Unlocking the Secrets of Real Estate: Kelly Lynn Cronin’s Journey

Dylan Silver (00:00.994)
Hey folks, welcome back to the show. Today on the show we have a senior sales executive in the veterinary space and rental properties, cozy spaces in extraordinary places, in places like Alaska, Puerto Rico, and Wisconsin. They’re doing a big deal, 80 acres in Wisconsin. Kelly Lynn Cronin. Kelly, welcome to the show.

Kelly (00:25.156)
Thank you so much for having me.

Dylan Silver (00:27.904)
It’s great to have you on here, Kelly. I always like to start off at the top of the show by asking folks how they got into the real estate space.

Kelly (00:36.974)
think like a lot of people, fell into it. We actually had a house that was on land lease and Indian Reservations land leased this land out and at the time that we needed to sell it, just, it was not gonna sell in a traditional way and…

I rented it for a few years, really figured out that I enjoyed renting, but maybe not on a remote place out in the middle of New Mexico. And when that, when that ended and I really wanted to get into some vacation rentals, some really personalized experiences, I made the same mistake and bought places in incredibly remote areas that we just absolutely fell in love with. And it’s been a struggle, but also one of the best things that we’ve

ever done.

Dylan Silver (01:24.206)
So you would say that you love travel.

Kelly (01:28.138)
Absolutely, yes. And I love the idea of having to travel and having an excuse, a business excuse to travel to the places that make my heart flutter a little.

Dylan Silver (01:39.573)
And it’s a tax write-off, right?

Kelly (01:41.344)
Absolutely. And I don’t know if you’ve ever heard of travel hacking, but if you haven’t, know, go do a little bit of research on travel hacking because that’s really been one of the things that has made this, you know, starting this business and launching this business so incredibly impactful for us is just being able to travel for free on points.

Dylan Silver (02:00.45)
Now, when you got into the rental space, did you have an idea in the back of your mind, hey, we might rent these out, we might turn this into an Airbnb? Did you have people maybe in your sphere of influence, family or friends who were in the real estate space who might have been influencing you one way or another?

Kelly (02:17.92)
No, definitely not. I…

I deep dove a little bit after I started renting our New Mexico house, just in terms of, what are best practices? What should I be doing? And that was a long-term rental. And what I’d say is that deep diving into, you know, different rental podcasts, listening to, you know, bigger pockets and some of those big rental podcasts, I really got the taste for, could I create something that was not only a destination for someone, could I really put hospitality to

work because that really drove me.

And could I do it in a way that was sustainable to my love of travel? And so I would say that I heard a lot of influence, really close to home. honestly, when I told my family and friends, other than my significant other, about wanting to buy an off-grid property in Utah and buying it sight unseen or buying a geodesic dome in Alaska sight unseen, everyone pretty much thought I was insane.

Dylan Silver (03:22.028)
Yeah, I know that feeling.

Kelly (03:22.34)
And so there was a little negativity there. And you know what? That’s OK. Not everyone has to be on board with my dreams.

Dylan Silver (03:31.808)
I’m with you know, I going down this rabbit hole, I had that experience to the nth degree. And what I realized is certain things you kind of have to, like you mentioned, it’s not for everybody. But also some people you curate in your life, like I had a friend group that I’ve now stopped being friends with them, because I realized, if they’re just constantly saying this is a bad idea, what are you doing? What are you doing? And I’m spending, you know, 80 % of my time with them when I’m not working, that’s gonna

seep into the way I think about things. And so I started doing this audit every so often of the people that I choose to have in my life. And I’m like, if they’re not at least critical but supportive, like, I don’t know if that’s going to work, but I support you, then I don’t know if this is going to work for me. But to the flip side, mean, if you have family and they’re like, well, you’re crazy, you kind of got to just let that one go for the ride, I guess. Because I get that. I tell my parents what I’m doing. And they’re like, you’re doing what?

know, moving out to Santo Domingo, can you even speak Spanish? And I’m like, claro que sí, pero yo aprendí anteriormente el año pasado. And they’ll be like, how did you learn Spanish so quickly? I’ll be like, they don’t speak English out there.

Kelly (04:38.872)
Yeah, yeah. And I think honestly, when I found my significant other and he jumped on board with wanting to build a school bus and wanting to travel to our different vacation rentals around the world and wanting to go find this crazy dome house in the middle of Alaska.

You know, I knew I found my person who does have that voice of reason. He has occasionally said, I’m not allowed to buy an additional place until I finish the one that I’ve started. But other than that, he’s all for it.

Dylan Silver (05:12.856)
I want to pivot a bit here, Kelly, and talk about some of the destinations that you’re involved in currently. you have the place in Alaska. Remind me the name of the town.

Kelly (05:23.51)
It’s called Kasilof, Alaska. It’s down in the Kenai Peninsula.

And if you haven’t heard of the Kenai Peninsula, it is the number one and number three salmon river fishing destinations in the world. So it’s incredible fishing. They’ve got halibut fishing. They’ve got seaports. They’ve got all kinds of destination things that you can do. We are one street away from a caribou migration path. And so seeing 150 caribou, you know, come down the street right next to you is pretty amazing. Waking up in the morning, you’re cooking breakfast and watching out your

picture window to watch our moose Natasha walk through the yard. That’s pretty incredible. The northern lights are epic. If you go in the summertime it is light constantly. If you go in the wintertime it’s dark and you can see the northern lights and it’s beautiful and it’s just a cozy space where you can go hide away and do some fun, you know, self-reflection or go learn how to mush some dogs down the Alaskan sled trail.

Dylan Silver (06:23.01)
I know you like to travel because you have that place, Alaska, right? But then you also have Puerto Rico. So polar opposite, Caribbean, right? So how’d you get to Puerto Rico place? Was this another one where you said, really like that area and you decided I’m going to get a rental out there?

Kelly (06:29.816)
Yes. Yes.

Kelly (06:38.18)
Absolutely. Yes, we, my daughter and I decided that we were going to do a couple states. We were going to travel a little bit. We went to Puerto Rico because it was on our list of states. We arrived there and I tend to travel with very little thought or planning. And so

Dylan Silver (06:57.134)
Show up.

Kelly (06:58.06)
We arrived in Puerto Rico, found out that we had a place to stay for the night but didn’t have any plans thereafter, met a family that she really vibe with their kiddo and they said, hey, we’re going to Vieques, Puerto Rico. I’d never heard of that place in my life. And we said, well, we don’t have any plans. Should we come with? And all it took was having a very small herd of free range horses trot in front of us as we got off the ferry. Before we were, we were sold, we were in love with the place.

spent the next two days taking a horseback ride on the beach and seeing Playa Negra the Black Beach and you know.

Effectively like spending all of our time on the seashore and really loving it going to the bio bay and seeing the brightest bio bay in the world It’s just an epic situation and Honestly as we were coming to the end of our two days there we kept seeing Savenda signs for sale signs as you know, speaking Spanish and And in looking at it. I realized that they weren’t that far out of my price point and so I started really looking at different

Dylan Silver (07:56.418)
Yeah. There you go.

Kelly (08:07.156)
places in Puerto Rico that potentially would fit and came upon a really exceptional deal just by setting a low price point and waiting until something came up that was appropriate. What I’ll say is that when I fell into starting the vacation rentals, I fell a little bit hard. I had three different places that over the past two years I had tried to make offers on and had gone really far down the path, had looked at their value ratio, had looked at what they were

going to produce in terms of overall rentals. Had done all the research, had done all of the work on these three places. None of them came to fruition. And then all of them came to fruition within a month of each other.

Dylan Silver (08:48.096)
Mmm. Wow, so this was all over, not just in Puerto Rico.

Kelly (08:53.068)
Yep, had a place in Wisconsin that didn’t work out. We moved on to Vieques and that took forever to negotiate. We moved on to Utah and found a little 250 square foot off-grade tiny home and that worked out and then didn’t work out and then worked out again. And then we had the dome house, the geodesic dome that we found in Kasilof, Alaska, and that took a long time to negotiate as well and all three

Dylan Silver (09:08.355)
Huh.

Kelly (09:22.982)
of those last three properties actually all came to fruition within two months of each other. So that was 2021.

Dylan Silver (09:29.218)
Wow, so what year?

Dylan Silver (09:35.18)
So what was it like putting three deals down within a couple of months? That had to be a lot, right?

Kelly (09:44.632)
It was stressful.

Dylan Silver (09:45.986)
Yeah, I can imagine.

Kelly (09:47.732)
And it led to some interesting situations. It actually led us to purchasing two of them without having ever seen them and purchasing another one on a handshake deal effectively. And so it definitely changed the way that we were looking at them and it changed the overall structure. But thankfully, you know, coming out of veterinary medicine where we just don’t make a lot of money, all of them were very, very low purchase prices. I had found very, you know, income-savvy.

places to try and buy so I was able to still buy all three of them. VEKUS we got for $73,000 but on owner financing. Kasilof we got for $40,000 straight cash and then Utah I got for $17,000 straight cash.

Dylan Silver (10:26.69)
Yeah.

Dylan Silver (10:36.216)
So owner financing, was that something that the seller had proposed or was this something that you came to the table with? So you came to the table with it. I’m assuming you have some type of real estate background or maybe circle that is influencing you to say, we can do a seller finance situation.

Kelly (10:52.578)
So I learned about seller financing from our house in New Mexico when we sold it finally. The only way that that…

that person could purchase coming out of a Pueblo situation was she could only purchase on owner financing. She had no credit whatsoever. She was never gonna get to a point of having credit and she had never owned anything in her lifetime. so looking at that owner financing, which was proposed to me to purchase this really interesting land lease type of situation, that really taught me a lot about what owner financing could do

And then, you know, when I, when I came into this, I knew that I didn’t have a lot of cash to start with. just knew that I had to do it on a shoestring and that I had to keep all my operating cash for any kind of remodels that I needed to do. so if I, if I look at anything that’s a little bit bigger in terms of a purchase price, I always try and pitch owner financing to the, to the seller. And I will tell you that most real estate professionals do not understand what that looks like. So you have to do a lot of education of both

Dylan Silver (11:57.102)
They don’t. Yeah.

Kelly (12:00.916)
the seller and the retail in order to get there and you have to really look at what the seller needs to really identify hey do you know do you want to get out of paying all of your you know your cap gains or do you want to make sure that you don’t have a taxable event or do you want to have you know long-term income from that that financing option and and really tailor the way that you pitch it to what they really evidently need from that sale.

Dylan Silver (12:29.944)
I want to ask you a granular question about seller financing. When you’re making the payments or when you’re proposing it, do you suggest going through like a debt service company like a third party, some type of maybe attorney or whatever type of third party? Or do you say, well, it’s easier to just go direct to the seller?

Kelly (12:49.442)
So I generally talk to the seller directly about it and then we usually utilize and I have what three of these deals, four of these deals under my belt now. For those four deals, I’ve done them through a title company to set up the structured payments.

Dylan Silver (13:07.182)
Will most title companies be aware of what that is and be capable of taking monthly payments? Or is it you have to find a specific one that’s comfortable with creative deals?

Kelly (13:17.582)
So I’ve talked to five title companies at this point about it, and all five have really understood how to set those up.

Dylan Silver (13:23.886)
That’s good. That’s good. I’m a real estate agent. I understand where you’re coming from with the idea like not all I would say maybe even most hope I’m not speaking out of pocket here. Most real estate agents are not really truly familiar or comfortable with the creative space. And it’s almost like a bad word. But I think a lot of these cases like you talk about, you know, being able to finance these deals with someone with limited credit. But also, you know, we’re seeing right now where I’m from in the East C+oast, starter home is

going to be, you know, six to $800,000 plus if you’re lucky. And so in order to qualify, you need to make like $220,000 a year for these homes. So like what other way I mean, maybe alternative housing, but also seller financing, I do want to pivot and ask you about this 80 acre deal in Wisconsin. So that’s a lot for rentals. And you’re breaking it up, I believe you said before hopped on here, 13 or so. How did this deal come about?

Kelly (14:02.243)
Yes.

Kelly (14:23.532)
I was trying to purchase one acre to place a school bus renovation on. I thought that potentially my neighbors here in Milwaukee were sick of seeing the yellow school bus. And so in the process thereof, that one acre deal just did not go through for a variety of reasons. And the realtor on the other side of the one acre deal said, well, that’s not going to go through, but I have this other 80 acres if you want that.

And while I thought it was completely insane, it was in the right area and it was an interesting piece of property. It has a cute little river that runs through it. It has a little pond that it touches. It was pretty near where our families are from. So we thought at the very least we get a little bit of hunting land out of the deal. And then we got there and it was just magic.

It was just magic. So thankfully the seller was totally open to doing that on owner financing. We set up that deal and when we got there, I was just in love with the idea of doing a tree house rental and then.

Started to fall in love with other things as well. Bell tents are so incredibly cute. I hate camping and so anything that is camping with heat and a mattress and a place to shower and a outdoor kitchen is just it’s it speaks to my heart

Dylan Silver (15:49.699)
Yeah.

Kelly (15:51.436)
We really just started developing this idea and other people have jumped on board. I have a friend who does tree house builder camps. If you ever want to check those out, look up relaxy shacks and has agreed to at some point do a tree house builder camp out there and.

I have a friend who puts together buses and has agreed to use that as her staging ground for buses that she’s going to be selling after renovations and and bell tents and all kinds of you know just super fun little kitsch and interesting places that you can stay out in the woods and then this family experience so along the trails we have plans to do giant Jenga and to do you know a giant chessboard and to have a place where you can you know pull down your

easel from a tree and have some art things there to do a beautiful picture of the river running through the land. I think that honestly if you can make a place really interesting to families and really off-grid, can be just so magical for reconnecting people.

Dylan Silver (16:57.066)
I completely agree. would even go one step further with that and saying that because of where we’re at with housing, and it being so, I would say, unaffordable for even like college graduates in many areas of the country. What would not shock me is if we started to see more of these alternative housing as housing, because if people are like, you know, looking at, let’s just call it where I’m from in northern New Jersey.

Kelly (17:19.501)
Yeah.

Dylan Silver (17:25.432)
and they’re looking at how difficult it is to purchase and qualify for those homes. Or they can be living in maybe a more remote area, but they could also get remote work and they get to be in nature without camping. Like they get to see the nature. They get to have all the first world amenities, drinkable water, hot shower, know, Wi-Fi, you know, you have your smartphone and all these things. You’ve got a place to cook. But then you’ve also got nature right there.

I think we might be unlocking a lifestyle that was previously inaccessible to past generations.

Kelly (18:02.276)
think so too. And I think that there has to be that bridge of the gap, right? Like if you are, if you’re someone who’s lived in a city all their life, who may have lived in an apartment, camping sounds pretty atrocious. And you have to all the gear and you have to have, like you have to spend $5,000 to go camping at a $29 camping site these days. The reality is, that,

you know, we’ve all gotten accustomed to a certain way of living. And so how can we make nature a little bit more natural?

and how can we make it a little bit less natural so that people can actually enjoy being out there. I don’t want to sleep on the ground. I’m not going to lie. There’s just no point in my life where sleeping on an air mattress is something that I really want to do. We just tried it this last week when we went on a family road trip and I’m sorry but the rest of the time was in a hotel.

Dylan Silver (18:51.502)
That’s right.

Dylan Silver (18:58.434)
Yeah, that’s right. I’ll just need a Tempur-Pedic in Wisconsin, right? That’s what it’ll shape out to. Kelly, we are coming up on time here. Where can folks go to learn more about your rentals or to maybe get in contact with you?

Kelly (19:01.336)
Yeah.

Kelly (19:13.964)
Absolutely. So we do have a website www.croninscastles.com Cronins with an S, castles.com and We would love to you know, love to connect if you ever see me on social media I am pretty out there I have Instagram and Facebook and Tik Tok and all of the things and you know, just reach out I love to talk to folks about this if you have some interest in trying to do this down the road I did put together

Just a kind of an overview of all of the different things that I had to have in place in order to do vacation rentals as well. That’s on our website.

put it together as a course just because I really felt like I had done all of this leg work that didn’t have to be done. You know, creating the different email paths and creating how you actually put things up on a listing like an OTA and, you know, trying to tell people exactly how to actually value a place to figure out if it’s going to be a halfway decent vacation rental. Dealing with guests, like automatic guest replies. I’m so into automation. just don’t

Dylan Silver (20:16.91)
Sure.

Kelly (20:23.038)
want anyone to do this and have it be a slog. I really want people if you’re interested in doing it to have it just be a click it and forget it and enjoy the place that you just invested in.

Dylan Silver (20:36.896)
I may take you up on that if I end up getting a place overseas, I may say, Hey, I need to automate this. Kelly, thank you so much for coming on the show today. Congrats on your success. And thank you. Thank you for coming on the show here today.

Kelly (20:42.381)
I love it.

Kelly (20:48.94)
Absolutely. Thank you so much for having me. It’s been so much fun.