Turn Your Vacation Home Into Cash Flow | Maine and Florida Real Estate

Jeremy Chapman (00:00)
Primarily the lifestyle decision, which I’ve found, you know, the the better your lifestyle, the the higher capacity and better work you can do. But to your to your question, I think I’m usually kind of the one that’s like they have the desire, they wanna do be a snowbird, and they come to me, they’re like, Jeremy, how do we how do we do this? You know, guide us through how are we gonna afford this or can we even afford this? And so I can kind of consult with them, you know, there’s different options as far as renting when you’re not there, as far as where you place your, you know, the certain requirements, but as long as you can potentially pr- place your residency in either place. So there’s tax implications. And so the if you mix up that cocktail of maybe some tax benefits and some rental income, people are often really surprised how affordable I can get them into that snowbirding lifestyle.

Dylan Silver (02:26)
Hey folks, welcome back to the show. Today we’re joined by Jeremy Chapman, investor and entrepreneur, as well as sports entertainment realtor with eXp. He’s also an endurance cyclist and DJ who blends business, adventure, and personal growth into everything he does. Jeremy, thanks for joining us here today.

Jeremy Chapman (02:46)
Hey, thank you so much, Dylan, for having me on here. I’m really excited to be here and I excited for our conversation.

Dylan Silver (02:52)
Great to have you on. You’re a sports and entertainment realtor. What does that encompass?

Jeremy Chapman (02:58)
Well, first of all, just say I love my job and I love the people that I get to work with, both on the client side and through my brokerage. Really love my brokerage and my division. And we basically kind of tailor the real estate buying and selling experience to professional athletes and other high-net-worth individuals that may value privacy and have just kind of different requirements than that of a typical home buyer.

Dylan Silver (03:26)
Now, when you’re working in this segment specifically, how important is it to nurture these client relationships over a long period of time? And are folks typically reaching out to you when they’re ready to buy right then and there?

Jeremy Chapman (03:41)
What a great question. I think that there it’s I’m I’m someone that’s very relational and I’m kind of like long game. So I think that fits in well. This isn’t kind of often one-offs, it’s something it’s like really truly a relationship where you kind of help people and stay with them for for their journey. So it’s it’s very very much relational and very much getting to know people and and if you can really address and take care of their needs, then they end up taking care of of you and st- and staying with you for for the long game.

Dylan Silver (04:19)
Now you’re active in Maine and Miami, is that right?

Jeremy Chapman (04:23)
Yes, I’m I’m active throughout the East Coast, but I have my licensure in Maine and we’ll soon have it in Florida. I really love the South Florida, so many things about it down there. And it’s a really interesting contrast from where I live up here in Maine.

Dylan Silver (04:39)
You know, one of the interesting things about those two markets, right, is that you mentioned the contrast. I imagine there’s also a lot of people who and probably more by the day are looking at how they can divide their time between, you know, Maine and Florida or South Florida.

Jeremy Chapman (05:46)
One hundred percent. Becoming a snowbird myself is something I saw. Some other people, you know, growing up here in Maine do. And they just they come back in the in the spring tan and happy. So it’s you know, it’s great. And then I was down, you know, I was I’ve been in New York a lot, but I’ve been in Miami a bit this winter and going back and forth just just so very interesting. But it’s a excellent point. The the snowbird lifestyle I think got supercharged here with all the remote work and the internet.

Dylan Silver (06:21)
You know, when folks are snowbirding, we haven’t discussed this on the show, I don’t believe. How did they typically handle the time periods when they’re not in their Florida home?

Jeremy Chapman (06:34)
Sure. Well, there’s you know, variety of different ways. You can certainly just kind of you know let it set and but you also have options now, you know, short and midterm rentals, all sorts of like things like PadSplit where you could rent out by the room, for instance. Plus just also kind of the comfort of being able to check on the other property. If you’re in Florida and you wanna look at, you know, your your your Ring door cam or something like that, you’re able to kind of check on your properties through technology a lot easier. So that’s another interesting aspect about that.

Dylan Silver (07:14)
We’ve actually had Atticus, the CEO of PadSplit, Atticus LeBlanc, on the show. And one of the things that you mentioned is there’s so many opportunities for folks to really have their investment turn into a cash flow opportunity when they’re not there. When you’re talking with folks who are snowbirds themselves or considering snowbirding, do they approach it as investors first or second, or is this something that they’re primarily doing because of a lifestyle decision?

Jeremy Chapman (07:44)
Primarily the lifestyle decision, which I’ve found, you know, the the better your lifestyle, the the higher capacity and better work you can do. But to your to your question, I think I’m usually kind of the one that’s like they have the desire, they wanna do be a snowbird, and they come to me, they’re like, Jeremy, how do we how do we do this? You know, guide us through how are we gonna afford this or can we even afford this? And so I can kind of consult with them, you know, there’s different options as far as renting when you’re not there, as far as where you place your, you know, the certain requirements, but as long as you can potentially pr- place your residency in either place. So there’s tax implications. And so the if you mix up that cocktail of maybe some tax benefits and some rental income, people are often really surprised how affordable I can get them into that snowbirding lifestyle.

Dylan Silver (08:38)
There’s a lot that goes in there. You mentioned the tax implications. So it’s it’s a you know, pretty it’s a pretty, I would say, challenging conversation at times if I’m not if I’m not overstepping and saying that because there’s so much that goes into it. It’s not just a matter of, hey, I’m gonna go get a second property and then I’m gonna go live in South Florida. Now you’re looking at, well, which state am I a resident in? Where am I paying taxes? Am I gonna be able to afford this? What am I gonna be doing when the when I’m not there in the property? When you’re having these types of conversations with with folks, what what is the flow? What’s the cadence? And, you know, are they typically wanting to have, you know, multiple perspectives on this and, you know, get their CPA and their attorney involved? What’s the conversation like?

Jeremy Chapman (09:22)
I think that can really depend on the client. But one thing I try to bring to the table, I say, look, you know, if if there’s something you need to buy and it’s a commodity, probably just buy it without thinking, without necessarily enjoying it at the lowest price. But if it’s something you want, you know, these people like to get into especially with the internet now, they like to get involved in the research about things and they like to either depending on the person, you know, get into some of the details and things like that. So one thing I always try to remember to bring is, hey, let’s enjoy this a little bit. This is a big purchase and you wanna kinda have your head on straight. And I find being in a positive mood, especially if they’re, you know, getting into it, enjoying this enjoying the process a little bit, enjoying the journey. And I find that clients that do enjoy that journey often end up at the best destination, so to speak.

Dylan Silver (10:51)
We haven’t had too many folks on our show from Maine, although we have had several. What are you seeing these days in the Maine market as a whole?

Jeremy Chapman (10:59)
Sure. I think Maine is I’m a little biased here, and this is a big a big call, but I would say that Maine in the summer is the number one place to be on Earth. That’s a big one, and it’s coming from a Mainer, so you can take it with a grain of salt, but I think that Maine is just the place that everywhere everyone around, you know, the Northeast region and beyond wants to be. In the summer it’s just it’s cool, it’s green. There are a myriad of outdoor activities to take in and and not to mention just the beauty and the the could go on to the incredible food. So I think Maine is absolutely a a hot place to be considering real estate. It’s a great place in the winter as I highlight a lot. Things are good in the winter. But I feel like Maine really shines in the summer as a destination.

Dylan Silver (11:57)
Now when folks are looking at, you know, summer destinations, Maine specifically, I would say is is it fair to call it an underdog? I don’t know if that’s again, I don’t want to overstep here, but when you think about summer destinations, it could get you know sometimes lost in the stack. Where are you seeing as maybe the most up-and-coming areas of Maine?

Jeremy Chapman (12:17)
Well, I think and to your to your last point there, I think it is becoming more and more recognized you know, everywhere, even globally now. I I think that recognition is maybe it’s coming out of its underdog status into a into kind of a premium premium spot. But as far as like where I see a lot of people you know, placing their attention. It’s always kind of been in the southern part of the state. And Portland is Portland, Maine is a really great city. I grew up going down there and skateboarding, biking, going to restaurants and music. A really great city. That is growing and kind of evolving. The the Roux Institute has been a phenomenal component of that city. And so I see most of the to answer your question, most of it’s kind of been relegated to the s- southern part of the state. But as it’s becoming even more and more popular, more people are coming here to live and to visit, I see them now spreading throughout the rest of the state, which wasn’t really happening as much in the past.

Dylan Silver (13:24)
If if folks are looking at a summer spot in Maine, of course prices will will vary, but what have you seen as a standard, you know, purchase price for a single family home at a vacation destination in Maine?

Jeremy Chapman (13:39)
Sure. I think that there’s a lot of variables. So I don’t know if I could just spit out a a a certain number on a average house, but what I would say is the values and and prices, the market numbers have gone up quite significantly, especially since COVID. It’s the Maine’s become very popular and at times we may not have a huge amount of inventory. So that has kept the prices pretty strong. That being said, and I speak in generalities usually to be relevant, I think that the it got ex- extremely hot during COVID and has it cooled slightly since then, yet remains strong, is is probably what I would say.

Dylan Silver (15:06)
Now you’re an investor yourself a and when you’re looking at deals, whether in Maine or elsewhere, is there anything specific that you’re looking for these days?

Jeremy Chapman (15:16)
Well, I I had been kind of blessed to really get the good timing with a lot of my portfolio, which I’ve since exited out quite handsomely. And I just have one investment property besides my house right now. And that’s doing very well. But I I would say a lot of the numbers and kind of the economics of multifamilies, even here in Maine, have changed. And a lot as you know, as I kind of mentioned, and s- you know, since COVID and and beyond.

Dylan Silver (15:48)
It has been an interesting time for multifamily developers and syndicators and you know fund managers. In Maine, is there a shortage of multifamily housing?

Jeremy Chapman (16:00)
I would say it’s not necessarily easy to to get you know, there isn’t just a plethora of good multifamily investments like there was before there was and kind of it I would say it goes back to that point I made earlier where I feel like the outside you know, out of staters or you know, outside eyes are are going throughout the state, not just in southern Maine and Portland area. They’re going throughout the state. And I think when they did that, they and I don’t blame them, I would have too. They kind of ate up the good deals that that were had and then, you know, increased kind of the demand. So it can be challenging to find the correct multifamily for for an investment for you. But that’s something I I do specialize and know a bit about. So fortunately I’m able to get folks into into into multifamilies and other investments when you may not see just out there on the internet.

Dylan Silver (16:57)
Now, when folks are looking for those types of deals, do you recommend that they really partner with someone who has, you know, substantial experience in that niche? Or you know, if they’ve got the cash to invest, that you know, looking at a larger multifamily deal, you know, could be okay for someone who is a newer investor.

Jeremy Chapman (17:17)
Would definitely say partner with someone, you know, what someone you know, maybe someone that’s in one of all these cohorts and groups online now. You could partner with a a local investor savvy broker like me. And where I if I were to I would look not only on market, but I would, to be honest, you know, speak with that that knowledgeable or savvy person and see are there also, you know, off market opportunities to be considered.

Dylan Silver (17:48)
Yeah, off market can be a huge acquisitions channel. When folks are looking for off market deals specifically, sometimes people don’t necessarily know where to look. And that’s why, you know, having someone like yourself can be so useful because you have the prior relationships with investors and so forth. When you’re finding off market deals, have sellers been open to, you know cash offers and seller financing and maybe some alternative types of offers, or are they only looking for, you know, what they could get if it was, you know, listed on market at this point in time?

Jeremy Chapman (18:23)
Great question. I think it depends on their life situation. Because you get some people that, you know, their their hand is a little bit forced for different reasons. They have to sell. And that cash, no hassle, just cash offer is great. And then someone with a little more time, they kind of really want to squeeze the fruit and get every last drop out of it, may kind of have a different, you know, approach to kind of to meet their needs. That’s why it’s so important to just be open and hon- you know, I feel like it’s best to be just open and honest with your realtor or broker or whoever’s helping you. The more we know, the more we can help.

Dylan Silver (19:03)
Yeah, that that goes a long way. Pivoting here, Jeremy, you’re an endurance cyclist. How’d that come about?

Jeremy Chapman (19:10)
Well, I’ve just always been into long distance hiking and been a off and on biker my whole life. So what happened and around that COVID time is I had less business on my plate and I really dive in and and go into things pretty pretty hardcore. So I got into moved into road biking from mountain biking and I was just talking to someone the other day about this. St- learning to road bike or really getting into road bike when everyone was on lockdown from COVID and the streets were empty was the most incredible yet eerie experience for me.

Dylan Silver (19:52)
I can imagine you’re the only one out there. People are saying, “What are you doing?” Right. We are coming up on time here, Jeremy. Any new projects that you’re working on? And then also anything you’d like to mention directly to our audience.

Jeremy Chapman (20:05)
Well, I’d just like to thank all the people at eXp, in particular sports and entertainment and luxury luxury divisions. I really appreciate you all you guys and I enjoy being at my brokerage. Some new exciting things going on. Absolutely, there always is. I’m gonna be starting a twice-a-month webinar and newsletter, and that’s going to be called Chapman Capital Currents, and I’ll be able to feature. Kind be a a connoisseur or a sommelier of s- of sorts of investments. Mostly real estate related, but also not necessarily. They could be business or other investables. So that kind of came about people just wondering if I would do something like this. And then I think it just it fits it fits a need that I’ve been asked about about what you know what. I wanna learn more about investing and I what sh- what should I invest in? Particularly from athlete segment.

Dylan Silver (21:05)
Yeah. I I that’s it’s huge, right? People definitely need that that guidance and that expert opinion. We are finished with the show here, Jeremy. Thank you so much for your time and thanks for joining us here.

Jeremy Chapman (21:17)
Dylan, it’s been a pleasure, man. Thanks so much. And I appreciate you having me on here.