Winner of The Shortyz 2026 Best Travel Influencers of the Year
Oct. 15, 2026

Pour Decisions: When Guests Wreck the Home, Who Pays?

Key Takeaways

  • High-end vacation rentals and premium nightly rates do not guarantee well-behaved guests, meaning destructive behavior can happen in luxury properties just as easily as budget accommodations.
  • Relying solely on major booking platforms for damage recovery can be an uphill battle, especially when guests delete their profiles or offer minimal compensation for severe property damage.
  • Working with a specialized guest protection and screening solution like Safely allows property managers to streamline damage claims and avoid complicated insurance workflows.
  • Proactive communication with homeowners about guest protection policies builds deep trust and reassures them that their valuable investments are safeguarded.
  • Regular monthly inspections and a high-touch management approach help operators catch maintenance issues and potential property misuse early before they escalate into major disasters.

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests.

And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache.

In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex and Annie are joined by Alexandra “Ali” Chaney of 30A Beach Stays & Vacations, alongside Amanda Martins and Zach Grimes of Safely, for a candid conversation about the unpredictable side of vacation rental management.

Ali brings firsthand stories of unexpected guest incidents and the challenges of managing damage claims, while Amanda and Zach share insights from Safely's experience helping operators navigate these situations.

Together, they explore the realities of guest-related risks, the challenges of recovering costs through booking platforms, and how the right protection and processes can help property managers safeguard the homes entrusted to them.

We discuss:

12:55 - Why luxury properties are not immune to destructive guest behavior

14:53 - The challenges of recovering damage costs through booking platforms

21:52 - How the right protection can support homeowner confidence

24:08 - What operators can learn from real guest damage incidents

27:47 - Why documentation and a clear claims process matter

30:14 - How different types of insurance and damage protection work together

36:48 - Where guest waivers fit into a broader protection strategy

From shocking guest stories to practical insights on damage protection, this episode offers plenty for property managers to think about before the next stay goes sideways.

Connect with Ali: https://www.alexandanniepodcast.com/guests/alexandra-chaney/

Connect with Zach:

LinkedIn: https://www.linkedin.com/in/zach-grimes-9242b478/

Connect with Amanda:

LinkedIn: https://www.linkedin.com/in/amandakatmartins/

Learn more about Safely:

Website: https://safely.com/alex-and-annie
LinkedIn: https://www.linkedin.com/company/safely-stay/
Instagram: http://instagram.com/safely/
Facebook: https://www.facebook.com/safelyprotection

This Episode's Cocktail: Ali's Special

A classic margarita with a fresh citrus twist.

Ingredients:

  • Tequila
  • Triple sec
  • Sour mix
  • Fresh lime juice, optional
  • Fresh orange juice, optional
  • Ice

How to make it:

Combine the tequila, triple sec, and sour mix in a shaker with ice. Add fresh orange and lime juice if desired. Shake well and pour into your favorite glass.

#vacationrentals #shorttermrentals #damageclaims

Send us a message!

Frequently Asked Questions

Who is Alexandra Chaney in the vacation rental industry?

Alexandra 'Ali' Chaney is a property manager and founder of 30A Beach Stays & Vacations, managing a curated portfolio of premier properties along the 30A area in Florida.

Why are luxury vacation rentals not immune to guest damage?

Regardless of a home's nightly rate or property value, guests can still exhibit destructive behavior, proving that upscale demographics do not automatically guarantee respectful treatment of the property.

What role does Safely play in short-term rental property management?

Safely provides vacation rental operators with integrated guest screening, damage protection coverage, and a streamlined claims process to handle accidental or malicious property damage efficiently.

How do property managers handle severe guest damage when booking platforms fail to pay?

When booking platforms offer insufficient reimbursement or fail to assist after a guest deletes their profile, specialized protection services like Safely help operators recover repair costs without bearing the financial burden themselves.

00:00 - Why Stays Turn Into Nightmares

00:41 - Meet The Crew And Today’s Guest

02:11 - Margarita Setup And Vacation Rental Culture

04:16 - Building A High Touch Management Brand

09:31 - From Cleaning To Monthly Inspections

12:55 - Whippet Canisters And Platform Frustration

20:24 - What Safely Changes For Operators

23:32 - Grayton Beach Brawl And Damage Claim

30:03 - The Insurance Stack For Short Term Rentals

32:19 - Faster Claims Through Better Documentation

36:48 - Waivers Versus Proactive Protection

41:46 - Contact Info And Closing Cheers

Why Stays Turn Into Nightmares

Alex Husner

Not every stay goes as planned. Sometimes it's a small issue, and sometimes it's the kind of situation that turns a story into one you'll never forget. This is poor decisions when stays go sideways, presented by Safely, where we talk about the moments that no one puts in the highlight reel, but what actually went wrong and what operators can do to handle it better next time. Join Annie and I and the Safely team for cocktails and commiseration as we swap jaw-dropping tales of the good, the bad, and the downright outrageous. And trust me, there are plenty of them. Laugh, learn, and pick up a few instructor tips to help you handle and hopefully prevent future poor decisions. Come for the cocktails, stay for the stories.

Meet The Crew And Today’s Guest

Alex Husner

Welcome to Alex and Annie, the Royal Woman of Vacation Runnels. I'm Alex. And I'm Annie. And we have a crew here today. We are back for another edition of Poor Decisions brought to you by Safely. And we've got Amanda Martins, who is a returning guest on the show. We also have Zach joining her from Safely. And then we have a special guest today, Allie Chaney from 38 Beach Stays, that's going to add just a whole lot of color to all the conversation. But we want to make sure that we introduce everybody that is maybe not familiar with the to the audience. Um, Zach, let's start with you.

SPEAKER_00

Yeah, hey everybody. My name is Zach Grimes. Um I'm a I'm a licensed insurance agent here at Safely, uh, where I work with vacation rental managers and property management companies to help protect their properties, guests, and businesses. I've been with Safely for several years, and I take more of a consultative approach to helping vacation rental operators understand their coverage options and help them find solutions that fit the way they actually operate. Great.

SPEAKER_02

And Allie?

SPEAKER_05

Hey guys, I'm Allie. I am a 27-year-old property manager of 37. It may be 37 as of my signed contract today. Um properties in the 30A area. And um I focus specifically on the premier 30A beaches, and I'm here just to talk to you guys about my experience with Safely and my experience as a manager overall.

Margarita Setup And Vacation Rental Culture

Annie Holcombe

Awesome. So we are back for the poor decisions show that we've been doing. And before we get started with every episode, we have our mixologist here, Amanda, who gives us a drink. That's our theme for this episode. What is the drink for today that we have?

Amanda Martins

So no fun names, no frills, Allie special. This is a classic margarita. I have mine in a little mason jar. So if you want to mix that up, it's typically a little bit of sour mix, a little bit of triple sec, some tequila, shake it up, pour it in your glass, and add some flavor if you want. I did um some fresh squeeze orange and lime juice because, you know, I like that fresh stuff. And that's it.

Alex Husner

Love it. I uh I didn't have a margarita glass necessarily, but normally when we're drinking margaritas, we use just a regular solo cup. But I found this in my cabinet that this is from years ago. It's a red solo cup on a um quote unquote. It's not crystal, but it looks like it's a crystal bottom. So that's that's my rendition of it. I like some Grand Manier in my margaritas. I don't know, that's that's kind of my my favorite. I didn't have any today, but the the traditional recipe that Allie and and Amanda you guys sent us was was great. So we're excited.

SPEAKER_05

I love that challenge. It's like very classy. It's like red and classy. Toto cup on a piece of crystal is like something you should have on my bookshelf. That's plastic.

Annie Holcombe

That is that is the southern way. Is you you know, you want to be you want to be classy, but you also want to be a little, you know, down to earth.

Alex Husner

I'm pretty sure my dad got it for us for Christmas one year from Bass Pro Shop. So it kind of explains it.

SPEAKER_05

You really want to be southern, but also classy.

Annie Holcombe

Exactly. There you go. So crystal on the beach, this way you're not gonna break your glass, right? So, okay, so we're on 30A and Safely is all over. We've we've discovered that safely is literally everywhere. But um, Zach, I think you you met Allie in a roundabout way. You kind of discovered her. And so why don't you tell us a story about

Building A High Touch Management Brand

Annie Holcombe

how you met and and how you and Allie started working together?

SPEAKER_00

Yeah, so I I actually came across Allie and 38 Beach Days through the perfect in Walton County Awards. I was looking through some of the winners and I saw that 38 Beach Days had been named. I think it was the diamond winner for Best Boutique Vacation Rental Company under 50 units. It caught my attention, so I started looking a little closer at what Allie and her team were doing. And the more I learned, the more I thought this is someone that I'd I'd like to talk to. So really a lot of what stood out to me was how intentional they were about staying local, keeping the portfolio curated, focusing on the guest experience, and really just being involved in the properties rather than trying to build the biggest operation possible. So I I ultimately reached out to Allie to learn about how they operate and see if they felt safely could be a good fit for their program. And I guess as kind of transition to Allie, Allie, we talked about this before, but as you've grown your company and built that reputation, I'm curious or maybe you want to talk a little about uh what you look for in a company that you're gonna trust with something as important as protecting your homeowners and their properties. And is that part of what made Safely a good fit for 38 beach days?

SPEAKER_05

Yeah, so for me, as someone who went from zero to almost 40 properties in less than three years, um, and I am not trying to scale that quickly. So this has been all word of mouth. And so as soon as I got in contact with Zach, I realized, oh, there's a lot of other people talking about safely and how they've been benefiting from using that service. And I realized really quickly that I threw myself into management after cleaning and after doing a couple other things that weren't so fun, but I learned a lot. But the one thing I didn't have any knowledge on was protecting the home specifically from, you know, consumer damage and things like that. So I found that once I talked to Zach and then I looked him up on Instagram because I'm a creep, and I also looked him up on Facebook, I noticed that we had a lot of mutuals. And so I'm thinking here, you know, okay, so he works with a lot of people around the area, and I I generally go for people who um, you know, have good rapport and and and good feedback from other people. And so I thought, let me take the call. Uh it won't hurt absolutely. I I I'm a hundred percent for like anytime someone has something to offer, something that I don't know anything about is a learning experience. So we took the call and I think I had maybe signed on that first call. It may have taken two, but I was I was ready to make the jump after a few um a few horror stories.

Alex Husner

Well, and Allie, I think it's interesting to back up just a little bit too and make sure that we you know give credit where credit is due, that you grew, you know, 36 properties in 30A is a lot of properties. This isn't you're not in Myrtle Beach or Panama City where you have to have huge, huge volume to still have a a really nice business there. And these homes are are are difficult to get because there's a lot of competition in the area. But I'm curious, I mean, how did you grow it that quickly? Like what was your I know you said referrals, but it couldn't have just been because you know how to clean properties and you had referrals. There had to be something else in there.

SPEAKER_05

That is hilarious because it like truly is not like a mailer door-to-door, um, you know, cold calling situation. I have a background as a financial advisor. Um, I I used to have a Series 7, 66, and MBA and finance, all of that, where I had to cold call professors and people at uh different like companies and try and get them to contribute to 401ks when they're only making X amount of dollars a year. And that was horrifying. But this company, as soon as I got my first client and became the number one revenue producer in that neighborhood, it turned into kind of a spiral situation where people were like, oh, you're in X neighborhood. How much do you make? Oh, I make this much a year. And then as soon as they started hearing the figures we were able to produce, because I treat every property like it's my own. I approach everything as almost like a self-management with multiple inspections by me or someone on my team personally a month. It's like there are 800 other companies out here and probably less than five that are giving the homes that kind of touch. I mean, we are high touch, very high touch, high turnover, and really just treat your asset like it's our own. So the growth was, I really don't know how it happened. It was a lot of people just calling me, man. I don't know what happened.

Alex Husner

Yeah. Well, and it's interesting because it's like I think everybody wants to figure out what that magic recipe is. But in a lot of cases, it's not necessarily recipe. It's it's you, it's who you are, it's the connections that you've made, it's the opportunities that you're able to spot, maybe that somebody else didn't see, you know, and that's kind of where the magic happens. But the the magic can sometimes

From Cleaning To Monthly Inspections

Alex Husner

change to disaster, though. And that's part of uh the poor decisions series where we talk about the things that that have gone wrong uh within the property. And so maybe take us back to before you were working with Safely, like what happened and then what made you realize, oh my gosh, like I I I can't keep doing this anymore.

SPEAKER_05

So I um was a ma uh obviously I was high up at a financial advisory firm and I got moved over here, and it turns out that I uh didn't want to do financial advising because it is hard to get people to can to put money into investment portfolios that won't return for 30 or 40 years, and they don't even make enough money right now to be putting large amounts away. So I realized that there was a gap in the market for really, really high-touch cleaning services. And I started a company called Quick Turns, was cleaning all these homes, um, got up to about 50, 55 homes cleaning me and myself and two other girls and um a couple of their teams. And then I was like, wow, these are managed so poorly. I should not be the only person looking at this um air filter for the first time, literally written on it in 2022, and I'm there in 2023, and it's not December to January. I mean, 12 months this air filter had been in there. And I was like, okay, turns out the managers are are pretty much relying solely on the cleaning staff. And I don't think the management is really trying all that hard. And so I took a step back and was like, I if if everyone else out here can have a management company, all five or eight hundred, I'd like to start one, but I'd like it to be super intentional. And the intention is just on being present and high touch and being someone that people can trust, someone that puts eyes on their property every single month. And and that just spiraled into something that I couldn't have ever dreamed of.

Annie Holcombe

So the intention was the attention, like that, you know, you were very intentional with the attention you were paying. And I think I live in the Panama City, Panama City Beach market, very familiar with RDA, and it is kind of astounding because some of these homes are 10, 15, 20 million dollar homes. And the lack of attention that can be paid to is is quite astounding with some of these companies. And to your point, like air filters. I mean, an air filter in a beach property needs to be changed out like quarterly, if not more than that. You know, these these so it's interesting that you notice that because I don't think that a lot of managers go in with that like thought, they'll like take a broad look at things, but you understood that there's there's value in the like Alex always says the riches and the niches, but there's value in these nooks and crannies in the houses that need to be need to be taken care of and need to be monitored. So you grew your business, and so um you just you got into the management, and somewhere along the way, you had some experiences that were less than ideal, um, dealing with guest damages, dealing with guests who maybe weren't playing by the rules. Why don't you tell us a little bit about some of those that you had prior to Safely, how you dealt with them, and then you know what Safely was able to do if you, you know, now that you're dealing with different guest

Whippet Canisters And Platform Frustration

Annie Holcombe

issues.

SPEAKER_05

Yeah, absolutely. So uh the first property I ever took on, I can say it was in Grand Point, which is on the wrong side of 98. If you are a frequent flyer on 30A, it's not the side you want to be on. But again, at the time I was like, anyone who will work with me, work with me. I did hours and hours of research into software and you know, managements and blah, blah, blah, blah, thought nothing about insurance. I just assumed based on the caliber of homes, you know, from one to twenty million dollar homes, that the guest experience would be similar, which is really silly um and was really a poor decision. So I took about two months to have my first what the heck moment. And I walked in. At this time, I was still cleaning them. So for the first three homes, I had that background in cleaning and I cleaned every single one myself, which was a lot, but it was nice. I retained my management commission. Retained the cleaning. I walked in, found about 16 whippet canisters, which, if your viewers are not familiar, that is um essentially a giant whipped cream canister without the whipped cream. And I found a room full of explicit items that I won't go into detail, but I felt like something very inappropriate had been going on at my rental. Once confirmed, after spending $400 to get rid of said canisters, because you cannot put those in your trash can. By the way, you'll set the local fireman or the local trash van's the whole thing on fire. If you blow that's not good. Uh, I realized that I needed to do some arbitration with uh a certain platform that they had booked through, and that was a nightmare. I mean, truly, I I had proof of smoking in the beds, explicit material probably being filmed at my home, whippet slash nitrous oxide canisters, and the like every part of what you would use to do something not good in this home, about a hundred photos and got like roughly $200 back from the platform they booked on. And so I that's when I realized that was the first inkling that I was going to have an uphill battle for probably the rest of my career in management, especially with said platforms. If you're not booking direct, you are at their mercy for a lot of things.

Alex Husner

Yeah, I bet you never anticipated getting into this that you were gonna have to learn how to dispose of whippets as part of the job.

SPEAKER_05

No, and the fire people at the office. So I brought them uh the local station that you could dispose of them legally, which again, like lifting batteries and whippet canisters, was a fire station. So I walked in like seven canisters, they're about this big in hand, and they all just looked at me like this. What is she doing? And I was like, These aren't mine, I promise, but you don't have to believe me because this is where it says to get rid of them.

Amanda Martins

Something that stands out to me about this story, Ali, is that there's an entire service dedicated to whip it canister removal. So there's like a market for this.

Annie Holcombe

Really?

SPEAKER_05

Wow. There there certainly is a market marketed towards getting rid of things that cannot go into your local trash persons. So so lithium batteries is on there, um, uh things, anything that can set fire with pressure and or uh any sort of like electrical, like if you're in a compacting machine and you compact something and it could blow up or set fire, there is a service on the sites they do list out canisters of nitrous oxide, which means that there is a lot of people doing this. So if you haven't had it at your rental yet, you just might. Wow. Zach, correct me if I'm wrong. This is a new one for us, right, Zach?

Annie Holcombe

Yeah, you dealt with that, you've now had suspect things filmed in this home. You've had to throw away nitrous oxide canisters, and you realize I've got to do something about this. Like I can't be the one doing this, right?

SPEAKER_05

I took an ear of trying to collect security deposits and whatnot myself. Because again, at this point, I only had three homes. So it was like three that I'm cleaning. I was like, this is over.

Annie Holcombe

You can handle it, right?

SPEAKER_05

Yeah. I mean, what are the odds? I have another whip it video.

Alex Husner

That's why there is no real school of vacation rentals, because there's every day is a different story, and I feel like you could go into any property management company within where I live, there's probably at least, you know, 20 in a very small radius, and every single one would have a shocking story of something that's happened today.

SPEAKER_05

So there's never never an end of uh good stories, but it took a couple years to one, one and a half more to realize that um I wasn't protecting the asset, which is the most important thing to me for homeowners, because the owners here on 30A are not people just willy-nilly renting out their, you know, home for some extra cash during the popular times in their hometown. These are second, third, fourth, fifth home investors that are expecting these homes to appreciate. They are using tax strategies and praying that they're going to make, you know, more be worth more and more and more value over the years, and then they're gonna gift them probably to their heirs. And and if the home is destroyed, I've done a disservice as a property manager, in my opinion. So I realized that I had to do something differently.

Annie Holcombe

I think what you just said there is really important because I think that I deal a lot with channels, and I don't think that the channels have an understanding of what a property manager has to do to protect an asset. And I really feel like if they understood more of it, and maybe this is where Safely comes in to like share more of these stories, they they would understand like why it's important to hold these guests accountable for stuff because these are people's investments. They are, they are, you know, again, we're talking in some of these markets, multi-million dollar deals that people have gotten involved in. And some of these people have, like you said, three or four of these, and they might be in a group of investors. And the channels don't, I don't think they appreciate what a manager's trying to do to protect that. So this is where Safely can come in and help you navigate with those channels.

What Safely Changes For Operators

Alex Husner

This episode is brought to you by Safely. One of the realities of running a short-term rental business is that things don't always go as planned. Whether it's accidental damage, guest-related issues, or the unexpected, these situations are part of the business. The challenge is figuring out how to handle them without adding more friction to your operations or your guest or owner experience. And for a lot of operators, that's where things can get messy. Safely is designed specifically for short-term rental operators, combining guest screening, protection coverage, and a streamlined claims process into one solution. Instead of relying on large security deposits or navigating complicated insurance workflows, Safely helps operators put a system in place that's both more efficient and easier to manage. And what we love about Safely is that they remove a lot of the back and forth that usually comes with these situations. When something does happen, you're not starting from scratch or trying to figure out what the next step is. There's already a process in place that helps you move forward without slowing everything down. For teams that are growing or even just looking to operate more professionally, having that layer of protection without disrupting the guest or owner experience can make a huge difference. If you want to learn more about how Safely works, click the link in the show notes or visit safely.com and be sure to mention that you heard of them on the Alex Nanny podcast.

Annie Holcombe

When you did finally engage Safely, what did that what did that mean for your peace of mind in being able to know that if you take a guest and you have a problem that you didn't have to navigate this challenge anymore?

SPEAKER_05

Yeah, so I immediately like went to my app of certain channel where there's a support chat and just like deleted it. It and was like, I'm done talking to you. Goodbye. I don't need to even look at this support chat anymore because I'm tired of dealing with it. And that was that was huge. Then I sent out an email to all the owners. Hey, you know, XYZ is happening. There might be a tiny bit slight increase in in cleaning fees because I decided to work it into that fee because I was already low on the very low end of cleaning, not knowing what I was doing when I started this company and realizing. And so I was like, you know, here's the slight increase, but in in exchange, you get X amount of coverage for negligence or accidents, as well as, you know, liability coverage. Are you okay with that? And I expected a little bit of pushback. I had zero. Every single homeowner emailed me back and said, you know, at the end of the day, they were like, whatever, because you're increasing the cleaning fee to the guests, but they don't get to see that money. So it makes their gross revenue number look higher. And I mean, that money passes through to me to safely and whatnot, but it didn't matter to them because at the end of the day, they felt like their investment was going to be better protected than it was before. And that just knowing that zero people felt like I was making the wrong decision made me know that I was a hundred percent making the correct decision moving forward with them.

Alex Husner

Yeah. And Allie, you've got some interesting specific stories of some things

Grayton Beach Brawl And Damage Claim

Alex Husner

that have happened too that we haven't quite touched on yet. And I want to make sure that we get to them in this episode. And this is all painting the whole picture. And I think that's the the reality is, I mean, this is it's super important to talk about because until you actually get into these situations, a lot of managers don't even know that they need to have something like this. And so your context is critical here. But there was one story that stood out to me that was the boxing ring in Grayton Beach. And I'd love to first hear your take on what happened, Allie, and then Amanda and Zach, if you can maybe give your input on how you saw that situation from your side.

SPEAKER_05

So um my favorite thing to wake up to, obviously, at 6 a.m. is a message of a guest like saying, We vacated the property because of XYZ. And I'm like, you know, okay, I'm in a panic. Thank you, cortisol spike 500. I start to read through what they said. And it was agre at a home, no less than six or seven hundred dollars a night, I will add. Not that that matters. I do not like to think that a certain demographic is gonna treat the home one way or another, but you do sort of think that at the homes that are two, three, four, five million dollars, you'd get a little bit more respectful um appreciation of the homes. At the end of the day, doesn't matter who, it really doesn't. If it's $50 a night or $5,000 a night, and I learned that the hard way, I about had a heart attack because they sent about 40 photos in a row, which is never good. If you're in property management and you open the app and you have 40 photos coming in, it's someone either complaining, right, about how bad the home is, or it's something that happened. And um, I woke up to them saying, We're gone. Don't worry about it. We're never coming, you you never have to worry about us again. The whole profile was deleted within about 30 minutes, which is another reason why these um these other platforms aren't protecting you. But they had had a domestic violence dispute, which is never funny, never something I would joke about 100% of the time, would have had them call 911. But the majority of the group was out at the bars in Grayton, which are very popular. Red Bar, Turingo, AJ's, those are the fun places to be. And two of the patrons had headed back to the home about 10 minutes away and decided to beat the living you know what out of each other in the home. And then they left. And the friends came home, and that's what they found, and that's what I was given in terms of photos at 6 a.m. on a Friday morning, which was something I will say that was shocking because you you expect people to possibly wreck a golf cart or break a bike or you know, small things. They chipped a tile here and there, they broke a coffee maker, and we're not like we're not that mean about stuff like that. If you report it to us, and they had to have gone at it for at least 30 minutes with each other in this home. So that was crazy. But I did end up using safely um and reported all of the damage in the repairs. There was a screen that was broken through, two walls that had holes punched through them, a large expensive vase, I guess, from like the some region of China that I never even heard of. I tried to Google search it, couldn't find it, just smashed. You could tell they like smashed it into the wall because the top part had cracked off, and then the wall had the exact, like overarching bottom piece in it. One of the back door latches was broken. The what do you call those like fancy doors that have a bunch of little panels all broken down, like someone had been thrown into it about as hard as they could. And um, they just they left. They left apparently. They just left and let their friends come home.

Annie Holcombe

Oh, so what what's not you called safely, and and what does Safely do at this point?

SPEAKER_05

Didn't even have to call them. So I immediately texted my maintenance person and um was like, I just need quotes for all of this. Like, just get them, get them to me as fast as possible, make sure that they're accurate because uh the next guest coming tomorrow is my owner.

Alex Husner

Oh wow of course. Bad timing.

SPEAKER_05

So my handyman, one of my handymen went to work. I mean, Google image searching and da da da da da da da da. And he sent me like six different invoices, you know, the drywall repair, mudding, painting, fixing the slats on the whatever, the screen, which the screen repair ended up being not that expensive. I was shocked. Um, the latch on the door, whatnot. And so I had a figure and I uploaded to Safely. I did it all in like separate uh dialog boxes so they could see. So screen and then receipt. Here's the screen and receipt, this and then receipt. And I did that like nine different times and then inputted what the full amount was. Um, and because I I was gonna go back to the guest and say something, and their profile was gone. Oh, what a surprise. Even though they admitted to me what all happened and sent the photos, apologized profusely, they no longer existed on said platform, which is amazing that the platform even allows them to do that. So I could go into someone's home, light it on fire, and then delete my profile. Wow. Wow in theory, um, and then safely took like I think 19 16 to 19 days. It was a larger amount that I was claiming. So, you know, you got to keep that in mind. And then um they just they covered it all. So it got deposited into my escrow. I had already paid for all the the repairs. The homeowner came and unfortunately it couldn't all be fixed in time, but he understood that the process of getting it fixed was happening. Again, I I have lost zero homeowners in three in three years because of not just safely, but just being proactive and honest with people. So he was totally fine with it. He was like, you know what, that area of the wall probably needed painting

The Insurance Stack For Short Term Rentals

SPEAKER_05

anyways.

Amanda Martins

Volleying to Zach over here, I'd like to hear your perspective on what's that, what's a solid insurance stack and where do we fit in in the ecosphere?

SPEAKER_00

Yeah, no, I that's a good question. I think there's a couple of different policies, and Allie, we can kind of volley back and forth on this too. But I think from a property management perspective, you should have a standard general liability policy, right? To protect you, your business operations, your employees, your staff, your cleaners, your technicians. You should have that general liability policy with your errors and emissions intact. Um your homeowner should have a standard homeowner's policy. Uh that policy is in place for when they're at the property, uh, when it's unoccupied, when it's vacant, or when they have friends or family staying at the property that are not paid guests. And then safely is kind of that in-between. It's a commercial renter's policy. So it's the commercial policy. And when I say commercial, when there's a commercial transaction or when somebody pays to play, that's when our policy kicks in. So it's uh after the general general liability policy when your team vacates the premises and before a homeowner arrives, it's that in-between time when there's a paying guest from check-in to check out, essentially. So I think those are really the three main pieces that you need with a short-term rental. You need from the property manager side the general liability policy, you need the commercial policy for the commercial transaction, and then you need the homeowner's policy on the back end.

Amanda Martins

Thank you, Zach. I I had another question too, unless Alex or Annie uh wants to interject.

SPEAKER_02

Yeah. No, no, please. Yeah.

Amanda Martins

Yeah. See, this was for this uh this question is for Ali. I'd like to go back to that um that brawl in the home, let's say. Um you know, you mentioned you were talking about how um how the claims process and what you did. I didn't know yet. I actually didn't look into your account yet. Did did our um customer happiness team work with you at the beginning to show you how it all works, or did you just kind of figure it out on your own how how the system works, how to file a claim?

SPEAKER_05

Zach showed me one when we first like did our thing. He was like, here's where you upload, here's what you say, yada, yada, yada. And then to be honest, I just um started using chat GBT. I mean, I I need it to summarize what's happening. And a lot of times I'm like, the guest got into fight.

Faster Claims Through Better Documentation

SPEAKER_05

Like I'm like illiterate, and like I so I put into Chat GBT all the screenshots of what happened and all of the photos, and I said, summarize this so that I can tell safely what happened in a way that is concise and has timestamps and yada yada yada. And it and it you didn't really need to walk me through it because unless you're very, very behind technologically, I mean, it's one of the easiest uh systems I've ever used for making a claim. It's like what day did it happen? What happened? Did you think they were negligent or it was an accident? Yes, no, and then you upload. What I have learned is if I upload all of the um, if there's multiple problems at once, if I upload them as separate sections with those photos, that receipt, that description, those photos, that receipt, that description, it seems to go through a tiny bit faster. It might be easier on the adjuster's end to not have to sift through 400 items at once. So I usually classify like say the guest popped a bike tire, broke a coffee maker, and walked through a wall. You want three different ones and you want to have the receipt for what you're gonna have to order already or what you have ordered to replace it, and then at the bare minimum, an estimate. Because if someone walks through a wall, that could go anywhere from 400 to $1,000, depending on who's doing the repair. How is it drywall? Is it she rock? Is it blah, blah, blah? So you really want to wait for that part until you have it at least an estimate. Um, for me, uploading just the estimate and then receipts for anything that's like smaller, like a coffee maker or a printer that got broken or whatever, those have gotten um pushed through really quickly. And if there's any flack back, they just email me and say, hey, we need a little bit of additional information.

Amanda Martins

You made a joke earlier about somebody body slamming into a wall. But if if whoever's listening goes back to our first episode, we actually have that. We talked about that, yeah.

SPEAKER_02

Yeah, yeah, it's happened.

SPEAKER_05

Yeah, people in walls, like after a couple drinks on vacation, like they do not get along. It seems, I mean, even and especially like even kids. I had a person text me, like, oh, my kid fell off the bunk. I'm like, oh my god, do you need urgent care? Yada yada yada. No, this kid's fine. Just you have like a large head-size hole now on the wall. I'm like, okay, thanks. They're like, yeah, he fell. I'm like, okay. They were not offering to pay, they were just letting me know. I'm like, just letting you know there's a head-size hole. They were like, this is the size of his head, and there's the hole.

SPEAKER_02

Oh my goodness.

SPEAKER_05

Yeah. Well, I'm glad you didn't try and sue over some bunk bed climbing BF. So I'm like, whatever. We'll drive all repair it and move on. I mean, 90% of the time you can have safely and you can have uh homeowners insurance and you can have your comprehensive. And if somebody is trying to come after you, they're going to be able to come after you. So what the best thing you can have in place is some really robust uh waivers in place, some rental agreements that they sign, and a manager like us that really goes to the properties and checks on them and knows that they're there, there's no negligence there. I mean, I I have photos of every home every month right now, actually after every clean from cleaners, but myself. So you're, you know, it's really hard to sue someone for a uh a bunk bed that someone fell off of when I just climbed it and made the bed yesterday and I'm 150 pounds and your kid is 12. So at the end of the day, you you you can have your stack and people can still come after you, but safely is gonna make it 40 times easier to get reimbursed for all those things that that your homeowner is gonna come at you about, you know, the uh piece of art or the chandelier or the vase or the ring on the bunk bed. I mean, you can protect yourself all you want, but as long as you, as long as you are inspecting your homes and you have those three things homeowners, yourself, and then some sort of policy that's protecting you that is protecting the guest day, you're going to

Waivers Versus Proactive Protection

SPEAKER_05

be okay.

Alex Husner

And actually, I'm glad you brought that up, Allie, about the waivers, because that was one question that I wanted to get Amanda and Zach's opinion on because I know that you had used waivers, guest fees are kind of a different approach prior to using safely or maybe still in combination. But I think property managers often get that uh confused with whether they need one or the other. I mean, Amanda, how would you look at that?

Amanda Martins

So um, I want to get the definition of waiver right first. Um, because you have damage waivers and then you have waivers, you have liability waivers that your guests sign. I think, Ali, you were referred, were you referring to the liability waivers? So, like, I won't sue you if I fall down these stairs or my child punk.

SPEAKER_05

There's a super robust in our management agreement. It's both. It's it's liability and damage. Yeah. The bikes aren't my problem, and the golf cart's not my problem, and the pool's not my problem, and the hot tub's not my problem, and anything your kid does is not my problem. I mean, you should have that regardless. But like I said, someone can still try whatever they're gonna try. So as long as you're protected, safely is probably gonna cover whatever silly stuff they break. And that's the most important part to your homeowner for sure.

Amanda Martins Profile Photo

VP of Business Development | Safely

Amanda Martins is the Vice President of Business Development at Safely. She has been with the company since 2019 and has worked across multiple parts of the business, including onboarding, customer experience, sales, product, and partnerships. Her broad view of the customer journey gives her firsthand insight into the challenges property managers face and the kinds of guest-related incidents that can quickly turn costly without the right protection in place.

Alexandra Chaney Profile Photo

Property Manager / Real Estate Advisor

Alexandra “Ali” Chaney is a Northwest Florida entrepreneur, licensed Realtor, and founder of 30A Beach Stays & Vacations, a boutique luxury vacation rental management company serving Florida’s scenic 30A corridor and surrounding beach communities.

With a background in marketing and finance, an MBA from Florida State University, and experience in finance and real estate, Ali combines a business-minded approach with a genuine passion for hospitality, luxury properties, and building successful brands.

Ali founded 30A Beach Stays in 2023 and has grown the company into an award-winning vacation rental management business known for its hands-on service, attention to detail, and elevated guest experience. She has since expanded her entrepreneurial pursuits into real estate through 30A Beach Realty and design through 30A Beach Designs.

Driven by an appreciation for beautiful spaces, smart investments, and creating opportunities, Ali is passionate about helping homeowners maximize the potential of their properties while connecting buyers and guests with the lifestyle that makes 30A so special.

Zach Grimes Profile Photo

Account Executive / Insurance Agent

Zach Grimes is an Account Executive at Safely, where he works with vacation rental managers and property management companies to help them navigate guest damage and liability protection. With several years of experience at Safely, Zach takes a consultative approach to helping operators find coverage solutions that fit the way they actually run their businesses.