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

Summary

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She Started Investing in Her 50s, Now She’s Retired with 4 Rentals — Sandy Lee’s Story

BiggerPockets Real Estate Podcast
Date: May 25, 2026
Hosts: Ashley Kerr & Tony Robinson
Guest: Sandy Lee

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Episode Overview

This episode tells the inspiring journey of Sandy Lee, a Houston-based investor who began her real estate journey in her 50s after a 35-year career in engineering and construction. Sandy shares how she acquired four vacation rental properties across different states within four years, allowing her to retire early and create a life centered around travel, flexibility, and family. The episode is packed with actionable tips for late-starters, short-term rental strategies, and the importance of applying corporate skills to real estate.

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Main Discussion Points & Insights

1. Late Start but Fast Progress: Why Sandy Entered Real Estate (00:52–07:46)

• Background: Successful 35-year career in engineering/construction, senior leadership, but began seeking ‘more’ at age 50.
• Turning Point: Subtle realization: “I could see that I didn’t want to live out the rest of my years in an office setting and keep doing the same exact thing that I was.” (Sandy, 01:16)
• Motivation: Wanted to diversify investments away from stock-heavy portfolio and create more flexibility for travel and personal fulfillment.
• Preparation: Spent two years consuming content, reading, attending open houses, evaluating if long-term rentals fit her goals.
• Fear & Safety: “Maybe it is about redefining safety and seeing it in other places. But I think it’s also okay to go chase something as long as you have some sort of a backup plan.” (Sandy, 06:24)

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2. The Ski Condo That Changed Everything (10:30–19:46)

• Catalyst: Son’s suggestion: “Ski condo, ski condo.” — led Sandy to consider using real estate for personal enjoyment as well as investment.
• Decision: Purchased a $1.3 million short-term rental in Steamboat, Colorado, sight unseen until closing.
  “I went from safe... to hey, let’s buy the most expensive, most ridiculous condo. And I’ll see it the morning at closing, it’ll all be fine.” (Sandy, 13:18)
• Market Research: Analyzed local market, upcoming resort expansions, limited supply due to new regulations, chose a four-bedroom in the “green zone”.
• Renovation: Invested $65,000 in light remodel and furnishings. Brought her trusted contractor from Texas for the job.
• Self-Management Mistake: Initially used a management company, realized self-managing was more profitable and practical—even from out-of-state.
• Financials:
  • Yearly gross now $135,000, expenses $72,000.
  • “If I could do it over again, I would. Your big cash cow. That’s right.” (Sandy, 16:33)

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3. Scaling (Thoughtfully) to Four Vacation Rentals (20:47–22:44)

• Branding: Each property named and branded (“Whiskey Ridge,” “Whiskey Sands,” “Whiskey Hills,” “Whiskey River”) for personal/family use and rental appeal.
• Acquisition Approach: Properties span Colorado, Alabama, North Carolina, and Texas—chosen for lifestyle flexibility and family travel.
• Finance:
  • First two: mortgaged with 20–25% down.
  • Last two: bought all-cash by liquidating investments.
  • “Scaling to me looks like getting rid of all mortgages in my life by a certain age.” (Sandy, 22:10)
• Life Design: Prioritized properties that could be enjoyed by family in off-seasons, not just pure financial gain.

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4. Picking Markets and Managing Risk (24:07–29:02)

• Geographic Diversification: Purposely didn’t concentrate all in one market; wanted travel options and to avoid Texas property tax.
• Market Selection:
  • Some chosen for family appeal, others for unique investment opportunities. Example: Mars Hill ski property was purchased just before the resort reopened.
  • “I’m not much of an analysis paralysis 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.” (Sandy, 27:10)
• Personalized Strategies: Even bought in places she had never visited before; relied on data, market trends, and gut intuition.

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5. Navigating Oversupply & Improving Operations (29:05–34:41)

• Operational Adjustments:
  • Faced occupancy challenges in Orange Beach due to new supply.
  • Improved occupancy from 51% to 77% in a year by:
    • Remodeling the backyard and kitchen bar to boost listing appeal.
    • Aggressively revising pricing strategy and hiring a revenue manager.
  • “I’m going to have the price that gets me the most overall revenue, period.” (Sandy, 31:37)
  • Used tools like Price Labs; values data-driven, dynamic pricing.
• Revenue Management:
  • Hired a revenue manager for $8–10k/year for four properties.
  • Highlights cost-benefit for higher grossing rentals.

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6. Transferring Corporate Skills to Real Estate (34:41–39:47)

• Problem Solving:
  • “If you’re really going to be a great manager in a short term rental world, you also need to solve problems right away.” (Sandy, 36:56)
  • Example: Fixed a broken 85” TV for Thanksgiving guests within hours, leveraging corporate crisis management skills.
  • Stresses importance of fast, transparent guest communication.
• Processes & Systems:
  • Runs all four rentals on a few hours of work per week via automation and remote systems.
  • “Having the right tech stack in place is the most key issue for me. It works while I sleep is what I like to say.” (Sandy, 40:52)
  • Recommends robust management software, reliable local teams, and automation from day one for anyone starting out.

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7. Advice for Late Starters & Personalizing Your Journey (41:09–43:13)

• Use Your Previous Experience:
  • “Absolutely, taking those skills from your W2...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.” (Sandy, 41:09)
• What Would She Do Differently?
  • Start earlier—would have bought properties 10 years before retiring, even while working full-time.
  • Self-manage from the start: “If you learn it yourself first, you’re going to be a better owner in the long run.” (Sandy, 42:26)
• Scaling isn’t the Only Path:
  • Advocates for ‘enough’ properties vs. endless growth for a simpler, more comfortable retirement.

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8. Preparing for the Future: AI & the Next Era of Short-Term Rentals (43:13–45:56)

• AI’s Role:
  • Recommends having a direct booking website with clear, quantifiable descriptions and strong branding—essential as platforms like Airbnb use AI to serve guests faster.
  • “AI wants clarity. Having descriptor words like beautiful is not going to help AI at all. It needs to be amenities, bed sizes, beds and bath. Be really clear about who this home is for and say that in your listing.” (Sandy, 44:26)
  • AI will hold owners accountable—overstatements won’t survive as property images are correlated to listing text.

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Notable Quotes & Memorable Moments

• On Safety and Risk:
  “Now I’m counting on myself and that definitely took some inward looking...” (07:14)
• On First Big Investment:
  “I went from safe... to hey, let’s buy the most expensive, most ridiculous condo. And I’ll see at the morning and closing, it’ll all be fine.” (13:18)
• On Occupancy Issues:
  “That I had to make a huge pivot to make the property work...” (30:37)
• On Bringing Her Contractor:
  “Find yourself somebody that’ll travel for you.” (17:48)
• On Tech and Automation:
  “It works while I sleep is what I like to say.” (40:52)
• On AI & Listings:
  “AI wants clarity...Be really clear about who this home is for and say that in your listing, even several times.” (44:26)

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Key Timestamps

• 00:52 - Sandy’s career background and initial search for more after 35 years
• 03:29 - Readying for first property—consuming real estate content
• 07:14 - Redefining ‘safety’ in financial life and investing
• 10:30 - The “ski condo” idea—how her son inspired her first purchase
• 12:25 - Buying Steamboat condo, market research, and remodeling strategy
• 15:39 - Short-term rental financials and use
• 17:48 - Bringing her own contractor from Texas—a key efficiency hack
• 20:58 - Scaling up: branding, family use, financing methods
• 24:07 - Why choose different markets? Retirement vision and life design
• 29:19 - Navigating oversupply, pivots in Orange Beach
• 31:55 - Revenue management: working with a professional to increase revenue
• 34:41 - Translating corporate “fixer” skills to running short-term rentals
• 39:47 - Operations: running 4 properties remotely in a few hours/week
• 41:09 - Advice for late starters and adapting career skills
• 42:26 - What she would do differently: start earlier, self-manage first
• 43:13 - The future with AI: direct bookings, data-driven listings

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Final Thoughts

Sandy’s journey defies the notion that it’s “too late” to start real estate investing. Her story is a lesson in blending life design, family, travel, and financial freedom—and proves that focused effort and corporate experience can be powerfully applied even after age 50. Whether you’re a rookie or late-bloomer, this episode champions thoughtful scaling, technology, self-management, and personal fulfillment over chasing numbers for their own sake.

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Connect with Sandy: strjumpstart.com | @strjumpstart on Instagram & Facebook

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Transcript

[A]

Hey, everyone. Dave. Here today on the feed, we are publishing an episode that previously appeared on the Bigger Pockets Rookie show. It's the story of investor Sandy Lee from Houston, Texas. Sandy didn't start investing in real estate until she was already in her 50s, but she was still able to buy four properties in just four years and retire early from her day job. So here's rookie hosts Ashley Kerr and Tony Robinson with Sandy. And we'll be back with a new episode of the Bigger Pockets podcast a couple of days.

[B]

This is the Real Estate Rookie Podcast. I'm Ashley Kerr.

[C]

And I'm Tony J. Robinson. And with that, let's give a big warm welcome to Sandy. Sandy, thank you for joining us on the Real estate Rookie podcast today.

[D]

Thank you so much for having me. I'm a fan girling over here. I've been a big fan from the beginning.

[B]

Well, we are so excited to hear your story today and the journey that you've been on. And you actually started out with an engineering and construction degree working for two companies for 35 years. You had senior leadership roles and really a career that most people would call a success story. So what was actually happening inside the story around the time you turned 50?

[D]

I mean, I absolutely loved my career, so. So you won't hear me speak too ill of it. I was so lucky to have it. I worked my way up from pipe stress engineering into some senior leadership roles, and I loved all of those different experiences along the way. But I could see that I didn't want to live out the rest of my years in an office setting and keep doing the same exact thing that I was. So I was kind of just looking for more when I turned 50 and trying to figure out, like you said, how to get to retirement.

[C]

So, Sandy, I mean, 35 years is. Is a good amount of time to invest into a career. Was there, was there a moment at some point in that journey where, like, a light bulb went off or was it more of like a subtle shift or subtle realization that you need to do something different? Like just take us back to that moment where you realized that maybe a change was needed.

[D]

It was very subtle, and I think you hit on it with the long time that it was. By the time I was at the end of my career, I had had such great roles, but I was running our private equity division. I was still helping out a little bit on the services side, but it wasn't a role that necessarily fit any of my background or really my skill sets. Fantastic education. I didn't even realize it at the time but, but it wasn't really me. And so I was starting to just feel like, I wonder, wonder what else there could be. I longed for more travel. I grew up with a mom who was a travel agent. So travel was in my soul from a very early age and I was looking for flexibility.

[C]

And what about from a financial perspective, Sandy? I mean, to work 35 years, do you feel like you had put yourself in a position to kind of coast into retirement or was there something from the financial perspective that motivated you a bit as well?

[D]

I was in a position that I could have stayed in the same career, company, industry for another five years and then coasted into retirement. I wasn't quite there yet, but I certainly had more resources and I was very lucky to have been there. But no, I wasn't ready to just hit the button and be done. Even if I was, I don't think that would have felt great to me. I think I'm the kind of person who always needs something to focus on and I was trying to figure out what's that next thing going to be

[B]

now what were you doing before you actually bought your first property as far as getting yourself ready? And how long were you consuming content like bigger pockets and reading and listening to podcasts before you actually pulled the trigger?

[D]

I feel like I was doing all of those things and for at least two years I was thinking about how to diversify my portfolio. That's really how this started. I was all in stocks. I had a lot of stock in my actual company. I was thinking about, I don't want to be so invested in the stock market. So I started going to some. After listening to you guys forever and reading books, I started going and visiting some homes in Houston, Texas, which is where I live, thinking about long term rentals. How could I just get a few long term rentals, sort of the bigger pockets mentality and get something else in my portfolio, but it just wasn't feeling great. So that's what led to this big two year time span where I was just listening to a bunch of content. It kind of started in Covid and trying to figure out what I wanted to do. But the long term rentals just didn't feel like me. Everyone we walked into just, I just couldn't picture it.

[C]

So Sandy, when you say that, that it just didn't feel right or that it just wasn't clicking, was it like mathematically like you, you look at the numbers, the numbers weren't working out or was there, was it like a fear that you had about actually pulling the trigger. Like when you say it wasn't working, what did that actually mean?

[D]

I don't think it was a fear though. I am a single mom with one son, so there's always a fear of jumping out and doing something crazy that comes back to bite us. The numbers were fine, not fantastic. Long term rentals are good, right? They're, they're solid. But it just didn't feel exciting to me. And I'm the kind of person that wants to feel excited, joyful, what's next thing going to be and how's it going to benefit me? Not just from a money perspective, but from a joy perspective.

[B]

Now with this version of your story, most people decide that they're going to grind it out till 60, 65 and just work that safe career that they've had. What made you decide that that wasn't the life, the path that you wanted to take?

[D]

And, and for a long time I thought that's exactly what I would do. So many of my friends have and are doing exactly that. More power to them. That's great. But I'm kind of the crazy one, which doesn't sound like it when you hear about my career. But I'm, hey, you're among like minded people. We would not do the same, right? Things were changing rather quickly in my industry. I don't know how much you guys knew about what was happening with oil and gas over the last 10 years, but things were shifting and it seemed like the right time to come up with a clear exit plan. So I wasn't panicking because like I said, I had resources. I had had this great career. But I started to wonder, what could it look like if I didn't work in an office at all and started to just supplement that retirement by taking some of my money and putting it into real estate? Didn't know I'd take all of my money and to put it into real estate, but hey, we're getting ahead of ourselves.

[C]

But you talk about like the safe piece, right? Like, you know, you said you have a son, right? You think about what's safe. Did you have to maybe redefine what safe looked like for you? Or how do you, how do you reconcile that, that desire for safety with maybe taking this bet on yourself?

[D]

Well, to tell you the truth, I'm not sure I'll ever reconcile that need for safety. And I think that's okay. About two, three times a year I still have to get deep into financial models and convince myself that, yep, the value is still there, the equity is still there. Yep. I still have money. It's just not, you know, it's just not in a big pile in the stock market that it used to be. So maybe it is about redefining safety and seeing it in other places. But I think it's also okay to go chase something as long as you have some sort of a backup plan, which could just mean like turning a corner and doing something different. Right. Believe in yourself kind of thing.

[C]

So you said redefine safety. So how was your definition changed as someone who has a, you know, climbed the corporate ladder, checked all of the boxes of typical American dream. How has your definition of safety morphed as you've gone on to do real estate full time?

[D]

Well, now I'm counting on myself and that, that definitely took some inward looking and some deciding that I could do that on my own. But that's what's happening is now I'm counting on myself. I get up every morning and I look at my own spreadsheets and my own things to do for the day and I think about maybe how to grow my own businesses in a different way instead of going to an office, sitting down and seeing what's needed of me. They're just very different, different paths. I loved them both. Right. Like I'm having so much fun with this. But I also loved that too. It was very safe.

[B]

So Sandy had the career, she had the knowledge. What she didn't have was the right entry point. Until her son kept whispering same two words over and over again. That's right after this break. We'll be right back.

[A]

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[B]

investor okay, so welcome back. We are here with Sandy and her son kept whispering ski condo. Ski condo. And you know what? I hope my kids start whispering that in my ear and it manifests me to get a ski condo. But Sandy, you had spent years consuming every every piece of knowledge of real estate education and you still couldn't find the right entry point. That was perfect for you until Covid happened and your son actually went off to college in Colorado. So what happened from there? Right?

[D]

This is where everything changes, right? I certainly never thought I'd be going to buy a ski condo, but it was about midway through my son's college career. Like I said, he was in Colorado and his friends and he were leaving Colorado to leaving their campus to go skiing every weekend. I don't know. Side note, I don't know how they got mechanical engineering degrees and went skiing every weekend, but somehow they pulled that off. I guess they don't need a lot of ski or could afford to ski

[B]

in Colorado while In Colorado, boy, do

[D]

they find out cheap ways to do it, right? Like you can do that wherever you are, right? Like they figure out these college things they can do. But anyway, they had so much fun doing all of that. And meanwhile, Jackson and I had gone every year at that point for 20 years in a row to Steamboat. It was kind of our love. We did skiing every year. We skied as a mother and son. And so you know it, because we loved Steamboat so much. I laughed at him at that point though, and said, no way, we're not doing that. We'll still be able to go every year. Don't worry about that. But it didn't sound like an investment to me. It kind of sounded like a toy. But internally I hadn't really dismissed it. I started thinking more and more about it. I started going down those rabbit holes that we all do in the evenings where you're on your iPad or your phone thinking, I wonder what this could look like. I wonder if it could pay for itself even partially with some short term rentals. Because I just hadn't considered it all before then. But boy, that rabbit hole works. And before you knew it, I was looking at properties.

[C]

So you eventually end up buying a condo. So walk us through. Like how do you get from, you know, up late night scrolling through on your iPhone to actually finding a property, turning it into an investment property, like what, what happens in between those two steps?

[D]

During this time in the market, everything was moving fast and furious. So we, we scheduled a short ski trip and I knew that on a couple of those days I would just walk the neighborhoods, really get familiar with what is where in the area so that I'd be ready to pull the trigger when something came on the market. This was spring of 22 and so things were still really booming in the market back then. So found a couple. It took me a couple of offers to get the right one. Biggest purchase of my life, $1.3 million. I still can't say it without choking a little bit on it. And I didn't see it until the morning of closing.

[B]

Oh my God.

[D]

Wow. So I went from saf that we just talked about to hey, let's buy the most expensive, most ridiculous condo. And I'll see at the morning and closing, it'll all be fine. My family thought I was ridiculous, but it all, it all turned out just wonderfully. I had done enough research at that point to really believe in Steamboat. There were a few things happening at the resort that made me think, this area is going to boom. Aspen had bought Steamboat a few years earlier. They were midway through a big expansion on the mountain where they were adding a second gondola which was the longest, fastest one in the world, but it wasn't there yet. They were adding a bunch of land, but the ski area wasn't getting any bigger at the base. They also had just gone through all of that talk that so many towns are on the regulations and put in a bunch of new regulations in Steamboat. So the opportunity to pick up a four bedroom in the Green zone seemed a little bit infallible to me. Like, how could this go wrong? At least I could sell it if this doesn't turn out to be our thing.

[C]

Yeah, Sandy. Well, you answered my first question, which was how did you build confidence in that decision? You kind of walked through what you saw there. But if, if part of the initial tension that you were feeling was around this idea of safety and, and, and somewhat protecting your investment. And you even said it now like, like saying that the purchase price you still kind of get, get caught up on, on saying 1.3 million. Why start so big? Why, why not go buy something maybe in a different market for half the price? What, what push you to, to such a big purchase price to begin with?

[D]

Well, at this point, I really didn't know that this was going to become a business for me. I thought it was going to be one investment that would sit alongside the rest of my investments. I didn't realize you could get a mortgage that was for. In my case, I think I put 20, 25% down on that property. So it was still a big cash investment for me, but it could sit alongside the rest of my portfolio. So I was able to convince myself I'd be able to sell it. Things were still rising rapidly there. Sure enough, in the first year it went up another 25% in. So it turned out to be a great decision even early. But I convinced myself that I could always just sell it. That's how.

[C]

So you buy it for 1.3. What do you have to put into it? Well, I guess first, what strategy are you using on this? I'm assuming because it's a ski town, this is a short term rental, is that correct?

[D]

That's right. It's a short term rental and we use it about two weeks a year, a little bit more sometimes in the off season if we want to go hiking and things. But we use it very little. It's definitely a rental. It's there to make money.

[B]

I just have two questions on the money piece here. The first One is, how much are you making on average at this property?

[D]

So right now? Well, last year my revenues there were 135,000 gross. When I started out, they were about 80. So in that few years, it's gone up pretty material every year there. And my expenses there are 72. So it started out just breaking even, basically, but now it's my biggest money maker, even with much more equity in some other places, but continues to be my big. My big. If I could do it over again, I would. Your big cash cow. That's right.

[B]

My second question is, when you and your son would go on your yearly trip, how much were you paying to rent somewhere?

[D]

Boy, that's a really good question. So this was a while back, but still close to a thousand dollars a night. I mean, it's hard to get anything for less than $1,000 a night during ski season around these places, so. So certainly, yeah, now we get free ski trips, which is huge.

[B]

You said two weeks you're going. I mean, that would be $14,000 you would be paying if you didn't have your own place. So really that's, you know, added on to the benefit, the bonus, I guess.

[D]

Absolutely. So Tony asked how much I had to put into it. I did have to put some into it. We didn't talk about that. I put about $40,000 into a light remodel. I did some light remodeling on all three of the bathrooms, painted the whole thing, and then I completely refurnished it. So that was another 25,000 or so.

[C]

That's actually not bad, you know, 65 grand. You said it's a four bedroom?

[D]

Yeah, it's a four bedroom.

[C]

Yeah, that's actually. It's a pretty good price to set up a four bedroom, so. And to be able to net, you know, you said maybe like 60 grand a year, give or take, on. On that same property. That's an amazing return.

[B]

Yeah, I already paid that back in one year. Just the rehab and the.

[D]

I brought my own contractor from Texas. That was another thing. One of the things that I did really right was you can't find a contractor in ski town, especially if you're from Texas, especially if you're from out of town. They don't want to work for you. They've got so much work that they can do there locally. So I packed up my contractor from Texas and I asked him to drive to Colorado and do a remodel for me. And now he's done that at every single one of my properties. So I kind of Love that story. It's like find yourself somebody that'll travel for you.

[B]

Does he just stay in the property then while he's working on it?

[D]

Exactly. I just tell him what I need done. He takes his sons, he goes and has a vacation and works for a couple of weeks. When I, when I need him to do something, I love it.

[C]

That's fantastic. We actually, we did the exact same thing for the hotel that we bought in Utah. We were having a very hard time finding contractors here locally. It's a smaller town, you know, outside of a national park. We took our, our crew from California and they didn't stay there the entire time because it was about a, I think it took maybe three months to do or maybe four months to that full rehab. But they would drive up from California. It was a, you know, six hour drive. They drive up every Sunday and then drive back every Friday. Right. And they would stay at the property in the meantime. But, but if you do have a connection to someone, I think it does help tremendously to kind of skip that part of finding someone to actually do

[D]

the work for you and lower the cost because there's that mutual trust on both sides. Absolutely.

[C]

Now given that this was your first one, Sandy, did you, did you self manage this because you were still working a full time job at this time as well, right. Or had you left already?

[D]

I was still working a full time job and this was. If you were to ask me what my biggest mistake was, this is it. I did not self manage at first. I hired a management company and so that cost me all kinds of money. And as soon as my contract let me get rid of that managed company, that's what I did. That was just a confidence piece and that's something that I haven't looked back on since then and try to educate other people on now of, you know, this is not as hard as you think it is. You can do this from afar. You know the tools will let you do it from afar these days.

[B]

And you probably realize you could do it better too, for sure.

[D]

And I don't, I don't like to say that too much out loud because these folks are doing their best. It was actually a fairly small company, but nobody cares about your property like you do. If you really want all 5 star reviews, you're the one that's going to get it there.

[B]

Right. That would be like an interesting comparison to look at like some of these bigger nationwide companies and like gather all the reviews and like see how many of them are actually five star reviews compared to like individual owners.

[C]

You know, like that data has actually been like put together already and it's, it is 100% verify that as your number of listings increases, there's like a direct relation to your review score decreasing. And the people who are, you know, one or two listings, they're the ones that are really at the top when it comes to review scores. When you see the people with tens of thousands of listings, like, you know, the vacas, the, you know, evolves of the world, they're the ones that are really suffering when it comes to that. So you're absolutely right. As, as the portfolio gets bigger, it gets harder to maintain those review scores.

[B]

Now from that first property, you went on to build distilled destination. So how did this plan evolve from one ski condo into four properties within two years?

[D]

Right. So that ski condo, we branded it from the very beginning. We called it Whiskey Ridge. And like I said, about six months into it I started to see, hey, this is doable and I enjoy this a lot. And that's when I started really thinking about actual retirement, what could this be? And then, yes, in the next year and a half I bought three more properties. Whiskey Sands is in Orange Beach, Alabama. I've got Whiskey Hills just north of Asheville in Mars Hill, and then Whiskey river in Texas and the Hill country in green. So have loved putting it together. It just started seeming like how can I make this brand into something that we would enjoy? The theory was always the same vacation homes that the family could use. Both my son and I and our extended family, we're real close to my brother and sister in law and their three kids. So how can we all go vacation and enjoy some holidays but also by the way, pay for my retirement along the way? So that's what this became. What's that? Minimum number of homes that I could do exactly that with.

[B]

Now for each of these properties, did you do the same kind of financing where you put 25% down for each and where was this cash coming from for each of these down payments?

[D]

For the second property, I did do 25% down and I have a really large mortgage on that one. That was the Orange beach property. The third and the fourth were lower entry points and just to be blatantly honest, really liquidated some investments and went all in cash on those last two. My long term goal, different than some, maybe different even than what's the smartest, is to have no mortgages. So I'm now in that case where I don't think I want a lot more properties so scaling to me looks like getting rid of all mortgages in my life by a certain age. So that's the big goal.

[B]

And I don't think we hear that enough on the podcast as like that as an option it is consistently put into your brain. Scale, scale, scale. Grow, grow, grow, buy, buy, buy. The bigger the portfolio, the more successful you'll be. But really I, I think it's refreshing to hear that that that's not the case. You don't need a ton of properties to retire or to cash flow or to build the life you want. And some cases you could have these four properties and make as much money as someone with, with 20 properties that's over leveraged on them, you know. So I think it's very refreshing.

[D]

Well, that's the goal, the path to be on.

[B]

Yes.

[D]

Right. And now in the market, as you guys know, short term rentals have been seeing some struggles over the last couple of years. And especially in some markets, the goal is going to be to stay with them, to make just enough money to get by, to keep my own personal expenses fairly low and not quit, not walk away. Because I have a lot of faith that in five years this is just going to be the greatest decision I've ever made. I really do believe that. I think that sticking with it is the big key right now.

[B]

And like you said, the worst case scenario is that you sell the properties.

[D]

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.

[C]

Sandy, 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.

[B]

Right.

[D]

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 tried us to see when things aren't booked and get there. Couldn't have really done that if we had four altogether. 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. So I've been trying to get out of Texas and away as much as I could.

[C]

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, hey, I don't want a big portfolio because I want to take up too much time managing. So I'm, you know, 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 timeframe. Was it just places that you already knew and liked to vacation yourself, where you felt the numbers made sense, or. Or some of these markets that maybe you hadn't considered before? Just how did you land on all those. All those cities?

[D]

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 Hatch Point. And it was going to reopen within six months of when this house was for sale. So 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 and Gulf Shores just having gone public. I see some different things happening there with a beautiful beach town. So that's why Orange beach and then Green and 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.

[C]

But. But Sandy, I think, even taking a step back, and I appreciate the. The insight there, but. 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?

[D]

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 I 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, 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 Florabama. Let's go take a quick trip for a couple 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. I'm not even much of a beach person and I love it there. So I just was really sur. 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.

[C]

Just really quick. I've never heard of the phrase florid Bama before. I had to like google that to, to like oh really?

[B]

Wasn't there like an MTV TV show

[C]

that was called that popped up. MTV TV show Florida.

[D]

It's definitely the redneck version of Florida. And I am right there, right? Like I'm from Texas, my dad's from Alabama. Like this, these are my people. This is where I should be.

[B]

I actually went to a Mastermind once and stayed in one of the houses right there on the beach. And it was like super nice house. Like great light layout. Like every room had their own ensuite and it was beautiful beach and it's like house, house, house, house. And there's like where we were, at least there was no hotel. So it was all just residential and super nice because it wasn't like overly busy.

[C]

Yeah, there you go. Learn something new today.

[D]

There you go. It's worth a visit. It's pretty neat.

[B]

So even in this same market there was actually a new build community, right. That 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.

[D]

I knew, 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 in 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. We are the best lot for us anyway, has the most land. It backs up to the Gulf State Park. Like I said, it's got four ensuites 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 generations 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.

[C]

Now, I know one of the other things too, Sammy, that you focused on was improving the occupancy. So I think you went from 51% occupancy in 2024 up to 77% occupancy in 2025. And given that occupancy is only one metric. Right. We also want to look at revenues, but that's a big jump. 51 to 70, 77. What did you do that actually moved the needle?

[B]

Right.

[D]

That's a big jump. And it tells you, since I just told you my revenue was 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. I. I 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 to the pricing and I hired a revenue manager, 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 eco pricing because I was like, oh, I'm never going to have a night that would be less than the cleaning fee. Well, 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, for both of the full years that I've had it.

[B]

Tony, you had hired a revenue manager before, right?

[C]

I did, yeah. We have one right now for our entire portfolio.

[B]

How for somebody like me that has two short term rentals, what is the process to find and kind of vet a revenue manager?

[C]

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 got kind of got to chatting with him. But my process for vetting 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, you know, 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 talk 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. And then we kind of started with a few listings. Then we kind of scaled up to the whole portfolio from there here. So it was, we dated first and then once I saw some initial results that gave me the confidence to give them everything. And now, you know, basically our entire portfolio has been up year over year since we started working with them. So it's been great.

[B]

And how does the pricing look like, the cost to hire a revenue manager? Is it a flat fee? Are they getting a percentage of how they grow the profits? How does that actually work?

[C]

We pay on a per listing basis. I would be very, I think against anyone that charges on like a, like a Rev share type model, you know, because we handed over, you know, like a bunch of listings at one time. I think we're somewhere around like 100 bucks 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 bucks 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.

[B]

Sandy, is that the same kind of for you?

[D]

Yeah, that was exactly my thinking for, I mean, if I'm going to spend 8 to $10,000 on a revenue manager a year, but my entire revenue for my four properties is about 350,000. Is 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 Prices 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. But for now it's a really complex, complex tool with a lot of data science behind it.

[C]

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 fix 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 word from today's show sponsors. 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, your background in corporate again being thrown at something and fixing it directly translated into running your short term rental business. Can you give us like what is an example of what that looks like in, in action?

[D]

Sure. I think, 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 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 rentals specifically, you've got to have all the same skills. You 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 had a, 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's broken, there'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 4pm 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, where problems don't wait and you have to solve them right away. If 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 8pm 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.

[B]

I think one thing that I've learned on that piece, as far as the problem solving and trying to deliver customer service, 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, you know, keeping them updated as to what's happening, how you're solving the problem and update on, you know, he's arrived at Walmart, he's got the TV, he's gonna be there in 20 minutes. You know, like those. Updating people and telling them goes such a long way. Like every work order we receive, we are immediately acknowledging it, that we have received it. We immediately acknowledge that it has been assigned to a contractor. They've been called. We not acknowledge are they going to schedule it? Will we schedule it like 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.

[D]

And you feel like no one cares. They need to know that you care. And so, oh, I got the best review from this guy. So it was fantastic. Everybody wins.

[C]

Now you, you mentioned Ash, like systems and processes and Santa, 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, that maybe holds new rookies back from investing in Airbnbs is that they, 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?

[D]

Yeah, 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. Building automation into my processes has been a 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.

[B]

Now, a lot of rookies are actually trying to to get out of their W2. They want to escape from it. But what you're saying is actually something you brought with you. What would you tell all the rookie rookies listening who've been dismissing their own resumes as an investing asset?

[D]

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 W2 or from whatever your life is and translating them to the next part of life. I'm going to sound a little, 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. So the further you go along, don't leave behind anything that you might have learned there. It always voice 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.

[B]

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? You know, for somebody that's listening to this, what does this path look like for somebody listening right now? And what would you have done differently?

[D]

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 run, 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. I 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, that is just really important.

[C]

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 Rickies need to do right now to maybe stay ahead of that curve?

[D]

Right. So whether that's right or wrong, it's definitely a curve that I want to stay ahead of. Right. So you'll get lots of stories around AI. But I am sorry, 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, right? For. 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 help AI find your home better. But Airbnb and VRBO are already using AI to overlap. What how we used to think they were showing homes to people and trying to show the home that will get the guest 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, what they're saying is that AI wants to 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 bath. 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. Try 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, 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.

[B]

That's such a great point. Like I'm thinking about if I were to ask ChatGPT about a property. I'm, you know, 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 like, you know, I. It's going to be, I need four bedrooms, four bathrooms. It needs to have a deck, it needs to have a dock to the lake like you're. That makes complete sense.

[D]

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.

[B]

Well, Sandy, thank you so much for joining us today and sharing your story and all of the knowledge that you have learned, learned from your real estate experience. Where can people reach out to you and find out more information?

[D]

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 [e-mail] 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. Financial 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.

[B]

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 Eaterookie, and you can find us on Instagram at A Bigger Pockets Rookie.

[A]

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. Our new episodes come out Monday, Wednesday and Friday. I'm the host and executive producer of the show, Dave Meyer. The show is is produced by E and K. 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. You should only risk capital you can afford to lose. And remember, past performance is not indicative of future results. BiggerPockets LLC disclaims all liability for direct, indirect, consequential or other damages arising from a reliance on information presented in this podcast.