Sarah Bradford Unfiltered: Fix These Vacation Rental Mistakes Before 2026
In this unfiltered conversation, Sarah Bradford joins us once again to break down the most common and costly mistakes she sees vacation rental operators still making today.
Drawing from more than two decades in the industry and her experience building, scaling, and ultimately selling two successful vacation rental companies, Sarah revisits pivotal moments that shaped her leadership, operations, and decision-making.
This episode is practical, direct, and rooted in real situations. From financial missteps and weak owner communication to outdated technology, unhealthy competition mindsets, and tolerating the wrong homeowners, Sarah shares what she would fix immediately if she were starting again today.
As the industry heads into 2026, this conversation offers a timely reality check on what needs to change and what operators can no longer afford to ignore.
We cover:
1️⃣ The financial habits that quietly put operators at risk
2️⃣ Why trust accounting, budgeting, and clean books are non-negotiable
3️⃣ Common owner relationship mistakes that lead to unnecessary churn
4️⃣ How silence from homeowners can signal problems long before complaints
5️⃣ Why competing on commission is rarely the right move
6️⃣ The danger of delaying technology and PMS upgrades
7️⃣ How weak company culture shows up in performance and retention
8️⃣ When to say no to homeowners
9️⃣ Why outdated homes hurt your brand more than you think
🔟 What operators should fix now to stay competitive heading into 2026
Connect with Sarah:
LinkedIn: https://www.linkedin.com/in/sarah-bradford-032129b1/
Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).
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#vacationrentals #shorttermrentals #propertymanagement
00:00 - Meet Sarah Bradford And Her Story
05:18 - Trust Accounting And Budget Wake-Up Call
12:18 - Open-Book Finances And Profit Sharing
18:45 - Love Your Homeowners Or Lose Them
27:56 - Competition Panic And Pricing Confidence
36:10 - Focus On What Matters And Website Failures
41:20 - Sponsor Message
43:10 - Branding In The Field And Owner Touchpoints
49:40 - PMS Migration And Embracing Technology
56:05 - Red-Flag Owners And The Power Of No
Alex Husner: 00:02
Welcome to Alex & Annie, the real women of Vacation Rentals. With more than 35 years combined industry experience, Alex Heuter and Annie Holcomb have teamed up to connect the dots between inspiration and opportunity. Seeking to find the one story, idea, strategy, or decision that led to their guests' big aha moment. Join them as they highlight the real stories behind the people and brands that have built Vacation Rentals into the $100 billion industry it is today. And now it's time to get real and have some fun with your host, Alex and Annie.
Alex Husner: 00:37
Welcome to Alex and Annie, the real woman of Vacation Rentals. I'm Alex and I'm Annie. And we are joined today by Sarah Bradford, who is an industry celebrity and veteran, former owner of Winter Park Lodging Company and Steamboat Lodging Company, as well as former host of the Sarah and T podcast. Sarah, it's so good to see you. Great to see you, ladies.
Annie Holcombe: 00:58
We're so excited to have you. And I feel like I'm I'm at your wallpaper, so I'm really, I'm really digging it.
Sarah Bradford: 01:03
I know you you got to get some wallpaper in the back there.
Annie Holcombe: 01:06
Well, I thought I had enough going on back here. My pale walls. But before we get started, why don't you give us just a little snippet about your background and who Sarah Bradford is?
Sarah Bradford: 01:20
Who is Sarah Bradford? Uh well, I always wanted to be a celebrity, so thank you, Alex. Now I can say I've been introduced as such. Uh let's see. I got into the vacational industry in 2004. I guess we're at 20 over 20 years now. We started Winter Park Lodging Company in Winter Park, Colorado. Then we moved to Steamboat Springs, Colorado and started, guess what? Steamboat Lodging Company. And in the middle of all that, I also started a podcast with Tim Cafferty of Outer Banks Blue and Sam Bridge Blue over in North Carolina and Virginia. And we did not ever record as many episodes as you two at this point, but uh we did quite a few. We did it for seven years. And it was, as you said, Alex, it was called Sara and T. Uh, it was actually called the Vacation Run Managers Podcast with Sara and T. But if you if you search up Sara and T, you'll find it. So uh just been really in involved in the industry. And then three years ago, three and a half years ago now, actually, we sold both businesses to continuum and left that day, walked away with a big smile on my face, and haven't looked back. And now I just do a little tiny bit of consulting in the industry.
Alex Husner: 02:41
And many, many lessons learned over those years. Anybody who's been to conferences has heard you share stories and you know different tidbits, and certainly on the podcast, you guys did an amazing job on the educational content that you provided people. But at the VRMA executive summit this past May, you had a really interesting session that was called uh Dear Diary, What I Wish I Had Known 15 Years Ago in the Vacation Rental Industry. And I remember before you went on stage, you were showing us you literally had your diary entries and you were going back through and you picked out some of the main lessons that you learned. So we've been wanting to have you on, and finally we got schedules aligned today because I think there's just a it's just a treasure trove of information and knowledge that our listeners will will love to hear if they weren't at the conference. So uh let's get started and and I'm excited to hear what you picked for the first lesson.
Sarah Bradford: 03:34
All right. Sounds great. Yeah, I do have a teacher. I'm a teacher at heart. I used to teach high school way back in my 20s. And I also have a pet peeve that I just hate to see someone remake the same mistake I made, right? Like I want to share with everyone possible in our industry so we move forward instead of keep repeating our previous errors. So I had so much fun sharing this talk, I guess you'd say, um, this format uh in Miami. So if we just pick some highlights and we'll go through them and see how much we can fit into the podcast. But in before I do, I just did want to tell the audience those watching on video, I pulled up my original diary from the 80s. This entry is 1984. It's not gonna be that kind of diary. This diary says something to the effect of I went to Emily Hoke's house, we saw Matt, what a massive babe he is. So we're not gonna do that kind of diary. This is just confessions of a vacation rental manager. So I'll read the entries for another episode. Yeah, exactly. Oh, and Alex, you were the awesome person that at the end of the talk, you were like, I can't believe you had a diary that whole time. I was like, I made this up, I wrote it all up from my memory. So I just love that you thought it was authentic. Well, some people don't journal every day. So I mean, I wouldn't surprise. I'm not, I was only like that in 1984. But it's a quick little entry I'll read and then I'll kind of share why what I learned from that, and you guys chime in. So the first one we picked was from May 2009, Dear Diary. We're not doing trust accounting. I'm not even totally sure what that is. It sounds like something people with CFOs worry about. Oh, meanwhile, I'm in Mexico on vacation with two toddlers, one panicked husband, and exactly one bar of self service. I'm praying for a last-minute booking today, so it'll go into our account by 4 p.m. and we can cover payroll tomorrow. I have zero chill and my dignity is currently operating at 2%, just like my phone battery. So this is not what a terrible.
Annie Holcombe: 06:00
I mean, I remember when you said that. And I remember being in property management where we were worried about like, how are we gonna make payroll? Like, like that was because trust accounting just hadn't become a thing yet. And now it just seems like, why didn't we know that that was that was even a thing? So when you said it, there were so many entries that you had that like resonated with me from my experience. But I remember that that panicking feeling of not knowing if you were gonna be able to pay the bills or the payroll or like the insurance or whatever. And so, like, what what what did you take away from that? Like looking back on it, did you think, like, how did I get through that? Like, I mean, it had to be the feeling.
Sarah Bradford: 06:38
Yeah, it was a horrible feeling. We didn't have a bunch of money in the bank personally. We were still pretty young. We had just had kids and we were borrowing from Peter to pay Paul. And I gotta tell you, Annie, from what I've learned in the industry, it's still happening a lot. I know. And that's why I bring it up. Everything I bring up, I feel like is relevant even today. I wrote like something to just kind of summarize it is that future reservations are not your personal piggy bank, and everyone needs to hear that loud and clear. And there's plenty of people out there like, it's fine, we still have money in the bank, or my dad'll give me money, or it's okay. It's not okay. When you have reservations that come in and you don't live in North Carolina and you're not forced to have trust accounting, when you have reservations come in um for let's say six months from now, that's not your money to spend. And that's just such a dangerous thing to have that money look at it and think it's yours. So that's what I learned. Um, what I really should have done was made a budget to start with. We didn't have a budget for the first five or six years. Again, I think that's very prevalent still. I'm sure your listeners, there's a couple of people driving around right now, um, making them feel guilty because they don't have a budget. But if I had had a budget, I would have known per month how much money I had, see how it's going, and be able to go, whoa, we're in trouble, right? Yeah. And so a budget is so important. It's so important to track a budget. This is probably my number one thing, and that you stick to the budget and you don't overspend. The other thing is we always hear this at conferences, but I think it's just you can't say it enough. You should run your financials like you're about to sell your business, even if you're not gonna sell your business. I mean, run it like you could tomorrow. If someone said, Let me see your books, you could just open them wide up and someone would go, dang, that's good. Yeah, like organizer.
Alex Husner: 08:35
Yeah, yeah.
Sarah Bradford: 08:36
When we did go to sell, it was very easy because our books were beautiful. And so the rain catcher who represented us were just like, Okay, you actually have your act together because we had worked so hard to never have the feeling again that I had in May 2009.
Alex Husner: 08:54
Yeah, yeah. Well, and I think a big part too of why, you know, accounting in this industry is so complicated is a lot of us are in very seasonal markets. In your side of the world, I mean, you're mostly in the wintertime. I assume that you're getting the majority of the revenue, but in beach markets like where Annie and I are, you know, it's June, July, and August. I mean, that is your time to really make the money that has to, you have to make sure it's there and can work for you in the off-season because there's there's just not enough to January, November. I mean, those off-season months, it's really quiet in a lot of these destinations. So I think newer companies fall into that as well of just not planning ahead.
Sarah Bradford: 09:27
It's so true. Most of us are cyclical, right? In our businesses. And I mean, hopefully COVID will never happen again. And I'm not going to read the COVID entries from here. If you guys remember, I shared the horrible story of COVID at our business. COVID's a perfect example of why you want trust accounting. Because when COVID happened, it happened in our very height of our season, March. You know, for beach communities, that would be like it happens July 4th.
Annie Holcombe: 09:53
Yeah.
Sarah Bradford: 09:53
And we had to refund everyone. So we refunded over a million dollars in two weeks. Wow. And if that was back in 2009, I wouldn't have had it. And like we would have stayed in Mexico and never come back.
Speaker 3: 10:06
Yeah, exactly.
Sarah Bradford: 10:08
Oh my gosh.
Annie Holcombe: 10:09
Oh my gosh. Okay. So you got past that panic moment. And then what was that? What's our next entry that we're going up?
Sarah Bradford: 10:15
Okay, yeah. And the other thing I wanted to say, since we're not going to talk more about budget and it's my passion, is I really believe the only way a budget works is if you share it with your team and don't keep it a secret. And even more so, I think you should do profit sharing and let everybody experience the joy of getting a little of the money that you profit.
Alex Husner: 10:33
Can I actually ask one more question before we move on? Because I know this is something that I've heard you and Tim talk about on your show quite a bit. That Tim always said he let the whole company see the PL and everybody had access to see what was going on. Did you run your business the same way? Was it that open for everybody?
Sarah Bradford: 10:49
I did. And when I done some consulting with other vacation rental managers, it seems to make everybody nervous when I tell them I think they should do that. Yeah. You know, they they get nervous that someone's going to see how well they're doing or how well they're not doing. It they think it might make the the staff jealous that, you know, you made 500 grand or whatever. I never had that problem. I shared the entire thing with them. We went through it in detail, and then we did updates every month, and they had a goal, they knew the profit we wanted to make that year, and then they got a percentage of that if we hit it.
Alex Husner: 11:26
Yeah. I mean, I think having giving your upper employees an opportunity to have skin in the game, that's the most important part to that. And then when they understand, like not just of them just to earn more, but what they need to be thinking about looking at their own budgets within their departments of like, it's not just free money to go out and spend, like, this is also going to impact what they get at the end of the year there. So I think it's great philosophy.
Annie Holcombe: 11:48
No, I was gonna say, like, I think it kind of goes into like something that I've been doing with managers, is talking about from like business development standpoint, like your owner acquisition, like your whole team needs to be bought in on the ethos of your company is so because they are the front line and they're running into other owners and they they they should be equally as excited about the property manage or the owners that they're bringing on the plan as you are, and you shouldn't have one person focus on it. The whole team needs to be part of it because you need to build these relationships from every aspect of your business with these owners. And I think that kind of goes into your next entry was kind of dealing with owners.
Sarah Bradford: 12:22
Yes. Oh, nice segue. Thank you. Here we go. Uh yeah, I could do a whole episode talk with you guys about that last entry about budget. It's yeah, really forgotten. It's forgotten about. Okay. So we are moving to 2010. We're going at rapid speed here. Uh dear diary, we signed on two new homes this month. Yay, right? Except we lost four. So yeah, technically we're growing just in reverse. They all said it was for little things, they're going in a different direction, or my personal favorite, they're taking a break from renting, like it's some kind of toxic relationship. But here's the kicker I realized I couldn't pick most of those owners out of a lineup. They might have had three little boys or a cockatoo. I it's hard to say. This is maybe my second biggest one to share is that I see so many uh owners of vacation rental companies not loving on their homeowners the way that I feel they should be. If you don't have homeowners, you don't have homes. And if you don't have homes, you don't have a product to sell. And so I think a lot of vacation rental managers are just trying to grow so much. They just focus on like who's the next owner we're gonna get? Who's the next owner? Instead of, I need to love on the ones that are with me, right? Love the one you're with. Right. And so I just wrote in kind of some lessons I learned from that is that some vacation rental managers they send their monthly statements to their owners, they send that annual 1099 and they're like, I don't know, they didn't call and complain, so I guess they're happy.
Alex Husner: 14:07
Yeah, silence is not golden in this case.
Sarah Bradford: 14:11
Silence is not golden. In fact, it's funny you said that. I used to go through our all of our homeowners, even when that we had 200 some with my team, and we'd say, Have we talked to this person? Have we talked to this person all in the last month? Has anybody talked to you know John Smith? Nobody's talked to John Smith for like three months. Oh, that's a problem. And then we'd reach out to John Smith proactively. And um, John Smith would be like, Yeah, I wasn't gonna complain, but we are kind of looking around, you know, it's like, what? So a proactive call means everything. Um, I think you should meet every homeowner in person. I'm sure that's controversial, but I do. I think you should send monthly informative newsletters that aren't too wordy. They have maybe three articles in there. You put a picture of your staff, not just you. You make them really personable every month. You have to be the expert. That is probably something I didn't realize until six or seven years before we sold is you are the expert. They don't know about our industry. So you have to tell them. And if you don't tell them, then they're your competitor might tell them. And they think, oh, well, Sarah didn't tell me that. She must not know. So you have to be the expert and share information with them. Uh, we surveyed them two times a year, just the net promoter score. I know you've talked about that on your show, that metric, very easy.
Speaker 3: 15:33
Yeah.
Sarah Bradford: 15:33
Survey them and don't just survey them, but then you sit down with your staff and you say, let's go through every answer and how do we want to, you know, correct anything that we heard about? We would go, oh wow, they like us. I didn't think they liked us. Um and then we also did something that I think probably 0.05% of vacation rental managers do, but it was magic. Are you ready? Oh, I can't wait. Every six months we ran reports of how everybody did all the homeowners versus last year on rate, occupancy, and you know, overall revenue. And then we separated those into categories like revenues up, but ADRs down, you know, revenues up and ADRs up, revenues down, ADRs up, you know, you get it. And then we created emails for each one of those sections and then did that thing you can do in Excel. What's that called? Mail merge. Yep. And that each owner, every two times a year, got an email telling them the performance of their home, very customized. And half the time like them, yeah, half the time they didn't even know they had done better than last year because a lot of homeowners aren't sitting around adding all those numbers up like we are. Yeah, and it was just a great way to say, we're killing it for you. Don't even open that mailer from the competition. Right. Yeah. Yeah.
Alex Husner: 16:56
Well, and I mean the hard thing is too, I think in our industry, it's like uh owners have, you know, most softwares do not give a lot of transparency for owners to be able to see what's going on in the property or to be able to pull any information like that themselves, unless they, you know, downloaded their statements last year and added it up. But that's something that I think is is continuously getting better these days. But back then, you know, that was that's kind of you know, it's a heavy lift. I mean, because really because it's like you've got to go you property by property and you know, that whole program. But it definitely makes sense why, you know, you just you you have to tell people you're doing a good job. You can't just assume that just because you're up that they know it because they might not be paying attention.
Sarah Bradford: 17:34
Yeah. I mean, really, I think the goal is that you have a touch point with them at least every month. Um, and then my other one is that so many home so many uh VRMs forget to copy their homeowners on their e-blasts, their marketing e-blasts.
Alex Husner: 17:48
Yeah, yeah.
Sarah Bradford: 17:49
And you want to just show them you are marketing like crazy.
Alex Husner: 17:53
Yeah. Here's a question. What did you let owners when they came to check into their property, did they get the same flow of communication as a guest would?
Sarah Bradford: 18:02
We didn't write to them like they were a guest, because we that would have sounded odd. We let them, we that they definitely got all the check-in emails and things, but we had a whole system of what they got because they were a homeowner.
Alex Husner: 18:14
Because it was different. Okay. Yeah. Cause I've I've had different conversations on that. I think on one hand, it's good for owners to see what you are sending to guests. I mean, like if you explain, I know that you're not a guest, know that you're an owner, but I want you to see how much time we've put into these guidebooks and the information and stuff like that. Um, but was just curious.
Sarah Bradford: 18:32
No, that's a good question. We did have, and we also had one that went to owner guests because we had a lot of owners that had their friends come and we had a special email for that because you have to say, like, I know you're not paying, but this is how it works when you leave. Yeah, right. The rules, non-paying guest of owner. Yeah, non-paying escalation. That's right. Um, one thing I wanted to read here, I have this little book of all these quotes from John DeJulius. You know, he's my favorite person in customer service in the United States. And Peggy, my old staff, wrote these quotes out for me. And this one applies to this topic, which is relationships are the biggest differ differentiator in customer and brand loyalty. So, one more time. Relationships are the biggest differentiator in customer and brand loyalty. I don't care what your marketing looks like. If you don't have relationships with your homeowners, it doesn't matter how pretty your e-blasts are. It's all about a relationship. Yeah. And that's painful to hear because some of you guys don't want to have those relationships because they're maybe not your type of people.
Alex Husner: 19:42
And how many how many people did you have in your owner relations team to manage all those relationships? Because when you you had how many properties? A few hundred.
Sarah Bradford: 19:49
We had various amounts, but at one point we had probably 200 properties between winter park and steamboat. We varied on how many people we had. We really landed on one or two people, it wasn't like Like five people, but it was a big job. And checking all the statements, making sure you're you don't have no errors on your statements is probably my another number one thing I didn't put in the diary. The second you have an error on an owner statement, you've lost trust for maybe ever. So we we had dedicated people that were working with homeowners and knew what should be on the statement and reviewed all of those, but we probably had like one per 50 homeowners. Let's say that. Interesting. Yeah, it's a pretty crucial role.
Alex Husner: 20:33
Yeah, for sure. All right, well, I'm moving on.
Sarah Bradford: 20:37
Okay. I'm gonna keep going here. Those were two really big ones, so we can kind of fly now. All right, the next one we've jumped all the way to 2013. My kids were six now. I have twin boys, and they were six years old. Oh, this was a rough time. Dear diary, there's a new vacation rental company in town, and I'm convinced they're younger, cooler, and probably give away puppies with every booking. I spent two, I spent two hours stalking their website and spiraled. So far, I Googled how to compete when you suck. So this really happened. I didn't necessarily Google how to compete when you suck, but we get the gist. That was the mentality of your mind. It was for the impact. This happens all the time. It was really happening to me back then. And I let the fear come in. And then the fear was trickling down to my staff, right? I wasn't saying, hey, you guys, we're good. Like this is the deal. Don't worry about it. Um, instead, I was kind of letting it feed on all of us. And as you can imagine, it was a company that started with the V and end with an A that was coming in, right? Yeah. And they looked big and fancy. And we were so scared because they had lower commission. We had a really high commission rate in the mountains. I won't say what it was, but it it shocks people. They had these slick handouts, they had, you know, all this stuff we didn't have. They were they were talking corporate talk. And you guys, I'm not kidding, they were the best thing that ever happened to us, especially in Winter Park, because they didn't take over. And actually, anybody that went to them in those days, I think I can say this now that you know it's kind of uh become a different company. They would all just leave them and come back to us and love us, and they never even left us to go to them. It was just like a brand new customer that called and said they were with some of these more fly by night companies that didn't have staff in Winter Park, they they could just couldn't perform the way we could. And so be confident, like don't you need to have a healthy fear, but you don't need to get obsessed and you need to understand what your differentiator is and why you shouldn't be afraid. And then I would say that you should go ahead and befriend them. So besides the, you know, the V that ended with A, I never did know who owned that. I never knew who worked there because they didn't weren't really in Winter Park. But the other competitors we became very close to. And then when I went to Steamboat, you know, one of my best buddies is Robin Cragen. And he was, whether he'll admit it or not, was my direct competitor in Steamboat. It's incredible to be buddies with your competition because there's plenty to go around. And then you can share, like when some when you have a leak in the roof and you can't have the guests stay next week, I could call Robin and be like, help me, you know, or when all the regulations went down in Winter Park and Steamboat, all the vacation rental regulations, we could work together instead of being like, Oh, that's my competitor. So I just tell everyone to please chill on the competition. And I also wanted to say that just don't start lowering your commission because someone tells you they're looking at the competitor. That is the kiss of death.
Annie Holcombe: 23:58
Yeah, because once you get once you go down, it's hard to get back up for sure. Exactly.
Sarah Bradford: 24:03
Also, when you lower your competition, we could role-play the conversation, but let's say Alex, you go, you know, would you take would you do it for 20? Because that's what your competitor is doing. And if I said, Oh, yeah, I'll do it for 20. You just said that you weren't worth the 30 that you started with. It's almost like you were lying. Yeah. Right? Yeah. And there's a like a popular story in our company where this one homeowner said to me, you know, the competition's five percent less. We do want to go with you, but will you match that? And I said, No, no, I won't. And you'll be back to me. And he goes, Okay, I was just asking. I'm going with you anyway.
Annie Holcombe: 24:40
Just had to see what you would say. I think it we were actually talking to somebody last week, um, down here on 30A, which is in my neck of the woods. But, you know, I when I was in property management, it it was it was the scarcity mindset, you know, and it was just like everybody was operating on this, like, we need to like hoard everything and get everything. And you couldn't share. And just I I see how that is that has changed and people are understanding the need to work with each other because not every owner is gonna be a good fit, not every guest is gonna be a good fit, not every, you know, every situation is exactly the same for each one, and you can learn from each other. And I think it's it's it's the world has gone more to that, you know, there's abundance, there's plenty out there. Why not we all work together? Because regulations are gonna affect us more than these homeowners jumping ship all the time. And so we need to communicate. So I think that that's a really um salient point and really important right now, as there are companies going back to like all these other things we've talked about, there are still companies that operate in that and they want to get everything and they don't want anybody to know, and they think that they've got some magic that nobody else can replicate or or you know, or or or do. And it that's just not not it's not a way to foster a good feeling in the market. And I think it it makes me feel like you know, karma will take care of those people, but wouldn't it be easier if everybody was just on the happy karma train? You know, we're all helping each other out.
Sarah Bradford: 26:02
Yeah, I just thought of something also when I'm telling you all my mistakes. So here's another one in this topic. When I used to meet with a new homeowner, I would rip on the competition. Yeah, okay. That is a huge no-no because the homeowner would be like, Well, I don't like X, Y, and Z company. They we had them for two years and they did this, and I'd be like, Yeah, they're blah blah blah. And the second you start ripping on your competition, you look weak and like a small person, and you lose the respect of that homeowner, even if the homeowner's ripping them to shreds. I would encourage everyone to not rip to not just start falling into that same conversation of agreeing with the homeowner. In fact, I think it makes the homeowner want you even more to say, Yeah, I'm I'm I'll just use Robin for fun. Um, yeah, I'm friends with Robin. They have a good company over there. So if you go with us or you go with them, uh either way, I think you're gonna be, you know, make a decision.
Alex Husner: 27:05
Yeah.
Sarah Bradford: 27:05
And they're like, Oh, she's so confident. I kind of want to be with her. Yeah. So don't rip on your competition.
Alex Husner: 27:14
Yeah. And we were talking to somebody last week also about, you know, when they meet with the new owner, they ask them, I mean, not not to like shred the other company, but they say, What, why, like, why are you even here? I mean, what are you not happy about that the other company is doing? And it they use that kind of as a way to also know if the things that they're complaining about are things that are like don't make any sense. Like this could be the chance for the company to say, I also don't think that we're gonna be a good fit for you. Um, but it's not about getting that information. So you're sitting there bashing them, but just trying to understand, like, you know, what are the things that are important to these owners so that you can be able to carry on a good experience with for them when they switch over.
Sarah Bradford: 27:56
I've had many experiences of them saying, one time we came and there was a piece of food in the sink. Yeah, and I need I got finally I got better at my craft as I went along and I knew to stop right there. Don't tell them later. I told them right there. Oh, we'll have a piece of food in your sink. That's yeah, I gotta tell you right now, yeah. We're all gonna have a piece of food in your sink.
Speaker 3: 28:23
Yeah, yeah, exactly.
Sarah Bradford: 28:25
Right? Exactly, yeah. Um, you can learn a lot by asking about their experience. Okay, I'm moving on. Is that all right? Let's go, let's go, let's do it. Let's keep moving. December 6, 2013. Dear diary. Turns out you haven't been able to book on our mobile site for at least three days. The first few guests who called got the classic. Have you tried clearing your cash? That used to be a big thing. But today, when we heard the same thing yet again, we finally checked it. Yep, totally busted. No one could book anything.
Alex Husner: 28:59
Yep, yep. No, it's I remember those days so well of like this was when desktop was more, and we would get calls from owners saying that. And I'm like, no, no, it's working fine, it's working fine. And that same thing of like, okay, if I've heard this two or three times now, there's probably something wrong. Yeah.
Sarah Bradford: 29:16
And I so wish that this wasn't it the case anymore, but I think it still is.
Annie Holcombe: 29:22
Well, I think it goes to the point of like check your processes, check the check the steps that everybody has to go to, whether it's an owner or a guest many times a week, because you just don't know. It could be an internet outage, it could be your provider outage, it could be it could be anything, but you have to be aware of it and try to be ahead of it because if an owner finds it, that goes back to like finding something wrong on the owner statement. That trust is like they're thinking you're not watching the store, you know, you're not minding the store, you're out there skiing and not paying any attention to what's going on.
Sarah Bradford: 29:49
Yeah. Totally. And I wrote in here, you know, I didn't notice because I was too busy debating what color the bag should be to hold the dirty linens versus the clean ones. And I want to just crawl under my desk. This kind of just got it's an easy lesson. It's just one that I think many people don't do. Make sure you're keeping the eye on the ball, focus on what matters. You know, you have a certain finite amount of time and a day. Do the thing that matters, do the thing that moves your company forward, do the thing that, well, like you said, you don't get a homeowner calling about the website not working. And the biggest thing here is to get out of your inbox. And I know this is still true because a home VRMs get so many emails, chats, texts. Am I right? And you just you gotta get out of there and actually do the project, spend time with your staff, go to properties, do the things that really push the business forward. Can I get an amen? Yeah, amen. Yeah, no, absolutely.
Speaker 3: 30:55
Yeah, yeah.
Sarah Bradford: 30:57
And then I added a little thing to that, which is if you really just got you get out of your inbox and you're like, Sarah, now what am I supposed to do? I would challenge you to call a homeowner out of the blue. You know, maybe a homeowner's called and you're waiting, you're scared to call them back because they're gonna tell you they found that piece of food in the sink. Go ahead and just make the call. The less time you wait to call an homeowner back, the better, no matter what the issue is. And even if they didn't call you, call one of your homeowners completely at random and just go, Hey, I just wanted to know how we're doing for you. Nothing's wrong with your house. I mean, that goes so far. And also, most homeowners don't answer the phone, but you leave a voicemail and you get extra credit. Yeah, true.
Annie Holcombe: 31:44
And as the teacher in you is trying to give everybody opportunities to get extra credit, and I love that. Exactly.
Alex Husner: 31:50
Even just starting the call by saying, just everything's okay. You know, like saying that word. Some people, it's like when you get that dreaded call, it's like, oh no, the AC is out or the fridge is out, but like, yeah, start it on start it quickly, like everything's good. I'm just, you know, blah, blah, blah, calling to check in. We'll start the show in just a minute. But first, a word from our premier brand sponsor.
Speaker: 32:10
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Speaker 5: 34:02
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Alex Husner: 34:25
We had somebody else on the show last week, too, that they their team will go to properties and they take selfies when they're at the property. Or if it's a rainy day, they show them out there in the rain or in the snow and like just showing the homeowner and send it in a playful way, just so that they understand like you're out there day and night, not just on check-in day taking care of these properties.
Sarah Bradford: 34:46
That is one of my favorite uh little fun things to do is to take a picture from their property. And I used to just text it to the homeowner and they're like, You're at my house, and it's so fun to see what it looks like right now because I haven't been there in three months.
Alex Husner: 35:01
Yeah.
Annie Holcombe: 35:01
Yeah. Well, and they don't they don't typically get to see their property in any way other than when they're there, or if you're sending them something to say, hey, here's a damage, it needs to be fixed, or you know, like they're not getting it just out of fun. And I think I actually we talked about this because at VRMA this year, there was a session that I introduced and was in um doing questions, and it was like, what are you doing to engage your homeowners? And it was this particular manager that was talking about it. And they were saying, like, how the homeowners, like they now like love getting these texts, they're like, because they're doing fun things of like them standing in the bathtub or like, you know, just weird, weird, like quirky places within the house that that like the homeowner's never gonna see a picture of somebody doing this, but then also the guests next door, or maybe the owners next door, see the staff in and out of the properties, and they're like, wait a minute, my manager's not going in and just checking on stuff, like so it goes like it goes a long way to just build up trust completely in your market and and with everybody, and then and the staff gets to have fun too.
Sarah Bradford: 35:60
Absolutely. That's such a great way to take that to the next level. The other thing you just made me think of there's so many things we could say, but another one is to make sure anyone that goes in that property is wearing your logo gear, looks professional, and uh that that's how you get more homeowners.
Alex Husner: 36:17
Yep. I mean, your your vehicles, wraps, all those things that are super important.
Sarah Bradford: 36:22
Driving the vehicle wrapped person. I love wrapped vehicles. I do too. Actually, you don't have to wrap them, it's much cheaper to just put decals nicely classy on them. Yeah, yeah, if you want to save a buck. Yeah, the big magnets on the side of the door work too.
Annie Holcombe: 36:38
If you need to slightly yeah, I mean, it just depends on, you know, are you using do you have a dedicated vehicle that you can do this with? Some people are starting out, you know, crude and using their own personal car. So we gotta that's true.
Sarah Bradford: 36:52
Okay, I'm gonna let it slide. Thank you. It's better than nothing, but if you put something on the car, you know, if you put a decal or a magnet or you wrap it with the phone number, we got calls of hey, your staff is driving poor.
Alex Husner: 37:06
We're driving, yeah.
Sarah Bradford: 37:09
So they behave better.
Alex Husner: 37:11
Mm-hmm. Yeah, very interesting.
Sarah Bradford: 37:15
All right, what is next on tap? All right, here we go. August 27th, 2014. Dear Diary. We were forced to move off rent one online, and anyone out there that's gotten in the industry recently has no clue what that is, but that was an old vacation rental software that a lot of people had. So we were forced to move off of Rent One Online because they called me last month and said it was being turned off in a month. Um, excuse me. Today we migrated to Streamline some new PMS that had a cool booth at the last Verma conference. And I think we just lost all records of all future reservations, as in all of them. Some head dude named Carlos called me and said not to panic, but that's exactly what someone says right before you do panic. You know, this is I'm sure still happening, people switching PMSs, and it's just not a pleasant experience. Yeah. Can I is that true still? Yeah, I personally think it is. Yeah. Yeah. Yeah. But my lesson is that moving is hard. But in the end, you need to do it before it's an emergency, like I did. We had no choice. And you will be better on the other side if you pick wisely. And having a PMS that's powerful and that they're adding features and they listen to you is a game changer for your business. And so I just encourage people to not stick with an old PMS just because they just can't deal with the idea of switching.
Alex Husner: 38:48
Yeah, totally.
Annie Holcombe: 38:49
No, I was gonna say, well said. I think people just kind of put it off because it is the perception of the pain is is in their mind is it's gonna be worse than if they waited, and then it becomes a necessity, and then your whole life spirals out of control so quickly. Yeah. And your staff too.
Sarah Bradford: 39:07
One of my clients, I guess you'd call her, she just switched to us to a good PMS. And I mean, she texts me and like, oh my gosh, I can't believe you can do this. It's so great. Like, just all the possibilities open up. But wouldn't you guys also agree? Because I know you're very involved in tech more than I was, is just stop avoiding technology, don't turn a blind eye to it. Embrace it, what's out there, what works. And like with artificial intelligence, go for it, try it. It's incredible if you don't try to just turn a blind eye. Does that does that resonate with you guys?
Alex Husner: 39:44
Yeah, for sure. And and the ability to even turn a blind eye is going to become basically a nail in the coffin, you know, much sooner and at much more of a escalated pace for companies that I think companies have been able to still kind of hobble on with older systems.
Sarah Bradford: 40:00
systems or doing things manually and using you know multiple different tools and it's like that era is is gonna go away because the competition is gonna who gets on to newer tech is just gonna start out smoking you so absolutely yeah do it or die kind of situation yeah I think uh I love chat GPT I if I had had chat GPT 10 years ago oh my gosh I might have actually spent more time with my kids yeah I'm gonna skip this one that I really wanted to go through but I want to for time's sake but the biggest the takeaway of this journal entry that I just have to say is that the culture of your company is everything. If you want to talk to me more about that you can go listen to the podcast we recorded about it but your staff has to love you. They have to love your company they have to be behind your mission and everybody needs to be included in it. And it does magical things when your staff are bought into the goal with you. So there's lots I could talk about there. But I'm gonna move all the way to 2016. Okay. Okay, this is a big one. We officially opened our doors in Steamboat minor detail we don't actually have any properties yet so how do you get your very first one mailers of course we just got one call just one but hey it sounded promising I went to see his townhome today this owner's location perfect layout perfect potential through the roof him an absolute walking red flag oh yeah you could tell even his wife was exhausted by his existence that happened way more than I can tell you how the wife was like oh my god at one point he literally pointed at a picture on the wall this is true and he raised his voice and demanded can you tell me what's wrong with this and I blinked and I said it's a little crooked and he said exactly my current management company didn't even notice oh boy and so I the the I'll just summarize what I did next I had this feel that my brain is going right like oh my gosh I can't work with this guy but I also don't want to leave and then tell him later so I'm just gonna tell him right now and so right there and then I said you guys are really nice it's been great to meet you we're not a good fit I'm not gonna make you happy oh man and they were like no we're we're fine we we're good we we we want to work with you and I was like nope nope bye not a good idea and I mean the lesson is to trust your gut and even if it costs you a listening that was the one of the first ones we got a call on like we really needed properties but I knew from my experience in Winter Park that it would just be a nightmare and it would fall into that rule that we all hear about right that 95% of your time is spent on five percent of your homeowners which is not okay. Yeah and just think about that your my staff would have murdered me if I had taken that guy on that would have hurt us more than it would help us and just be so ready to say no to homeowners that are coming under your program if they are a red flag and even harder to do break up with homeowners who are a PIA.
Alex Husner: 43:29
Yeah that was my next question was when you got to that point that they already were an owner and you decided this just wasn't working out like any tips or tricks uh for how to get rid of them nicely oh yeah I I became like the expert at we called it breaking up with a homeowner.
Sarah Bradford: 43:46
Um sometimes there were reasons not that they were jerks sometimes it was that they wouldn't upgrade their home and I just said well then sorry I really like you but we can't manage that or there were they were using it too much or anything like that. But if they were personality conflict people, the ones that call all the time and torture my homeowner manager, I would call them and I had a very direct conversation. I didn't beat around the bush. I just said you're not treating my staff with respect they feel bullied they feel they can't make you happy and we need to be we need to stop the we need to end the relationship and honestly most most homeowners groveled I had a man grovel and I was like nope because they won't change they won't change and you have to do it that is the hardest thing I would say about this business is having homeowners that treat you poorly and it especially happens with women they treat women poorly often that is the case and they'd be really nice to Al my manager my GM you know Al Ferlone they'd be pretty cool to him and then they'd be super rude to me or the homeowner manager who was a woman and I was like no we're I'm not in business for this I'm not that desperate. Except when I was in Mexico without money I might not have done it that time that's the only time oh my goodness okay moving on from that we're moving to March 9th 2016 this is an easy one this doesn't require that much conversation I don't think dear diary the realtor who just got busted for raiding medicine cabinets in vacant homes to feed his opioid addiction that that really happened he called me today super eager to sell me the warehouse he owns with two apartments on top totally casual nothing says safe investment like a pitch from a guy facing felony charges we're still we're still out hopefully he doesn't hear this we're still outsourcing our laundry to a man down the street and owning our own space sounds kind of dreamy. Can we afford it? Of course not am I considering it anyway obviously over the course of 15 years we bought our office in Winter Park we bought this warehouse from this guy to build our own laundry that then ended up servicing Steamboat as well and we bought our office in Steamboat and they were all scary purchases but I want everyone to hear if you are ever going to sell your business I highly encourage you to purchase your office if you can or build your own laundry first of all while you have your own laundry it's the greatest thing ever because you can control that part of your business but then if you ever sell your company most groups out there buying companies don't buy the real estate they don't buy the office they just rent it from the former owner and that then becomes your monthly income yes very smart pretty cut and dry yeah yeah okay July 5th 2017 dear diary wanda called again she's the homeowner who wants more bookings for more money but her house still has a wall mounted rotary phone floral valences oh that's the best a DVD rack labeled new releases and plastic blinds that go full ninja on guests when the windows are open I draft a brave email recommending upgrades then I delete it but in all seriousness uh I didn't delete it I but I well actually I would never have emailed a homeowner that they needed to upgrade their home I was always the one calling or I eventually trained my homeowner managers to call this is about upgrading homes and I think this is one of the biggest problems in our industry. Oh I the the old bear couch that's really not good to sit on, it's fine. We don't want to bother him we make a hundred grand from his home we're not gonna enforce it and I just feel so strongly about this that if you avoid this and let your properties go into you know bad repair or not the latest technology or old furniture old the old look it just looks gross and dirty one home ruins your brand because a guest stays in that home that one home and what do they think of your company and it's not that yeah yeah um so I just want to empower everyone to get out there talk to your homeowners with love and kindness offer to help them if you're up for doing that and get them to upgrade their home and keep it on your brand standard. Yeah.
Annie Holcombe: 48:35
Let me ask you a question on that um we had a lot of properties that had been built like in the late 70s 80s and then there was brand new condominium product that came on so you had this disparity and stuff that had you know some places still had shag carpet you know I mean like brown tubs, you know, all this kind of stuff. And so we put together um with a local company basically a new like a refresh kit that we would take to homeowners like at the homeowners annual meetings and say like okay we'll do this for you and we'll take it out of your rent rental proceeds for next year but but you're not going to go on rent until this is done. And we would get a pretty good um response to it because people are like oh I don't have to put any money out this is this is really good. And I feel like people have gotten away from like being more proactive to do that that they just put all the onus on the owner and if the owner says no they're like okay fine and maybe they break up with them and is that you know but but they might be in a building where if they did upgrade it could do really well. So like I mean what do you think would be your guidance? Would you say do that or or not? Because I've suggested that to people and like oh no no we want the owner to like completely own that process and it's like well if you give them a way to do it where they're less there's less friction for their the or less responsibility because if they are responsible to follow up and they're living halfway across the country odds are they're not going to do anything about it because it's just more work to their day. So do you have any thoughts on that?
Sarah Bradford: 49:54
I'm so glad you brought that up Tom Goodwin's actually great at doing this. He is they are upgrading homes and reaping the benefits. They're willing to do that though um we were absolutely willing to do that so I would encourage everyone to consider it you can get a a designer that's what we did a designer that understands vacation rentals not a just a designer because a designer is going to maybe make it fancy and stay everything stainable sustainable yeah but you get a designer that will work with the homeowner or you have a designer in house whatever you want because the homeowner a lot of times wants to upgrade it's just the idea of it sounds daunting. If they have a house in Hawaii and they live in North Carolina or what you know to to figure out how to upgrade my house forget it. Oh you'll do it for me and you won't really charge me that much extra because you're gonna benefit from the rentals right you're gonna benefit from higher ADR so we wouldn't charge some big fee to do it. Of course the designer got their money they got and then the homeowner paid for all the upgrades and if we had to do something that really took longer than an hour we would charge for it. But we could then control the process we could kind of push them to buy the things we wanted I mean the worst thing is when you convince them to upgrade and they buy a different floral couch. Right.
Annie Holcombe: 51:25
Yeah yeah or they buy more touch keys that you have to place in certain areas like that's that's they always go crazy. Yeah.
Sarah Bradford: 51:32
Yeah and it this also really comes back to whether the homeowner sees this as a business or they see this as their home they've had for 50 years that their family has all these memories in if it's seen as a business which is really the homeowners you want then of course they're like great okay 2000 but I can make 2000 more in a year I'm doing it. And a lot of times this is also I saw this so much the woman would be like thank you for doing this now my husband's saying yes to fixing the place up or he wouldn't listen to me wanting to do it because now you the expert are saying that we can make more money. And so he's agreeing to it because she wanted to upgrade it anyway right yeah so my answer to you is I 100% love the idea of having a upgrade operation in your company.
Alex Husner: 52:21
Yeah I think it's it's definitely something that I'm seeing companies do more of these days. And just to be able to have that that control over the inventory and make sure that you've got something that's going to you know get good reviews and also uphold your brand values of the company it's great.
Sarah Bradford: 52:37
Yeah and be really really specific with homeowners about what you want them to do. They don't always know go for the tell them what's the best biggest bang for their buck show them examples of the look that's selling make sure they're doing their beds you know at least get them that information don't just be like you need to upgrade bye make sure they know it too yeah okay um okay so we're all right we already went over that one we are almost done are you ready? Yep yep how you feeling you're getting to the diary we are flying oh wow we are really flying forward there's so much more I could share here but maybe I'll write a book okay there you go best seller any day now I'll get on that yeah the last one I'm skipping is that you need to I call it dumping properties you need to break up prop with properties that are not making you a reasonable profit to stop holding on to the ones that don't make money. Okay we got our final entry here we go November 17th 2025 that's the day we are recording here ladies so you better make this uh go public or it's gonna sound really old dear diary my life looks wildly different now we sold our business three and a half years ago we never once regretted it but I also not for one second regretted building it for 15 years it was chaos comedy keyless locks and purpose now I'm mom first and always a halfway decent wife my husband deserves a medal a more present daughter to two aging parents and a really solid friend the kind who remembers birthdays shows up with snacks and books the court for pickleball I skied 43 days this past year I played mahjong like it's my job and if joy were a metric I'm finally off the charts. Oh I love that wow and one of the entries that I skipped Alex one of Alex or Annie one of you told me you liked it was the one about how I missed a lot of soccer games.
Annie Holcombe: 54:44
The soccer that was at the soccer game yeah I was at the soccer game I was the same I was the same thing like just missing those or getting there at the end of something and just having missed all of it or being I think yours was you were there and they scored and you didn't see it because you were taking a call or something. I mean that a hundred percent resonated with me.
Sarah Bradford: 55:03
Yeah yeah yeah yeah I decided not to cry on your podcast so I didn't read that one. Yeah but I guess I would just finish it by saying I loved running our vacation rental companies I loved my staff I loved most of the owners I loved the guests I loved the whole idea of hospitality and I loved making money and I do think you need to like making money and like hospitality but now I'm so glad that I worked hard and made it a profitable company because we can now go into the next stage of our life the way we have being more present with our kids experiencing things in a different way and it's great on the other side but it also doesn't mean you have to want that tomorrow it's just when you're ready make sure your company is ready that you can make enough money to live freely yeah what's the thing that you miss the most about it um it was it was time for me to go um what I miss the most I mean I'm gonna sound like the biggest capitalist but I'm gonna give you my real answer. I loved getting bookings like every single day I own that company I would look and be like oh $37,000.
Annie Holcombe: 56:24
Yeah yeah it's like a game it was a game yeah I know when I was I missed that it's it's proof of what you're doing is is being received at all levels when you get those bookings like your marketing is good and people saw your brand and you've got the operations in place and so it's just it's like a a lot I mean I know when I when I was that close to it when I was working inside the company for 13 years like I I had it on my phone and I was checking it all day long.
Alex Husner: 56:52
I mean it was like a stock ticker but like yeah you'll be sitting there watching and then all of a sudden you refresh and you're like oh my god somebody just booked a $20,000 condo online like that's crazy. And then you want to see where they're from and like wow like where did they come from? You know it's it's I don't know it's it's fun to watch that for sure. It's not fun when nothing's coming in but when when you're rolling in in booking season it's a lot of fun.
Sarah Bradford: 57:15
Yeah I miss that I mean I was so psycho that I used to look at Google Analytics and you can see where different users are on your website and I would watch someone and see where they were from and then I'd see them get to the booking page and all of a sudden I'd get an email that said you have a booking and it was like they did it.
Annie Holcombe: 57:34
I've been spying on them the whole time I love that well Sarah thank you so much for sharing all this and and I think we could have you back and talk more about some of these specifics like in in more detail if you'd be open to it. We'd love to we we know you're out of the business and you want to like spend time with your family and play pickleball and now ski but um we don't want to let you go. We love having you in the industry and and your personality is infectious and the way you share your stories is heartfelt and and it's just fun and it's it's nice to see it on the other side just you know learning from your learnings and you're sharing that with other people and I know you've you've been coaching some people in the industry so thank you for doing that and thank you for sticking around.
Alex Husner: 58:14
Oh yeah I love it I love it I just love doing it without the pressure yeah that sounds great well you've earned it for sure thank you for coming on coming on Sarah so much uh we've been excited for this since May so this was a fun one if anybody wants to get in touch with you and go a little bit deeper or just you know connect with you what's the best way for them to get in touch uh probably by email Sarahmbradford at gmail.com okay great that's you can always go back and listen to your podcast too so oh yeah you can get real sick of me if you want to go listen to all the episodes yes for sure and I want to thank you all you have been pioneer S's pioneer s is that a word um I love what you're doing out there it is so important to share get different people on here so that again we don't all make the same mistakes and we can learn from each other. Yeah absolutely thank you if anybody wants to get in touch with Annie and I you can go to alex and anniepodcast dot com and until next time thanks for tuning in everybody
Sarah Bradford is a vacation rental industry veteran with more than two decades of experience building, scaling, and operating successful property management companies.
She co-founded Winter Park Lodging Company, which grew to manage over 110 luxury vacation rentals in Winter Park Resort, the third-largest ski area in Colorado. In 2016, she launched Steamboat Lodging Company, building the business from the ground up using the operational lessons learned in Winter Park.
In 2022, both companies were acquired by Sunset Management, a boutique vacation rental owner and operator with properties in South Carolina and Big Sky, Montana.
Sarah lives in Steamboat Springs, Colorado, where she and her husband, Chris, are raising their twin sons, Nicholas and Willem. Since selling her businesses, she has remained active in the industry through consulting, mentorship, and speaking, sharing hard-earned insights with operators focused on building sustainable, well-run vacation rental businesses.


















