5 Powerful Strategies for Thriving in Real Estate and Building Wealth

John Harcar (00:01.046)
All right, hey guys, welcome back to our show.

I’m your host, John Harcar. super excited. We’re here today with Caitlin Cucchiella. I said that right. And we’re going to talk about how to live the life you love. Guys, remember here at Investor Fuel, we help real estate investors, entrepreneurs, service providers, really 2 5X their business. And we do that by providing tools and resources to grow the business that you’ve always wanted to grow to live the life you dreamed of, which kind of falls in line with our topic today. So Caitlin, thank you very much for our show.

Caitlin Cucchiella (00:07.922)
Hi guys.

John Harcar (00:33.552)
Welcome to our show.

Caitlin Cucchiella (00:34.524)
Thank you, thank you so much for having me. I can’t wait to get started.

John Harcar (00:39.308)
Yeah, I’m super excited to talk about this because a lot of folks obviously get into business and then the whole goal is to make money, right? But if you’re not doing what you love, you’re going to kind of get burnt out. So I’m excited to talk about that and hear from you about it. But before we talk about and get into the weeds, tell our folks about you, your background, how you got into real estate, and kind of what got you here.

Caitlin Cucchiella (00:44.466)
You

Caitlin Cucchiella (00:47.996)
Absolutely.

Caitlin Cucchiella (00:59.602)
Sure. So my background was actually in college athletics. essentially from a little kid wanted to play for the women’s national team. I wanted my trajectory on the coaching side of things to go to that level. And after I had my two little boys, I realized I shouldn’t probably be on the recruiting trail every single weekend. And I should probably raise my own kids versus everyone else’s from 17 to 23. So I won a few championships coaching college soccer.

John Harcar (01:25.312)
Right?

Caitlin Cucchiella (01:28.754)
played my entire life, played a little bit professionally, and then transitioned to real estate. And I really looked at real estate as the same sort of competitiveness that you’d have in athletics, but now let’s just transition to the market and how do we beat the market and how do I help my clients win the game or win the market? So now I’m a top producer. I’ve been doing it. going into year nine and I’m a top 1 % producer sold about 18 million in 2024.

John Harcar (01:31.491)
Wow.

John Harcar (01:49.547)
bright.

Caitlin Cucchiella (01:58.902)
And I’ve just steadily increased my trajectory every year and I’ve learned something different about real estate every single year. And I love to learn.

John Harcar (02:09.838)
So you were a professional soccer player and you were a soccer coach and doing all that. Why real estate? I mean there was probably a lot of other things that you could have got into that maybe even something that more aligned with the soccer and the sports world but but why real estate?

Caitlin Cucchiella (02:24.22)
So real estate, I would find myself actually in the evening looking at design trends. I would look at prices. I would look at rentals to how much you would have to put down to buy something. And it just always really fascinated me and intrigued me. And for some reason, it gave me this calm at the end of the night. And that’s what I would lean toward was my Pinterest board or designs or houses. So there was real estate.

John Harcar (02:50.418)
it sounds like my wife, before we got into real estate, would always call it house porn. So she would look at the luxury houses on Zell. like, know what, why don’t instead of you just keep looking at it everyday, why don’t we try to start doing that? So I kind of get that part. So you went into traditional real estate, right? You became an agent, got your license.

Caitlin Cucchiella (03:02.354)
Exactly.

Caitlin Cucchiella (03:10.93)
Yes, I took a two week vacation and never took a vacation before. So got my real estate license within two weeks of my vacation and retired from college coaching. And in December, let’s see, I took the test in December of 2016 and January, 2017, I was off to the races.

John Harcar (03:20.887)
Mm-hmm.

John Harcar (03:31.034)
OK, did you know about real estate investing back then or was it just you had a focus on wanting to sell luxury homes or get into traditional?

Caitlin Cucchiella (03:37.01)
Yeah, so not really. I didn’t know the investment side whatsoever in 2017. I knew people were doing it to make passive streams of income, but I myself had no one in my family that had really invested in real estate. had an aunt who had a couple of multifamilies, but nothing we’d ever really talked about growing up.

John Harcar (03:57.472)
OK. Yeah, and that was going to be a question. If you had any prior influence in your life that kind of led you to real estate, because that is sometimes what folks have. So did you join a brokerage, or what did you do?

Caitlin Cucchiella (04:09.36)
I did. was with Coldwell Banker in Saratoga for seven years. And then about a year and a half ago, I switched over to Core Real Estate team, which is a small independently private owned brokerage. And I helped them grow their Saratoga Springs branch.

John Harcar (04:25.038)
What do you think were some of the first challenges that you came across or obstacles or struggles when you got into real estate?

Caitlin Cucchiella (04:31.762)
My first week in real estate, I had a client who looked at a property, wanted to put it in a contract, and they don’t teach you how to do the contract in the real estate course. So I remember my first thought was, I need to get with the best of the best, and I need to learn how they do it, and that’s exactly how I’m gonna do it. So I was at this mentor’s house at 730, and we put a contract together.

John Harcar (04:41.518)
Hahahaha

John Harcar (04:57.814)
That’s awesome. mean, and that’s the best way to do it. Learn from other people’s mistakes. All right. So in this whole journey of your traditional real estate piece of your life, how many total homes have you sold?

Caitlin Cucchiella (05:09.308)
You know, that’s a great question, John. I have no idea, but it’s a lot.

John Harcar (05:14.658)
That’s a good thing. Too many. Too many to count, right?

Caitlin Cucchiella (05:17.008)
even know. I just know every year if I’m doing X amount a million, I know I’m doing good.

John Harcar (05:23.358)
Right, right. So at what point or did you or what point did you turn, like transition to real estate investing or add in real estate investing into what you do?

Caitlin Cucchiella (05:33.01)
So 2021, I bought my first investment property. I had already bought my primary because I knew that was important just from the start. So I had already bought my primary years before that. And I remember in 2021, I said, I want to buy my first investment. I didn’t want to fix her up or I wanted something that was positive cashflow. My mortgage was this and I could bring an X with the rental. And that’s what I did. I started with a condo and it was great.

John Harcar (05:42.926)
Mm-hmm.

Caitlin Cucchiella (06:00.178)
It was only less than five years old. It had one prior owner and I knew that was a good investment in case something went wrong, but yet the outside would be covered.

John Harcar (06:08.032)
Mm-hmm. Right. Got it. And when you bought this property, did you do any rehab to it, or was it just kind of a turnkey situation?

Caitlin Cucchiella (06:16.154)
I didn’t, the only thing I did was I did a little paint, a couple touch-ups, and like I said, it was less than five years old, so it already had the quartz in it, it had upgraded bathrooms, updated kitchen, everything that a renter would want, it already had. Just needed to deep clean, some paint, and we were ready to go.

John Harcar (06:28.728)
Nice.

John Harcar (06:36.482)
Did you have any pains in that first rental?

Caitlin Cucchiella (06:39.65)
Yes, I did have to track down some rent from time to time It was a higher-end unit. So the the rent was a little higher but there was times where I would have to call and say hey, it’s the first of the month where’s my rent and Thankfully, I was able to get it. But you know you have to be Beyond people because their life gets busy your life gets busy and I would have preferred to have the auto pay set up from day one

John Harcar (06:55.33)
Right?

Caitlin Cucchiella (07:06.738)
But those are kind of just the growing pains you go through and sometimes not every client, especially if they’re 1099, can do that. So I was able to secure from that month forward after the first time a certified check moving on from there forward. Never had any more issues from there.

John Harcar (07:10.658)
Mm-hmm.

John Harcar (07:27.768)
Do you think having your real estate license prior to doing any type of investing is a benefit or was a benefit for you?

Caitlin Cucchiella (07:35.792)
Absolutely, I would say the knowledge that you get going on multiple inspections, the things that you understand and become familiar with within a house, to understand that everything really is fixable. It just has set prices and you have to know how much the labor is versus the actual product that you’re fixing or I’ll call it flipping.

John Harcar (07:59.15)
Got it. Okay, and then have you done full flips? Have you done like what type of level of rehab is your comfort level?

Caitlin Cucchiella (08:05.02)
So a few years ago, I would have said I had no comfortability on actually doing a flip. But I will say I did take on the oldest house in Saratoga. It is actually the house I’m sitting in right now. We just won a ton of awards for the Saratoga Showcase of Homes. But we essentially, thank you. We had to bring it down to a lot of the studs. We kept certain things in the home. But this was a challenge, a renovation verse, you know.

John Harcar (08:19.311)
nice.

John Harcar (08:23.554)
Congratulations.

Caitlin Cucchiella (08:34.278)
keeping a lot of the exterior architectural features the same, keeping the wood beams from the 1700s. There’s a lot of details. The floors aren’t always perfectly even, but it was a challenge, but I will say it’s probably one of my most favorite homes and I absolutely love all the hard work that went into it and now we get to call it ours.

John Harcar (08:41.806)
Mmm.

John Harcar (08:46.168)
Yeah.

John Harcar (08:56.436)
Yeah, what do think was a mistake you made in that flip or any flips that you did that you kind of look back and go, wow, why did I do that?

Caitlin Cucchiella (09:03.804)
Think, whoo, I would say thinking it’s gonna be easier than it is. But no, I would say always double or triple checking exactly what’s going on on the site. So originally I wasn’t the builder and contractor when I started the project. And I would say the mistake was actually thinking that someone else could probably do it just as well or keep it on track the way I would.

John Harcar (09:09.902)
Hahahaha

John Harcar (09:23.107)
Mm-hmm.

Caitlin Cucchiella (09:31.448)
and believing that they would do it to the same level of integrity. So we actually had to fire that person and we took it over ourselves and thank goodness we did. So negative to a positive.

John Harcar (09:36.118)
Mm-hmm.

John Harcar (09:42.762)
Right. Yeah, there’s always a severed line to every cloud. Do you prefer investing in the property and doing the flips, or do you prefer traditional real estate?

Caitlin Cucchiella (09:56.526)
that’s a good question. I love the design aspect, right? That’s easy, but it takes so long to get to that place. And I think a lot of times the consumer thinks that it’s just gonna be this granite countertop that comes in, the appliances that they’re picking out, but there’s so many other features that go into it, like the subfloor and paying attention to those details and the plumbing and where you have cutouts for different things. And really taking the time to plan is what I think that…

John Harcar (10:16.27)
Yeah.

Caitlin Cucchiella (10:24.784)
you don’t see on the HDTV show and there’s so much more that goes into it. And a subfloor itself can be a lot of money. So you wanna make sure that you are laying a good foundation. I know people talk about it, but you really have to be paying attention on a day-to-day basis.

John Harcar (10:39.267)
Right.

John Harcar (10:43.982)
for sure, for sure. So what is your business look like now? Are you focusing more on the traditional versus investing? Is it a 50-50 thing?

Caitlin Cucchiella (10:51.506)
So I would say at this point in my career, real estate is the heavy focus working with clients. And then my partner, Chevy, he focuses on our rentals. So we have a few Airbnbs that we’ve run for a couple years. And we love that. We love meeting new people all the time. We love the feedback that they’ve had a great stay where they come into our city. They’ve never been here before or they used to come as a kid. And it just makes us feel really good that we get to share part of our life.

John Harcar (11:05.006)
Okay.

Caitlin Cucchiella (11:21.102)
with them and we’ve had repeat clients and it’s just it’s really great and some have turned into buying in our town which is icing on the cake.

John Harcar (11:29.454)
That’s awesome. Yeah, yeah. So what got you to do Airbnb? Like what prompted that as opposed to just holding for traditional rental?

Caitlin Cucchiella (11:37.148)
So I would say the first one I bought, wanted a long-term hold and I wanted to do a long-term renter. But in Saratoga specifically, you have a lot more transient guests that come in and out for the weekend. And when I bought my first investment property in Saratoga, I just knew that I wanted to use it sometimes. I knew that I wanted it to be available for friends and family. And honestly, we woke up one morning and I said, I’m just going to throw it on Airbnb like a listing.

And I pretended it was a listing, a professional listing, had professional photos, and I just learned every day a little bit more about it. And over the years, I learned how to price it properly. I just did it exactly as I would as an agent, but I ran it as a full-time business.

John Harcar (12:20.344)
Mm-hmm.

That’s awesome. Yeah, and a lot of people buy, know, turn things into Airbnb just because it’s a place they want to go visit. Like you said, family may be coming in. They can monetize that, you know, to have that available, but also be able to make money the rest of the year. That’s pretty cool. In your bio that you sent over, you kind of talk about a couple of things I want to touch on, you know, a big strength is relationships, integrity and communication, right? And I want to touch on that a minute and why that’s important and what the business we’re in.

Caitlin Cucchiella (12:51.568)
Yeah. So I tell all of my clients when I meet with them day one, communication is free. If you have a question, a concern, you don’t understand something, please reach out and ask. It’s free. I can literally talk to you, text you, email you at any point of the day, pretty much, and make sure that you know what’s going on. And it’s even gotten to the point now where I think some of the basic questions that every new home buyer asks or somebody who’s sold and bought a lot,

but maybe it’s been a couple years. Things change year to year, and I’m even thinking about coming out with some videos for those people to just give them updates and pointers on commonly asked questions that just come up. And so that’s something I’ve been working on lately, but I think text is easy, it’s immediate, and even if you can’t respond, you can always say, I’m in a meeting, I will call you back. Give them something because that’s what’s really gonna have them trust you and know that

John Harcar (13:24.558)
Mm-hmm.

John Harcar (13:30.427)
cool.

Caitlin Cucchiella (13:51.727)
They’ve been heard, right? Everybody wants to feel heard.

John Harcar (13:54.862)
Yeah, sure, sure. Yeah, and that all builds and slides into the relationship part, right? By having that communication, you’re able to build honest relationships with folks. So you mentioned your partner, right? What does your team look like now? Is it just you two? Do you have people going out and sourcing properties for you? What’s your team look like and how are you finding the properties you’re finding now?

Caitlin Cucchiella (14:19.452)
So I’ve actually kept my circle pretty small. It’s always been me at the front. Chevy does a lot of the back end lifting, especially if we’re getting a house actually ready. And then I’ve got a home stager that if it’s a larger property and I need an extra hand on deck, I’ll have her come in with me. And I’ve got my assistant behind the scenes that’s just doing all computer work when I need something prepped, especially if you see a house, you need a contract prepped. And by the time I get home, we’re already signing everything.

John Harcar (14:31.512)
Mm-hmm.

John Harcar (14:37.07)
Okay.

John Harcar (14:49.366)
Sure. Sure.

Caitlin Cucchiella (14:49.65)
Yeah, so I would say I’m open in 2026 to actually growing that larger. But I was waiting to finish this renovation and now that this is done, that’s kind of the next step.

John Harcar (14:56.769)
Okay.

John Harcar (15:02.483)
How are you sourcing your properties? mean, obviously, I know you have access to the MLS, but are you doing any type of off market marketing or anything like that?

Caitlin Cucchiella (15:09.712)
I would say it’s a little bit of a combination. So obviously I’ll reach out to past relationships and past lenders that I know. At this point, I’m not looking for me specifically. So right now I’m just looking for my clients. So the relationships with the agents are actually the most critical in my opinion and the lenders because they will either know of properties coming on or you will have agents that are getting properties prepped.

John Harcar (15:29.368)
Mmm.

Caitlin Cucchiella (15:37.56)
one to three months before they hit the market. So definitely having conversations, even if you don’t know the address, at least you know the price point and you can possibly get a heads up on something that’s coming to help your clients. that’s how I sort of, I guess, look and prep for properties, but there’s obviously the wholesale properties and the foreclosures and things like that. And the investors are always searching for those, but the inventory is just very, very low. So those relationships I find.

John Harcar (16:04.12)
you

Caitlin Cucchiella (16:06.64)
seem to do better than just waiting around to see what happens on the internet.

John Harcar (16:13.038)
Got it. And you being an agent in the realtor would know what is the best way because if someone’s getting into the business, right, and, you know, they say, you know, go talk to realtors, go talk to agents, right? Some people are afraid to, some people are intimidated to because maybe they don’t know as much as they want to. So how do you think a best way, whether it’s, you know, through questions, whether it’s mindset, to go and approach realtors to be able to have that relationship, that valuable connection?

Caitlin Cucchiella (16:39.974)
Well, I think there’s a multitude of ways. I think you can reach out via email. If you can’t find their cell phone or their email on their social media or they’re not on social media, you probably, in my opinion, in this day and age, probably shouldn’t work with that agent. They should be actively working. They should be actively showing up. And they should be easy to contact. And if they’re not, then that’s probably not the agent that you want to choose.

John Harcar (16:57.066)
Yeah.

Caitlin Cucchiella (17:06.662)
You want somebody who’s doing it full time. This is one of your biggest assets, whether you’re buying, selling, or you’re doing this multitude of times. And you want to know that they’re going to be available for you to help you throughout the entire process, not just in the beginning. And that’s something I do see is sometimes the agents will fall off, like they’ll get them the house and then, you know, the client feels like they’re just kind of like wading in the water.

John Harcar (17:22.784)
Right.

Caitlin Cucchiella (17:31.94)
Make sure you have somebody from day one that’s explaining it to you. Make sure they’re working for your best interests and ask them how many homes have you sold? Like ask those questions because it really is not you digging. It should be like an interview. You should be interviewing the agent and they should be interviewing you. And if you can’t be your authentic self and they can’t be their authentic self, like you need to make sure that the personalities match up. Just like dating. It’s just like dating.

John Harcar (17:44.792)
Mm-hmm.

John Harcar (18:00.778)
Sure. Yeah, of course, of course. So if I find an agent, should I just call up and say, hey, I’m an investor. What do you got?

Caitlin Cucchiella (18:01.916)
You

Caitlin Cucchiella (18:07.278)
Absolutely. And I think also just realize that that agent’s also going to ask you to work with them on a buyer agreement. And, you know, we don’t work for free. This is how we put food on the table. And so I think that’s really important, too, for people to realize, because you do have some investors that get that, understand it, and they just want the deal. But if your agent is working for you every day and touching base with you, then you know you’ve got a good agent. So

John Harcar (18:20.216)
Sure.

John Harcar (18:33.952)
Yeah, yeah.

Caitlin Cucchiella (18:34.502)
Be ready to commit to them because they’ll be ready and willing to commit to you.

John Harcar (18:39.788)
Yeah, and it’s a relationship that can be beneficial on both sides. So let’s talk a little bit about how do we live a life that we love.

Caitlin Cucchiella (18:47.76)
Yes, lifestyle. You should love the house that you buy, number one. You should love the city you live in. And something that I’ve put into practice in my business is I don’t always just talk about real estate. I talk about different things that I like to do. So whether it’s fine dining, grabbing a cocktail, going to the park, taking a walk. There’s so many different things that are going on in the city that you’re positioning yourself.

John Harcar (18:51.416)
Tell me… Okay.

John Harcar (19:06.574)
Mm-hmm.

Caitlin Cucchiella (19:16.924)
But I think it’s really important to share that with the community and clients that are coming into your sphere. So I actually joined American Dream TV and that is a nationally broadcast show. And I really enjoy that because I get to produce positive media on the local businesses that support me in my area and also help my real estate investments grow. So I support the local businesses and I share.

John Harcar (19:28.876)
Mmm.

Caitlin Cucchiella (19:46.596)
about them all the time on the show.

John Harcar (19:50.19)
Right. If someone’s stuck in a rut, right? Someone’s stuck in doing something they don’t like. They don’t love the way things are going in their life. I mean, what type of mindset do they need or what type of resources or tools or, you know, things they can maybe look into to help them flip the script.

Caitlin Cucchiella (20:05.938)
Sure. Well, I’m really big on manifesting positive feelings. I’m also a high believer in action. So you can manifest all you want, but if you have no action behind what you want to happen in your life, nothing’s going to change. So I’m a firm believer if you’re feeling a certain way and actually doing an action that counteracts that feeling or that like tenseness that you are feeling, it can change your entire day.

So one change, one action, let’s say you don’t feel like making the call today. Like make the call, like just make the call, do the call, just do it. Like literally just do it because you doing nothing is gonna make you feel worse and then that feeling is gonna go into your behavior, your behavior is gonna go into your action and it’s just this cycle. And so if you can break the cycle in some capacity, then you are going to change your.

John Harcar (20:37.666)
Hmm.

John Harcar (20:46.03)
Just do it.

John Harcar (21:00.952)
Yeah.

Caitlin Cucchiella (21:05.604)
outcome and you’re just going to start changing the way you show up on a daily basis.

John Harcar (21:11.918)
And it’s about building that muscle, right? It’s about doing, taking one little step, right? What do they say? You know, how do you eat an elephant? One bite at a time. Yeah. So you, but you got to take a bite, but you got to take, yeah.

Caitlin Cucchiella (21:17.682)
One bite at a time. Same with, same with, yes. Same with working out, right? You haven’t done anything in a long time. Literally do one pushup, one sit up. Or sorry, one pushup, one squat. Like just start with one. Don’t try to tackle it, just do it.

John Harcar (21:38.478)
Let’s do something. For folks that might want to get into real estate, whether it’s traditional, whether it’s investing, what kind of advice would you give them, resources would you recommend, et cetera?

Caitlin Cucchiella (21:50.898)
would say if you’re getting into real estate, know that you’re going to be promoting yourself and your own brand, whatever that means to you. You don’t have to have a full answer on who and what you are going to be. You don’t have to have a specific niche to get started. But get with your local MLS. Go and sign up for the course. You can do a hybrid online or you can actually go to the course, whatever is best for you.

And just know that you’re not going to be able to have all the answers on day one. I constantly am learning every single day. I sign up for different webinars. You know, I came across your podcast, John, I’m so thankful we’re here and just be growing and be open to different ideas. Something that you may have never even thought about, for example, like AI technology. just spent a couple of thousand dollars doing a few courses.

John Harcar (22:33.838)
Yeah, yeah, it’s me too.

Caitlin Cucchiella (22:47.964)
just to make sure that I was ahead of the game. So every year something will change in the world. Every year there’ll be something new. And the moment you think you know it all is the moment that your career is pretty much flatlined, in my opinion.

John Harcar (22:54.136)
Mmm.

John Harcar (23:02.722)
Yeah, yeah, always be learning and, you know, to tack on to all the great suggestions you had. Find maybe someone who’s in the lane that you want to be in and learn, right? Learn from their mistakes. Don’t stumble on your own.

Caitlin Cucchiella (23:12.219)
Yes!

Caitlin Cucchiella (23:15.984)
Yeah, and you don’t have to build the wheel. There’s so many people out there that are doing such a fantastic job. And honestly, like copying their idea to a degree, but putting your own spin on it is just as much a compliment to those people as it is for Mew making it from scratch.

John Harcar (23:36.186)
Right. Well, I mean, you know, and like we said, it shortens that curve, you know, gets you to where you want to be faster and you don’t learn from your own mistakes. You learn from others. Caitlin, this has been an awesome conversation. I’m so glad I had you on here. It’s really great to meet you. If there are folks out there that, you know, some of the stuff you talked about resonates with them and they want to reach out, what is the best way that they’d be able to get in touch with you?

Caitlin Cucchiella (23:44.229)
Absolutely.

Caitlin Cucchiella (24:00.366)
absolutely. They can call me directly on my cell phone. I don’t know if you want me to drop that in here, but I’m

John Harcar (24:07.47)
You can, we’ll put it in the show notes also.

Caitlin Cucchiella (24:08.945)
Sure, so that’s 518-852-3665. And I’m on Instagram, Facebook, Twitter, LinkedIn. You can find me anywhere. It’s Caitlin with a C. Sometimes you’ll look up real estate Kate with CAIT. But literally, you can find me anywhere. If you can’t find me, then I’m not doing a good job.

John Harcar (24:33.998)
In the TV show? What’s the TV show’s name?

Caitlin Cucchiella (24:37.466)
Yeah, so American Dream TV, it’s a streaming platform and they’ll be hosts, they’ll be about five hosts per episode. And usually the episodes come out once a month or once every other month. And I just recently shot the Albany Firewalls, which is an indoor pro lacrosse team. And I just met all these fantastic people and I can’t wait, that’s coming out April 12th.

John Harcar (25:03.17)
So cool. Everybody go take a look at that and you know, get with Caitlin and talk to her about her experience and she’s got a lot of great information to help you get along. Thank you again so much for being on here. I really enjoyed it. And guys, I hope you enjoyed it too and I hope you took some good nuggets away. I had fun. I’ll see you’re welcome and I’ll see you guys on the next one. Cheers.

Caitlin Cucchiella (25:20.198)
Thank you, John.