a bunch of good people and hotel people all the time. You, uh, know, I've had people like, um, you guys are, like, a lot of fun, you know, And I. I just think, because there's not this side of the business, everybody works hard, plays hard, loves hard. It's such a great place to be, and I can't imagine being anywhere else.

Speaker C: I agree. They're the nicest people in the industry. And I think about the people that I love that are not my family.

Speaker A: They're in this industry.

Speaker C: They are in this industry. They are people like, have my back that I know I could call at 2 o'. Clock. There are people that we don't call at 2 o' clock in the morning that we could.

Speaker A: Absolutely.

Speaker C: There are people now that are gazillionaires that now have so much responsibility that I know I could text and they would answer me that. I was really surprised when I had this data issue how many people really were willing, including yourself. Thank you.

Speaker A: All I did was tag Bill Gates.

Speaker C: Well, thank you. But a thousand people. But, uh, 70,000 people that saw it did not tag Bill Gates. I appreciate what you did and I do appreciate Microsoft for reaching out and I will. I am going to put together a campaign about that. They were really awesome, the people there. So thank you for that and thank you for just being such one of the best people in the industry. When I think about the nicest people in this industry and people you really would want to invite to dinner, you're top of my list. Give Alex my love and, uh, thank you for being on the show.

Speaker A: Thank you. And I hope to see you in person soon to get a big whole hug from you.

Speaker C: I'll see you at the industry events and you keep on keeping on with booking.com and help them understand the industry so that we can integrate better with them. That's beautiful.

Speaker A: It's a lot of fun and they have a lot of potential and they can help a lot of people. So it's definitely good.

Speaker C: It could change the way people do this.

Speaker A: Absolutely.

Speaker C: It could change people's lives. So, yeah, that's important, 100%. Thank you, Annie.

Speaker A: Thanks, Lynell.

Speaker B: This episode of the Vacation Rental show is brought to you by Streamline. To find out more about how Streamline can grow your vacation rental business, visit streamlinevrs.com make sure to search for the Vacation Rental show in Apple podcasts, Spotify and YouTube or anywhere else podcasts are found and hit subscribe. Subscribe so you never miss an episode. On behalf of the team here at Inhabit, thanks for listening.

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