How This Dentist Built a $600K Short-Term Rental Portfolio Across 5 Markets

Ned Markey (00:00)
Yeah, so I I take the philosophy of not ready aim fire. If you sit and think I’m gonna wait until I’m ready, you’re never gonna do it. You just gotta do it. You just make it happen. You just pull the trigger on something that the math works on. So number one, do the math. Make sure that the math works. If it does not cash flow, do not buy it. You do not buy for appreciation only. I think that’s a fool’s errand. You buy for positive cash flow and the appreciation is a nice to have. Remember financial freedom?

You don’t get there with net worth. You get there with cash flow. Huge, huge point right there.

Scott Bursey (02:06)
Welcome back to the Real Estate Pros podcast powered by Investor Fuel. I’m your host, Scott Bursey Today’s guest brings a rare combination of discipline, precision, and high octane strategy to the table. He is a board certified dentist, an experienced pilot, and a short-term rental powerhouse who has successfully built a seven property portfolio, generating over six hundred thousand in annual revenue across five distinct markets. He’s here to show us how to navigate.

the complex skies of real estate with clinical precision. Get ready to fuel up because we’re about ready to take off. Please welcome Doctor Ned Markey. Doctor, welcome to the show.

Ned Markey (02:44)
Thank you, Scott. Pleasure to be here. like a lot of you, I’m a husband, a father, and someone who wants to live a life by design, not drift. Excited to talk about it with you, Scott.

Scott Bursey (02:46)
is

Yes. And we’re excited to to have this conversation. And for our listeners who may not be familiar with your journey, please give us the short version of how your career began and where you’re pouring your fuel now.

Ned Markey (03:06)
Sure, yeah, my wife and I started out very intentional about how we built built our life and our family. And our early motto was small house, fast airplane. So we decided how do we gonna make that happen? and so we started buying initially some residential, duplex, multifamily stuff while I was still in dental school.

So we were house hacking before house hacking was even a thing. We lived upstairs, the tenants downstairs paid the rent. that one went so well. I bought a sixplex, that one didn’t go so well. but it ended up being okay with enough time. currently we have five commercial properties and seven short term rentals, three in Florida, one in Wyoming, two in Colorado, and one in Washington state. And we use our airplane to fly between So that’s kind of the

back of the napkin sketch of where we’re at right now.

Scott Bursey (03:52)
that’s awesome. That’s awesome. So what really caught my attention about you, Doctor, was the way you’ve been able to leverage the high level discipline of a pilot and a dentist to scale a high revenue STR portfolio across five distinct markets at once. You know, that’s powerful stuff right there, and it’s not easy.

Ned Markey (04:59)
Yeah, well, I think it goes back to the life that by design concept that we’ve kind of planned out and then I sort of started really thinking deeply about it and I realized that there’s kind of a a freedom stack. I realized I don’t have this vision to become free financially and time and independent, all the different things the levels of freedom, which I’ll go over in a minute here.

But it was thinking about that and being very intentional about how do we achieve those things. So the first freedom of the Freedom Stack is agency. You have to decide for yourself that you are gonna do this thing, whatever that thing is. If it’s gonna be, you know, have abs, you gotta decide you’re gonna have abs and you’re gonna have to commit to eating healthy and working out. And if it’s gonna be to fly TBM turboprops in them across the country, then you commit to doing that. You have to be safe and and keep current and all of your things. But

You have to decide for yourself what are you going to do and be committed to it. So the first freedom is agency. The second freedom is financial freedom. You have to figure a way to get free. For us, my wife and I, we started off, like I said, with a duplex and a sixplex, and then we moved on to actually a small inn. We had a 26-room inn after that. and then we sold the sixplex that didn’t go so well. We we 1031 exchanged that into a beach house.

And then we continue to grow our short term rental beyond that.

as you mentioned, we have about six hundred thousand dollars in top line rent coming in these days. continue to add to that by adding a property every probably year. We’ll add another property. and we could be financially free at this point, but I’m committed to my dental practice and my kids are in high school, so we’re gonna stick around for a while until they’re done with that. but the third freedom then would be time freedom. Once you’re financially free, you can be your time can be free. You don’t have to go to work any longer.

You have the choice of what you want to do every day. For me, I still want to go to work. I like what I do. but you don’t have to. You can go to the beach or do whatever you want. After that, I think health freedom is super important. You can have all the time and money you want, but if you don’t have your health, what good is it? So a lot of high W2 income earners spend a lot of time with their heads down in books and they neglect their health, or they spend a lot time building their businesses and they neglect their health.

But by the time you’re financially free and time free, it’s time to really focus back on the health because that’s key. the number five freedom is relation relational freedom, relate relationship freedom. So go deep with your friends and relatives and just really build those relationships and your family. people have floated this past have said maybe the relationship should be higher up, like I guess lower down. I build it from the bottom up, but I don’t know.

They thought it should be, you know, one, two, or three, but I don’t know. I have it as number five. after relationship freedom, it’s creative freedom. I think everybody needs to be creative in their life. They maybe somebody likes to paint, maybe somebody likes to do architectural things. For me, I like to design spaces and I use that in my short-term portfolio. So I really enjoy basically doing a burr method, which I’m sure your your guests know, but it’s buy. Let me see if I get this right. Buy

rehab, rent, refinance, repeat. but we do that in the short term rental world. So we buy some fixer upper kind of deal and we really make it special. and that’s where my creative juices get to come out. I also use my creative juices to write books, which I have one coming out in the fall. Probably be called the freedom stack about this very principle here that we’re talking about. ⁓ But the creativity can also lead to impact freedom.

Which is number seven. So I think it’s important that people give back. Give back to the world somehow be a positive influence in in in my case in children’s lives. I do a lot of mission work. I’ve been to the the Dominican Republic, been to Cuba, been to Panama, do stuff around the United States, like so however you want to impact for the good of the world, go out and do that. number eight is geographic freedom. once you have all these other freedoms.

So far you can go anywhere in the world and you can live and do what you would like. You’re not geographically tied to your business at home any longer because your mailbox money keeps coming in. and then and and I and I don’t have that right now, to be honest. Like I’m I have my practice here, I have my kids in high school. Like we’ll we’ll get there in a couple more years, but I choose to do that now. and then the ninth freedom is adventure freedom because in my opinion everybody needs to

have an adventure in their life and life is an adventure. But that’s what I really, really love doing is just my my plan is to sail around the world, actually. I have my boat picked out. It’s a sixty two foot boat. Costs about two point five million dollars. And so that’s my plan. Gonna take about sixteen months to go all the way around. So that’s the nine freedoms of the freedom stack.

Scott Bursey (09:47)
Life by Design The Nine Freedoms of the Freedom Stack When’s the book due out?

Ned Markey (10:27)
Probably November, December, if I can get done with my final edits in the manuscript and get it off to the publisher, which should have happened a week or two ago, but I’m I’m a little behind.

Scott Bursey (10:37)
Love it. I love it. Thank you for sharing that, Doctor. And we’re always looking for the fuel that keeps an investor’s engine running through any market cycle. So are you ready to burn some rubber? So you’re operating in five different markets. What is the number one operational strength that allows you to maintain that level of consistency?

Ned Markey (10:49)
Yeah, let’s do it.

I think getting just doing it every day is just being in it. Like you’re just gonna do a little bit more than the next guy. You know, I learned in dental school early on, like if you’re the last guy to the party and the last guy out of the library and therefore the last guy in the into the party, you’re two steps ahead of everybody else. So I think it’s just putting that little extra effort in to to go above and beyond. In our world, in the short term rental world, we are selling vacations on the internet. I mean, that’s basically it. People are spending twenty thousand dollars for a week

property they just clicked thro through a hundred pictures on the internet. That’s kind of crazy. That’s the price of a car. but but that’s what they do. So we just try to, you know, underpromise and over deliver.

Scott Bursey (11:39)
Absolutely. And I love that. Now, Ned, even a pilot encounter is turbulence. What’s one operational speed bump you’ve had to smooth out recently to keep your portfolio running at a at a peak efficiency rate?

Ned Markey (11:52)
That’s a great question. I think I had a lot more problems in the sh in the long term world than I do in the short-term world. We buy quality assets in quality markets and we charge a premium for We don’t have any kind of crummy assets like I did when I had Section 8 housing. And so I had a lot of he headaches with that stuff. I will never go back to that that market. So the speed bumps in the short-term rental world.

We don’t really have any. We have really great teams on the ground in the markets that we’re in and those are not hard to find and put together. If you’re if you’re a new investor in short term rental, ask the realtor, like who are you gonna recommend as a cleaner? Who are gonna recommend as a handyman? Those people, those those realtors, they have those people on a list and they’ll share it with you. So that’s an easy one to build your team. C call a couple of those people off their list, interview and

It it’s not hard to build a team wherever you’re looking to invest.

Scott Bursey (12:52)
You know, Doctor, it’s the operators who adjust the flight plan midair that win. And that was well said. With STR markets evolving, where do you see the biggest blue ocean opportunity for an investor today?

Ned Markey (13:06)
Yeah, I that’s a great question, Scott. And I don’t look at the Great Blue Ocean. I I absolutely only go where I wanna go. Like if I think it’s a cool market, I’m gonna find my own niche in that market. It has to be someplace where I’m passionate about. It can’t just be like this one makes the most money, so I’m gonna invest in it. Because if I hate it, I’m never gonna wanna go deal with it. It’ll just be like something I just push on the back burner. But if it’s a place that I like to go and it’s a place that I’m proud of owning.

Then I like to go there and I like to, you know, tinker with stuff a little bit here and there and just make it as awesome as it can be. So I don’t care what the market says. It could be the most saturated market in the country or the worst investment market in the country. I don’t care. If I like that market, I’m gonna find the place I like, the h the the property that I like, and I’m gonna make it the way I like it, and I’m gonna sell it and I’m gonna win.

Scott Bursey (13:54)
I

I appreciate that transparency. And Ned, if you would walk us through, you know, regulation is a is a major headwind in the STR space. How are you hedging against market specific log regulatory shifts?

Ned Markey (14:49)
Yeah, you know, a couple of our proje s okay, I didn’t I didn’t mention this, but we started buying air properties on runways. So our very first property was actually one in Wyoming. and it’s on our private runway. And that place actually blew up with with billionaires. So I got in there early and it’s been a great it’s been a great property. but we just fly our plane right in there, walk over to our house and spend a week. We’ve got a Jeep and a Range Rover out there, so we just

go hang out and go rafting and horseback riding and all the things. But we started off with that one as our first one. and then we started with the theme of let’s buy where we can fly right into. So then we bought our second one. That’s where at 10 31 exchanged that six unit building into the beach house. That’s also on a little island. That’s that’s on an island with a runway on it. The island is called North Captiva Island. There are no roads, there are no bridges, there are no grocery stores, there are no street lights or pavement.

It is sand roads only accessible by boat or small plane. That is a really unique property. and we ended up buying a second property on the island because that one rented so well. So we started off with the theme of like aviation related. And the whole thing was driven by like how do we afford to buy our turboprop airplane? Because remember, I said we want a small house, fast airplane. Well, we ended up with a lot of houses and

fast airplane and a lot of houses pay for the fast airplane. So I don’t know, did I answer your question? I might have I might have gotten off course on that one.

Scott Bursey (16:13)
That is it it does and I’m curious, where

is that slice of heaven located, the island?

Ned Markey (16:20)
the North Captiva Island is right off of Fort Myers in Florida. So it’s on the Gulf side of Florida. So if you look at a map, you go off of Fort Myers to see Sanibel. Most people have heard of Sanibel Island. Connected to that is Captiva Island, and you can drive to Captiva. But then in the early nineteen hundreds, I believe, the the island was cut in half and we then we got North Captiva separated from Captiva and there are no bridges or cars.

There’s no cars on the island. It’s golf carts and sand roads. It’s really, really cool. It’s really unique. It’s there’s there’s nothing else like it in the US that I’ve ever seen. So and I’ve traveled a lot. Sounds good.

Scott Bursey (16:50)
Awesome.

Well, I’m ready to hop in your plane and let’s have a barbecue this weekend. You know, Doctor, running

seven properties across five markets is a logistical marathon. How do you keep your team aligned so you aren’t stuck fixing every fire yourself?

Ned Markey (17:10)
Yeah, that’s a good point. Well, my wife is is a stay at home mom and she runs our real estate portfolio. And so she is the team leader of the team. And at each location we have the teams in place, mostly that we found through word of mouth and initially started with the realtor. And so if we have any guest issues or anything like that, Molly will usually take them initially. Molly’s my wife. and then if and then if we need to pass it on to somebody else on the ground, we need to get

something to the property. We usually just call the cleaning people and say, hey, can you drop off this thing for the guests? And usually we end up paying them a couple bucks, but they are happy to do it. Pay your people promptly and they’ll drop anything to take care of you. So and and then

Scott Bursey (17:50)
Sure. It’s all about know, those relationships

and so forth.

Ned Markey (17:54)
Yep. We also have a VA in the Philippines. and so she helps with a lot of the social media and marketing and stuff like that. She’s awesome. She’s eight dollars an hour and she can crank out a lot of lot of social media marketing stuff that gets just posted automatically to help drive the you know, drive the the tenants or the guests to our to our pages and our properties.

Scott Bursey (18:17)
And what is the occupancy? How many guests can it handle your property?

Ned Markey (18:21)
well, which one? they all they’re all a little bit different in sizes. We’re we have one that were that actually got absolutely destroyed by Hurricane Milton. We ended up scraping the ground. And so one lesson I learned is don’t don’t go without flood insurance in Florida. So I ended up eating that whole the whole thing. but that’s almost rebuilt right now, so they’re putting drywall this week and then we should have that back online this fall, maybe early

winter. So we’re planning on being down there for Christmas and and putting all the furniture in there and decorating it up and taking all the photos and then it should be online and available hopefully in January. So

Scott Bursey (19:00)
awesome.

Awesome. We’ll be looking forward to seeing that. And Ned, if you were sitting down with someone who has the capital but lacks the strategy, let’s say, what is the one habit they need to build today to ensure they aren’t just surviving, but actually dominating the market?

Ned Markey (19:17)
Yeah, so I I take the philosophy of not ready aim fire. If you sit and think I’m gonna wait until I’m ready, you’re never gonna do it. You just gotta do it. You just make it happen. You just pull the trigger on something that the math works on. So number one, do the math. Make sure that the math works. If it does not cash flow, do not buy it. You do not buy for appreciation only. I think that’s a fool’s errand. You buy for positive cash flow and the appreciation is a nice to have. Remember financial freedom?

You don’t get there with net worth. You get there with cash flow. Huge, huge point right there.

If you don’t take anything away from this, take that away. You want to buy for cash flow so you can get financially free. I know people with twelve million dollar net worths who can’t afford a week off because everything falls apart because the redlined and their lifestyle costs more than their passive income coming in. It’s not a it’s not a good place to be.

Scott Bursey (20:13)
Ned, this has been absolute rocket fuel, but we can’t let you go yet. You’ve given us so much good illustration and words of wisdom. Is there any additional golden nuggets that you could leave with our pros here today?

Ned Markey (20:25)
well, first of all, Scott, I would say to your listeners, like drop Scott a like and subscribe to this to to his podcast. This is awesome. So thank you, Scott, for the opportunity and and hopefully everybody will hit the thumbs up button for ya. lastly, I would say, you know, you can check me out at Nedmarkey.com. But the last little nugget I would say is your income is not your wealth.

your optionality is. So you gotta have options. So not your net worth.

Scott Bursey (20:51)
Hundred percent couldn’t agree anymore. And if our listeners want to follow your journey or collaborate with you, what’s the best way for them to reach you?

Ned Markey (20:58)
Yeah, you can reach out on nedmarkey.com. There’s a link on there. You can email me. You can email me at [email protected]. But I get a lot of emails.

Scott Bursey (21:09)
Awesome. Awesome. I can

imagine you do. Thank you for joining us today, Ned. This has been an absolute pleasure.

Ned Markey (21:18)
Thank you, Scott, appreciate it.

Scott Bursey (21:19)
And to our listeners, we appreciate you. If you got value from today’s episode, please subscribe. We’ll be filling your tanks with elite guests, just like Ned Markey, who are accelerating and setting the pace for the rest of the industry. Until next time, keep your standards high and your vision clear. We’ll see you in the next episode, everyone.