An Inside Look into Short-Term Rentals

In this episode, I wanted to come to you with something that’s been on Wall Street. It’s actually been in a lot of publications and national news. It’s a form of real estate investing that a lot of people have made tremendous returns in this area of investing over several years. Now, we’ve hit this (I would say) why on the road as to where we’re going to take it. 

If you’re not familiar with this type of investing, what I’m referring to—if you haven’t figured it out yet—is short-term rentals. I have had a short-term rental property for a time in Hawaii, and I found it wasn’t for me.

I sold that property to an individual who had several other properties there. I occasionally went back, monitored what they’re doing with it, and I can see they knew how to run the business. That’s really what it comes down with any real estate—knowing how to treat it as a business.

I thought with this episode, we would talk to one of the experts in the field when it comes to short-term rentals i.e. Airbnb-style investing. He’s a good friend of mine. I’ve known him for many years. I’ve been on his podcast. We’ve worked together to help people structure it properly. This is the expert, and I’m glad to have him on. His name is Richard Fertig. Richard, thank you for coming on.

Richard: Thank you so much. To all the listeners, I really appreciate your time and interest. Clint, I would love to get a better sense of why it wasn’t for you because there’s probably some listeners that may come across some of the same challenges. If they could avoid it and get into a good investment, great. But if I can also add insight as to how to overcome some of those challenges, perhaps they can be a great investment for many.

Clint: That’s a great way to start off with this. I think I know what it is. I didn’t have the education. I didn’t know what I was doing. I thought this is something I’m just going to dabble in, and I think that happens a lot for people. They think, I’m going to try something. It fails, they assume that it’s not for them, and they never go back and try it again. The problem was with me not understanding what I was doing because I didn’t get educated.

Richard: Right. That’s actually a great segue. I started Short Term Rental University because I was experimenting with the Airbnb platform. This is now five or six years ago. I found it really interesting and amazing what kind of return I was generating relative to a long-term rental—a 12-month rental. 

I really started to dig down a little bit deeper. What I realized was I was in the process of creating a portfolio of assets, lifetime legacy assets in places that I wanted to go and visit. Basically, other people were paying my mortgage and then some.

If I was able to do this for 15 years—those were the 10-year mortgages that I have at that time—then I would earn it out, own it outright, and people will continue to pay me and with cash flow. Once I’d realized that vision and that opportunity, I created the Short Term Rental University YouTube channel to educate individuals about what to do, what not to do, what mistakes we’re all going to fall prey to, how to avoid them, and ultimately, how to run a successful business. That’s really what it comes down to. 

It works really well for two different types of individuals. One isn’t better than the other. You just have to know what type of individual you are. My girlfriend’s father (for instance) got started and he loves the hands-on. He loves meeting with the guests. He loves telling them about the neighborhood and what’s going on. That’s where he is in his life. It gives him a sense of purpose, satisfaction, pride, and joy.

For me, I take a totally different approach. I automate as much as I possibly can. I outsource everything and then I scale. Consequently, I have to figure out how to have a personality and a relationship with these individuals while not doing it myself. 

Clint: Yeah. That is key. You said a number of things that we can unpack. Number one, you like to go to those places. I’ve seen your place in Wyoming. You’re in North Carolina right now. You have places all over the country that are desirable locations that you, yourself, would want to stay. 

The biggest mistake I think I made is that the property I bought in Maui, I wouldn’t stay there. It’s not an area of Hawaii that I want to go to in the Kaanapali area. I like the big island. I like other places, so we never stayed there. That’s important. 

You also said there are two different personalities. There’s the person who wants to engage with the tenants—talk to them and tell them all about the area. Not my personality to want to do that. But then it was needed to set up the business side of it—the automation. I never fully invest in myself to learn how to do that. I was just treating it like I do my rentals thinking I can get by that way. That’s important. If you can go more into that aspect of how people should approach it, I think it’ll be enlightening for them.

Richard: Absolutely. I would say the following. I was attracted to the short-term rental space because it has the single largest rate of return out of all real estate investments that I’ve reviewed. For those of you who don’t know me and my background, I used to run a $4 billion hedge fund. I’m constantly looking all over the world for value and opportunity. I like to get there earlier and before other people. Commensurate with that risk is also a higher reward. That’s what attracted me to the short-term rental space. 

Many of those things exist today, although we have matured quite a bit. Airbnb is about to go public. There are hundreds of thousands of hosts all over the world. The competition has increased. That said, you can still do incredibly well.

The key thing is to know what it is you want to do and what space you want to occupy. It’s like that in every single business. For instance, if you try to appeal to everybody with a very generic home, a very generic listing, neutral colors, it’s in the middle of nowhere, suburbia, plain vanilla, and it doesn’t offend anyone, the flip side is it doesn’t excite anyone either. You’re going to have to compete on price. 

Everything that I do, I try and find a niche. Then I charge a premium for that because once I attract my tribe, they want what I have. I’m the only one doing that, and they’ll pay a premium for it. The key thing is this business that doesn’t exist in other real estate businesses is there are this trust and review process from your peers where guests rate hosts and hosts rate guests. Believe it or not, studies have shown scientifically that people trust those anonymous reviews as much as somebody who they know and respect telling them the same thing.

For instance, somebody saying, Clint Coons has a great podcast. You should really go and listen to it, coming from someone’s brother has a lot of meaning. When you read the reviews about Clint Coons’ podcast, and they’re also positive, people value that just as much even though they have no idea who left the review.

The key thing in the Short Term Rental University teaching is about knowing what it is you’re trying to do, differentiate yourself, delight your guests so that they’ll give you five-star reviews, and that’s your marketing. Then it just propels in a positive fashion.

Clint: Okay. What I got out of it, a lot of people saw this as an opportunity to make quick money—I would say easy money—to make more than they would off a normal property. They were buying properties in just some normal areas like Downtown Tacoma or Silverdale, Washington—not desirable locations. You’re buying in places where people want to go or people would mean, especially, to want to go. Has that been your niche, then?

Richard: Yeah. I think that the key thing about real estate—and this should come as no surprise to anybody who’s listening to this podcast and interested in real estate—is location, location, location. You always want to buy the best location that you can afford. When you overlay the short-term rental thesis on top of it, in an ideal world, you’re not the only person who wants to go to that location. There are reasons that people are coming to those locations anyway.

I’ll give you a real-life example. I’m sitting here on the Outer Banks of North Carolina. Two years ago, the Outer Banks of North Carolina was on sale. Nobody was coming here. Nobody was buying. There was an old bridge making access to North Carolina Outer Banks safe. During storms, you couldn’t get on the island or off the island. 

I realized—and so did many other people but they didn’t act on it—that the state of North Carolina just invested $700 million, and has built a world-class bridge that they’re guaranteeing for 100 years. My thesis two years ago was that once there’s a safe passage here, this island is 87% national park. They’re not making any more islands, 87% of it is a national park, something like 3,000,000 visitors come here during summer vacation, and there’s no new lodging. 

I’m in the process right now. I think I’m the single largest landowner in the area. We own 50 acres of waterfront property that we’re developing into single-family vacation rentals for people to come in and enjoy something new and modern. 

Now, is it risky? Yes. Are people coming to the Outer Banks of North Carolina and the Hatteras Islands specifically? Yes, by the millions. Has COVID accelerated that? Yes. While I don’t want COVID for anybody and it’s a terrible tragedy, it’s been a real boon for our business because we were positioned correctly in advance of the herd. 

Clint: Okay. You brought up COVID. If you read Wall Street and you’re listening to the media, they said that a lot of people that started with Airbnb are in a tough bind. Maybe they were referring to a couple of months ago where they couldn’t meet their mortgage because they couldn’t cover it because of the restrictions that Airbnb was placing on the tenants coming into the property. The turnover time—72 hours. How is that impacting you, and where do you see that going forward for the next year?

Richard: What I would point listeners to is go check out my YouTube channel, watch the videos that we filmed in late February and into early March as COVID came out. Listen to the predictions that I made then, and then fast-forward to where we are today. Most of them are extremely accurate. 

What I’ve been teaching on the channel for years is about location, location, location but in the right places for vacation rentals. What a lot of people were doing was second nature to them, and they thought it was less risky. What do I mean by that? If they had a successful Airbnb in, let’s say, their primary home in Tacoma—to use your example. They’re doing well. It’s cash flowing. I want to scale. I want to improve my business. I want to have more. 

What do they do? They got the unit next to them down the hall, above them, or below them. They concentrated all of their risk into what seems safe, convenient, or easy to do. But the challenge with that is that’s actually a lot more risk than diversifying and having places. All of my places I run remotely. I’m not on location for any of them. I build a scalable business with a team behind me so that I can operate a place in Crested Butte, Colorado, Costa Rica, Outer Banks, Jackson Hole, Alabama, and it goes on and on. It doesn’t matter where I am. 

I pick locations where people want to go. I diversify the risk. I run them remotely. What that has allowed me to do is pick really world-class vacation spots. I, fortunately, have been selling out of urban areas and going into more rural vacation, beach, ski—places where people want to go and spend vacation dollars.

Now, that traveler is more discretionary. If times get really bad and we go into a recession, one of the things that get cut back is vacation spend. What I try to do personally in my niche—again, where I want to stay. I’m at the higher end of the market. People in that category have means through good times and bad, and they value experiences. 

What we found through COVID right now—to address your question about the WallStreet Journal and others’ saying that a lot of people had a hard time, there was a ton of uncertainty. We didn’t know what this was going to look like. We didn’t know if people would be able to travel or when they could resume traveling. 

But I made a prediction back in March and it’s on the YouTube channel. I said that when we come out of this thing—I think it’s a couple of months away—we’re going to have so much pent up demand that I predict if you’re in the right locations, you could have your best year up. That’s actually what’s happening.

If you take a look at the more recent articles, the proper locations on Airbnb and VRBO are having our best year ever. Our prices are through the roof. Our occupancy is as high as it could possibly be. The responsible hosts are leaving people little windows so that it’s not back-to-back. We’ve enhanced our cleaning, so it’s nice and safe. 

If you’re positioned properly, this is possibly the best thing that’s happened to vacation rentals in remote areas where there is not a lot of crowding. People can get away with their loved ones and family and relax, enjoy, and realize that life goes on. People are flocking to them.

Clint: Okay. I’ve always wanted to have a house in Jackson. I know how much they cost. It gets up more than I want to stay in. What do they look at then? If you’re going to borrow to buy one of these types of properties and you’re going to the bank, do you position it as a short-term rental property and you use projected income to help qualify for that? I’m just thinking about the individual investors that are listening to this, and they’re liking what they’re hearing but they’re thinking, how am I going to afford a house in Outer Banks that is in that desirable location?

Richard: There’s a variety of different ways to do it. When I first got started, I had to qualify based on my own income and it was a vacation home. Over time, I would change the vacation home into a vacation rental that I would still use.

As I’ve scaled, gotten bigger, and the industry has matured, there are now what’s known as non-QM loans where the underwriter isn’t underwriting Richard or Clint the individual. They’re underwriting the asset and its earnings. They’re looking at it as if you’re buying a business, and there are tons of data. There’s a company out there called AirDNA where you can literally put it in an address and it will project what the rental income is. It’s about 95% accurate or something like that. I have no affiliation with them. I don’t even get a commission or anything. I don’t know what their exact accuracy is. 

My team and I, I always go by gut. I have a very strong intuition about what works. Then I use that as a sanity check and double-check it. And then I make sure that that covers my DSCR—my debt service coverage ratio—which is what the underwriters are going to look at.

If you put down 20% to buy that $100,000 home, you financed 80%, what is the mortgage payment? What are the taxes? What is insurance? As long as the rental income covers all of that, you can get a loan in the non-QM market whether you have income yourself to support it or not.

Clint: Okay. Right now, if I was interested in this, what area should I be looking at (would you say) in the country?

Richard: Well, that’s a very good question because the real estate market—as many people would have bet against—has rallied to levels we haven’t seen, and the demand is unprecedented. Again, you have that pent-up demand. There were no real estate sales for a quarter. When people come out, there’s a lot of pent-up demand that is just buying everything. 

The areas that are really in focus and what I like to think about COVID are that it didn’t really change the trajectory of the world. All it did was accelerate it. Whatever trends were happening before is hyper-accelerated. If you think of the businesses that have suffered the most, for instance, restaurants—it’s a very low margin business, it’s a very competitive business. It serves a great purpose. It’s quite satisfying to own a restaurant than to dine in a restaurant, but it is a very hard business. That business is having the most difficult time through COVID. It just accelerated the challenges.

The flip side of it, some trends that we’ve been seeing historically—I’ve been betting on these and positioning myself through this—is about quality of life, experience over luxury, things that are memorable, things with loved ones, and things that you can Instagram. It’s all about experience and sharing that with loved ones. The places that are doing incredibly well during COVID are new and unique. People haven’t been there. They haven’t seen it before. Everyone wants that first Instagram shot. Everyone wants to discover it.

In a nutshell, what I would encourage your listeners to do is to think about places that they would love to go that are off the beaten path. Maybe they’re on their bucket list. Maybe they’re hard to get to. They had to take two planes. The reasons you didn’t go there before are now the reasons to go there. You can go find places that other people haven’t looked at and find great opportunities.

Here in the Outer Banks of North Carolina, we are still trading below 2004 highs. Maybe as much as 50% below. That’s very rare in the United States anyway. If real estate traded in 2004— let’s just pick a number, $100,000—the Outer Banks right now, you can still buy things at $50,000 or $60,000. Whereas in most parts of the country, we’re at all-time highs and going higher. Now, you’re picking something at an all-time high. 

Go try and find a place that’s really remote, that is really desirable, and that doesn’t have a ton of competition. Try and find a place that you would like to go. Because if you’re wrong, you have a wonderful vacation home, and you can go enjoy it yourself. It’s all about experiences. But chances are you’ll be right.

Clint: All right. If you’re looking for that property. Are there some general guidelines? It needs to be at least four bedrooms. It has to have these many bathrooms, garages. Within so close to an airport or something like that?

Richard: Yeah. It really depends on the budget. I can tell you what I do personally. I focus on the higher end and the bigger stuff. I take the risk that many people aren’t comfortable with. I’ll buy a multimillion-dollar place and bet that people will spend $3000 a night, $4000 a night. 

The average listeners are not going to do that or should they to get started? But the one thing I would say is people really care a lot about bathrooms. Don’t go get a discount and be like, I got a four-bedroom but it’s got two baths. People are going to choose something that has four bedrooms and four baths. If you can’t afford the same number of bathrooms as bedrooms, then just go smaller. Get a three-bedroom, three baths. Get two bedrooms, two baths. 

Think about it. People are on vacation. They’re having a good time. They don’t really want to wait to shower. They don’t really want to wait for somebody to come out of the bathroom and then go in. Try and get the number of bathrooms consistent with the number of bedrooms. Whether people need it or not is irrelevant. That’s just the way that they search on Airbnb and other places.

Clint: Typically, you’re going to buy these properties where you anticipate that you have to do some rehab work, or do you try to get them where there’s no work really involved other than maybe some paint?

Richard: Again, it depends on the individual and their level of comfort. If you’ve never done a renovation and that’s not your business. Let’s say you’re an accountant, you work at the desk, and you’re now buying a place, try and make it turnkey. Don’t learn a whole new trade and start hiring contractors, electricians, and taking time off work. This is supposed to be a value add to your life and to your income. It’s not supposed to be a distraction. 

By the way, it doesn’t have to be perfect. Everything will clear at a certain price. If you buy a fixer-upper, rent it out for a year, two, or three. Just get less income and don’t worry about it. Your basis is lower too because you haven’t taken $50,000 or $100,000 and renovated it. 

Try and find something that is unique. What I mean by that is to find that really remote cabin that’s deep in the wood but has an insane view. Try and find something that has an architectural interest. It’s a treehouse. It’s a modern design and everything else is traditional. Try and differentiate yourself because then you’re no longer competing with all the other people. 

What most people do is go for something that fits everybody, fits their price point, fits every other Airbnb host price point, and fits all their needs too. Chances are you’re overpaying for it. Where you find tremendous value is you go and find something that’s a little bit off the beaten path, a little bit different size, and a little bit eclectic. Maybe it’s funky, maybe it’s fun. It doesn’t matter what it is.

I hate condo investing. Don’t buy an Airbnb in a building where there are 300 other people competing with you.

Clint: That’s what I did. 

Richard: Don’t do that.

Clint: Well, I know that now. 

Richard: You know what I mean? The only thing you’re doing at that point is you’re competing on price.

Clint: You always […] too. That was one of the things. I’d look at VRBO, and I was always trying to put the price bands in there based on what other people were doing in that same area.

Richard: What ends up happening is you start to compete in price because you’re not getting booked, so you drop your price $10 or $20. You get a booking. I teach people to be the exact opposite. Find something really interesting and then price it at a premium. Attract your tribe and you’re much more profitable. It’s okay. 

One of the other mistakes that people make is they view occupancy as the KPI—Key Performance Indicator—whether they’re doing well or not. If you’re at a 100% occupancy, you’re doing really well. Anything below that means that you’re not doing well. That’s silly if you think about it. I can guarantee you 100% occupancy is no problem. 

I don’t know where you are right now. It looks really nice. It’s got a wine cellar. Maybe it’s your office or something. If you wanted to rent that thing out and you wanted 100% occupancy, I guarantee you if you put it on Airbnb and you charge $1, you’d be sold out. Are you profitable? Are you fulfilled? Has it done anything for you?

The right way to do this in today’s world—we use dynamic pricing just like airplanes and hotels. We change every single one of our unit’s pricing every single day based on supply and demand in our immediate vicinity. I always like to price higher than everyone else as I’ve indicated because it’s more profitable. I’m okay having 20% or 30% vacancies.

Even with 20% or 30% vacancies, at my price point, I’m more profitable than 100% occupancy at a lower price point. There is less wear and tear. It gives us days between people for turnover. We can go and have maintenance people going on those days. Overall, it just runs much more smoothly and more profitably.

Clint: Anybody listening in right now can tell. What you’re talking about, that’s the experience of someone who’s actually in the business that’s doing it. Because these little nuggets that you’re throwing out there that I hope people are writing down and paying attention to. There’s a lot of people that teach this stuff, but they don’t do it. I listened to a ton of them. There’s a big difference when you get on and you start talking about these. Where was that link again where they can get more information?

Richard: Go to Short Term Rental University, that’s our YouTube channel—STRU. We also have a Facebook group with 22,000 hosts from all over the world. Peer-to-peer, people ask, hey, this happened to me. How would you handle it?

When you’re first getting started, in particular, every situation is new. Someone checked in late. Someone checked in early. Someone wants to check in late. Someone wants to check out early. There are all these uncertainties. We’ve created this tremendous, completely free community where hosts share. We don’t view each other’s competitors because we’re not. It’s just a great place to learn and hangout.

I’ll just give you an example. My girlfriend’s father—who I mentioned earlier—always wanted to have a house in Lake Tahoe. That was his dream. His dream was like his kids coming home from Christmas, everyone’s around the big table, and it’s snowing outside. You can have your own dream. Maybe it’s at a beach or a lake. It doesn’t matter. But he didn’t think he could afford it. He’s semi-retired. The vacation home was outside of his […]. 

He started doing some diligence on me like, who’s my daughter’s dating? What is this YouTube guy? What is this all about—Airbnb? He started watching some of the videos. Before you know it, he got really interested and inquisitive. 

When I met him the first time, about the second or third day we started talking about his dream, his vision, and what he wanted to do. I shared with him the numbers. We ran the numbers on AirDNA and I said, look, I think this thing can be profitable. The worst-case scenario, it breaks even. The worst, worst-case scenario, do you have any budget that you could throw towards a vacation rental? If this thing doesn’t work out, I’m just totally wrong, and it costs you $500 a month, could you live with that? Maybe you can’t live with $3000 a month, but could you live with a little bit?

He was like, “Yeah. Totally. That makes perfect sense.” We helped him get started. He watched a bunch of videos. He went and found a place. Again, unique, different from anyone else. He totally loves being there, as I said earlier. It’s been in his semi-retirement like his pride and joy. It’s something that he looks forward to, and is incredibly successful. It’s cash flowing. Not only is it paying the mortgage, but it’s actually profitable.

Just yesterday, I got an alert from him that the same person booked five different reservations this winter. The same group is coming back five different times. He found his tribe. He priced it properly at a premium so that they know what they’re getting. The challenge with pricing at a premium is just this, you have to deliver. Once you’re in that stratosphere, people don’t mind paying more than they have to, but you have to over-deliver. I put the burden on Austin—our host that we teach—to delight the guest, to make them keep coming back, and that’s the perfect example.

It went from, I don’t think I can do this. It’s not going to cash flow. To he has his dream. By the way, we’re going there on Christmas and the snow is going to be falling. His life is fulfilled, and he’s getting paid for it. He gets to use it when it’s not rented. It changes lives.

Clint: Jackson Hole or Sun Valley, which one?

Richard: For me, Jackson Hole because as you know, Wyoming is a tax-free state. It has no estate taxes. By the way—as I started earlier—I’m a very big believer in macrotrends. For me, while inequality is unjust and it’s only getting worse than this country, that divide is going to continue for the foreseeable future. I think you’re going to see a huge continuation of people leaving high tax states like New York and California and going to places like Wyoming, Texas, Tennessee, and Florida. Places that have no estate taxes are absolutely on fire, and I think that continues.

Clint: What was the worst investment you ever made in this space and why?

Richard: I made an investment about 12 years ago. It was pre-Airbnb, although VRBO was alive back then. I actually just exited it. It took a pandemic for a buyer to actually come to buy this thing off my hands. That was in the Hamptons of New York. It was a charming 1830s home with really wide planks and uneven floors. If it was in the town of Southampton, people would’ve paid millions of dollars for it because it has that certain mystique and allure, but only in that one area.

The mistake that I meant that I did was I bought it in an area that I thought was up and coming. I bought an old home that looked like what people wanted in Southampton. I thought people would get priced out of Southampton. There’d been some urban sprawl. They’d come to us just on the outskirts. The exact thing that I thought would happen did not happen.

It turned out, no one came further away. Everyone just bid everything up in the town of Southampton. Those prices went up. The things on the outskirts where people wanted were brand-new construction at their price point. Nobody wanted the headache, the fixer-upper, the white plank floor, and the uneven stuff that wealthy people look forward to getting. I can’t wait to get away from my brand-new condo and go live in that antique cottage.

Clint: Charming, I think, is the word you used. 

Richard: There you go. The charming cottage. But it turns out the people that are on the edge that really can’t afford it, they want the brand new, vinyl siding, half the tree stuff. You live and you learn.

Clint: Wow. You’ve given us a link. I’m going to have some information on the show notes. I know you have a special for everyone as well. They can click on those links in the show notes to get more information about this. 

It’s just so much in the real estate arena. As I stated earlier, Richard, you really dialed it into a niche that could be very profitable, if you know how to do it the right way and you don’t take the approach I did. It just takes a little bit of education. I’d encourage the listeners—check it out, get the education, and best of luck with your investing. Anything else you’d like to leave?

Richard: No. I just want to say thank you very much for your time, Clint. It’s been a real pleasure working with you over the years. I just want to say, I’ve looked at all sorts of real estate investing from industrial to retail to multifamily to single-family and short-term rentals. The short-term rental space, in particular, not only is it the most profitable when done properly. We get paid for that vacancy risk. 

In the multifamily world, you’re basically paying up for the comfort of knowing that someone’s going to cut you a check every 12 months. I’m taking that vacancy risk, but I’m getting paid that vacancy risk. Besides the cap rate, besides the return on investment, it has the opportunity to really do things for many people. We see it all day long where now they’re doing something with their family. You can get the kids involved. They can come to paint, do the lawn, and they can start to learn about being an entrepreneur. Your family can vacation there when it’s not being rented out.

There’s a ton of benefits. It’s completely flexible. You can take it on the market one day, and take it off the market the next. You can go to 12-month leases, you can stop doing that. It just gives you an incredible amount of opportunity that many other real estate investments don’t allow. That flexibility is worth a premium, but it’s not priced into the market yet. It’s a mispriced market. It’s still in the early stages.

Clint: This goes to show you, don’t believe everything you read in the media because they’re not doing it. They don’t have an idea of what’s really going on. That’s why I brought you today. Thank you.

Richard: Clint, thank you very much. I appreciate your time. Listeners, keep listening to Clint, and be tax-smart.

Clint: Thank you. Bye-bye.

Richard: Have a good one.