Cale Delaney runs Mountain to Sea Cabins in the Smoky Mountains and Florida. He left his W2 job in two years after starting short-term rentals, but his wife got stuck in Ecuador for six months during a family medical crisis while he scaled the business. He credits grit, family support, and the Hospitable Hosts community for getting through it.
Questions this video answers
South Florida, just north of Miami.
The Smoky Mountains, Tennessee (primary); additional properties in South Florida.
About six months.
Three children: ages mentioned as three, nine, and twelve.
About two years (left W2 in roughly two years).
Chapters
Hey. Hey. Welcome to the Boostly Podcast. This is the podcast host. The tools, the tactics and the trainings and most importantly, the confidence that you can go out there and get more direct bookings. Today we're going behind the host with a successful and interesting short term rental host who's actually featuring in hospitable hosts too. So if people aren't aware of this, I've got the book holding up. If you can see us on the so we've got Cale Delaney joining us today. He's one of the hosts within the book and we're just going to dive into his business. His business is called Mountain to Sea Cabins and Cottages and we're going to find out what tips we can find from him. So welcome along Kale. Thank you for joining me.
Thank you very much, Liam. And it's a pleasure to be here. You, of course are one of the OGs in the original hospital host, so it's a pleasure to be in the company.
Thank you. Thank you. So why don't you introduce the yourself where your business is in the world and anything else you'd like to share.
Sure. So I live in South Florida, just a little bit north of Miami, and my business is it's primarily in the Smoky Mountains in Tennessee, but we do also have some properties down in South Florida. It's primarily long term rentals though, in South Florida. We do have one short term rental here and then the rest are in the Smoky Mountains in Tennessee. And yeah, we call it, you know, Mountain to Sea Cabins and Cottages because that's kind of what we like to offer. You know, we have our, our mountain properties and we have our, our ocean properties and we're looking to expand on that brand as we, as we grow our portfolio.
Why did you get involved in the Hospitable Hosts project and how does it feel, you know, writing your own chapter?
Yeah, that's awesome. I mean, the reason I joined it really was because of the, I think the community that it offers you access to, you know, people like yourself and the other authors in both books. I mean there's some real, real powerhouses, real successful, you know, giants in the industry in these books. There's people like myself kind of in the middle and you know, there's people, you know, starting out as well that are all a part of this. And everybody has a very similar reason for why they get into short term rentals for the most part. But everybody has a very unique journey and it's really cool to learn and see, you know, how other people have gotten to their point of financial or time freedom through short term rentals. You know, that was my goal in getting into the short term rental game and I've achieved that thankfully. But yeah, it's really the community that the hospitable host offers. And I mean, writing the, the chapter was, it was enjoyable. Honestly, the hardest part for me was really trimming it down. I, I wrote the, I wrote everything in two days and it was more than double the, the allowed word count. So it took a lot of trimming and trying to scrape out pieces and, and still keep the story intact. So that was the most challenging part of it.
What word would you use to describe hospitable hosts? If you had to contain it down to one word, what word would it be?
Inspiring. And I think that's really the intent of the books, is to provide the readers with inspiration to start their own journey or continue their own journey. In fact, just earlier this week, I had somebody reach out to me that had picked up the book and read it and just sent me a note just thanking me for giving them inspiration that day, you know, that they could continue on and do something like that.
Talk us through the journey. How did you go from that first unit to the units that you're on now? And yeah, what were the kind of steps to success along the way?
Yeah, I mean, I was committed once I decided on short term rentals and even a step back from that once I decided on real estate as my, my path to financial freedom. You know, I started out with the goal of I wanted to replace my W2 income, right, so that I could, I could leave that job to get the financial and time freedom which I think most people are looking for. And so I decided on real estate as my, my vehicle for being able to do that. And that's why it started out with short term or long term rentals. And it was just, you know, it was just realizing that it was going to take a lot longer to achieve the goals that I was looking for. And by happenstance, I, I happened to come across another podcast that was talking about short term rentals and the Smoky Mountains in particular. And I just, I mean, it sounded too good to be true. So I google mapped where it was because I didn't even know where the Smoky Mountains were. And then I, I saw it was, you know, 17 hours or so away is a week before Thanksgiving. And we packed up a minivan full of seven people and, and drove out there and, and checked out the area. And, you know, about three weeks later or so, we Were under contract on our first cabin. And you know, from that point, like I said, I was just committed and I knew I was going all in. So it was just a matter of finding the, the right deals and I knew that I'd figure things out as I went.
What was the biggest challenge and how did you overcome it?
Yeah, I think the biggest challenge for me was it was really just a personal, personal challenge that came about unexpectedly. And you know I, I mentioned it in the, in the chapter there, but shortly after I'd gotten started, I think we were, we just bought the first cabin and we were under contract on the second and third and converting that one in Florida from a long term rental into a short term rental. So it, a lot going on still very, very early in the short term rental stage and learning things and we kind of got hit with a pretty big medical issue with, with my wife. Long story short, she was in Ecuador and had to have a procedure that really went awry and she got stuck there for about six months unexpectedly, almost bedridden. And you know, I was still working the W2 at that time of course. And we have three kids including a three year old, nine year old and a 12 year old. And so we kind of get hit with that out of left field and you know, in the midst of all that, everything else going on, growing the short term rental business. And so it took a lot of, it took a lot of grit to, to keep going through that. You know, I think that's one of those things that can really be a showstopper if you don't have, like I mentioned before, if you don't really have a strong reason for, for why you're doing it. But I was, like I said, I was committed and I knew that I, I couldn't stop. I saw the light at the end of the tunnel in terms of what we had started with the real estate and I knew that it was going to, it was going to be getting me to that goal. And so to stop at that point, frankly for me just wasn't an option. So from there it's just, you figure it out. Right. So we, you know, leveraged family and friends both in Ecuador and, and here in the US in different states. We sent our two older kids up up north with our grand, my parents to spend some time there. Yeah, we brought in my father in law from Ecuador to here to help out with the three year old who was around two at the time. So you know, we did everything we could and thankfully after six months or so we were able to get my wife back here to the US but it was still several surgeries that had to happen once she got back here. And so it was very long, long, long process going through all that. But that was probably the hardest thing for me, trying to tackle those, you know, personal issues while trying to build a fledgling, you know, short term rental business.
What would you say is the biggest wow moment or a perception that's changed since you originally started this business?
I think. I think the biggest wow was just seeing how quickly I was able to achieve the financial goals that I had set out with, you know, when I had started or come up with that, hey, you know, real estate, how I'm going to get out of this, this W2 world and set myself up for, for building generational wealth. It was a five year goal. And to me that was like extremely aggressive. And like I said, it happened in less than two years. I mean, a lot less than two years. But I left the W2 in about two years. And that just really blew me away at what was actually possible with this and particularly with short term rentals. I mean, when it comes to cash flow, like if that is what you're looking for, which, you know, most people are, if they're looking to leave their W2 and replace that income, it's hard to beat the cash flow that you can get with short term rentals. And you know, I started out with the long terms and it was small, multifamily, and like I said, it was just going to be a lot of those units to get me where I wanted to be, and it was going to take a long time. And then I stumbled across the short term rentals and lo and behold, it just blew those goals out of the water.
Thank you so much, Kale. And yeah, thanks. I look forward to seeing you at the next wealth conference or online for the network. And so thanks again.
Bye for now.
Having a blast. Gonna get it on the Bruce Lee podcast. Bruce Lee, Like Bruce Lee. Cause it's so hard and the tea is loosely making up those rhymes. Don't write it, just do it loosely.
