Girlfriends' First-hand Experience Watching Jeremy's Portfolio Grow

Quick Summary

The Short-Term Rental Pro Podcast shakes it up, where Jeremy, the usual host, gets interviewed by his girlfriend, Kate. The discussion provides a personal look at Jeremy’s journey in short-term rental investing and property management, highlighting his successes, challenges, and lessons learned. It blends professional insights with personal anecdotes, showing the interplay between business growth and personal life.

Key Points

• Jeremy started his Airbnb business by co-investing with friends and managing properties remotely.
• These partnerships allowed him to scale quickly, leveraging shared resources and responsibilities.
• Unexpected guest behaviors, maintenance emergencies, and operational hiccups are common but manageable with proper systems.
• Jeremy emphasizes the importance of flexibility and quick problem-solving in this business.
• Utilizing virtual assistants and robust processes has allowed Jeremy to manage properties across multiple states while traveling.
• Thoughtful design choices and unique touches, like murals, help properties stand out and enhance guest experiences, often translating to higher booking rates.

Full Transcript

Check on the full podcast on:

1. YouTube
2. Spotify
3. Apple Podcasts

Jeremy: What's up, guys? Welcome to the Short-Term Rental Pro Podcast! I am so excited today. This is going to be such a special episode. I'm joined by my beautiful girlfriend, Kate, who—actually, today—it's Kate's podcast. She's going to be interviewing me.

She's been along for the ride, been at pretty much every single one of our properties, and has been a huge part of this whole experience. I'm so excited to have her here with us.

Kate: I love that, guys. I'm taking over today for Jeremy, the host of the Jeremy Warden Podcast,

Jeremy: Short-Term Rental Pro

Kate: Short-Term Rental Pro Podcast. Either works, though.

Jeremy: We'll make it work.

Kate: Um, and yeah, I'm excited to be here.

Jeremy: Awesome, Kate. I guess you're going to be interviewing me, but can you share with everybody your background? Where are you from? And then I want you to, like, share—in your perspective—what it's been like, like, dating me and all these different properties.

Okay, going from my portfolio being like really nothing to where it is today with 25 listings. I guess, what are some things that are some experiences that you've had along the way?

Kate: It's so crazy because, yeah, so Jeremy and I have been dating for almost two years, but I've known you for, I guess, five years.

Ever since, like, before the pre-Airbnb business, when you just had one property, which is so cool to think about—like how long I've known you for—and seen you grow and develop into this awesome person and, like, with this amazing business.

But yeah, I guess, did I intro myself first and then get into that?

Jeremy: Yeah. Okay, okay.

Kate: So, I'm Kate.

Jeremy: Other than seeing your beautiful—what else is there?

Kate: Yeah, no. So, I'm Kate. Some of you guys might know me as Kate Max, the NYC Runner Girl. I spend a lot of my time running and interviewing people throughout New York City and wherever I'm traveling to. Maybe LA this summer—TBD. Maybe Chicago.

But yeah, I'm a host of a running interview series that's been really fun that Jeremy really was one of the pioneers behind. I'm so grateful for him for that. But yeah, I live in New York City. Jeremy and I actually just got an apartment together—our first.

Jeremy: Signed a lease.

Kate: Yeah, signed a lease—our very own apartment. I'm so excited. We're moving to Dumbo, Brooklyn. So, I've been in New York City for almost 10 years, and this is going to be my first time living outside of the city. I've done a ton of boroughs, but I'm super pumped to do Brooklyn.

Jeremy: When you haven't been in New York in the last couple of years, where have you been?

Kate: Yeah, when I'm not in New York, I am traveling with Jeremy. Like, we are going to his Florida Airbnbs, his North Carolina Airbnbs, Colorado. We're in California occasionally—we're staying up in California at somebody else's short-term rental kind of property, like your cousin's.

But yeah, typically, it's Jeremy and me traveling, setting up new properties. But to take you back into what I remember about the early stages, it was St. George. I remember St. George.

Okay, it was almost two years ago now. I was fresh out of a relationship, and I said to you—and I said to Jeremy—I was like, "I need to get out of New York City."

Which is a common theme throughout, like, our entire relationship—me being like, "I need to get out right now."

Jeremy: I was like "Alright, fine. If you want to come, you can."

Kate: Yeah, and he was like, "Okay, my friends and I just bought this house. If you want to come set it up with us, you can." So I immediately was like, "Lake house, warm weather, not in New York, let's fckin go!"

So, of course, I was like, "Let's send it," bought my flights, and it was then that I witnessed the first property that you set up with a group of friends, which was so cool.

So fun. Felt like a little home renovation TV series, in a way. I kept saying to Jeremy while we were there—and this is probably me missing the point of what we were there for—but I was like, "This would be an amazing reality TV show."

Jeremy: She did say that a lot. And I was like, "Alright, that sounds nice, but yeah, we've got work to do."

Kate: Because to be real, like, when you're setting up these properties—and like when you first started out—you were setting up the properties with friends.

And, like, setting up properties with friends, A) makes for great reality TV show content, but the reason why it makes for that is because there's so much drama when it comes down to it.

Jeremy: It was a lot of drama, and I think Kate definitely was a huge, huge contributor—maybe the MVP—of the drama.

Kate: I don't think so. That's not true.

That's not—guys, that's actually not true. What happened was, I was like, "I'm here because I need some time to relax. I need to be by the lake."

So I decided that I was going to paint a mural in the backyard, on the dock—which is what I did.

Jeremy: I love the initiative.

Kate: Yeah, and Jeremy was like, "There's a lot going on. Can you—let's not talk about me being like—I maybe overspent the budget on the dock."

Jeremy: Alright, well, Kate—I would say that the murals she’s drawn—she has drawn murals at multiple of our properties at this point. She’s drawn that first, that house she's talking about at the lake, and she’s drawn murals in Florida. I love when she draws murals. She does a great job.

She doesn’t tend to finish it. She likes the concept of doing it.

Kate: Yeah.

Jeremy: And then, a lot of these things require multiple coats of paint. It’s definitely a big process. Ideas are definitely there. The vision’s there. She definitely finds them on Pinterest. And I love the one time—

Kate: I’m really good—I’m so good at vision boarding, guys, and it’s super helpful.

Jeremy: Both of the murals she’s painted—the one at the lake that’s behind the bar—that’s one of our top five photos. Photos. That’s one of the early moments.

Kate: It is, to be fair.

Jeremy: Florida—same thing. It’s—I think it’s our first photo. Has the mural in it.

Kate: It’s true. You guys, like, love when I’m doing these murals. Everybody’s hating on them. They’re like, "It’s going to be a disaster." And I’m like, "No, just trust me. Trust the process." It ends up amazing, and it ends up literally being the main photo.

So you guys were all like, "Kate’s not doing anything. Kate’s, like, painting on the dock." Fast forward a few weeks, a few months, and the first photo in all of these listings—or the first—one of the first few photos—Okay, maybe not the first photo—happens to be my mural. I don’t know.

Jeremy: Yeah. So I would say—and actually, I do think for the two listings you did the murals—there actually are the first photo, or it’s in it. I’m not gonna say it’s the whole photo, but, like, it is in the photo.

I will say that the first property you said you’re gonna do a mural, I was so excited. I gave you my credit card. I said, "Go do your thing."

Kate: Okay, so this is what happened. Let me talk about what happened, and then let’s get into you, okay? This is a lot about what’s going on with Kate’s brain when she’s at these properties.

I like to make things pretty, and as a girl, I tend to like to bedazzle things. And so I saw this table in—on the dock. Basically, to paint the picture, Jeremy has this beautiful lake house that he bought in North Carolina.

And a lot of your lake houses that you have now for Airbnb purposes have a nice dock on them where you can pull your boats into. And some of the docks have the bar area, like a little lounge/TV area, looking out onto the water. This bar area was, like, rotting, decaying.

So I know nothing about construction, right? So I'm like, "Let's just patch it up."

Jeremy: “Let’s, bedazzle it. Make it look pretty.”

Kate: So, uh, I went to Home Depot, and I bought a lot of tile—all different colors—and, like, a glue stick, basically. And we mosaic-ed the deck, and you guys didn't like that very much.

Jeremy: It wasn't that we didn't like it and think that they were nice tiles and that they were pretty. It was just the fact that after a day, I could go there and literally, with one of my fingers, poke a tile and have it just come right back up.

Kate: Yeah, it wasn't the sturdiest situation.

Jeremy: It wasn't the right materials for the surfaces and the humidity. In addition—yes, there was a problem. It was a disgusting bar. It had plugs and stuff in it.

Kate: There were, like, so many wasps under there.

Jeremy: Yeah, the wasps weren't even the issue, but the actual boards themselves were, like, wet and definitely eroding. So the first thing you do with any renovation project—not even just saying this bar, but in general—if you have something that's broken or decrepit, you demo it.

It's called demo. Demo day.

Kate: Yeah. So, okay, okay. But you learned…

Jeremy: Out with the old, and in with the new. Okay, what Kate did in that time was, instead of going out with the old, she bedazzled the old. So she put this very nice—they happen to actually be kitchen tiles—on top of the outdoor bar. So, it just wasn't the right material.

Kate: It ended up being pretty expensive. Okay, let's, though, let’s pivot—we can talk for a very long time about that because it honestly was really funny what happened. But yeah, it ended up being so fun, though.

Jeremy: Yeah, and it forced me—that particular project forced me—to have to—

Kate: I think that made you like me.

Jeremy: Because of the bar situation?

Kate: Yeah, the bar situation.

Jeremy: Yeah, I don't think that made me like you.

Kate: I think it did. You want to know why I think it did? I think it made Jeremy like me because—this is when I knew he liked me—was because this was an expensive error, right?

Jeremy: Yeah, it was. And it was at a time when I personally did not have a lot of money. And I was raising money from literally my 24-year-old peer friends, and we were down to our last dollars. Like, we didn't have any room for error. Like, we ran out of money on the project.

Kate: Jeremy still covered the cost of my error.

Jeremy: I did. I put that on my personal credit card. I gave my personal credit card, and I ate it. I just ate it. I had to eat it because everyone was looking at me like, "Dude, what? You really just let her do that?"

And I'm like, "Just—I don't want to talk about it. Yeah, it's on my credit card. It's okay."

Kate: Okay. And it's fine. It was fine.

Jeremy: It ended up being fun. The mural was beautiful. And, yeah, incredible job with the mural.

And, I mean, I went to Home Depot, and I got wood, and I broke out the old, and I put in the new. And it looks great now.

Kate: It does, yeah.

Jeremy: It forced me to have to spend a day and drive to Home Depot and actually do it the way it probably should have been done to begin with. But whatever.

It's fine now. The bar's still there. Yeah, we found out the mural's still there. We haven't done any touch-up paint on it, and it still looks good.

Kate: Okay, okay. Yes, so now, let me bring this back to you, okay? So, North Carolina, as you guys can tell, was an experience, right? It was very fun to be with a group of people decorating a house—really reality TV show content.

Okay, I want to ask you: what made you want to do that? What inspired you to—because you already had an Airbnb, you had your family's lake house that you guys were listing out—what, like, sparked something inside of you that you were like, "Oh, let me buy this house with a group of friends"?

Jeremy: Yeah, so I had, at that point, I was managing several houses. One of them being a house that I partnered—yeah, partnered with my family on—was one of the houses I was managing.

But the rest were just houses I was managing for external homeowners, and I could see, "Wow, all these houses at this time on this lake were making a lot of money." And we had—if you recall—we had friends. You came, too, July 4th, beginning of COVID, so 2020 July 4th. Had several friends, including yourself.

I think this was another instance of you being like, "Get me out of New York," and I'm like, "If you want to come, you can come down to North Carolina for July 4th."

So, at that point, I had started my boat rental business, and I had several boats on the lake that were renting out. I had a couple—or several—co-hosting clients, and I remember just, like, showing—like Kurosh, for example, who was with us down there—my Airbnb account.

Just being like, "Yo, dude, people are, like, paying a lot of money for these houses." And he was an investment banker. Like, he knew investing, and he was just like, "What the heck? What is this? Numbers?"

I was like, "Yeah, people are paying four or five thousand dollars a week for these houses to rent them." And he's a smart guy. He could do the math in his head. He knew it was very lucrative.

Kate: Okay, so you've had friends that were interested?

Jeremy: Yeah, I had friends who just expressed interest.

Kate: Okay, so then?

Jeremy: I was like, "Alright, I'm down."

Kate: Okay, so then…

Jeremy: My family—I could only—we were tapped out as—yeah, personally. Like, I was tapped out. I couldn’t do it with my family, like, I had to do it with other people.

Kate: Like, I—okay, so then—Okay, so then walk me through. This was after you figured out that this was a good investment. You knew that this lake was going to be profitable. What was the process of finding that first house?

Jeremy: Yeah, so at that point, I had a comp set because I was managing several. So I could see that, you know, this—one of these houses is pulling in—let's say that our six-bedroom house is pulling in a hundred and twenty-five thousand dollars a year.

Our four-bedroom house is pulling in, that I'm managing, is pulling in 90,000 a year. Our three-bedroom house is pulling in seventy thousand. Alright, looks like the six-bedroom houses are the ones that pull in the most. So, I found a six-bedroom house on the lake.

It was technically a four-bedroom, but we converted it to six. That was, I think, like $585,000 at the time. So, based off the purchase price, based off our comparable property, I could say I have a pretty high confidence that the place will make about this much money.

And obviously, I can tell how much it costs because that's what it's listed for online. Do the math and figure out—it’s just—it’s called a pro forma financial analysis.

Do the math. I have actually built software at this point to do pro forma financial analysis—shoutout BNBCalc. And just run the numbers and get an idea of how much it's going to make and how much profit it'll have for the investors.

Kate: Yeah, no, that makes a lot of sense.

Jeremy: I know talking about numbers and profit is not Kate's favorite—favorite. That's where she gets disinterested.

Kate: No. I'm like, "Numbers and profits," and I’m like

Jeremy: She would have rather I said, like, "How did I know it’s good? Because it was so pretty."

Kate: No, that's not true. That's not true. That's not true. "Listen, I think that everybody brings different strengths to a relationship, a friendship, a work partnership." Let me tell you, I bring a lot of strengths, and they are not crunching the numbers.

Jeremy: Hey that's my job.

Kate: So, you got your friends. They were down. Okay, so now tell me—how do you then, once you have the house—how do you then manage the house? And how do you ensure that it's going to be profitable? And how do you manage those relationships?

Because you, I think, are the property manager for that house that you invested in with X amount of friends.

Jeremy: Yeah, at this point—so that was—even that was two years ago, and it's crazy to think how far we've come in two years. And there's—I mean, there's a lot of—how Kate has been to, like, many of them. But there's even a lot more that have been stood up, and I haven’t even really been to that.

Like, some of them I set up completely remotely at this point. So, yeah, at this point, I'm accustomed to doing pretty much—like, we closed on the last house we bought.

Kate and I were in Paris, France, yeah, when we closed on the home. It got rented a month later. So, it got renovated, furnished while Kate and I were in Europe. It got set up, and Kate was mad at me for working while I was in Europe, but I was literally—

Kate: Jeremy worked… Let's just say this—every girl's dream for a trip to paris.

Jeremy: I was buying a house.

Kate: Jeremy worked the entire time. When they say "passive income," trust me, guys, there is no such thing as passive income.

Jeremy: All right, that's—I think that's true. And Kate took the time literally off her job, whereas I was like, "Oh, I'm gonna go remote work in Europe." So, it was definitely a difference in our Paris trip.

Kate: Our Paris trip was a whole other situation because I don't—so what happened was Jeremy's passport ended up being not eligible to travel. So we—so, whatever—we were supposed to leave a week prior, which is, I think, when you had blocked off your calendar.

Jeremy: Yeah.

Kate: And then what happened was, we ended up leaving a week later because we got to the airport, and we were initially supposed to fly out, and they were like, "You actually can't travel today. Your passport expires in less than three months."

Jeremy: And, you know, yeah, a tangible tip for you guys—not short-term rental related, but check your passport expiration date when you go out of the country. Yeah, that was something I had to learn the hard way.

If your passport doesn't have a certain month period of eligibility left on it, you can't go to certain countries. So, I learned that the hard way. But essentially, all that made it happen was we had to leave a week later.

But yeah, I literally have a benefit to being self-employed because, like, I don't—also, at this point, I don't only do Airbnb investing. I also have a software business. I have a coaching program, so, like, people block times with me.

Kate: Yeah, so you were able to block off your own calendar.

Jeremy: So, yeah, I blocked off the week that we were supposed to go, but then we didn’t go that week. So the next week, I had things on my calendar. So, I'm so sorry. Yeah, honey, I was at a—

Kate: it was fine. It was fine because he got another property. Okay, so I want to do some rapid-fire questions. Okay. So, quick answers kind of thing.

Jeremy: To answer your question, how do I do things completely remote—

Kate: I didn’t—I don’t think I asked that.

Jeremy: Oh. Like, how do you do things from afar?

Kate: Well, we can—I can ask you that. Apparently, Jeremy wants to answer it.

Jeremy: No, you're in charge. Sorry. Sorry.

Kate: No, that’s a good question. Let’s add that in.

Jeremy: All right. Okay, if you insist.

Kate: Yeah, I am insisting.

Jeremy: So, you have a virtual operation, and you have an in-person operation. A virtual operation for short-term rentals is guest communication, ordering supplies, dealing with the calendars.

So, I have a team of virtual assistants in the Philippines who is in charge of guest communication.

Kate: Okay, but let me slow you down. When did you decide that it was a good time to hire virtual assistants? Because for a while, you were doing it on your own.

Jeremy: I was. I was, and I will admit that I was doing that, and that was really in the thick of things when I was physically setting up properties too. Like, I was literally going house to house. Kate would come for a lot of them, and actually, a lot of times, I was doing physical work with my hands on the house too.

Yeah, I think when I got to 13 listings—it’s probably like May of 2021—I think I just had a realization at some point where I was like, "Alright, first of all, this is the last house. I am not going to do another house until my business—this is, for better or worse, automated."

And I knew that I needed a team—a virtual team…

Kate: because at that time, you had—so basically, to back it up for people—so when we were talking earlier in this podcast about Lake George, like St. George, the prop—the lake house that we set up in 2020, 2021. Okay, so can you explain to people what happened from 2021 until now?

So, let’s go, like, rapid fire. Like, 2021—you, at that time, had your family’s home, and then you had your group purchase, and then what happened?

Jeremy: And then I had several properties that I was managing.

Kate: Yeah. But so what happened?

Jeremy: So we did St. George, and the property did great. Got it up, started getting booked. So, my group of friends—my group of friend-vestors—well, that was the first time I've actually ever said that word.

Yeah, friend-vestors. Was stoked. They were super happy and wanted to do more. So, decided that the next place we would buy—at that point, the lake—unfortunately, the numbers stopped working at the lake, so we had to go somewhere else.

And it was—we wanted to try somewhere else out. So then we did Florida. So, we did Florida in October of 2021. Kate was there for that. She drew a mural.

Kate: Yeah.

Jeremy: And that went really well too. Got that set up. It was cool. The weather was incredible.

Kate: So then we were like, "Let’s do another. Let’s do another."

Jeremy: Let’s do another. And then set up and then did another. And at that point, Florida started becoming—actually went from Florida and then did one in the Smoky Mountains.

Kate has actually never been to that one. And then did another one in Florida. And keep in mind, while doing this—so these are properties we bought—but also was just adding arbitrage properties too.

But for arbitrage, all you got to do is throw in furniture. Like, you don’t have to actually renovate the home, so you really don’t actually have to be there because you just need furniture assemblers.

Whereas, when you buy the home, you actually do—we do a lot of renovations on them. Which…

Kate: okay, so yes. So, what is happening moving forward now? nSo, you have a lot of properties with friends, right? Like, co-investments? Or you have a few?

Jeremy: Yeah, I have several.

Kate: And now, where is your mindset? You want to do something, like, individual?

Jeremy: Yeah, the thing is—I, the reasons I couldn't—in a perfect world, I would have just—I would have just come out the womb buying my own houses. I would have done that as a baby. Yeah, in a perfect world.

Kate: As a little baby.

Jeremy: As a little baby, like the little E-Trade baby, except for buying Airbnb properties. But didn’t have the—didn’t have the money, didn’t have the financing. I didn’t get a credit card until I was like 21-ish years old.

Yeah, so that’s a huge component in getting a loan from a bank—is like your length of credit history. Which, at this point, I was 23, 24, so I didn’t have long credit history. So, I couldn’t get a loan personally. So, I had to work with other people and leverage their cash, leverage their financing. And also, it just made it more—definitely made it more enjoyable, right?

Kate: So, let’s talk about it.

Jeremy: But now, I can—now, I actually, knock on wood, I can buy a house myself. So, I’m actually under contract right now to buy a property. Honestly, by the time this probably gets released, hopefully, I’ll have actually closed on the house.

Because I just feel like it’s like—you guys don’t understand—I’ve been doing this for a couple years. I’ve been grinding. Like, blood, sweat, and tears. And I’ve had a dream—even though I’ve bought, at this point, eight houses—I’ve had a dream of just buying my own house.

And this month, it should happen. So, hopefully, by the time you guys hear it, it’s actually happened.

Kate: Yeah, Jeremy’s really excited about getting his own property, which is awesome. And it’s a beautiful house.

Jeremy: So then, I’m gonna do another—right?

Kate: Okay, let’s switch it up because I like the fun—I, these are like more technical questions—but let’s get to the fun questions.

Jeremy: Okay, this is a fun, fun episode.

Kate: Yeah. So, we’ll do some rapid fire, okay?

First question—what’s the craziest or most bizarre experience you’ve had with an Airbnb guest that stayed at one of your properties?

Jeremy: I’ve had a lot of weird things happen. I’ve had traumatic things happen.

Kate: What about the last one? There was one that happened very recently.

Jeremy: The thing is, I have so many guests at this point. Like, I have so many—that’s—when you have 25 listings— Can you give me a hint? I can’t even remember. I wanna—

Kate: One crazy—

Jeremy: I can think of a couple of the last few weeks.

Kate: Just tell me. The one that pops into your mind. It doesn’t have to be your craziest because I’m biased, because I only know a few of them. So, what’s your craziest Airbnb experience?

Jeremy: Okay, the last craziest—So, during COVID, there was a lot. Like, bars weren’t open, there weren’t really many outlets for partying, and a lot of people—what they would do is rent Airbnb properties and have bangers. Fortunately, that’s subdued.

But I did have one instance where a property I managed—they had a Project X-like, an insane party that literally—At the time, I was actually looking—like, I was looking and I was under contract on a house in Florida. And I just packed up my bags, got in the car, and drove up to North Carolina because…

Kate: It was so bad.

Jeremy: Honestly, at the time, I thought it was like the worst thing ever. Like, I literally thought it was like the end of the world. Like, that feeling in my stomach, I remember—I, I like couldn’t breathe. Like, it was—yeah, it was nauseating. It was extremely traumatic.

Kate: It was traumatic too because you were managing a high-profile person.

Jeremy: I was, I was. Yeah, that was definitely a variable. It was something…

Kate: The person that owned the property that he’s renting…

Jeremy: I don’t want to say who it is.

Kate: We don’t have to. Yeah, but she—it was like a celebrity.

Jeremy: Yeah. And she was also a very dramatic person. Like, literally, that’s what her celebrityness was. Yeah, a dramatic human being. So she, honestly—and she, to be frank, wasn’t even as dramatic as one of her family members, who was, like, so dramatic.

Okay, but that was an extreme situation. I was like—this isn’t—I just remember thinking, because I’m, like, in my own, like, my stomach is—it feels like an endless pit. And I was just like, "Oh my God, this is nuts."

Kate: Okay, so let’s go through—give me quickly, like, some of the details.

Jeremy: I’m not a dramatic person.

Kate: Why was it—why was this project—why are you classifying this party as a Project X party?

Jeremy; First of all, I personally have videos. Yeah. They have not been shared, and I promise I will not share them.

Kate: But wait, I’ve never seen the videos.

Jeremy: I keep them to myself. I don’t even know where they are.

Kate: Wait, I want to see them!

Jeremy: I will show you. It looks like I’m showing Kate the videos. First of all, it looked like—I’ll just say—you had, like, people jumping from, like, the rafters and other people catching them.

Kate: They were like gunshots.

Jeremy: So that—yeah. Physically seeing it there was one. Another was I called the local sheriffs, and I was like, "Hey, do you guys have a report of this?" And they’re like, "Oh yeah, we have a report. Yeah, we had police go there, like, multiple times." I’m like, "Why didn’t they stop the party?"

And they’re like, "I don’t know. It just says here because they were repelled by gunshot bullets." And I was like, "What?" And then my heart and my stomach even sank even farther because I’m thinking cops got shot. Okay, sorry. Not funny.

Kate: That’s crazy. Okay, next rapid-fire question. What is the most unusual or memorable request a guest has ever made during their stay?

Jeremy: Unusual or memorable request—is this something specific you’re asking about?

Kate: No, this is top of mind.

Jeremy: This is top of mind?

Kate: Yeah, I’m just like—I don’t know.

Jeremy: Oh, okay. I was like, "Are you asking me something specific?" Okay, like, that you know about?

Kate: No.

Jeremy: Unusual request. See, the thing is, once—I’ve just had so many guests at this point, like, it’s just—there’s so many things to think of.

But I’ll just say one group—they didn’t necessarily request this, but they booked the house to film, like, what they said was, like, an indie film.

Kate: Oh, God.

Jeremy: And which I was like, "Oh wow, that’s really cool. Make sure—send it over, that sounds fun." And then, it turned out that they actually shot…

Kate: An adult film?

Jeremy: Lke, an adult film, like, a pornography at the property.

Kate: Yeah, that’s true. That did happen. That was crazy. And you just had something recently like that, Jeremy. We won’t say it, like, in detail, but basically, Jeremy got a very graphic video sent to him the other day over Airbnb messenger. That was—

Jeremy: Oh yeah, yeah. It was a guest—"Thank you guys for the property. Like, I used it to film an OnlyFans, like, photo shoot."

Kate: Yeah.

Jeremy: "I hope you guys like it."

Kate: Yeah, and she, like, sent it to them.

Jeremy: Yeah, I saw the—file. I don’t really try to open the Airbnb app and look at messages at this point.

Kate: Yeah. You have people that are doing it for you.

Jeremy: So I got it screenshotted and sent to me, and I was like, "Oh crap."

Kate: And then, that was the only time Jeremy hasn’t let me, like, see his phone. I was like, "Let me see!"

Jeremy: I was like "I don’t—you don’t want to see this."

Kate: Yeah. Okay, next question. What is the most unexpected thing that you have learned from Airbnb?

Jeremy: Unexpected? I would definitely say, with Airbnb, to expect the unexpected. Like, anything that can go wrong will go wrong is the mentality I have.

Like, for instance, whenever you buy a house, I have the belief now that pretty much every system in the house is going—because, like, a lot of these houses I buy are rural houses that no one's lived in for a long time.

So, this past weekend, for example, the water heater went out at the newest lake house property. And it was a holiday. It was Labor Day.

Kate: Yeah.

Jeremy: So there was literally no—and this is a super rural area—so there was no plumber who was willing to go out and replace the water heater. And that's just the type of thing. Expect—it’s expect—I should expect the unexpected. What was your question?

Kate: It’s just, what have you learned? So, it's basically like, you have so much random sht happen that you're, like, constantly learning.

Jeremy: Like, random new things are gonna happen. Yeah, like, things are gonna happen that, at this point, it's like something new, unique that happens, I'm not, like, in shock by it. Yeah, I'm like, "Oh, okay. All right, on to the next one."

Kate: Okay, so this is my next question. This is personal, guys. So, Jeremy, as somebody that decorates homes for a living…

Jeremy: This is personal.

Kate: I knew this would be personal. How do you feel about me decorating our apartment together? Our home.

Jeremy: Honey, darling.

Kate: And, guys, just to clarify here—I have a design background. And this is how crazy he gets. Yeah, tell me.

Jeremy: I don't think it's crazy. Yeah, so I do create these experiences, these short-term rentals. So I have a pretty—I don't want to say like I'm an interior designer, but I feel like I'm good at it.

And also, I have a pretty good thought for functionality, whereas I would say Kate—I love her to death—I would say functionality is not her strong point.

Kate: That's actually—guys, let me just clarify—that's actually not true. The problem is that Jeremy has never seen me create a space before. And remember when I renovated that closet that we had?

Jeremy: She did a great job with the closet.

Kate: And you, at the time, were like, "Oh, she's functionally off," and I was like, "No, trust me. I know it's going to be good."

Jeremy: She did a good job with the closet.

Kate: So then, I don't understand why you keep saying, "I'm letting you do this against my grudge—my grudges. I'm allowing it. I'm giving you the green light." He's such, like, a little control freak over this whole situation.

Jeremy: I'm just trying to do my office. That's the one thing.

Kate: No, we're not putting black up in the office. Jeremy wants, like, a full black wall. I'm like—

Jeremy: "I want to make a studio for you guys. I want to literally make a recording studio.

Kate: But look at, this is beautiful and white with plants and—"

Jeremy: Yeah, but it also helps to have one in your apartment. I'll still be here, don't worry.

Kate: That's going to be part of our—don't worry, we're going to be making—because I want to be able to film stuff too. So, we're going to make—we have our set, the stage of our new apartment.

Jeremy: Kate's very excited about our new apartment.

Kate: I'm so excited.

Jeremy: She would only let us get an apartment that had a wooden beam that came from the top.

Kate: Listen, I have had this goal of having a loft-style apartment in my head for years. And, like, personally, I haven't had my own apartment since pre-COVID because I subleased from, like, different people, lived at my parents' place for a little bit. So, this is, like, my first home.

So, I'm just so excited to be able to decorate it and make it like a really calming and beautiful space.

Jeremy: Kate calls me, like, several times a day right now.

Kate: I've put together…

Jeremy: To talk about the design, setting up…

Kate: Listen,listen, I've put together mood boards. I've put together a 3D model of the apartment, which was very—

Jeremy: She's never done any of this for any of my Airbnbs. She's never even—

Kate: Yeah, you don't know what I'm capable of, Jeremy.

Jeremy: I'm excited, and maybe you can use this strength, and you can see—put you to work on maybe the house I'm buying right now or maybe the one we'll do after that. Yeah, now that I know, you're such a—she's literally been creating 3D models for the house.

Honestly, I was shocked when I saw it, and I was like, "Dang, this is actually pretty—because we don't even have the dimensions."

Kate: Yeah.

Jeremy: And I was like, "Actually, it's pretty accurate."

Kate: Yeah, I figured it out.

Jeremy: Did you, like, take our videos and create a 3D model off it? Like, yeah, did you draw it yourself?

Kate: Yeah, I watched a bunch of YouTube videos on how to create a 3D model.

Jeremy: So that's what all you've been doing the last few days?

Kate: I spent probably six hours doing this, guys. And let me tell you, I figured it out.

Jeremy: So, she'll never—she hasn’t done it for the Airbnbs, but for her dream loft apartment, that is when she actually…

Kate: This is why I am a firm believer that you have to visualize the life that you want. And right now, I'm literally visualizing and crafting my new apartment, my new home.

Jeremy: Can you visualize this next vacation house we're gonna buy? But we're gonna also have guests stay there, paying for it…

Kate: The North Carolina one?

Jeremy: I'm not gonna say where I'm doing it, but some—it will be somewhere, I don't know where.

Kate: Yeah, for sure. I can't wait to see that one.

Jeremy: We'll see. Time will tell. Maybe we'll have Kate back, and she'll have done a 3D model for—yeah, an Airbnb property.

Kate: Maybe my next. Oh, that'd be fun. Yeah, I should do that.

Jeremy: She can show it. She can pull out the phone.

Kate: But you have screenshots of the 3D—

Jeremy: I do. I can't—it's hard to show on this, but if you look at my Instagram or DM me if you want to see Kate's 3D models, I'll show you them. What other questions do you have, honey?

Kate: Okay, oh, here's a good one. How do you stay up to date on industry trends and what's going on?

Jeremy: I just look at a lot of Airbnb listings. I look at a ton. I look at them all the time. I see what amenities hosts are providing. I see who's killing it. I always am trying to see who's out there making money and what are they doing and how can I do what they're doing—and do better.

I see who the pros are. I go out there. I have a list of Airbnb accounts that I consider, like, my pro list, and I literally look at their listings. I look at where they're investing, what types of properties they're investing in, how they're setting up the properties. And I try to copy and paste it to what I'm doing.

Jeremy: And they try to copy and paste what I'm doing.

Kate: Okay, okay. That makes sense. Okay, so let's talk about this. So, five years from now, where do you see yourself? And then, 10 years from now—like, where can we see Jeremy Warden?

Jeremy: Where do I see us?

Kate: You can talk about—Yeah, if you want to do…

Jeremy: How many kids do we have in five years?

Kate: I don't know. How many kids? Maybe one, two.

Jeremy: Say two would be—yeah, maybe one and a half. Maybe one on the way.

Kate: Yeah.

Jeremy: Yeah, so honestly, like, I'm someone who—I feel like I don't—maybe one of my weaknesses is thinking, like, five years out. Like, I'm definitely very, like, "All right, this is what I'm doing now. This is what I'm doing next."

And I know that if I continue doing what I'm doing for a really long time, it'll be great.

Kate: Yeah. But guys, that's—that's actually—so, okay, that makes sense. And I feel like a lot of people do that, but I also feel like it's so important to plan.

Jeremy: And I've had some mentors I've talked to who say it can be like, "You gotta know what exactly your goal is."

Kate: You don't have to. I actually disagree with that. You don't—you do not have to know exactly what your plan is or what your goal is. But you should have loose ideas of, like, where you see your life going.

Like, for me, it's like—I have a running interview series, right? Like, I used to work in branding. I worked in advertising for six years before I was able to do this. So, like, I could see myself doing multiple things.

Like, I could see my interview series leading me into working in-house at one of the brands that I'm growing a relationship with, which—running community marketing—which would be so cool.

Jeremy: Literally running community marketing.

Kate: I could see myself, like—I could see myself, like, coming out with my own brand or, like, my own product that is really aligned with me and what I love. So, like, those are two specific avenues.

And I could see myself writing a book one day about something fun—and maybe a children's book. I don't know.

Jeremy: Yeah, so.

Kate: But okay, what—like, what could you see yourself doing?

Jeremy: Yeah, I mean, I’ve definitely found a business that I’m passionate about. I like creating these properties. I want to have more of them. Yeah, I want to own—I’ve done arbitrage, I’ve done co-hosting, which has been awesome, which have really allowed me to scale my portfolio, have more employees, have economies of scale, and build my cash flow.

But at this point, I definitely want to buy properties and just continue to do that. So, I think I’ll probably try to buy two a year. So, five years from now, we’ll own 10 more—10 more houses at least. And also, I’ll probably want to try to get into, like, boutique hotels.

And, like, all the 10 houses will—Kate, at this point, we’ll own them together, potentially.

Kate: Yeah. See, technically, our new apartment is—I’m solely on the lease because of this whole thing, so just…

Jeremy: There’s—we don’t have to get into that, but real estate, you gotta do things in real estate. Uh, whatever, let’s—that’s a conversation for another day. Yeah, but that’s a fun five years from now if you’re potentially—where things are going—these houses that I’m buying now are not my houses. They’re our houses.

Kate: Yeah.

Jeremy: And—How’s—did you blush?

Kate: But then I smiled. I would love the—but the thing is with me is, like, eventually I want to have, like, our own properties that people don’t stay in.

Jeremy: No, that’s totally

Kate: So, hopefully that’s part of your plan too.

Jeremy: Sure.

Kate: But I love your goals for Airbnbs, obviously.

Jeremy: Yeah, totally.

Kate: So, do you want to buy a building?

Jeremy: Yeah. So, also, I want to get into larger-scale projects. So, that would be a boutique hotel, a big glamping resort.Those will be things I’ll raise money for because those are gonna be things that cost, like, probably millions or millions of dollars.

Kate: like Under Canvas stuff?

Jeremy: Yeah, that would be awesome. So, to do some large-scale projects—that you guys listening are probably gonna ask—you guys are to—if you guys want to invest in them.

Kate: So, that’s big projects in addition to, like, personal portfolio growth. And then also, I like software. I like building our software company. I like creating tools that help people.

I like that I’m working with others at this point, helping them succeed.

Kate: Yeah, I want to talk about that. Okay, so you want to build out your software company, which I think is so cool.

Jeremy: Maybe do other software companies? Well, okay, it will be the same thing, but we’ll, like, we’ll, you know, we’ll pivot.

Kate: Yeah, because you guys have such a cool team for your software company that I think has a lot of legs.

Jeremy: Yeah.

Kate: But no, you said something that stood out to me, which was about, like, igniting your community. Do you wanna—so, do you see yourself in five years doing more, like, panel events for people and, like, really creating a community of Airbnb investors? Like, I know you love it—your coaching program.

Jeremy: Yeah. I like people. I definitely like human beings. I like people. Maybe that’s why I also do being in short-term rentals—because it is a hospitality business.

And I like when people are happy, when they’re having a lifelong experience. The thing with our properties is that people have memorable experiences that they’re going to remember for the rest of their lives.

That’s what they tell us. They said, “This will be my grandma.” They send us pictures of their grandma catching a fish on the dock.

Kate: Yeah.

Jeremy: I love that. Like, that does hit—pulls my heartstrings when I see little kids, like, smiling on our boats, like, whatever it may be. I do like that.

And then, for the coaching program, it’s great because ultimately my job is to help the trajectory of someone’s life. Like, short-term rentals changed my life.

When I started, I was working for someone else. I was going into an office—that’s actually not that far from here—every day. I had to be there by 10. And, like, I probably couldn’t—if I left at 5:30 or 6, that was like I was leaving too early.

So, I had to stay there—6, 7—so I didn't really have—if I went on a trip, like, Kate, if we went to Paris, France, I couldn't just block my calendar for a week and say no.

Kate: Because you have your own company.

Jeremy: Yeah, exactly. So, that has been something that I’ve been able to build for myself that has changed my life. I honestly think, to be frank, like, that's helped change your life. Like, me having the time to help you with everything.

Kate: Yeah.

Jeremy: If I didn't have that time and freedom and creativity—or ability to be creative on my end—I probably wouldn't have been able to be very helpful to you.

Kate: Yeah.

Jeremy: And my loved ones. Like, my loved ones—including yourself—but the people around me, like, I can give a lot of time and energy and thought to them in their situations.

Kate: Yeah.

Jeremy: So, that's what I'm doing for others.

Kate: Yeah, you are. You're really good at that. Jeremy is a very good connector of people. He also helps people a lot. You do—you give a lot of, like, mental bandwidth to other people, which is cool.

Jeremy: Yeah, for those who are willing. I mean, for my program, I'm like, "What is your goal and objective?" That's the first question—what do you want and can I help you? That's the first thing. And if you’re like…

Kate: I love it.

Jeremy: I can't, or maybe because it's unclear what you want, or like you want it but you're not going to appreciate the process to getting what you want—I'm not the right person for you. And I say that.

Kate: Yeah. But it's like finding a therapist—you gotta find the right coach. So, some people are a match, and some people are not.

Jeremy: Also, if you guys follow me online, I'm pretty authentic. Like, I'm pretty real. Like, I'm not trying to sell anyone on some fantasy. We live a great, incredible life. Like, we're about to move to a beautiful apartment. Like, we have incredible real estate all over the place.

But, like, I'm not—we're not just living some fake life. Like, we're real human beings. So, I connect with those people, and those are the people who reach out to me, which I love. I freaking love it.

And their goal is a lot of times—they're, you know, maybe they are in a job and they want to get out of it, and they know that short-term rentals are a great way to build an additional income stream to get them out of their job.

And I am uniquely well-suited to help them do that. And I am helping folk do that. I have a bunch of examples already where I've helped folk do that. So, that's—that is what I like. That is awesome.

Like, it means a lot to me to know that I can actually change the trajectory of someone's life and free up their time to do what they want to do on a daily basis.

Kate: Yeah, that's amazing. All right, what should we say for the final wrap of this podcast? What do you want to talk about?

Jeremy: Yeah, so normally what I ask people when I'm the host is—

Kate: Like, switching it up, guys. Jeremy is the host again.

Jeremy: I usually ask people, like, what their pro tip is. What's your tangible pro tip that you can share with our listeners? Do you have one? Do you have a tangible pro tip?

Kate: What do you mean by a tangible pro tip?

Jeremy: Like, a real thing that they can implement in whatever they're doing.

Kate: Okay. Yeah, I feel like I have—so, I feel like I have a few. I think that the one thing that has always helped me is consistency, and just being consistent in what you want to do.

If you really enjoy doing something, then just implement consistency in your life with that one thing. Do it over and over again, and eventually, you'll get better—or it could lead into something else.

But yeah, I think consistency and healthy aspects of your life are so important, whether it's career or your hobbies. Like for me, I've been so consistent with my running. Like, my entire life, I've liked running.

And then I started thinking a few weeks ago—I was like, "I love running, and I love running with other people, so what if I started doing an interview series online?" And that's when my running interview started.

At first, it was like, "Is this embarrassing? Is it?"

Jeremy: That's good to adjust the framework a little bit.

Kate: Yeah, yeah. But really, for anything that I've ever had success in, it has come down to not being the smartest, not being the best, but really just being the most consistent.

So, I think that's my pro tip to everybody: if you really love something, be the most consistent at it. Just keep showing up for yourself every day.

Jeremy: Beautiful. Are you gonna ask me what is a quote that I live by?

Kate: Yeah. What is a quote that you live by, Jeremy?

Jeremy: "You miss every shot that you don't take."

Kate: That's true.

Jeremy: For those listening on Spotify. I just kissed her.

Kate: [Laughter] For those listening on Spotify, I was just kissed.

Jeremy: But yeah, I would say a pro tip that—or something that I try to do—is don't overthink things. Like, I think a lot of people…

Kate: Like me, I'm an overthinker.

Jeremy: Kate's an overthinker.

Kate: I'm not an overthinker. I'm a spiraler. So, I go from overthinking into this endless wormhole down my brain, and I'm like—I think of every single—I don't know, I'm obsessed with the concept of how you're being perceived.

Jeremy: She is.

Kate: I'm like, "How am I being perceived right now?" That's a really interesting thing to think about that you guys honestly shouldn't spend that much time thinking about because it's—let me tell you.

Jeremy: She does social media for a living.

Kate: Yeah.

Jeremy: Whereas, to be frank, I don't really think about that, like, at all. Like, I—for example, with my business, I just think, "All right, what are my goals? Let's get them done."

I don't overthink it. I do lie in bed, and I have thoughts that are creative and, "Oh, I should do this, I should do this." But I just do it. I write it down on my list. I guess my tangible tip is: make a list of things and just do them.

Don't overthink it. Don't have—don't have analysis paralysis. I think a lot of people, they tend to, like—they need everything to work perfectly, and if it doesn't work perfectly, they think of it as a failure.

And I see that a lot of times with folk who are wanting to do a deal. You don't have to buy your first property if that's going to be a huge life make-or-break investment for you.

From a short-term rental standpoint, rent a property. If you don't even want to rent it, try to manage it for somebody. Try to co-host. And just do it. If you want to co-host, all right, what are the steps I need?

If I want a rental arbitrage, how do I get in front of landlords? Like, just think of it one thing at a time and just execute on it. And that's the only way you're going to get going towards your ultimate goal—if you decide on the path you want to take and you start walking.

If you don't lace up the shoes and get going down the road, how are you ever going to get to your destination? Just because you don't have a car or a private jet to take you to your destination doesn't mean you shouldn't try to get there.

You should be like Bryce Garris and lace up your sneakers.

Kate: I love that guy.

Jeremy: Shoutout, shoutout.

Jeremy: Yeah, we had Bryce a few weeks ago. Watch that episode. It's really funny. And then Kate actually had him on her running interview series.

Kate: Yeah, he's so great. I don't know if anybody could be like him, though. He is, like, a different type.

Jeremy: I know. I was just saying walking.

Kate: Yeah. But that guy is literally walking across the country right now. Yeah, he's camping in random places, staying with strangers. It's very entertaining.

Jeremy: Yeah. But my point being—yeah, it's just if you have a goal, don't switch between 10 different goals. Just set your path, set your trajectory, and make it happen.

Kate: Yeah. You can have multiple goals, I think, but figure out what lights your soul on fire. And if there's one specific thing out of those many goals that you've been testing out, run with that sht.

Jeremy: Then test them out, but just—yeah, just do it. My point is, I do think people overthink, or maybe they're gonna just do—they're gonna watch, learn about every side hustle online.

Kate: Just do it.

Jeremy: Because a lot of people, your goal is probably to get out of the nine-to-five hustle, out of that struggle.

Kate: Which is a great thing to get the fck out of.

Jeremy: Yeah, as two people here who have now gotten out of it. I am good at getting people out of it. I'm just gonna be fcking honest. I'm really good at getting people out of it. I have a case study right in front of me. I'm good at getting people out of their nine-to-five.

I don't know what—I mean, I'm good at some other things too, but that's something I've—I think I've proven. But, uh, yeah, guys, just take action. Make it happen.

Kate: Okay, so what can people stay tuned for? So, what's the next podcast episode?

Jeremy: Yeah, so we have some really cool people I've been interviewing. This podcast, generally speaking, is interviewing people full-time in the field who are pros. They're the best at it.

By listening to conversations with those who are doing this full-time—they're the LeBron James's of— Dude, I'm not going to say I'm the LeBron James. That would be way—I'm just not going to say it. Whatever.

Kate: These are people that are really good in investing.

Jeremy: Okay, so listen to us. Listen to my other episodes. We share markets, we share data, we share tax tips—like, everything.

Kate: A lot of good info, guys. And if you want Jeremy to interview me, just send us—

Jeremy: yeah, yeah—and let us know. I'm always open to also feedback from people and comments. Like, I do what the people want, so I'm—the world is me. I am your puppet.

Let me know what you want me to do. And I love you guys, and thank you so much for listening.

It really does mean a lot that you guys are along for this journey. I love when I talk to folk, and they're like, "Hey, I've been listening to you or following you for the last year and a half, and you've given me the idea to do X."

Like, that literally lights me up too. So, I really appreciate you guys listening, and stay tuned. We have really great folk on this podcast. Anything I can be helpful with, give me a holler.

But stay tuned. Until next time, hit that subscribe button, hit that follow button.

If you're listening on Spotify, please hit it with that five star. Really, just do anything you can to help this reach more people, and I would really appreciate that.

As always—Kate, any last words?

Kate: Any last words? No, but love you guys. This has been so fun.

Jeremy: Yeah, we'll be back, guys. Until next time. Yeah, until next time.