She Started Investing in Her 50s, Now She’s Retired with 4 Rentals

24:16I really do believe that. I think that sticking with it is the big key right now. And like you said, the worst case scenario is that you sell the properties. Absolutely. Go back into the market. I could even go back to work. Lord help me. Who knows? But hopefully, hopefully not. Hopefully we can just stick with what we're doing over here. Santa, you went into a few different markets, right? You're in Steamboat. You said Orange Beach, just outside of Asheville, and then Texas Hill Country. Walk me through your thought process on kind of casting a wide net versus just buying all four in Steamboat where you started.

24:50Right. It definitely would have been easier to buy all four in one place, but my vision of retirement was to travel during the off seasons at each property and spend even months there to where we could go and do some hiking or some other things, whatever was in the area. Still have that vision. Boyfriend lives here and we try to get out to, in fact, we're going to Orange Beach this weekend. We try to see when things aren't booked and get there. Couldn't have really done that if we had four all together. So I decided it was worth the operational headache to have four different states. I also did not want to invest much in Texas because the property taxes are so high here.

25:32So I've been trying to get out of Texas in a way as much as I could. But Sandy, I love that so much of your approach is really centered on what kind of life do I want my portfolio to support? And you said, I don't want a big portfolio because I want to take up too much time managing. So I'm making different decisions there. I want to be able to use them myself. So I'm going to these different markets. I love that approach. But how did you actually choose the other markets, especially that's a pretty tight time frame? Was it just places that you already knew and liked to vacation yourself where you felt the numbers made sense?

26:05Or were some of these markets that maybe you hadn't considered before? Just how did you land on all those cities? Actually, not at all. I had never even been to Orange Beach or to Asheville when I started all of this. So that's kind of an interesting aside. But the approach was to try to replicate what I had found in Steamboat. Asheville's a good example of that. The property in Mars Hill is on a ski hill where it was actually shut down, but new owners had already bought this resort and they were turning it into Hatley Point. And it was going to reopen within six months of when this house was for sale.

26:40So it was another one of these cases of I can see that this thing is about to happen and I can see that in three to five years it's going to be amazing. I'm willing to jump in now, maybe even take, you know, way less revenue than I'd like right now. Orange Beach was kind of the same. Some people will call it saturated, but I see something different. I see people coming from Florida and starting to vacation in some lesser expensive places. I see the airport in Gulf Shores just having gone public. I see some different things happening there with a beautiful beach town. So that's why Orange Beach.

27:11And then green in the hill country in Texas, we're on the river. We're walking distance to the oldest dance hall in Texas, and there's great concerts there all the time. So that was just more of a money play. It's kind of close to a lake house that we have. But, but saying, I think even taking a step back and I appreciate the insight there, but how did you go from 20 ,000 potential cities in the United States to even get, you know, Orange Beach and Asheville on, on the list of potential places? Well, I will say I'm not much of an analysis paralysis kind of person. If I get an idea and then I think something looks cool, I'll go look at it and I'll pull the trigger very quickly.

27:47I realized that the first 10 minutes of this podcast did not sound like that. But once I'm in on something, I'm in. So we looked at Florida. I had gone to Destin quite a bit. I wanted to maybe invest there. I had concerns about the insurance costs there and everything that was happening in Florida, even taxes. So I said, I don't know anything about Floribama. Let's go take a quick trip for a couple of days. Brought my son down to Orange Beach and we just fell in love with it. It's beautiful. It's more spread out. We back up to a Gulf state park that is hundreds of acres of just green area where there's all this hiking and biking.

28:21I'm not even much of a beach person and I love it there. So I just was really surprised by that. So it was kind of the same as Steamboat. We bought a house that we loved in an area that we loved and figured, okay, this will at least break even. And if it pays for itself, then it's doing its job. And if it makes more, even better. Just really quick. I've never heard of the phrase Florida Bama before. I had to Google that. Oh, really? Florida Bama. Wasn't there like an MTV TV show that would call that? There was. That was the third thing that popped up. MTV TV show. Florida Bama. It's definitely the redneck version of Florida.

28:55And I am right there, right? I'm from Texas. My dad's from Alabama. These are my people. This is where I should be. I actually went to a mastermind once and stayed in one of the houses right there on the beach. It was a super nice house, great light. Every room had their own en suite. It was a beautiful beach. It's house, house, house, house. Where we were, at least, there was no hotels. It was all just residential and super nice because it wasn't overly busy. Yeah. Or Bama. There you go. Learn something new today. There you go. It's worth a visit. It's pretty neat. So even in this same market, there was actually a new build community, right?

29:37That went up with 70 short-term rental units. So you knew the risk kind of going into this, but why did you decide to buy anyways and what ended up happening? Right. I knew the risks. Well, most of them. I had lost some money on a personal new build. So I knew it wasn't the smartest purchase unless I was going to hold onto it for a really long time, which is our plan there. But with a new build community, we were able to really get a vision for what it would be, get in fairly early while pricing was still good. We were one of the first six or seven houses in the community. We could pick the best lot, or the best lot for us anyway, has the most land.

30:12It backs up to the Gulf State Park. Like I said, it's got four en-suites in there, which we can fit all king beds, no problem, and really just make it into something that would work great, we thought, for multiple generation families. We were looking for how can we support multi-families, not just mine, but also other people who would want to go visit there. So we made it beautiful. We took a chance on it. It's stayed level in revenue, which I think for that area is a win over the last couple of years. Now, I know one of the other things too, Sam, that you focused on was improving the occupancy.

30:48So I think you went from 51 % occupancy in 2024 for up to 77 % occupancy in 2025. And given that occupancy is only one metric, we also want to look at revenues, but that's a big jump for 21 to 77. What did you do that actually moved the needle? Right, that's a big jump. And it tells you, since I just told you my revenue was stagnant there, that I had to make a huge pivot to make the property work. What I really did there was really just to take a huge fresh look at my pricing. Well, I did a few things. Let me back up. I did a remodel on the backyard to make it beautiful, put in a bunch of new plants, put some stone in, made it really nice.

31:26I put in a new bar in the kitchen area in a closet that always should have been a bar, very low cost, but just some things to make the property show a little bit nicer. But then I also took a look at my pricing and decided some of my pricing was just too high compared to the market. Along with doing that, I realized that I wasn't paying enough attention into the pricing and I hired a revenue manager. So that's something that I've slurged on over the last six months or so to really take a closer look at my pricing. Got rid of what I call ego pricing because I was like, oh, I'm never going to have a night that would be less than the cleaning fee.

32:03Well, of course I am. So I'm looking at it way differently right now. I'm going to have the price that gets me the most overall revenue period. That's what the house is for. It's not for anything else. So yes, higher occupancy, which I'm proud of, but the revenue has stayed right at$100 ,000 there for both of the full years that I've had it. Tony, you had hired a revenue manager before, right? I did. Yeah, we have one right now for our entire portfolio. How for somebody like me that has two short-term rentals, what is the process to find and kind of vet a revenue manager? Yeah, I think my process is probably slightly more unique because he actually came to one of our events and we met there and I just kind of got to chatting with him.

32:44But my process for betting him was I just asked him what his process was and I compared that to mine. And if I felt that everything that he was doing was maybe below the level of what I would be doing, would that be a red flag for me, right? But as we had conversations, a lot of his approach was similar to mine. And there were even a lot of things that I've learned from him about how to really put together the right pricing program. So when we talked through and he kind of walked me through his process, I was like, okay, this actually looks good. And we started off, I think, by just giving him, I want to say it was just a hotel first.

33:14And then we kind of started with a few listings. Then we kind of scaled up to the whole portfolio from there. So we dated first. And then once I saw some initial results, that gave me the confidence to give him everything. And now, basically, our entire portfolio has been up year over year since we started working with him. So it's been great. And how does the pricing look like the cost to hire a rep manager? Is it a flat fee? Are they getting a percentage of how they grow the profits? How does that actually work? We pay on a per listing basis. I would be very, I think, against anyone that charges on like a rev share type model.

33:50Because we handed over a bunch of listings at one time. I think we're somewhere around like$100 per listing. But I want to say if you've got like maybe one or two, maybe expect to spend a couple hundred bucks per month or$300 per month for revenue management. So if you've got a listing that's only doing like, you know, 40K a year, maybe it doesn't make a ton of sense. But if you have a listing doing, you know, 100K or 200K a year, spending 300 bucks per month to really optimize that revenue makes a lot of sense. Sandy, is that the same kind of for you? Yeah, that was exactly my thinking for, I mean, if I'm going to spend eight to ten thousand dollars on a revenue manager a year, but my entire revenue for my four properties is about 350 ,000.

34:30Is it worth it? Well, yeah, I hope so. But but, you know, that remains to be seen. I'm kind of early in the process. What I know for sure is that I've learned so much more about how Price Labs work and some of the things that that. So it's been a good investment no matter what, because I've learned a lot that I can take from this. So I'm not sorry that I did it. Price Labs is a really complex and simple tool. You can either set it and forget it and still get good value out of it. or you can really go into it and do a whole bunch of little tweaks that I think AI is going to make that a lot easier in the future, right?

35:04But for now, it's a really complex tool with a lot of data science behind it. Couldn't agree more, Sandy. And kudos to you for making that decision and seeing that value. Now, Sandy just told us how she nearly left money on the table and then fixed it by kind of killing the one thing her pride wouldn't let go of. But what makes your story really different is what she brought into this business from her 30 plus years working in corporate America. And we'll cover that right after a quick break to hear a word from today's show sponsors.

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37:11While supplies last, ends June 30th. Terms at aka.ms slash college pc. All right, we're back with Sandy. Now, Sandy, you went from, again, sold right at 50 to retired just a few years later, not by abandoning your career, but by really redeploying what you learned in your career into your real estate business, right? I mean, you were known at work as a fixer, right? You know, you got put on the broken department or a broken project or a broken process and you'd fix it. But it turns out short-term rentals are kind of full of broken things as well. So you said that your background in corporate, again, being thrown at something and fixing it directly translated into running your short term rental business.

37:50Can you give us like, what is an example of what that looks like in action? Sure. I think you hit the nail on the head. I'd have to go into situations without a lot of information. Often it was taking over a department where I didn't have any background and go in and learn the processes and then try to make everybody happy on the customer service side and within the department while I'm changing everything to make it work. Right. So lots of different moving parts when you manage departments or come up with new operations. But with short term rental specifically, you've got to have all the same skills.

38:24You need organized, clear, good operations. But you also need to be able to problem solve really quickly and efficiently in order to not let it take over your life or stress you out really badly. There was a really fun recent example. Everybody's got issues, but I don't know what I think is fun one now because it came out so good in my orange beach place over Thanksgiving week. I had two families arrive on Tuesday of Thanksgiving week. They're clearly big football watchers. I've got a big 85 inch TV again, Florida Bama. So we've got an 85 inch TV on the walls where everybody can watch their Southern football and they get there and the TV is broken.

39:02There's a big line down the middle of the TV. It's clearly just not okay. So Tuesday, Thanksgiving week, and they were definitely football watchers, like I said. So I learned this about 4 p.m. and I quickly went down a bunch of different paths to try to figure out what's the best way to get a TV into that house this evening and on the wall, right? Like that's hard. And I think a lot of people might just go, oh, shoot, that's hard. What am I going to do? I'll fix it in the next week or two. You can't do that. So everything I learned in my corporate business where problems don't wait and you have to solve them right away.

39:35If you're really going to be a great manager in a short-term rental world, you also need to solve problems right away. So between Costco, Walmart, Amazon, Best Buy, I found one at Walmart that worked. My handyman went and got it. He had it on the wall by 8 p.m. and everybody's cheering that this all worked out. But, you know, it's constant things like that. There's always a problem and it seems big and people can panic. Let the guests know that you care and that you're working on it really hard and then do your best and then let it go emotionally. It's just work. You've got to let it go. It's just work, right?

40:07I think one thing that I've learned on that piece as far as the problem solving and trying to deliver customer service, and this is more coming from my long-term rental side, but that just the more you communicate, it seems like the better, the the issue doesn't escalate. You can keep it more controlled. And I feel like with at least long-term tenants and sometimes with short-term guests, I've learned that keeping them updated as to what's happening, how you're solving the problem and update on, he's arrived at Walmart, he's got the TV, he's going to be there in 20 minutes. Those updating people and telling them goes such a long way.

40:48Every work order we receive, we are immediately acknowledging it that we have received it. We immediately acknowledge that it has been assigned to a contract or they've been called. We acknowledge, are they going to schedule it? Will we schedule it? Every little step of the way. Also, it's great to have that documentation too, but it's just letting them know and keep them informed and updated because what is the most frustrating thing to anyone is when you have no idea what's going on. Right. And you feel like no one cares. They need to know that you care. And so I got the best review from this guy.

41:23So it was fantastic. Everybody wins. Now you mentioned, Ash, like systems and processes and Sanana, that's been a big focus for you as well. Your portfolio for properties runs on just a few hours a week. And I think a lot of the thing that maybe holds new rookies back from investing in Airbnbs is that they feel that it's maybe too labor intensive for them to try and take on. So you're a few hours a week on managing, you don't live near most of your properties, and you're traveling constantly, right? So what does the actual operational reality look like? And what did it take to build to that level?

41:56Yeah, absolutely. I think this is really important. And I've heard you guys talk about it so much. Having the right tech stack in place is the most key issue for me anywhere. And that's something that I did from day one. Some people might not. I think it's great If you go ahead and put that property management system in place right when you set up your property and then it does so much of the work for you in terms of messaging and controlling your locks and your thermostats and everything else. I knew I was trying for a large revenue for every property. So I just have never stressed about small software costs.

42:31Building automation into my processes has been my key for me from the very from the very beginning. I think the software and the systems are the fun part for me also. So I've had a lot of fun with that. But remote management to me is so much easier with the right tech stack in place. I think that's the biggest key. Certainly the right cleaner, the right handyman. It'll work well no matter where you are. If you have a couple boots on the ground and then you have a system in place that is set to work without you. It works while I sleep is what I like to say. Now, a lot of rookies are actually trying to get out of their W-2.

43:07They want to escape from it. But what you're saying is actually something you brought with you. What would you tell all the rookies listening who've been dismissing their own resumes as an investing asset? I think there's a lot around this, right? Well, for one thing, it's never too late. If you would have told me 10 years ago that you could be in your 50s and start a real estate investing career, I might have thought you were nuts, right? But absolutely, it doesn't really matter when you start. It's just crafting this to look like what you want it to look like. But absolutely, taking those skills from your W-2 or from whatever your life is and translating them to the next part of life, I'm going to sound a little book-like on you, but that's just learning and improving and adapting and finding what's next and taking everything you've learned along the way.

43:54So the further you go along, don't leave behind anything that you might have learned there. It always translates. The leadership translates. The people skills translate. The team building translates. Certainly the operational skills, the Excel, the analytics, Tableau, all of that stuff translates beautifully to this career. You just have to sort of know where to deploy those skills and when. Now, looking back, if you could do this all over again, and what would you have changed? Would you have started earlier? Would you have only focused on fewer properties, maybe more properties? For somebody that's listening to this, what does this path look like for somebody listening right now?

44:34And what would you have done differently? I think the only two things I would have done differently is started earlier, which I think is probably not a surprise answer. I bet most people you talk to say that. I definitely would have started 10 years before I actually left work because it only takes a few hours a week, which really surprises me. I really wish I had bought two of these properties 10 years earlier and then just let them ride. Right. And had fun with them along the way. That said, love where I am. So it's totally fine. But I would have done that differently. And I wouldn't have hired a property management service from day one.

45:06I also think you guys have talked about this. If you really get into your own first property and understand how it works, even if you decide you'd much rather have it managed by others, totally fine. But if you learn it yourself first, you're going to be a better owner in the long run. I think all of that is just really important. Last question I have for you, Sandy. We've been talking more about like AI and how that's kind of seeping into the world of real estate investing. You said that you think guests will find their next Airbnb through like a chat GPT before they ever even open the app. What do you think rookies need to do right now to maybe stay ahead of that curve?

45:41Right. So whether that's right or wrong, it's definitely a curve that I want to stay ahead of. So you'll get lots of stories around AI, but I am so glad you asked this one. I actually just did two YouTube videos about AI and what I think the effects are that we're already seeing in the industry and where it might go. What an incredible tool for rookies that are already operating short term rentals. There are a few things that they can do even right now, I think, to get ahead of what's happening in the industry. having your own direct website with some sort of branding and a really clear description of what your home is, is really going to help AI find your home better.

46:18But Airbnb and Vrbo are already using AI to overlap how we used to think they were showing homes to people and trying to show the home that will get the guests to book the fastest. It used to be about keeping people in the scroll. And now it's how can we get that person with a shorter attention span to book quickly and get off the site, right? So it's just different than it used to be. And what they're saying is that AI wants clarity. So having descriptor words like beautiful is not going to help AI at all. They want it to be quantifiable. It needs to be amenities, bed sizes, beds and baths, be really clear about who this home is for, and say that in your listing, even several times who you're trying to attract with it.

47:04Try to call out a few specifics that makes your home better than your neighbors. All of this can be a game changer. I mean, I think we're all using AI in some ways, but keep in mind that the software products that we're using are probably all way ahead of us and using it in a lot of other ways that we need to be aware of as we go through this world. That's such a great point. Like I'm thinking about if I were to ask ChatGPT about a property, I'm going to this lake and I want to find a property that has this, this, and this. I'm not going to say I want it to have a beautiful living room. I'm not going to say I want it to look stunning.

47:40I need four bedrooms, four bathrooms. It needs to have a deck. It needs to have a dock to the lake. That makes complete sense. And then the other thing it can do is go through and compare pictures to words. So if you're overstating what your property is, you may not be able to get away with that in the future. I think it's going to be great for the industry. I think it's going to up everyone's game a little bit. I don't think it's bad, at least right now. Well, Sandy, thank you so much for joining us today and sharing your story and all of the knowledge that you have learned from your real estate experience.

48:13Where can people reach out to you and find out more information? Yeah. So I'm so happy to have been here. It's really been a joy. You can find me. I've started a new platform. STR Jumpstart is what it's called. So you can find me at strjumpstart.com. And on both Insta and Facebook as STR Jumpstart, it's really a step-by-step, really manual for if you wanted to get your first property or second, how you could do that. It's something that I wasn't able to find when I got into this. When I got into this, I was a little bit scared, as I told you guys. So having that step-by-step instruction, it's got 50 lessons in there and a lot of downloads.

48:50Financial modeling is really a key behind it. So if anybody wants to check that out, I'd certainly love to tell you all about it. So reach out to me. Well, Sandy, thank you again so much for taking the time to join us today. I'm Ashley. He's Tony. And thank you guys so much for listening to this episode of Real Estate Rookie. If you're not already, make sure you are subscribed to our YouTube channel at Real Estate Rookie, and you can find us on Instagram at BiggerPocketsRookie. Thank you all for listening to the BiggerPockets Real Estate Podcast. Make sure you get all our new episodes by subscribing on YouTube, Apple, Spotify, or any other podcast platform.

49:25Our new episodes come out Monday, Wednesday, and Friday. I'm the host and executive producer of the show, Dave Meyer. The show is produced by Ian Kay. Copywriting is by Calico Content. And editing is by Exodus Media. If you'd like to learn more about real estate investing or to sign up for our free newsletter, please visit www.biggerpockets.com. The content of this podcast is for informational purposes only. All host and participant opinions are their own. Investment in any asset, real estate included, involves risk. So use your best judgment and consult with qualified advisors before investing.

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