David Greene Show I This Simple STR Plan Could Change Your Life I Episode 124

Summary

The David Greene Show – Episode 124

"This Simple STR Plan Could Change Your Life"
April 3, 2026

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Episode Overview

In this episode of Real Talk Real Estate, David Greene sits down with Taylor, an Oklahoma-based investor, for a candid discussion about building wealth through short-term rentals (STRs) in practical, non-vacation markets. The episode focuses on the realities and strategies of managing a handful of properties in small-town America—far removed from the high-drama, high-risk, and high-maintenance world of "Instagram-famous" vacation rentals. Listeners gain clear, actionable insights applicable to the "bread and butter" real estate investor, emphasizing sustainable cash flow, automation, and the importance of keeping things simple.

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Key Discussion Points & Insights

1. Taylor's Background and Motivation

• Taylor is an Oklahoma native and dad of three, with a background in college ministry and oil & gas startups.
• His family motivates his real estate journey; he uses investing as a path to stability and legacy.
• Learned about real estate through podcasts (including David Greene’s) during the pandemic.
• Started with a single-family in Stillwater, OK, then expanded via cash-out refinances on his Colorado home.

Quote:
"For us, growing up, a rental property seemed so unachievable... But now, my kids see it as normal—that’s a huge mindset shift."
—Taylor [39:07]

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2. Market Selection: The Value in ‘Practical’ STR Areas

• Stillwater, OK is a classic college town—rural, small population, but with predictable cyclical demand (college sports, visiting parents, short-term work assignments).
• Unlike high-drama vacation markets, demand is steady and guest expectations are practical.
• Properties are small (700–900 sq ft), targeted to couples, college visitors, or workers—not luxury vacationers.

Quote:
"When someone has high expectations and they're paying a high price, any issue is going to be a big one. But when you’re paying an okay price for much more space than a hotel, you're just happy to be in a clean, nice spot."
—Taylor [15:12]

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3. Property Acquisition & Operational Model

• Started with a direct-purchase rehab (not MLS), renovated and furnished pragmatically (sourcing from Facebook Marketplace, only buying essentials new).
• Initially ran a “test” on a duplex: one side long-term, one side short-term. STR income outperformed long-term by 3x.
• Has automated much of the management via Airbnb’s messaging tools and uses PriceLabs for dynamic pricing.

Quote:
"Aim small, miss small. I wasn’t looking for a huge splash—I just wanted something attractive to a single person, a couple, maybe a small family."
—Taylor [09:23]

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4. Guest Types & Hospitality Philosophy

• Most guests are college-affiliated: visiting parents, traveling professionals, or attending local events.
• Guest expectations are moderate; Taylor focuses on practical cleanliness, comfort, and local touches rather than Instagram-worthy decor.
• Problems are rare and usually minor (“forgot the door code,” “saw a bug”)—and covered by a trusted local property manager.

Quote:
"Our properties are practical and they're pretty, but they're not going to blow your mind with the photos. People are just happy for a clean, nice spot."
—Taylor [15:12]

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5. The ‘Nightmare’ of Vacation STR Markets vs. Practical Ones

• David shares his theory (with Taylor backing him up) that non-vacation STRs have fewer complaints, less drama, and generally more satisfied, low-maintenance guests.
• Taylor agrees: his guests are easier to manage because they have specific business or family objectives (not “life-or-death” vacation expectations).

Quote:
"If you're thinking about getting into STRs, maybe it's better to stay away from the high-maintenance vacation areas and stick with the bread-and-butter, blue-collar, slow-and-steady properties."
—David Greene [18:46]

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6. Automation & Simplification

• Taylor uses only the Airbnb app and PriceLabs for management. No external property management software.
• Automates guest communication (pre-check-in, check-in details, check-out, thank yous).
• Leverages a local property manager for on-ground issues, and cleaners who self-schedule through the Airbnb system.

Quote:
"Airbnb app, baby. That’s it. Messages automated... I don’t have to think about it every single day."
—Taylor [23:04]

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7. Dynamic Pricing and Event Awareness

• PriceLabs automates nightly rates but Taylor manually adjusts for big local events (football games, graduations, etc.).
• Emphasizes the importance of monitoring local calendars and adjusting booking windows/minimum stays accordingly.

Quote:
"I got to be on top of when those schedules release because there's so few hotels in town... That's another benefit of these smaller town STR opportunities."
—Taylor [27:39]

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8. Design, Amenities & Guest Experience

• Minimalist and functional approach to amenities—king beds if they fit, clean decor, no over-the-top features like hot tubs or elaborate designs (not cost-effective in Stillwater’s market).
• Local touches (e.g., Hideaway Pizza gift cards for OSU events) enhance guest experience.

Quote:
"You're not coming to Stillwater to post a bunch of Instagram photos. If it's clean and nice, people are happy to be there."
—Taylor [33:12]

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9. Legacy, Family, and Keeping Perspective

• Taylor references involving his kids in property turnovers (“pack and plays in every property”) and modeling asset-building for his family.
• Addresses the “comparison trap” of social media-fueled real estate hustle culture.
• David underscores the pricelessness of present family life over chasing ‘door counts’ at any cost.

Quote:
"Comparison is the thief of joy... When I see somebody else—a 21-year-old with 50 doors—I think: am I doing OK? It's totally OK. I didn't have one door at that age."
—Taylor [44:58]

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Notable Quotes & Memorable Moments (with Timestamps)

• "For me, living up in Colorado, we worked in college ministry... but we'd always had a dream about owning real estate or having a rental of some sort. 2020 happened. 2021 happened... got real motivated."
  —Taylor [02:32]

• "My theory is that higher-maintenance STR guest headaches cluster around vacation markets... the people going to 'practical' cities like yours? Way fewer problems."
  —David Greene [12:23]

• "If I can fit a king (bed), I’ll do a king. If not, no big deal. It's clean. It's decorated nicely. It's as close to passive income as I can get."
  —Taylor [35:26]

• "It's not that much of a heavy lift in these situations. And I just want that to be the message of today's show."
  —David Greene [36:23]

• "One of my favorite feelings... is when I’m doing something else and I get the buzz—someone just booked two nights a month from now... That’s a great feeling."
  —Taylor [37:02]

• "Growing up, my family had one car for the whole family... we didn’t go out to eat, hand-me-down clothes—there’s actually a luxury to having less. You can choose not to participate in this consumer world."
  —David Greene [42:20]

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Essential Timestamps for the Busy Listener

• [04:36] Introduction to Stillwater, OK as a rental market
• [09:23] Taylor’s approach: buying, rehabbing, and targeting niche guests
• [13:45] The guest experience in non-vacation markets vs. vacation markets
• [23:04] How Taylor automates messaging and manages everything with just Airbnb, PriceLabs, and part-time help
• [27:39] Dynamic pricing strategies for local events and booking window management
• [32:25] Why extras like hot tubs and game tables don’t make sense in every market
• [37:02] Involving kids and teaching legacy asset-building
• [44:58] The value of keeping perspective and avoiding toxic comparison

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Tone and Takeaways

The episode’s tone is conversational, relatable, and forthright. Both David and Taylor demystify short-term rental investing, highlighting both the real frustrations of high-drama vacation markets and the practical, attainable upsides of investing in "regular" places. The message is clear: You don’t need dozens of doors to build wealth, and you don’t need to be an online influencer to win in real estate. Sustainable, automated cash flow is possible with “just a handful” of well-selected properties and a focus on simplicity and customer basics.

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For listeners considering STR investing, this episode encourages you to:

• Focus on stable, under-the-radar markets with real, cyclical demand.
• Keep operations lean, automate where possible, and avoid feature creep.
• Know your market—demand, expectations, local events.
• Get involved with your properties and your family; model asset-building for your next generation.
• Don’t compare your journey to the highlight reels of others—slow and steady can win the race.

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*"If I could just hit repeat on what we did, twice, I’d be ecstatic. There are ways to do this without making it your full-time job."

—Taylor [39:35]*

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To learn more or manage your STR more efficiently, visit PriceLabs or contact David for management via Coast to Coast Getaways.

Transcript

[A]

Welcome to Real Talk Real Estate, the show where we cover how to build wealth in real estate with no fluff, no BS and no sales pitches. I'm David Green and I've been doing this for over 10 years. I've seen the ups, the downs, and everything in between. This is the show where we pull back the curtain and show it to you, too. So if you want to build wealth through real estate or you just love learning about it, you found your home. What's going on? Real Talk Real Estate. This is the David Green Show. I'm David Green, and I'm joined today by Rainn Wilson of the office. Rain was kind enough to take a break from touring and talking about his new book to come on the David Green show and tell us how he broke into show business, what rentals that he's operating, and why he just can't get along with. Jim Rain. Thanks for being here today.

[B]

Thank you so much. I appreciate it. It's. It's tough to get away, but I'm happy to be here.

[A]

Yeah, my audience certainly appreciates you making the time for us. Taylor here did not know that I was going to do that, everybody. So he's just as surprised as all of you are. Although I didn't inter interview Matthew McConaughey at one point, so I might have been able to sell that if we'd, like, blurred out your camera a little bit.

[B]

Yeah, absolutely.

[A]

Yeah. So I met Taylor at a Bible study, actually, and he recognized me. He was like, hey, you're the guy that does the podcast. We started talking about rental properties, and he's got a pretty cool story. Now, in my opinion, the majority of the people that listen to these podcasts and that are rental property owners in America, contrary to what it may appear, don't have 74 units that they acquired in three years. They are mom and pop operators. They are trudging along, they got kids, they got bills, and they're trying to prepare for their future and doing what they can to acquire real estate. And depending on what's going on with the market, what's happening in their financial life, what's going on in their personal life at the time that deals pop up, sometimes people scale more than other people do. Sometimes you start off with three or four, and then you pick up five if you in one year and you triple your portfolio. And other times you go a couple years without doing much. And I just want everyone to realize it's normal to have a handful of properties and to manage them themselves. And so today I kind of Wanted to talk to just your average, normal, I guess I shouldn't say average, but your standard real estate investor. These are the people that are making the whole thing work. They're not managing massive portfolios, they don't have huge teams of people and they're not running incredibly inaccurate social media griffs trying to get a bunch of attention. So Taylor, thanks for joining me today.

[B]

Absolutely. Glad to be here.

[A]

Yeah. Tell me a little bit about yourself. How did you end up in life when our lives, when our paths crossed?

[B]

Yeah, man, I am from, I'm an Oklahoma native, born up in Miami, moved to Tulsa when I was about 2 years old. So I lived in Tulsa till I was, man, 23. We ended up moving to Colorado for nine years and then just moved back about midway through 23 and I've been back ever since and so been married 13 years. I've got three kids, a son who's about to be 10 and then twin daughters who just turned 4. And so they're, they're big motivators with all of this real estate investment obviously. And for me, living up in Colorado, we worked in college ministry for about 11 years myself, my wife worked a about 15 years in it and so we'd always kind of had a dream about owning real estate or having a rental of some sort, but Colorado for us and man, the career we were pursuing just wasn't likely. And then 2020 happened. 2021 happened. I was listening to a lot of podcasts, I was listening to a lot of you honestly, and got real motivated to try to figure out how could we use equity in our property there in Colorado and turn that into something else. And so my wife went to Oklahoma State and so we were familiar with Stillwater, we knew people in and around there and just started doing a lot of research, talking to people, trying to understand what that market looked like. And so ended up buying that property, that initial one back in 22 and then we bought or no, we actually bought it in 21 and then we ended up buying a duplex in 22. After my twin daughters were born, I had a month in the nicu and I could just think I just need to make more money, so that'll do it. We were able to do a couple of cash out refis of that property there in Colorado and that's really what turned into these, these two properties. So man, working in some upstream oil and gas startups right now had kind of a career pivot there back in 23 and learning like crazy and growing. But these properties have been an awesome, stable thing for us.

[A]

Now I'm unfamiliar with Stillwater. So where is that and what kind of a market is it?

[B]

Yeah, it's, it's, I think it's considered a rural market. It's where Oklahoma State University is. And so it is about an hour 15 west of Tulsa, Oklahoma, if you guys are familiar. So it's, it's small, it's north of a city called Edmond, which is a suburb of Oklahoma City. But a beauty of working within a state like Oklahoma is people love two things. They love college football. They're huge OU or OSU fans and they love the Oklahoma City Thunder. That's the only professional team our state has. So when it comes to football season, when it comes to where people go to school, it is OU or OSU typically. And so there's a ton of opportunity on the short term side, especially in a small town like Stillwater that would otherwise probably not have nearly the traffic that it gets.

[A]

That's what we're going to talk about today. When I first moved to Oklahoma, I was heavily recruited by both sides of this college football rivalry that as a California kid was very, very surprising to me. I didn't know I had to pick between being a Blood or a Crip within my first.

[B]

That's what it is. Yeah, absolutely. Yeah. I married into Oklahoma State with my wife. I personally went to the University of Tulsa. So I'm more of the stepchild when it comes to any sports. But. But we're osu, but it's a big deal. It's a big, huge deal.

[A]

Yes. I still don't quite get why college football is so big. It strikes me as somewhat odd that 40 year old men are violently cheering for 19 and 20 year old young dudes.

[B]

Absolutely.

[A]

With the vigor and passion that they are.

[B]

I felt that. I felt that in Colorado too. Like we would go to our son's soccer game or something. And my wife and I are vocal people. Right. We're there to participate. We want to help the team as much as we can from the sidelines. And we were kind of the only ones that were like really caring about the game or the outcome of the game. And it made us kind of go, man, maybe this isn't everywhere, you know, Cause we're, my wife from Texas, I'm from here. Like it just, it's just what you do, you're just plugged in.

[A]

Yeah. I mean it's probably the lack of professional teams because we have so many professional teams in California, I mean in like Northern California Alone, you've got two basketball teams to pick from, two football teams and two baseball teams. And the same in Southern California. There's two each major sport and we're not even at hockey yet.

[B]

I think it's a really good point. It is like life or death. College again, a lot of people support teams of schools that they did not attend. They just, their grandpa did or you know, it's some weird, like second cousins, third sister ended up going to OU for one semester, therefore, I believe.

[A]

And they're like loyal for life. Yeah.

[B]

Yes.

[A]

And I've noticed in other parts of the south too, Tennessee, same thing. Super big into college sports. It's a thing I'm gonna have to learn. Alabama, obviously, I mean, I know about that whole angel Pat Fields versus the McCoys rivalry. So you're in Stillwater and that's where Oklahoma State University is that they're the Cowboys. You know, it's actually funny. I, I'm theming one of the Airbnbs that I have in the Tulsa area. It's going to be called the Cowboy Inn because I think it's going to attract the OSU Cowboy fans. It isn't going to be all orange, but I do think it will catch people's eyes and they will be like, oh, if they're an OSU fan or if they're going to the area for some reason like that, it probably would catch their attention.

[B]

Absolutely, absolutely. Yeah, I think you're exactly right.

[A]

So you got your short term rentals. So tell me like you bought one of them and that was the two unit one and then you refinance and bought the other one, is that right?

[B]

Yep. So we bought a single family first. A little two bed, one bath, 740 square feet. I mean itty bitty house built in the 50s. We, we bought that from the owners themselves directly. So that wasn't like a traditional listing and I just immediately, we immediately converted it. So, you know, we're, we enjoy the grind. So we got down there, we just started working, we started finding stuff, sourcing what we needed. We weren't necessarily buying everything brand new initially, but we bought things that mattered new. But a lot of, you know, just kind of putting together what we could and got it listed on Airbnb right before the, the football season started, which is definitely a big part of what we're able to do. And it's been cash flowing pretty much ever since. Like it hadn't stopped. And so after about a year or so of doing that, my daughters were born. I had Time and then we our property in up in Colorado again we were able to cash out refi again because rates were still so low and properties that appreciated so much and we that's where we bought the duplex that all. So those two units are run as separate one bed, one bath. I mean little 500 square foot, aim small, Ms. Small was kind of my approach. I wasn't looking for a huge splash. I just wanted to be attractive to a single person, a couple, maybe a small family, like a couple with a single child where the kid maybe didn't necessarily need its own room. And so I think we, we've found a pretty good niche right there.

[A]

So both of them are cash flowing or all three units I should say are cash.

[B]

Absolutely, yes. Yep. Absolutely.

[A]

That's pretty impressive in today's market when not everybody is. When you bought them, did you intend on them being short term rentals or was of a back and forth there?

[B]

Yes, that was my hope. So I knew I only had a couple, you know, bullets to shoot. I knew I wasn't going to probably be grabbing a ton of properties over a short amount of time. So I wanted to maximize my cash flow as quickly as I could. And after doing as much research as I could, I'm also a big fan of Rob Abis Solo. I followed his channel a lot as well of just looking at Airbnbs and how could this be helpful as a short term rental option? And got fully convinced. And so we started. Yeah, correct. As a short term. And then when we bought the duplex we actually had a great experiment because I inherited a tenant. So I had one long term tenant for one year and then I ran the other side as a short term rental for that same year. And when I looked at the year once that tenant was leaving or his lease was up, I mean the cash difference was almost 3x on the Airbnb. So it was. Wow. It felt like a no brainer to just go okay, time to convert the other one and keep, keep this rolling.

[A]

And then that means you got to furnish it. Did you just do the Facebook marketplace thing for most of the furniture?

[B]

For the most part, yes. Yeah, we just found what we needed there in and around Stillwater. Even now in Tulsa, it's a lot easier to make a trip over to Stillwater and get something fixed if I need to, relative to when we were in Colorado.

[A]

Okay, what's the load like as far as guest communication strain on you or the family having to pay attention to stuff? What's that like with this property yeah,

[B]

so it's not too bad. Thankfully, I'm always aware when people are checking in because that's typically when I'm going to hear of an issue, right? If something's wrong or off or dirty. I'm hearing that night one. So when someone's checking in, I'm aware of my phone, but I've automated all messaging apart from just issues like that. So I know if I get a message from a guest, they're either saying, hey, we're in, and a thumbs up, or hey, we saw this, or hey, what can we do about this? And that's, that's typically it. And thankfully I've got great people there in, in Stillwater, my property manager, who, you know, is kind of boots on the ground to solve those fires and put those out. Great guy. And so I shoot him a call, we make a plan, and we typically get it handled within an hour or so. So it's been, I mean, there's been issues obviously, but nothing, thankfully to this point, super overwhelming or, you know, pulling me away from, from my responsibilities here.

[A]

So I have this theory and I want to run about you and you're under no pressure to agree with me because, say, David, you're completely off on this because it is a slowly developing theory. It's not dogma yet. My theory is that the short term rentals that I manage, I have a big chunk of them in the Smoky Mountains, Tennessee. This is a vacation market. And then I've got a smattering of them that are mine or I manage for other people that are kind of like South Florida, North Carolina, Hawaii, Virginia, Georgia, just like they're kind of a little different places. Texas, it feels like the percentage of unhappy guests, complaints, demands, refunds, bad reviews, just like almost all of my headaches, they seem to come out of the Smokies. And my theory is it's because you've got like people that are going on vacation with their kids. They don't travel a lot. They have a very high expectation. It's like, this has to be perfect. It's our one vacation for the year. And so they're also maybe incentivized to complain, to try to get good reviews because they know that I'm competing against 50,000 other cabins in the Smoky Mountains. But the stuff I've got in, in Maui, it's not as much of a vacation destination. And the people that are super picky are probably going to hotels. So I rarely get problems with my condos. The stuff I've got in North Carolina and South Florida is someone who's visiting the area, but it's not like they're throwing all their kids in the station wagon and they're driving to Disneyland type of an environment. I don't know if this is only my experience and so I am putting too much stake in this objective or subjective experience I'm having or if there's something to this. And other people who've got properties that are not in vacation heavy markets like Orlando, like the Smoky Mountains. What's another area that you get like a lot like Branson, Missouri where it's like, oh, it's terrible. These people show up and they complain all the time. What's your experience like with the small town person who's probably not taking a family vacation to Stillwater? They're going to visit their kids in college, they're going to check out the area. Whatever reason they've got, it's usually not a family vacation.

[B]

Yeah, I mean, I think you're exactly right. We don't have a ton of issues like that. Again, if someone's coming in town, they're typically there for one of two reasons. One is obviously Oklahoma State. They're there to see a kid or they're there to see a football game or they're there for something associated with the university. Their veterinary school is really strong. There's a local hospital that I know we've had doctors stay. So they're there to like work. They come to my house to sleep. And so our beds are great. We've got great amenities in that regard. But you're not going to look at the design of my properties and go, dude, how did you get, how did you do that? We're very normal, regular people.

[A]

It's practical, right?

[B]

Yeah, our properties are practical and they're pretty, but they're not, they're not going to blow your mind with the photos. And so that we, again, we. There are people who complain and there's a couple events that happen there in Stillwater where they're higher stake. So homecoming at OSU is like a very big deal. And so I want to ensure that, yeah, they have the best stay. And we. There's a local pizza place here now Oklahoma, but it started in Stillwater called Hideaway. So we always try to have like a pizza or something for them. Not, not ready for them. But a gift card for that spot or there's a big bike race that I'd never heard of. But it goes, it happens in Stillwater like every March. And so those are typically the two times that I'll see more of an issue or someone has a problem that's not just an oh for either miss on our cleaners part or they saw a bug or something, which we have all those, those properties sprayed quarterly, so it's not typically an issue. So that, that's typically. Yeah, I think you're exactly right though. We. You're not coming to Stillwater to, to exactly have a vacation that would take you maybe half a day to do the attractions. But if you went to school there, you're loving that you can go walk, you know, nearby downtown, if you have a child there, you're mostly out of the property doing something, you're seeing a game, you're out, you're doing something else. People show up late. Only other real issue we run into is just someone forgot the code to the door and it's late night. But that's pretty much it. So I mean, to add, to move this one notch closer to dogma, I think you're exactly right. When someone has high expectations and they're paying a high price, they have any issue is going to be a big one. But when you're paying a pretty okay price, maybe a little more than you thought, but it's so much more space in a hotel, you're kind of just happy to be where you're at in a clean, nice spot.

[A]

Yeah. My thoughts were the people who own them in areas like yours, which I need to come up with a clever marketing name for. I say practical areas. I don't know if people know what I mean by that, but it's like you're in Cincinnati, Ohio, you're in Jacksonville, Florida. It's just like I'm visiting the area and I don't want a hotel. Kind of what Airbnbs are meant to be before this whole crazy vacation surge took off, where it became a business. You probably hear me talk about these Airbnb complaints and the crazy guests and the bad customer service and you're like, I don't know what he's talking about. Maybe he's a bad property manager. It's not that bad. I don't have those experiences. Right.

[B]

But no, we, we, we've seen it.

[A]

Yeah, you've seen it, right? Or, or you deal with the people that are in Orlando, Florida, or Branson, Missouri, or the Smoky Mountains. Or maybe I guess you don't have a lot in California because it's so hard to run a short term rental out there. But I'm sure that there's like ski areas where people all go during Ski season and they're losing their minds right now. The people that are, they're either calling me to cry or scream or beg. Some people have had their listings completely taken off of Airbnb and they have no idea why. Other times, the guest is trying to hold them hostage for money and they think it's unfair and they get a one star review and they just plummet out of the rankings. They're. They can't even find their property anymore. And it's like it's, it's either a guaranteed for sale or if you can't sell it, a foreclosure. That's, that's how serious it can be. And I see like the desperation, a lot of their voices. So I think it's worth sharing the information that if you're kind of thinking about getting into this or if you've decided you want to get into it, but you don't know where, maybe it's better in the beginning to just stay away from some of these vacation areas where you're going to have very high maintenance guests and stick with the, the bread and butter, blue collar, slow and steady property like yours that just continually pays the bills and doesn't make you hate your life.

[B]

Yeah, I think, I think that's absolutely true. I think small college towns like that, today or no, yesterday we had a guest check into one of our properties and it's a business. They booked 50 days. Let's go like January, February for us. Very slow. So to have that booking, it's two superintendents for a construction company. Like, that's, that's who's going to be.

[A]

Those guys are not going to complain, man. Like, they're more likely to fix a problem than they are to tell you that there is a problem. You know?

[B]

Exactly.

[A]

They're like leaving and you're like, oh, that's pretty cool. Like the pictures were sideways.

[B]

Yeah, it's not squeaking.

[A]

Like the squeaks gone. The, the loose line in the fridge to the freezer's been repaired.

[B]

Yeah, exactly, bro.

[A]

It is so bad in some of mine that we have literally been sending gift cards to our guests that leave and don't complain if they come in and they leave it in good condition. And they, they just didn't complain to us. We're getting their address and sending them $100 gift card just to thank them for being a good human being that treats others the way they want to be treated. Because it is, it is so hard in some of these markets. You get people that trash the place. I had A. I don't think this happened. After I saw you guys, I believe I had like an impromptu flight out to Tennessee to go work on my cabins. And it's like the first I've been able to go back since I tore my bicep tendon when I was there the last time. And the night I get there, there's a huge party getting thrown in one of my cabins that the cleaner that cleans it saw going around on Tick Tock or Snapchat or something. And I drove out there and There was about 80 kids in this place and they had put so many cars in the driveway that they couldn't even get their cars out. It was absolute chaos. And I was like, just went inside. I called a cop, had him on the way, went inside and just started throwing 22 year olds out of the house, like, get out the party.

[B]

I was like, protect that bicep though.

[A]

That. Well, that was the thing is I had a sweatshirt on. I didn't want him to know that there's like major atrophy. I probably couldn't do much if he gave me a hard time. I just made up for it with a very stern tone. Yeah, time to bring back the cop voice. And I was like, I can't let one of them test me because if they sense weakness, the hyenas will all just jump on me. There's so many of these kids here, right?

[B]

Yeah.

[A]

But it was like chaos that that can happen. And if that does happen, like they advertise it as a Project X party and it could just like destroy your. I got so lucky, man, that this person just happened to say, hey, there's a party going on and it's your house's address. I think you probably want to go check it out. That's exactly what was going on. But if you got a property with 750 square feet, is it glamorous? Not as much. Is it going to be making 150 grand a year? No. But you don't have that type of thing. Right. It's sort of just something that's like literally an asset in your life that is a good decision that you're happy with, that you can build on when the time is right. When you don't have twin 4 year old girls that are constantly requiring a lot of attention, you can go pick up a couple more of these things and make it happen. So I think there's a lot of the people in your situation that listen to the podcast and then they feel bad about themselves. I'm not a 23 year old kid that has 50 doors that I'm managing or whatever. But a lot of those people hate their lives or they're not doing well and they're not telling you about it, whereas yours seems like it's going pretty good.

[B]

Yeah, I would agree. I think, you know, having the three properties or the three units, excuse me, two properties, has been awesome for now. And yeah, we, we would love to add a few more. My goal has always just been kind of five doors there in Stillwater. Not looking to overwhelm myself for the people I'm working with, but I think if we could just roll those and man, if my son or my daughters end up going to osu, down, down the road and they send up living in one of those for four years, like, man, that'd be awesome. And we'd love to keep those in the family as long as we can. So it's been, yeah, we're not looking for a quick flip. We're looking for cash flow. We're looking for, yeah, just supplemental income to help us live. And so it's been, it's been. And help us save, you know, to continue to grow the base.

[A]

Okay, now, what property management software are you using to manage this thing?

[B]

Airbnb app, baby. That's it.

[A]

That's it. You're not on vrbo, you're not on booking? None of those.

[B]

No, just Airbnb.

[A]

Interesting. Okay, and you said you have your messages automated. Can you tell us what that process looks like for you guys?

[B]

Yeah, totally. So we have probably three automated messages that go out to guests, I think three days before, one day before their stay, and then the day of, obviously, so they can get all the information they need. The check in again, I've got an automated message the night before they check out, just with any information around our checkouts, which again, small property, really easy, nothing crazy. And then we have a thank you kind of message at the end, a couple hours after checkout, just thanking them for their stay and all of that. So it enables me and allows me to not have to think about it every single day and make sure that, oh, did I make sure that's different or changed or whatever. But it's automated. It rolls. We use Price Labs for our pricing. And so that's the only other real automated thing I've got, is the dynamic pricing there. I have to go in every time that the football schedule is announced because even Price Labs couldn't get some charge. Their algorithm's not built for that big of a jump for one weekend in the year. So those two automated parts of messages and pricing has taken a lot off my plate, where I'll learn about an event, maybe after the fact. And I'm like, that's okay. Like, big concerts have been happening there in Stillwater the last couple years. And I find out because someone books some random weekend in April, like six months out, and I'm like, that's not normal. You know, graduations are normal, that race is normal, but that's not. And then I find out, oh, Cross Canadian Ragweed. This giant country band is getting back together and we missed out on probably a couple hundred bucks, but it's all good. I'm just glad I got it filled.

[A]

I'm glad you mentioned that because we are huge fans of Price Labs. Price Labs actually sponsors this podcast.

[B]

Awesome.

[A]

And a lot of investors at this stage kind of know that you need dynamic pricing, which just means, if you're not familiar, the prices go up and down based on demand of other properties in the area. It's pretty cool. But that, like, there's some people that aren't using that occasionally I'll come across and I'm like, oh, my God, you have no idea how much money you're

[B]

losing if you're not doing that.

[A]

But what a lot of people don't realize is that depending on the demand for the property and how many of others are in the area, basically, if it's not as much competition, this isn't as important. But if there's a lot of competition becomes more important. You need to be looking at Price Labs and dynamic pricing becomes like your foundation. But then you have to adjust it from there. So at coast to coast getaways every day, that's the first thing that we do is we look and we see what is not booked in the next couple weeks and we immediately adjust the prices on that. And we look and see. Like we. Let's say we've got 20 cabins and we noticed that two of them, like you just said, booked for a day in May. That's way far out. We're like, that's odd. Why is there two bookings at the same day? There's something going on. There's a car show coming into town, or there's a concert, or there's a big soccer game like you said. And then we go and we look at Price Labs will show us how what percentage of our competition happens to also be booking and what is still vacant. And when I can tell, oh, there's not a lot of vacancy in the market. We Know we need to go bump our prices up on the future stuff. And if for some reason I messed up and I bumped it too high, I can always bring it back down. But a lot of people will look at, I need to lower my prices to get a guest in the next week or two, maybe the next month. But you also want to be pushing them up for future bookings. You don't want your calendar all filled up in the future when you could have been getting more. So having price labs and knowing how to use price labs are not the same thing. A trend I think in the short term rental space is there's a lot of people that have a property manager and that person kind of handles guest complaints and does logistical stuff like cleaner turns and maintenance requests. And then they have a revenue manager that does nothing but plays with these tools to try to increase top line coast coast getaways. We do both of those. But it is worth noting that it's. You should be looking and doing exactly what you said, Taylor. You should be looking to see, oh, I could get a little bit more money. There's a football game coming up. There's something happening. The calendar's filling up. I need to increase my revenue.

[B]

Yeah. And making sure I get those, you know, two night minimums where I need them. And timing that correctly as well has been.

[A]

Yeah, talk about that a little bit. What's that like?

[B]

Yeah, it's great. Again, when we know there's an event again, especially football weekends there in town or parents weekend. Again, the university itself has its own calendar and stuff goes on. So if I know major events like parents weekend, game days, obviously homecoming, like I'm gonna make all of those changes ahead of time. Because there was a time, David, where I wasn't as aware of my calendar and how far out it was available and I had someone book in October. Typically October weekend is like when homecoming is, but you never know until the schedule comes out in January. And so this was like December of, I want to say maybe two years ago and someone booked a weekend in October and I was like, oh no, like, did I just miss out on one of our best weekends ever? Because I hadn't one reduced my schedule availability to more of a six month view, not a nine month view. And yeah, did I just miss out on homecoming? I'm going to screw up my super host status and all this stuff to try to cancel and convince this guest, whatever. So thankfully their guess was wrong. So it didn't, it didn't actually affect us as I, I was very Grateful for that. But yeah, I got to be on top of when those schedules release because that's when all these people. There's so few hotels in town, which I think is another benefit of some of these smaller town short term rental opportunities. I mean, Stillwater doesn't have a target just for context of like size and what this thing can, what this city can kind of keep. Now when OSU is in session nine months out of the year, it's, it's 30, 40,000 plus people in that, in that city or town, I should say. But it shrinks in the summer. And so the seasonality has just kind of pushed hotels away. There are some obviously that are around, but they're not, they're not making crazy investments in a small town like that because they know that they're going to be full for all those game day weekends like they have for the last 20 years. And so they don't, they're not going to add any or subtract any because people end up staying down in Edmond, which is about 30 to 45 minutes away. But they're there for homecoming because it's America's, it's America's brightest orange. And so people, it is, it's mind boggling. Hey, we will go in October if you're around and we'll do the walk around. And every Greek house there in Stillwater, they do these gigantic like just huge presentations like for the year. Like it talks about who is the coach and there's everything, osu, Pistol Pete, everything. Like it's, it is mind boggling. So people will pay money to walk around and do that on a Friday night in the middle of October and gladly do.

[A]

So is that where Pistol Pete played? Was he a cowboy?

[B]

He wasn't. But that is their mascot. So I think

[A]

Pistol Pete, right?

[B]

Yes. Is from actually Wyoming. But then Oklahoma State's had it forever. All these schools that started out as the state funded ag school, you know, Oklahoma A M back in the day, they've all got some sort of cowboy or horse, you know, as their, their logo and mascot now.

[A]

Okay, that's pretty cool. What's your normal vacancy like out there? Do you expect to be booked half the time or is it just wild swings depending on the season?

[B]

So I would say our slowest months are definitely January, February typically. And so again, having this one booking alone is like super exciting for 2026. Kicking off great. But I would say typical occupancy for the two bed, one bath is probably around 50% most of the time. And then the duplexes are probably closer, like 65 to 75. And again, we've got pretty good monthly discounts as well. So we actually had a guest in one of the side units. He's been there since December 1st. He's actually, I guess, played baseball there at OSU. He's a pro now, but he's just in town training, and so he just needed a spot to stay for a month and a half. So that adjusts my vacancy numbers. But in general, I would say those are where we're at.

[A]

And then some markets, like in the Smokies or in Hawaii, even if you can add things like a higher sleep count, you can increase your revenue. And then obviously, design is a big thing. Right. There's so many different properties to pick from. You get stinking, picky guests that are going other markets. It almost doesn't matter. They're like, I need a place to stay. It's me, or there's two of us. Do you notice that there's much you can do in that market if you want to decrease your average daily rate, or is it kind of going to be what it's going to be?

[B]

I think the only thing I could probably add to help my daily rate would be add hot tubs. But there's not a ton of groups there in town that clean hot tubs. Like, there's just not much of that amenity in the city to begin with. And so I've done the research. I think it would help. But the risk and the investment I'd have to make to get to that, I don't think it would be worth the average daily rate going up 10 or 12. That's a good point.

[A]

Yeah. I mean, even if you did increase it by like a hundred bucks a booking, and you're getting two to three bookings a month, you're talking about two to 300amonth. How long do you have to do this before you're paying for a $5,000 hot tub? Plus your increased electrical bills, plus now your cleaner is going to charge more.

[B]

And then they get to think about weird. Yes, you get the funky. Hey, my armpit really hurts after I stayed in your hot tub. It's your fault, and I would love to not deal with that. So I think that's the main spot. I think otherwise. Yeah, you're just looking at some people have gone kind of what you're doing here in Tulsa, the osu, like, orange and black, same font, same everything at osu. And I think those book and people love those spots, but Otherwise, it's. Again, if it's clean and nice, people are happy to be there. Like, they're. They're not. You're not going to Stillwater to post a bunch of Instagram photos and increase your follower count. Unless you're from small town Oklahoma, going, hey, look at me, I made it to Stillwater. That's probably it. Otherwise, it's just a great spot to be. And, you know, should we put a mural on the back of one of our houses for people to take photos at? No, it's not going to help.

[A]

Right? So, like, cool. Adding a billiards table you don't think would make a big difference?

[B]

One, I don't think we have a room that would hold one. Two. Just the size. But yeah, no, I don't think people would. Would use it. They. There is a pool hall there and still water. People want to go play billiards specifically. But if you're in town, like, you want to go to Hideaway, you want to go to the places you ate when you were in college. Like, it's just like any of us. And so you like what you know. And so the very first Sonic, if anyone cares, started in Stillwater. And so that's another spot a lot of people go to. Yeah, dude, when we go walk in October, I'll take you to that Sonic. And that's what people do. They love it there and they're big fans. And again, I think that ag background of the school is also really helpful because those are just salt of the earth people. Like, they're. They're great people to work with and talk to and interact with. So those are the. They're sending their kids to that school and the school is growing every year like some of these bigger state schools are. But again, my background being in college ministry, I thankfully know a ton of people who are really high character, great people in a bunch of these small towns. And so I think if there was an opportunity to expand outside of Stillwater in the future, like, yeah, I think I'd have people to call.

[A]

Do you worry about if it's a king bed or a queen bed or anything like that?

[B]

My rule is just as big of a bed as wolf fit is what I want to put in. Yeah. Like, I want to be comfortable, you know, Like, I try to think of it as I'm the customer. Like, I want to be in a king if I can. I'll sleep in a queen if I need to. But we've got the duplexes, each have kings and then the two Bed, one bath, both have Queensland queens.

[A]

The reason I ask is that a lot of the time in the short term rental community, people just get insane about these details. And the people that are teaching the courses are typically like the OCD type. People that love that level of detail and it gives this impression that if you're not doing that, you can't make this work. And here you are saying, if I can fit a king, I'll do a king. If not, no big deal. I don't have a pool table, I don't have a hot tub. It's clean, it's decorated nicely. It's more or less as close to passive income as I can get. I'm assuming that your cleaners get automated whenever there's a turn and you don't have to tell them directly.

[B]

Yep.

[A]

Yeah. And that your cleaner tells you, hey, there's an issue with this thing. You get a picture or something like that and then you got a handyman, you can pass the handyman, the thing, he has a door code, he can go in. It's not that much of a heavy lift in these situations. And I just want that to be the message of today's show. There are ways to do this with a little bit of thought ahead of time that don't require it to be a full time investment, that this is all you do and you are glued to your phone and this is a weight that you will carry around with me with you for the rest of your life. You still have your job, you still have your family, you've got these kids and you've got a property that a lot of the time you probably don't even really think about having.

[B]

No, I'm just one of my favorite feelings, and I say this to people when it happens, is when I'm doing something else, I'm working or I'm with the family, or we're just with friends, whatever. And I get the buzz. And I feel the three buzzes, right? The text message and then the app notification from every that, hey, dude, someone just booked two nights in a month from now. And this is something I tell my son, who's again about to be 10. We I'm trying to help him learn about assets and liabilities. Right. I want him to understand that, hey man, we're going to go to Stillwater every now and then and just clean the house ourselves. Just because I want to see it, I want to have my hands on it, I want to touch it, I want to make sure we're not missing anything or something's not broken. Because there's a difference. Obviously. My cleaners do an excellent job, but they're not going to always know exactly how things were before. And so I love that. I can run over there. See it? I can bring him. We've got a pack and play in every property as well. So even if I need to stay and the girls need to take a nap or something, like, now that they're bigger, it's not as much of a deal. But when they were younger, we used those pack and plays and I would have them on one half of the duplex. And my wife and I, she's super great at cleaning and design and all that, and so she'd help make all that stuff happen. And yeah, it's a family effort. And so for us, growing up like a rental property seemed like such an un. That's so unachievable. Like, I don't think I could ever get to that point. And, and again, crediting my family and my, my parents, like, man, they did everything they could. I'm super grateful for the, the foundation they gave me. But even as I, like, told them, I remember I called them, I was like, hey, I just bought a house in Stillwater. And their reaction was, oh, you're moving to Stillwater? Like, you only buy houses when you live in them. That's kind of, that's all you do. And so explaining, no, we're actually going to run these things as a, as a short term rental, you know. Okay. There's a lot of questions around that. And us, it's really fun to have the tactile reality that we can go help fix something too. Like if something is out of Tristan's hands, he can't deal with it or doesn't know how to deal with it. I can go over there and deal with it. And I like that part of this too.

[A]

Solid point, man, I love that. And now your kid is thinking subconsciously, when I grow up, I'm going to own a rental property. As opposed to how you were thinking, which is only rich people have those. Or the only reason you buy a house is because you're going to live in it. As opposed to, I have a mortgage being paid down for me by a tenant. And now your kid's going to think that's normal. And maybe when he gets his first job and he starts working, he'll be subconsciously saving, thinking, someday I'm going to want a rental property.

[B]

Yeah, absolutely. I would love to help him do that down the road. Love to help the girls do that. Down the road, if that's of interest to them. I mean, it just so happens that the amount of units we have is the same as the number of kids I've got. I've got twins and a duplex and a single son and a single. That wasn't the plan. It wasn't exactly what we were trying to do. But, dude, if we could just hit repeat on those things twice, like, man, I would be ecstatic because we. It'd be. Again, I think it's a market that there's other great rentals there, but if you can be there a long time, I think people just. We continue to get repeat people now too.

[A]

Do you think that God is incentivizing you to keep having kids by blessing you with another house? Depending on how many kids. I bought a duplex and he's like, well, for your twins, there you go.

[B]

Hey, I would love that. The twins for us were ivf. So it was. It was an interesting challenge getting them.

[A]

Well, maybe that's why you got the duplexes to pay you back for the IVF over time.

[B]

Here you go, man. It has. I'm super, super grateful. But, yeah, we were. They were born a couple. A couple of weeks premature and which is expected with twins, but they were in the NICU for about a month and I was just Groundhog Day in it, right? Every day was the same. We're in the hospital eight times to five. My wife's recovering from a C section. It's Covid time still. That was an end of 21. And Colorado took it obviously very, very seriously, so no one could come see them apart from us. And I'm just like, dude, we gotta do something right? You know, this one property is doing well, which is really cool, but it's only one. And so I called my. My loan guy and I was like, dude, no way I could do another cash out refi, right? And he goes, dude, it's kind of crazy right now, but I think you probably could. And yeah, to be able to pull the money out of that property and put it into others is, yeah, huge, huge, huge blessing. We're super grateful for.

[A]

Well, I call that the bigger pocket special, because that was kind of. At the time that the podcast was exploding with Brandon and I, the government was printing money. Values were going up, rents were going up. It was entirely possible to do good on a deal, and that deal would then be the down payment for your next one. And for some people, they carried that way for a while. I don't think that that is Nearly as possible now, or even that I'd recommend it in today's market. You got to be a little bit more conservative now. It's about, in my opinion, can you win the battle of running your budget as opposed to letting your budget run you. It's very hard when money's pouring in and it's coming in easy and work is easy. We were just talking about this on a show that was recorded yesterday. The work ethic in general has gone way down. And what people's expectations of what a workday is is significantly worse than what it was like when, like 10, 20, 30 years ago. Right?

[B]

Yeah.

[A]

At the same time, our cost of. Not our cost of living, our expectation of living is way up. And nobody likes to think about that. When I was a kid, my family had one car for the whole family. There was. We didn't go out to eat ever. We cooked every single meal. We had hand me down clothes for my cousins. We had hand me down toys from older kids. There was literally like wedding showers and baby showers where people would bring you their old pack and plays and you. That was a normal thing to do. Right. That was the version of China where we just ship it to us now. There were no gym memberships. There was no cable. There was not smartphones for everybody in the house. There was not an Internet bill. There's all these things that we have now that we just think everyone has it. It's not a big deal. That's actually a luxury that we've just become accustomed to having normally. And so for the people that are listening that may be thinking or just that here it's impossible to get ahead. Things are too expensive. It is kind of true. It's also kind of true that you don't have to choose to participate in that consumerism type of a world. You can choose to stay home and play board games with your family instead of going and buying a movie ticket for every single person. You can choose to play outside and throw the football around instead of having an Xbox or PlayStation 5 and getting all the new games all the time. It's harder. I do acknowledge that, but it's possible. And stories like this one are sort of that carrot of why it's worth making those sacrifices to get into that position.

[B]

Yeah, totally, totally agree. It's awesome for our situation. We've loved it. And again, we look forward to continuing to have our kids and our family learn more about this opportunity and hopefully be a part of it in the future as well. Well, so we're. But to the Work ethic piece. A thousand percent agree that people don't realize what it takes a lot of times. And yeah, it's easy to forget where you came from or how you got to where you're at and assume that everybody else is where you are. So the six, the six figure, seven figure social media personalities, I mean, comparison is a thief of joy and it's, it's what is true. And so when I see somebody else, just like you said, a 21 year old with 50 doors, I'm like, dude, am I doing okay? Like, should I have gotten 50 doors? I'm like, dude, I didn't have, I didn't have one door at that age. It's totally, totally fine. And I think having a plan and making sure you know what your plan is. Like we landed on Stillwater and said this is where we're going to be. I'd love to own these houses for, you know, 100k or less a door if I can. And that's around the edge of where we got to. And yeah, it makes cash flow and a lot of these other things a lot more achievable.

[A]

Yeah. I know in my world a lot of women that are running businesses and that have a big portfolio and now they're a little bit older because they gave their life to that purpose. I know a lot of men that are managing other people's money, that have syndications, that have a lot of doors themselves. And I know the talks I have with these people behind closed doors that aren't going to be on the podcast. I know the people I've talked off the ledge, I know the people that are absolutely just overwhelmed with anxiety and stress and they hate it that doesn't go on the Instagram reel. And I know they would give all of it up to go back in time and hear the pitter patter of four year old feet come running down the hall when you come in the door. And so it isn't something that you go put on Instagram reel or YouTube channel, but it is priceless, literally priceless to be in the position that you're in with these kids and a family. Just finding the ability to find a partner. Both men and women that want to be married in today's world is getting increasingly more difficult. So in the past 10 years, we glorified vain, shallow things and we called it financial freedom, but it was really just how do I look compared to everybody else? And now the flex is kind of where you're at. So I appreciate you taking some time off of recording the office. I appreciate taking some time away from being the assistant to the regional manager to come and record the David Green show. Michael.

[B]

Yeah, thank you. I appreciate. Yeah, thanks for making the time for me.

[A]

Yeah, Taylor, I look forward to getting to know you better. Thanks for sharing your story and we'll have you on again to get an update in the future.

[B]

Awesome. Sounds great.

[A]

All right. And guys, just in case you forgot, today's show is sponsored by Price Labs. If you've been considering software to help increase your short term rental revenue, Price Labs has cornered the market. They're the absolute best, in my opinion. And if you don't want to learn how to use that fancy equipment we got you, all you got to do is go to davidgreen24.com and you can get a hold of me directly and say, hey, I've got a short term rental and I don't want to manage it anymore. Let's talk coast. Coast Getaways can take that over for you. Thanks everybody for listening. We appreciate you. Please make sure you take a minute to subscribe to the channel if you haven't already done so. Leave us a comment letting us know what you thought about today's show and we'll see you next week on the David Green Show.