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Show Summary
In this conversation, Sandy Lee shares her journey from a successful engineering and construction career to becoming a real estate investor specializing in short-term rentals. She discusses the importance of understanding market regulations, the realities of managing short-term rentals, and how to effectively use technology to streamline operations. Sandy also emphasizes the significance of choosing the right markets and properties, and she introduces her course, STR Jumpstart, aimed at helping others enter the short-term rental space. The discussion highlights the potential for financial independence through real estate investment and the importance of providing excellent guest experiences.
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Investor Fuel Show Transcript:
Sandy (00:00)
So this is how this happened. And now we’re short-term rental investors and it’s become absolutely what I do. A few years later, later was able to retire with it. So that tells you how much I believe in it. Absolutely love, love the industry.Dylan Silver (01:52)
Hey folks, welcome back to the show. Today’s guest, Sandy Lee is a real estate investor and educator. She’s the owner of Distilled Destinations and STR Jumpstart and has a background in engineering and construction. Sandy, welcome to the show.Sandy (02:08)
So nice to be here and thanks for having me.Dylan Silver (02:11)
It’s great to have you on here and your background lends itself towards being able to break down processes and being able to identify systems, right? Engineering, construction. Walk me through how you went from a long career in engineering and construction into being a real estate investor. Was that something that you had on your ⁓ horizons?Sandy (02:35)
Boy, not at all, not at all. And I think most people don’t, right? So I went engineering, construction, services, and then sort of into the financial part of our business in my engineering firm. I was a bit of a problem solver at work. I was all over the place and ended up as a senior vice president. And then at the end of our career, I ran our financial branch of our investing part of our firm. And so that’s where I really started learning into investments.I was like, ⁓ wait, there’s maybe a better way to invest out there. Meanwhile, my son had gone to college in Colorado and kept putting this out there that, hey, we need a ski condo. And I was like, we absolutely do not need a ski condo. This is not what we’re going to do with our lives. But, you know, all of this kept plunking around in my brain. And at some point a year later, you know, ski condo. so then we…
Then I had an investment, right? And so,
this is how this happened. And now we’re short-term rental investors and it’s become absolutely what I do. A few years later, later was able to retire with it. So that tells you how much I believe in it. Absolutely love, love the industry.
Dylan Silver (03:43)
Now, when we talk about engineering background, engineering mindset, I’ve seen this go two ways. I’ve seen the engineers dive in and like yourself, probably figure out, how do I reverse engineer being a real estate investor? How do I do this step by step? But then I’ve also seen the folks who say, hey, there’s too much risk in that for me. I’m going to stay out of that entirely. Do you think that the engineers can sometimes fall into one of those two categories?Sandy (04:10)
Well, absolutely. And I laugh with my family that I’m a little bit of an 80 percenter. And I say that in the most love for myself. I don’t over engineer anything. I go almost to the end of everything and then I get it out. Right. Like you cannot be a perfectionist in this industry. I believe you have to get it done and get it out. And that goes for buying a home and not not working too much of the how risky is this. You’ve got to get it furnished. You’ve got to get it on the market. You’ve got to get somebody in there if it’s a long term.And then if it’s a short-term rental, you’ve got to get it out there and start getting people in there and start making the money, right? So I don’t consider myself that one of those really, really technical over engineering type of personalities at all. But you’ve got to, what I do consider in the engineering realm of all of this is document everything, be really organized. You’ve got to be a multitasker. Like there’s no tomorrow, right? Like that’s the part that really serves me well in this industry.
Dylan Silver (05:52)
Now, when we talk about short term rentals, I think this is part of the glitz and glamour part of real estate where people tend to think about short term rentals, fix and flip, HGTV, like, let’s do this. But it’s not so easy. You know, I’m licensed in Texas and I know in Dallas specifically, short term rentals, think to this day right now, you can’t do an Airbnb less than 30 days in Dallas. So there’s always the possibility that that,is no longer an option, but then you’ve also got to acquire these properties at the right price. You’ve got to make sure that they’re booked out. You’ve got to make sure that you’re staying highly rated on Airbnb. You can lose your whole account. There’s so much that goes into this. So walk our audience through really what it’s like being an Airbnb host, a short-term rental investor, and not just what they’re hearing.
Sandy (06:45)
Absolutely. So, so there is a glitz and glamour piece of it. And for me, I’ve chosen markets where they’ve already gone through the process of figuring out what the regulations are going to be in that market. I think that’s really important. That’s a risk that I’m not willing to take. I want to know that they’ve already figured that out and I buy in the green zone. Then I’ve chosen vacation markets and I’ve done that on purpose. I want here’s the glitz and glamour piece for my family to be able to use that as a vacation home when I’m not renting it out.That’s amazing. That’s a real, a real perk that I want for my family. But then also they do make more money if you pick the right properties than a long-term rental or then some of the other real estate pieces. That’s what I’ve loved about it. So you can take the risk out of it by picking a market where they’ve already done the work to come up with the regulations in that market and then picking the right property and doing a lot of the upfront work with the math. But then yeah, they can make more money. It does take a little more work if you manage it yourself, but
These days, the software is so fantastic. AI does a lot of the work for you. All you need is a great cleaner and a great handyman. And honestly, you can have a short-term rental in any market, many states away. I’m a big fan of it. I’ve got them in four states. I work realistically on my short-term rentals about six hours a week.
Dylan Silver (08:05)
Now, when we’re talking about managing these properties, what comes into my head is, well, most of the time people are going to be self managing until they get to a certain point. That does lend itself, especially in the short term rental space, they will now you’ve bought yourself another job. So if you have a job, it can be difficult to have a short term rental. Do you think that the SDR space really lends itself to people who have more availability or have the ability tohey, a cleaning crew, is it possible to self-manage these when you have a job already?
Sandy (08:40)
Absolutely. I think if you have a job already and you have an outlook of 10 to 20 years left in your career, get one or two short term rentals, manage them yourself, spend that five hours a week, have a good cleaning crew and a handyman that could really do a good job for you. But the software is so great. If you have the right tech stack in place, it will manage your pricing for you. It will manage the messaging for you. You set it up one time.There’s a set it and forget it thing that happens these days. So it’s about just knowing how to set it up the first time and then your problem solving. As long as you can kind of let problems get solved easily and roll off your back a little bit. It’s a five hour a week job. And then it’s making money for you a little bit of cashflow. It’s earning you equity each year. You’re having someone else pay down your mortgage. Real estate is magical. It’s just magical. I find it really a wonderful business.
Dylan Silver (09:37)
with you there. That’s why I’m still really in love with the business. And I got in in the distressed space. So foreclosures, know, probates, ⁓ you know, divorce, anything also distressing the home, right, that the home could be dilapidated older homes. But then I’ve also seen that it’s, I would say personality based as well, the same person who’s going to be an amazing short term rental hostmight not do so well in another
segment or niche within the real estate space. How did you identify short term versus say long term or corporate housing or multifamily?
Sandy (10:44)
Completely agree.think what I love is ⁓ again, setting up a procedure and an operations manual and having a sort of to-do list and a plan. And short-term rentals really lend themselves to that. The other thing I love is taking my family on vacation. And for two weeks a year, you can use your property for your kids, for your grandkids. And all of that, you still get the tax benefits.
As long as it’s, I believe it’s 14 days a year or less, it might be 12, without losing any of those benefits to your bottom line. So that’s the thing that really appealed to me. So I agree with you. Every personality is gonna blend itself to one of the different ways of doing business. And short-term roles was it for me. I like the vacations.
Dylan Silver (11:40)
Now,the Colorado, I’ve been, I love Colorado. think anybody who’s, who’s a vacation, who’s skied, who’s done any of the outdoors activities in Colorado has the same sentiment. And now I don’t know if it’s going to continue forever, but it does also seem to be the case that there’s a lot of people who are looking at Colorado either to move to or to have a short term rental.
Sandy (11:44)
Mm-hmm.Dylan Silver (12:04)
I’m curious to get your perspective. Do you look at some of this as you have to get in before the migration hits, so to speak, like you have to get into the market before everyone else is aware of it or once everyone else is looking at these places like the Denvers of the world and other cities in Colorado, that that also indicates that, there might be some competition there, but it’s an opportunity where I can hop in as well.Sandy (12:31)
think the trick is finding something special at about a specific market before everyone else does. For me, was in Steamboat, Aspen bought Steamboat, and I got in shortly after that, but sort of before everybody else figured it out. So it was after COVID, so prices had already doubled there, but they hadn’t gone up their full amount. So even after I bought, 2022 or something, it’s still gone up another 30 % since then, right?So it was still crazy, but it’s more crazy now. Then I bought another one in North Carolina where it’s at the top of a mountain and someone had just bought the ski resort there. It was all closed down. They’ve just reopened it. Now it’s been another year. In two years, it’ll be amazing. I just bought a property in Houston that’s not a short-term rental. They’re going to do construction on the freeway here for 10 years. But in 10 years, this place is going to be amazing. Right? So it’s like, so I’m always trying to get in way before
Dylan Silver (13:24)
Thanks.Sandy (13:28)
the market, it’s a long term view. Figure out what’s going on and look at something that other people won’t be willing to wait for. To me, that’s the secret.Dylan Silver (13:38)
I’ve said this on earlier on other episodes is that people in real estate specifically and especially newer folks are looking for the fast money in real estate. And that’s tricky. You’ve really got to be you’ve got to be on it. And I would say the fast money in real estate is actually slow money. It’s hey let me wait five years 10 years let me hold on to this. I have not yet met one investor who’s told me boy do I regret.Sandy (13:51)
Yeah.Dylan Silver (14:04)
Holding on to this property that I bought outside of this Metro 20 years ago. No one says that And so when we when we talk about, know, the the long-term strategy, it’s the consistency that counts now I know you’re also involved really with helping folks get into the space with your your STR jumpstart How did that come about where you having people come up to you saying? Hey, I see what you’re doing with these rentals these these short-term rentals. I want to get into that space How did it come about for you?Sandy (14:09)
That’s right.That was really just a product of my long-term engineering and construction career and how much management I did there. And all of this just plunking around in my head that when I started, I couldn’t find the course that I wanted. And I just kept feeling like I had something to say. And after retirement, have some time on your hands. And so at some point about six months ago, I just started writing a script. had something to say. Right. And so recently we launched about a month ago.
It’s about, it’s about a six hour.
course and it’s ⁓ 50 lessons just really detailed and I don’t think that’s out there somewhere else. It’s at strjumpstart.com so if people are interested in really getting the bones of how to do a short-term rental that’s what this could do for you. Really detailed stuff and the website kind of tells you all about it.
Dylan Silver (16:03)
when without giving away all the gold, maybe just a gold nugget. So they’ll go to the website when folks are looking at short term rentals in particular, there’s there’s really a number of different strategies. I’ve worked with a lot of these investors in San Antonio in DFW outside of Austin in the Texas markets where you’re looking at, you know, pre foreclosures, you’re looking at distressed properties, you’re looking at doing some type of value add rehab. then instead of, you know,Sandy (16:06)
No, it’s fine.Dylan Silver (16:33)
flipping it or instead of putting it into a long term ⁓ rental, it’s a short term. Do you have a preferred method for acquisitions? Whether it’s one of those or maybe something that I didn’t mention.Sandy (16:46)
So I talk some about how I picked each one of my very specific markets. But really what I’ve tried to do in my course is not that because I do think there’s a lot of that out there with great gurus who’ve been doing this for 30 years. What I’ve tried to do is what other people haven’t done, which is the nuts and bolts of the everyday operations. It’s what exactly should my tech stack be? What pieces of software do I buy and how do I put them together?Do I need to hire anybody and how? How would I scale up? What do I do each week? How much time is this actually gonna take from my day? So to me, it’s the boring part that no one wants to talk about, but I think it’s worth maybe spending a little money on to actually have a forever guide that they can keep forever and have six hours worth of videos to keep forever.
Dylan Silver (17:20)
Yeah. Yeah.Now, I want to dive into this a little bit again without giving away all the gold here. When we talk about managing specifically on Airbnb, which is which is what I’ve been familiar with. actually live abroad. live in the Dominican Republic. And my first experience coming over here was through Airbnb. can Airbnb just like the United States, whole homes, condos, townhomes, apartments and from all the way super upscale to something more rental grade.
Sandy (17:54)
Mm-hmm.Dylan Silver (18:09)
And what I’ve seen is that on Airbnb specifically, so much is riding on everyone else’s reviews, as well as the photos that you have up and not just that, you know, the niche that you’re providing for people. So if you’re in a college town, is it college themed, right? That might be a draw there. Is any of that, you know, super important? Do you think some of that is overstated? What’s your perspective on some of those topics?Sandy (18:29)
Yep. Right.Well, I think all of that is really important. And you’re really, you’re really at Airbnb’s mercy for where they’re going to put you in, their algorithm. But I think the most important thing is how many people will buy a property and just throw it on Airbnb. And that’s so important not to do. You should get, you should get the software that’s going to manage your property, which is only like 50 bucks a month so that you can have it copy it over to Airbnb, Ferbo, booking.com and your own direct booking.
website for no more effort and right away you’ll double your revenue. So just most people don’t know those very simple little secrets that as soon as they buy a property, so many people, more than half, that only put it on Airbnb. So just right away they can double their revenue just by putting it on four different platforms from day one with no more effort. Yeah, that’s a huge thing.
Dylan Silver (19:27)
That’s a huge, that’s, that’s,know, and I think to your point, most people are maybe going to, look at it from, I’m self managing this is going to be maybe a larger undertaking. I don’t necessarily want to have it on all these different platforms. ⁓ Yeah. When they end up doing that, it’s kind of like the same mentality of someone who says, well, I’m going to keep my own books. And then at the end of the year, they’re playing catch up, you know, with accountants and attack strategist.
Sandy (19:42)
All right, let’s keep it simple.Right.
Dylan Silver (19:56)
figure everything else out. When we talk about that upfront work that people are doing, they’ve got the actual physical property ready to go, they maybe have a cleaning crew in there, but then getting that up onto these other platforms and initially, you know, the maybe nervous energy from the first couple bookings, what’s the learning curve like for folks and can they expect that?within maybe a handful of months that it will smooth itself out for them.
Sandy (20:28)
Even less. mean, for me, it was a month or so and maybe I’m kind of easy going, but my first couple of bookings were really scary. But as soon as I had those first couple of bookings over, I mean, they got way easier. But now I never even look at a door camera anymore, right? Like it’s just, it just goes, you know, business just runs by itself. Everything’s fine. If I get a phone call, I’ll answer it and see what people need. And I get all five star reviews. I answer, you know, the messages right away and people loveThey have great guides. People love to hear from me, right? Like it’s just so easy to keep people happy by answering quickly and giving them what they need. I just find it to be a really easy and rewarding, wonderful business to give people a great vacation for very little effort. And yes, I think it’s really easy to do while you still have a job and such a great financial reward.
Dylan Silver (21:20)
I think one of the things that’s understated in this too, which you said is you’re able to provide an experience for people. And what makes a short-term rental host a great successful host is exactly that. That you got to respond quickly, right? And I think some of this stuff would be self-explanatory except it’s self-explanatory until it isn’t, right? You get a bad review and then your whole profile gets tanked. Some of this, would say,You don’t necessarily want to think about that, but you also want to be on these other platforms in case something like that does happen because, you know, one thing could happen. You’re diversified.
Sandy (21:57)
Absolutely.Yep, absolutely. would say of my revenues, it’s about a 30 % Airbnb, 30 % Ferbo, and then the rest is split between booking.com and direct bookings. So it really makes me pretty safe in case something goes wrong with one of the platforms.
Dylan Silver (22:18)
We are we are coming up on time here, Sandy. Where can folks go to learn more about the STR jumpstart? How can they maybe reach out to you? Maybe they’ve got ⁓ a property that they’re thinking about buying and not sure, but would like to learn more about the STR space.Sandy (22:32)
Sure, so I’m easily findable at sandy@strjumpstart by an email or ⁓ the website is strjumpstart.com. You can also find me at my distilled destinations. If you want to come find one of my properties, please feel free or on socials at distilled destinations or STR Jumpstart.Dylan Silver (22:53)
Sandy, thank you so much for coming on the show today.Sandy (22:56)
Thank you so much for having me. Great to see you. And I look forward to listening to all the podcasts coming
