Leaving a 30-Year Career for High-Cash-Flowing Short-Term Rentals

0:10Yeah, I've always kind of been of a bungee jumper at heart in a sense. Not that I'm the world's biggest risk taker, but I like I said, I think God gives us certain gifts that are transferable. If you don't know Excel, I can teach it to you. If I don't know PowerPoint, you can teach it to me. Skills are transferable. What's not transferable is the talents that you come with. You know, I can't teach you to be gregarious or love to speak in front of an audience. Those are things that you're born with. So what I tried to do was, okay, there's got to be a way that this recruiting stuff, the reason why I think I've been a good recruiter and and have been able to have teams, you know, global teams and all that is because what you see is what you get.

0:46And I think that if you have the right talent for something, I can help you further those talents. So you can I think it's easier to go from good to great than from mediocre to good. There's a lot of people that are really good out there. They just don't know how how to get that extra gear, get to great. And I take a lot of pride in that and and there's one thing I can take with me of my 30 years in in talent acquisition is that the people that I hired, I hired really good people that were even better than I was and now they're running the show. I look back on my LinkedIn profile and I see Diego and I see Erica and Hannah and folks like that that are now running Latin America talent acquisition and I love to take satisfaction and that I had some small nugget of of you know in that in their growth.

1:28So the the you know the the the the whole transition to real estate what I did was I I it got to a point where I said okay PR get off the pot. All right, you've been thinking about this for so long. — You have no excuse now. You've made enough money. You have your 401k there. When are you going to do this? And I said, I'm going to do this now. And it took my manager coming to me, she was the V the chief HR officer at a big company, wanting to give me yet more responsibility. And I said, you don't understand.

2:00I'm trying to throttle down here. I don't want anymore. You know, that's not really what you know, first of all, I'm a Christian. I'm I'm I'm a husband and I'm a father. Those are the three things that defined me. My work has never defined me. It's just been something that I do. So, I said, how do I how do I transition and how do I tell this lady that not only am I not going to take this you know new and improved role with more reach and scope, but that I'm actually she's given me the nudge to just take the leap.

2:30And I prayed about it for many, many, many months, maybe even years, to find when was my exit ramp, when when was the most propitious time to to leave. And this happened in December 2023. And I said, I think this is it. So after I said, "Yeah, I think I'll I'll think about it. I I may take that." I slept on it, talked to my wife, and she looks at me like, "Come on, really? Really? Is this what you want?" She always slaps me, you know, around a little bit. And and and I said, "No, you're right." So I called her right back. Can we talk in the morning? He goes, "What is it?" And then I resigned on the spot.

3:03— I would have I would I I think I left like $25,000 on the table because had I waited a couple more months, my stock would have hit and I would have gotten some money. But this was a time. This was a time and I said, "Okay, I am going to do it the opposite way. A lot of people look for real estate to you know to to to build it towards something so they can quit their job." — Since I'm older, — soft landing. — Soft landing. I'm older and I had some savings. I said, "All right, let's let's put it to the test. I think this is going to work. Let's do it." And then I — burn the boats.

3:35Burn the boats. And and I said, "But I I don't know how to go about it." And and I and look, trust me, I've looked at a lot of YouTube folks. And if there's one thing I do is I I analyze talent and I I read people well. And And this is not a plug or anything. It's it's the truth. I I've told you before. I came across your thing and there was something different about your spiel that it made me just book a call right away — and I said, "Okay, there's something that this guy's doing that I think is different from what everyone's saying. I think you were ahead of the curve because you were talking about investing in other geographies, not the prototypical, you know, Joshua Tree, Smoky Mountains, that kind of thing." I go, I'm seeing that.

4:15How does he do it? And that's really what piqu my interest and that's when I made the jump. So, I didn't have anything. I had the two cabins, one in Bryson City and one in Maggie Valley, both in North Carolina because that's what I knew. But I knew that, you know, six years later after buying the first one, I wasn't going to be able to cash flow the same way because the world had changed — and and and and rates had gone up and and prices of course, as you know, had gone up. So, how do I make this work? — Yeah. — and and that's really what what sealed it for me when I spoke with you.

4:48I said, I think he's on to something. I'm gonna jump it. — Yeah. Well, first off, it says a lot about Margaret that she was willing to support you and say, you know, you know what you want to do and stand behind you even though she was still working at the time, right? — She still was. She still was working and and that was kind of the, you know, you always have to have a why. I think you asked me in there why I did this or whatnot. — And my why was really to get her out out of her job, which she did this summer. And and it's amazing because soon after that we had our grandkid and it's it's a blessing because now she can hang out and and and be the helicopter grandma, you know, and all that stuff.

5:26So, but she was the one that kind of always sees because because you know, you you're hardwired to want to work and and you know, no, you're in your 50s. How the heck am I going to retire if I quit now? And what are we going to do about medical? God provides. — And if you're healthy, which is the main thing, you you'll you'll figure it out. So, was what this has done for me and I may be, you know, answering questions that you might want to ask is that it's allowed me to also rethink my retirement, you know, status or what I plan to do with retirement.

5:59— Because if I have this money, well, if I have this money coming in from rentals, I don't necessarily have to wait to get more money from retirement. I can do that even that earlier because although I'm going to get a little less by retiring at 62, which I completely plan to do, I can offset any losses by not waiting a little longer by the money that is coming in through my short-term rentals. — So, it's it's a win anyway you look at it. I don't want to give financial advice. That's not what I do. — But, like heck you know this has opened a brand new world of opportunities.

6:33I was able to quit my job. My wife a year later was able to quit hers and I think we're on our way and now it's just to find the funds to keep doing it over and over again because once you get the itch you can't help but scratch. — Yeah, that's funny you bring that up about retirement because I I've had a very similar perspective shift on it. We're trained to think of — working and retirement. It's like two polar opposites like you're either working or you're just sitting there in retirement, you know? It's like you can as I've grown cash flow I realized this is like a income that will be consistent forever.

7:10Like so I I don't actually need to build up this giant nest egg that I'm going to draw on until I die. I have enough income now that — I'm actually good. Like so does that mean you're retired? Well — to me it just means you can do the things that you love doing on a daily basis. And gives you flexibility and there's no age attached to that. It's just really a cash flow number that you get to to where you can support yourself. So — 100%. I don't see it as retirement at all.

7:41I mean, if I had all the money in the world, if I were, you know, Elon Musk, I'd be probably a Walmart greeter just saying hello to people, you know, for free, you know. So, it's not retirement at all. It's just redirecting your energies and your passions to something else, right? And if you're good at it, again, like I always told my daughters, they're all different. One is a marketeteer, one is a wordssmith, she's an editor, and one is a finance person. And they always would come to me since I'm the recruiter saying, "Dad, what do you think I should do?" And I'll be like, "I don't know. Find something that you don't suck at. Find something that you don't that you're great at." And and and you'll always love it.

8:13And it's true. They do. They each love their own lanes that they're in. Because like I said, it's better to be the world's best stitch digger than the worst dog to contract you. So, we're hardwired for certain things. Your job in life should be to find those things that you're hardwired with. If you don't like you know chemistry, you're probably not going to be a chemist or a doctor. If you are really bad with spelling, you're probably not going to be a writer. But if you like spreadsheets and numbers and you save and you know, you're probably going to like finance and accounting. So that's about the extent of the advice that I gave them and then just they pursued their own passions.

8:48So that's what retirement is for me. It's not retirement. It's is it's really redirecting your energies and your your stored energy into something else that you really love doing. I love this. I love, you know, as you know, I'm I'm on the calls that you have you know, every Monday because I don't have all the answers. You know, I used to work for Gallup, the Gallup organization, the polling company, and they used to have a survey question that said, "Would you rather know all the answers to all the questions or would you rather know the experts in the people in those fields that have the answers to the questions?" I submit to you the latter is better is is is to have access to people and learn.

9:26And I think through those calls, we learn a lot because we learn what other people are doing, the successes that they're having, and it makes our journey a lot a lot smoother, a lot easier. — Yeah. Yeah. I I agree and I'm I'm always learning as well and the goal is always just to improve from where you were yesterday. So for you I'd love to hear more and I think the the listeners would love to hear more about the the actual deals that you've done. Like how did you pick then the markets that you've decided on and the types of properties and that sort of thing?

9:57— Yeah. Well, it's always easier to work in your comfort zone, right? So most people by nature would just say, "Well, I know Florida. I live in Florida, by the way, in Orlando, Central Florida, and and you know, to venture outside of that periphereral perimeter, you know, like maybe outside of Jacksonville or South Florida, Miami, it's kind of difficult, right? Because that's an unknown. You don't know anybody there. You don't know the markets really well. Although nowadays, it's a lot easier with, you know, the information that you get on the internet and that kind of thing.

10:29But you know I in my case I just decided you know I didn't know I mean when I had my two cabins that's the reason why I bought them like within 45 minutes of each other is because hey I like it here. We like the mountains. If we make a little money let's do let's do it. But then I got to thinking and I said I'm investing a lot of money in these places that I could otherwise deploy somewhere else that would give me exponential growth on that money cash flow. And when I came across your your program, what it really did for me is it took away that fear because, you know, I tell you, you know, we can use the analyzer tool that we use in the program.

11:04And I went back in time and I plugged in that analyzer into the pro the properties that I had. And I I think I've told you this before, but I was within like $50 of what the analyzer sped out and and told me that that was going to be. I'm like, "This thing works, so I'm not going to worry about the geography. I think if I have a good cleaning crew and I get it that you should leverage your cleaners and your handyman. I get all that. But I was able to bypass that and those fears and trepidation by knowing that this is repeatable. If you know how to analyze them, you know how to spot them and you and you do your due diligence and you're a performer and you look at everything there.

11:40The sky's is the limit. So that said, okay, the whole country is open to me now. Let's go. Now, I had the freedom of not having Zoom calls like I used to, and I love driving, you know. I bought a little hybrid that does 50 miles an hour a gallon. So, I'm all over the place. And I I said, you know, this Kirby guy, he's having a lot of success in Michigan City. Let's go there and and let's check it out. And of course, I had already researched Michigan City. I mean, you mean to tell me that this beach bum from South Florida that you have a beach up there?

12:13Come on. Oh, it's snowing today. — Yeah. Well, I didn't believe it even though I went in the summer. And then I went and I went to Washington Park Beach and I go, "This is a beach. — There's just no salt in the water, but this is a beach. There's a lighthouse. There's a ton of people here. — Why don't more people know about this?" And I I said, "Let's keep it on the down low." But yeah, — I went up there and and and and I looked at a couple of properties and you were nice enough to meet me in person and and and talk me through the whole you know, I I just wanted to make sure that what I was looking at was legit — and and after almost a year being there, the numbers are are chewed up.

12:51I mean that I'm getting what I was supposed to be getting even though I've made some mistakes because I'm still learning the market, right? Like with pricing and all that kind of stuff. So the sky's is the limit. So that's that's one. Then by the same token, I was like, "Okay, well, hey, I'm not going to sit on my butt because if there's one thing I've learned is that when you have something, act quickly." — I think a lot of people fall to, you know, paralysis by analysis. — Yeah. — And they're always wanting to vet, you know, dot the eyes of cross the tees and and and they wait, next thing you know, it got snatched up — and you don't have that property anymore.

13:27So, the one in Michigan City, quite frankly, I put the offer on it without us seeing it. I showed up because I felt confident that it was going to it was going to work out. Yeah. I showed up for the inspection. You know, and and then, you know, that's it. We ran with it. After that, I went ahead and u purchased one in Savannah, Georgia. This is all in the span of three year of one year. Yeah. — Three properties and I'm looking at a fourth. And and Savannah was another market that we like Savannah. It just happens as icing on the cake.

13:59But it's not too terribly far from here. It's in Georgia. Again, a different state, different rules and regulations. But the same thing applies. You plug in your analyzer, you look at the geographies, you look at your comps and all the things that the program teaches and you feel confident that you're making a smart buying decision. And that's working out. It actually it's it surprised me a little bit. I'm going there after this call today, as I mentioned to you, just to put up some Christmas decorations. My wife is great about that. And you know, I mean, it's amazing.

14:29I mean, it's amazing that I can talk about putting Christmas decorations in the middle of December. All my friends are are are working and all that stuff. That's, you know, so, — so that's one. And then just two weeks ago, I I I like Georgia in general. And I decided that, Columbus, Georgia. I mean, Columbus, Georgia, really? I thought it was Ohio, Columbus, the only we had no Columbus, Georgia has for Benning, as you all know, close by. And I said, you know, this is and that's one of the things that we learned in the program.

14:59I'm not going to go over over every detail, but it has a an influx of people on a weekly basis who want to see the 120 folks, 20,000 folks that are stationed there, and you still have a nice historic downtown. So, I found one that was that was in a in a sweet spot that has an additional dwelling unit in the back. And I said, "Man, this is the one. Let's go. Let's do it." So, and I think it's going to do great. So, — yeah, — that's kind of the And I'm now looking at something else. It's crazy. My wife's like, "Aren't you going to slow down?" And we like, "No, because I love this." And and the key I think Kirby is, you know, once you have your portfolio, you can stand back and look at it and say, "Okay, that one may not be performing as much as I as I would like it to.

15:43— Let's play Monopoly. Let that's what I did with the one in Bryson City, my first one I ever bought." Yeah. — It had it had appreciated quite well and it gave me the ability to then spend in and those dollars in other properties down the line. So — you turn it into from lazy equity sitting in your property to cash flow then — on a monthly basis. — Yeah. — 100%. And you know if you look at the you know I think I read somewhere that 90% of the billionaires in the world have become billionaires through real estate. So I know if you I know there's peaks and valleys and dips and all that stuff but if you look at real estate on a on a line you know over 10 years you know it always appreciates.

16:23So we know that we make money through cash flow which is first and foremost extremely important especially in my case. Then you have the depreciation that you can take on your taxes, the appreciation and the principal buy down. So there's a lot of ways that you win in real estate. It's just out of all those ways I think short-term rentals after really looking into everything it's it's the way to go and that's the route that I've chosen. — That's awesome. And and there's a couple things that kind of stood out that I want to emphasize there that you said is number one is around running the numbers and and you know we always emphasize running conservative numbers so that you know in a worst case scenario it still makes sense for you and that deal still performs.

17:05And then the other thing is a lot of people just think of, you know, a property, a short-term rental is going to perform how a short-term rental performs in that market. But you guys have incred you do an incredible job. You design it well, you run it well, you're you're good to your guests, all the things that are they should seem common sense, but a lot of people are just in this to make a buck and it's like I'm just going to do the minimum and try to make as much as possible and you know charge the guests for every little thing and they don't do it the right way and and so the performance suffers as a result.

17:43So, it's incredible how when you do the right thing, you know, and you've run the numbers well, it it just it works, you know, and it it performs really well going forward. — 100%. That's a great point. And I think that, you know, anything worth doing is worth doing well, as the adage goes. I don't think that I'm average. I don't think any of the people that I've met in the program are average. So when we do our performer and we do our due diligence with our analyzer, we look at average and we use those average numbers and we plug them in because the way I see it, that's worst case scenario. I know I'm not going to be average.

18:14— Yeah. — And and you know, I have 299 reviews and 298 299 297 have been five stars and two have been four stars. And sometimes I lose sleep at night because of that. But very competitive. But but but what I but but you're right. I mean you analyze it, you use the numbers, but I think the rest really anyone can do it. If you are if you pay attention to detail, you know, whereas 7 10 years ago, you could just throw a cot and a cooler and have a nice view and you'd cash flow.

18:45Now the world has changed and there's more competition. But still, I mean, in the markets that that were investing, — I look at the comps right around me and I see they're crushing it. They're doing well and I'll be like, "Oh my god, if they would just throw a better couch with maybe a TV there and do something here, we could we could we could really do much better." And I and you know, so I think it's not difficult to do. I think it's repeatable. I think what the program has shown is, you know, the ways that we can, you know, improve the mouse trap, right? And the things and the tweaks that we can make that are going to make us not be average.

19:18But to your point, I am like you. When I when I do my my analysis of any property, I plug in the average to below slightly below average 50th percentile you know, kind of thing so that I know if even if if the worst happened, I would still cash flow and cash flow well. And and so far so good. And the three properties that I've purchased since joining, they're they're right on there. And one is is is is doing better than that. Yeah. So yeah, it's it's not rocket science, man. You just gota and again, it's like we're in a customer service kind of business.

19:52If you like hosting, you know, and if you don't, find somebody that's better than you at it. Maybe get a virtual assistant when you when you get more than three or four, that kind of thing. But I just enjoy it. I manage things myself with the help of some of the systems that you teach in the program — that kind of streamline conversation and all that kind of thing. But I I'm very hands-on and I think that's a recipe for success. Oh.