In today’s Behind the Host episode of the Boostly Podcast, we welcome back Kyle Stanley, an experienced short-term rental investor, entrepreneur, and the founder of The Fearless Investor. Kyle has built a thriving STR business, focusing on high-performing, uniquely themed properties that stand out in competitive markets.
In this episode, he shares the story of one of his latest investments—a Notre Dame-themed rental near the university that rakes in up to $10K in a single weekend!
[00:00:00] Liam: Hi, welcome to the Boostly podcast. This is the podcast that gives hosts the tools, the tactics, the training, and most importantly, the confidence. So you can go out there and get more direct bookings. We do a behind the host special on this podcast, where we dive into different hosts, uh, people who train other people in the industry, people who have got experience and the people who can help you on your journey today, we've got a special guest.
[00:00:22] Liam: We've got Kyle Stanley. Kyle has been on the podcast before. Uh, Both with Mark and with myself, and he's a regular here, so welcome back, Kyle. Thank you for joining us.
[00:00:32] Kyle: Yeah, Liam. Awesome to be on, man. I hope we can have some fun talking about this property today.
[00:00:37] Liam: Oh, I'm excited to dive into it. And, you know, just welcome back.
[00:00:41] Liam: And for the people who don't know who you are, Kyle, and I hope there's not many of them, but for people who don't, can you introduce yourself and share a bit about your background, like an elevator pitch?
[00:00:52] Kyle: Yeah, I mean, um, started doing short term rentals right after I got into real estate in 2019, and had been a serial entrepreneur, a failing serial entrepreneur up until that time.
Meet Kyle Stanley and his short term rental journey
[00:01:03] Kyle: Um, finally invested in myself in the real estate game, started flipping houses. Held on to my second flip as a short term rental in Fresno, California, where a lot of people were like, What? You're going to do a short term rental, vacation rental in Fresno? I was like, No, it's not a vacation rental. It's a short term rental.
[00:01:19] Kyle: So that tripled my profits compared to a long term rental. That was in 2019. And then I was off to the races, started doing the arbitrage model, started doing the co hosting model. I ended up getting to right around 70 units, a combination of, uh, ones that I own, plus ones that I was managing for other people.
[00:01:38] Kyle: and then took a pretty major step back from that model to then just start owning more properties in the last couple of years. And I've been very, uh, you know, I would say detached from the management company because I've been focused a lot on just my own, own portfolio and, uh, making some banger properties like, uh, the one that we're going to talk about today.
[00:01:58] Kyle: So yeah, that's kind of the background there. And then The Fearless Investors are the name of our channel, the name of our brand. I say ours because I have my good friend and partner. Hi, Lama, Kenny, doing some stuff with me. He shows people how to buy properties. He's bought over 200 doors in the last three years doing creative finance, which is just amazing.
[00:02:19] Kyle: and so I love talking about operations. He loves talking about the set, you know, buying properties and it's, it's a good combo.
[00:02:26] Liam: So Kyle, we've got, I know you've come on here to discuss, you've got amazing property that you've invested in. As you say, you've been focusing on those properties.
[00:02:35] Liam: Can you tell us a bit about this property and what made it a deal that stood out and what kind of experience and lessons you put into this, this, uh, this project?
The Notre Dame themed property and why it stands out
[00:02:45] Kyle: Yeah, this one was really cool because my wife and I, we were in Hawaii on vacation when this one came across our desk and Liam, I'm not the guy that does like 50 deals a year, I do like 2 to 3 quality deals per year and that's like, that's, that's what I hang my hat on and so this one, we were like, we need to get another house and literally within hours, my phone is ringing from a good friend of mine and he's like, hey, I found this place in South Bend, Indiana, it's close to Notre Dame.
[00:03:12] Kyle: And I have no idea what I'm doing. Can I pick your brain? I'm going to buy it. It's a really good deal. And so I started looking at this thing and it's, it's 4, 800 square feet and it's right by Notre Dame. And when I'm looking at all these properties in the area, I'm like, These people like are missing out on a ton of income and i'm afraid that my friend's going to do the same thing So I told him I was like listen I can I can like you can pick my brain if you want But I would love to partner with you on this and my wife is the interior designer I know what i'm doing And so, you know, I brought my piece of the value to that deal and he was like, yeah 100 percent so we partnered on this, uh own it 50 50 and My wife just went to town on this thing.
[00:03:52] Kyle: I told her I said, I'm assuming you're gonna link this property in the description. People need to go see this. They'll see it as soon as they click on it. But I told her, I was like, I want you to pretend like the Notre Dame leprechaun went in there and just vomited all over this entire house.
[00:04:07] Kyle: So it, yeah, it is green and gold, and navy, blue and gold, and it's, it's everything. Notre Dame. Um, that we, uh, we ran into a really special one and I can tell you the numbers, uh, on it were. Outrageous. We bought it for 185. We put in 200, 000 into the renovations, another 25, 000, uh, into furnishings. And so we were all in right around, what is that?
[00:04:33] Kyle: The like five ish mark. Um, and so, I mean, it ended up not, not even right. Like that four, four 40 right around there. Uh, it re, it rent, uh, refinanced for 7. 34. Wow. So we got all of our money back and then some, and, uh, now we have this just incredible property that, by the way, you know, during football season, on the weekends, during home games, is made between, uh, As little as 5, 000 for a two day stay to as much as 10, 000 for a three night stay during football season.
[00:05:07] Liam: I mean, as we say, we'll link it underneath, but for, for those of you on the audio, you'll have to, when you're not driving and you can pull over, go and check out this link, because even before we hit record on this, I was saying that I've taken some inspirational ideas around stuff, which, uh, which you do for this property, which we'll dive into.
[00:05:23] Liam: And what I love about it is it's very clear about what it is. Like, obviously you're going after the football market there. I mean, it even says fighting Irish on, on one of the walls, which is, uh, you know, it's, it's, it's amazing. And it's very, very clear. It stands out. So just backing up a little bit.
[00:05:45] Liam: So what made you so confident in that particular market? Was it just that other hosts, as you say, one doing what they could be doing, or was it a market which was emerging? How, how come you were so confident in it?
Why niching down creates higher profits
[00:06:00] Kyle: Well, I mean, you know, you look at the air DNA numbers, right? You start off and this is my first deal in a new market.
[00:06:05] Kyle: So I'm always looking at what the potential is. And there was a number of properties that were four bedroom, five bedrooms that didn't have the same kind of space as ours and were not. Niche down and themed like I knew ours was going to be, um, and they were making over 100, 000, uh, for the year in gross.
[00:06:25] Kyle: So that was enough for me to be like, okay, you know, when we first got this deal, we thought, you know, we thought we were going to have probably a 500,000 property by the time we refinanced it. But luckily for us, one sold down the street right before we closed at seven, it was like 729, and that's what just blew the lid off of our refinance.
[00:06:45] Kyle: And doing those numbers I looked at it and said, you know, that's like four thousand dollars of cash flow after you refinance this thing This is gonna be great. So that was the first piece. The second piece was that kind of confused me was Why are more properties in this area not themed for Notre Dame because it's within a mile We know how the Notre Dame fandom goes and when I started to learn about this town It's a hundred thousand person town and it literally doubles When there's home games for football, there's another a hundred thousand people that will come from out of town to go to a Notre Dame game.
[00:07:20] Kyle: There's, there's fighting Irish fans all over the country. Um, so for that reason, I was like, you know, uh, our realtor who actually has a management company for Airbnb, not a big one, she, she said to me. Um, don't, don't theme it Notre Dame. And I said, why? And she said, because there's other reasons that people come to see this town.
[00:07:44] Kyle: And I said, that's fine. I'm not trying to. Appeal to everyone i'm trying to appeal to very specific people I I want to if you if you don't niche down then you're just you know, you're just not Uh, you're not going to get the results that you want and that's what i've found in short term rentals You try to appeal to everyone you appeal to no one and so For that reason, I was like, yeah, I'm, I'm going all out.
[00:08:06] Kyle: I'm not listening to this person. Um, and you know, we, we, like I said, we've had this up since June. Um, just did the numbers the other day. We've netted over 25, 000 in six months. Um, and I want to say the gross income so far has been 12, 000 per month during that time.
[00:08:26] Liam: Is there any other features? Um, that you were like, Hey, I think this is going to work.
[00:08:31] Liam: Um,
[00:08:31] Kyle: Oh yeah. Oh yeah. I, I, there, there's a ton that I, I'd love to tell you about. So first of all, when we got into contract on this home, we said, you know, since this is the first time that we're doing one in South Bend, I think it would be a good idea for us to go there. When you see photos and you see videos of the place, you get some sort of idea.
Designing the Leprechaun Lounge for ultimate guest experience
[00:08:51] Kyle: But when you go there in person, like the basement. Was massive and as soon as I went down there, I was like, listen, I don't usually promote parties but like This could be a bachelor pad Haven and so we we decided that we were turning the the downstairs into what we now call the Leprechaun Lounge. And what that is, is it's a Irish pub.
[00:09:16] Kyle: So we have the bar. We have, we were thinking about doing a movie theater downstairs, but we found that, you know, uh, there was just going to be too much user air in that. So we just got a big ass TV and said, you know, it's a movie theaters type of feel. Um, we've got the pool table, like you mentioned, the foosball table.
[00:09:34] Kyle: Uh, we've got darts, we've got a poker table, we got all that downstairs, and we just said like, this is going to be if someone, even if they're coming for an away game, they're gonna pay top dollar because they know, hey, I'm not going to a game, but I am going to be in what feels like, you know, the, the bar for Notre Dame.
[00:09:55] Kyle: And so that was why we went all out downstairs. The cool thing that you can't tell unless you read in the description or unless you watch the, uh, the QR code, which is a tour of the entire place. Um, is that it's, it's separate rentable units. So 90 percent of our bookings are the entire house, but you can rent just the top half.
How Kyle maximises revenue with upsells and flexible bookings
[00:10:20] Kyle: And we did that on purpose because of exactly what, uh, you know, Kind of what my realtor had said, like, Oh, you know, there's a lot of different reasons for people to book. Okay, well let's give them a different reason. So what we did on the top half of the house is we just made it really nice furnishings.
[00:10:35] Kyle: Still went with that kind of navy blue and gold theme But there's nothing like really outstanding about notre dame about that So if if we have a last minute booking and someone is just looking to save money and our place is vacant Well, they can book the 2400 square foot three bedroom two bath upstairs And then what's cool about this is once they book Then they get a little notification saying, Hey, you only booked the top half of the house.
[00:11:02] Kyle: Here's a video of the leprechaun lounge downstairs. Would you like to upgrade? And we've had probably about 15 percent of people will upgrade to that because they're like, this is cool. Now I can go downstairs and. Play pool and I can, you know, play, uh, darts and I can bring the boys over and play poker. I can watch the game on the big screen TV.
[00:11:24] Kyle: So it's kind of an upsell for those that only book the top half. Um, and we never have anything competing because we don't, we don't offer just the bottom. We, it's either you book either just the top half of the house or you book the entire thing. Um, and that's been, that's been really cool for us.
[00:11:41] Liam: Kyle, that brings us to the very last question, which is obviously you've, you've had the, um, uh, you know, you've gone through a big journey basically with a management company.
[00:11:51] Liam: You've got the training, you've got the purchasing, you've got the creative finance. What's been the most rewarding part of the journey so far? And what can we expect in the future?
[00:12:01] Kyle: Ooh, that's a good question. the most rewarding is the ability to. To have time freedom for my family.
[00:12:12] Liam: And the cubs
[00:12:13] Kyle: And the cubs
[00:12:13] Kyle: Yes, yes, yes. Well, yeah, that, so I'll say something about that in a second. But you know, uh, two years ago we had our first daughter and leading up to that, that birth. Um, I've, I've just said, you know, what do I want life to look like? And the answer to that was I wanted to be, uh, the type of role model to my daughter that she was going to be inspired by.
[00:12:35] Kyle: And so the idea there was, well. When you're 90 years old and at the end of your life, do you wish you would have made more money or do you wish you would have had more experiences? And the answer is typically more experiences. So, we created a business that has been able to allow our family to not have to have a 9 to 5, not have to be in a certain place in order to do business, but be able to do this remotely.
The long-term rewards of short term rentals
[00:12:59] Kyle: And has given me the time freedom to be able to be dad when I want to be dad, uh, creator, when I want to be creator, real estate investor, when I want to be real estate investor and fills all of those, those needs in my life. But also I know when my daughter is. Going to start being three, four, five years old and starts realizing what dad is doing that she can do the same thing.
[00:13:21] Kyle: She doesn't have to go to college if she doesn't want to. If she does want to, we're going to support that. But this is the, the choices that we have in life. And, and that's, that's a beautiful, beautiful thing. And to your point, um, I'm a huge Cubs fan. And so I started a, a Cubs YouTube channel. And that's a lot of fun to be able to.
[00:13:39] Kyle: Pursue a passion every day and feed that part of my soul. So, um, I would say that's, that's my, my fun side. The rewarding side is definitely the family though.
[00:13:47] Liam: I love it. I absolutely love it. And it inspires me. I hope you, you know, for everyone listening to this, they feel inspired as well and ultimately having that time freedom.
[00:13:56] Liam: And even, and I know people listening to this, some will be on their first property, some will be on their 100th property, but ultimately just having the choice to decide where you're putting your time and attention into and creating things and doing all that is is part of the freedom isn't it? So, um, Kyle, thank you for today.
[00:14:13] Liam: This has been really fun. Uh, the links below this will be the link to the property that we've been discussing. Please do go and check it out. Um, give it a heart while you're there. Give it a like and also go and check out The Fearless Investor training link as well, which is all about, um, creative vendor finance and, um, Kyle, thank you so much for today.
[00:14:33] Liam: I really appreciate you joining. If people want to come and find out more, what's the best way to do so?
[00:14:40] Kyle: Yeah. Go to our Instagram @thefearlessinvestors is probably the best way to do that. And you know, see all of our content there on Instagram and that'll direct you to a bunch of other things that we got going on.
[00:14:52] Liam: That sounds good. So thank you so much. Um, we'll see you on the next one. Hopefully I'll catch up again in a few years. Sounds good, Liam. Thank you. Cheers, bye for now.
