Jay Chekansky’s Affordable Housing and Seller Finance Strategy

Jay Chekansky (00:00)
Yeah, sure. Happy to. I think that walking through how I’m able to structure these seller finance sales might help ⁓ shed some light or spark some interest in your listeners and seeing how they could apply some of the same strategies in their community. ⁓ as I ran through very quickly earlier, ⁓ I will find single family homes. ⁓ Maybe they’re in distress.

Quentin (02:00)
Hello, everyone. Welcome to the Real Estate Pros podcast. I am your host, Q Edmonds, and I’m excited to be here today. I am excited about my guest. I’m excited about what he does. I’m excited because I’m sure because this is one of his specialties, affordable housing, right? And that’s something that, you know, we talk about. I’m glad we get a chance to talk about it here. And I’m glad that he’s within this space, really serving people, serving the investor.

and people that need some affordable housing. So I’m really excited for us to peek through his lens, get to know what he does, some of the strategies that he used, get to know his journey. And so I’m excited to introduce you all to Mr. Jay Chekansky. Mr. Jay, how you doing today, sir?

Jay Chekansky (02:45)
I’m doing good. Thank you for having me.

Quentin (02:46)
Absolutely, man. Thank you so much for being here, sir. Hey, listen, I’m going to tell you, like to dive right in. So I would love for you to tell the people what’s your main focus these days. If you don’t mind, give us a little bit of an origin story, kind of how you got into this space. And we would love to know the hero’s journey and then let them know what part of the world you’re in, man. People love to know where you are, especially if they’re trying to connect. So what you’re up to, you’re up to, your origin story and where you are. Mr. Jay, sir, you have the floor.

Jay Chekansky (03:14)
All right. Well, thank you for having me. I appreciate the opportunity to speak with you. So, ⁓ Jay Chekansky, I am based in Charlotte, North Carolina. I have been a real estate investor since 2015. And ⁓ during that period, ⁓ I have invested in single family homes, manufactured homes on land, mobile home parks, self storage, vacant land, some new single family home construction.

Quentin (03:15)
Yes sir.

Jay Chekansky (03:41)
And those deals have been ⁓ primarily in North Carolina, upstate of South Carolina, Eastern Tennessee. Right now, the ⁓ core of the business work, probably 65 to 70 % of what we do day in and day out, revolves around creating affordable housing opportunities. It’s a little different take on that than what most people think in those areas. Basically, what we do is ⁓ we are able to borrow

private money from private lenders, folks looking for the stable secure returns in real estate.

We use that capital to purchase and rehab single family homes. And then on the other side, rather than reselling retail as a pure fix and flip, we resell those homes with seller finance to a qualified end buyer. And that permits them to buy a home, to generate equity. I truly feel that it improves things at the community level.

It improves things at the personal level by creating a homeowner rather than another renter. It improves the quality of life for my private lenders and private investors because now I’m putting their money to work

and generating monthly returns for them. And then of course on my side, it permits me to lead the life I want to lead. It provides for my family. It frees my afternoons up to play with my three year old son.

Quentin (06:05)
Yes, sir, man. Man, I love that. I really believe what we do should give us our time back. So we should use what we do, the money we make, the businesses that we’re in, to get our time back so that we have options to do what we want to do with it. And so how are you talking about playing with your three-year-old son? Absolutely. And this afforded you that opportunity. And I love it, man. I love the fact.

You’ve been an investor since 2015. Man, couldn’t even, was trying to, no, I was actively listening, writing things down, but man, you did mobile homes, single family, single family development. You, you rattled off some other stuff. I was trying to keep up, but man, you really done a lot. 70 % of what you do is affordable housing. And I love how you said you want to improve and what you do improves the community, the investors in the person that’s in the home. Like I love it. I absolutely love it. I I would go to say these things back to you.

For one, let you know I was actively listening. But two, I have a saying where I say destiny has no wasted moments, Meaning no matter what we go through in life, the moments build to where we are now. We’re building momentum to the things that we do, the mindsets that we have, the life that we get to live, right? So I would love to know throughout your journey, Mr. J, what has these moments taught you about yourself?

Have they taught you discipline, resilience? Like throughout the journey, throughout every step, what has it taught you about you, Mr. J?

Jay Chekansky (07:34)
Yeah, throughout the journey aspect of it, right? ⁓ I didn’t roll out of bed in 2015 and think about this ⁓ triple bottom line style of business, right? There was ⁓ lumps, mistakes, ⁓ lessons learned along the way, right? I got my start flipping houses. And the first house I bought in October 2015, I walked into it, I looked at it, and I thought to myself, I can do all this work.

Quentin (07:43)
Yeah.

Hahaha

Jay Chekansky (08:04)
And that’s what I did, right? Pulled out the tool belt, the hammer, the table saw, and I went to work. ⁓ Quickly realized that you can only do about two a year, three a year if you’re lucky doing it like that. Or at least with the skill set that I had at the time. You know, ⁓ I bought a house in 2017 and that was my real first taste of adversity in the business.

Quentin (08:17)
Yeah. Yeah. Yeah.

Jay Chekansky (08:32)
Had some foundation issues that I knowingly purchased it with those issues, thought that I could fix it. That wasn’t the case. And throughout the course of the next year… ⁓

You know, I had a lot of my money tied up in that house and another house and I started having to figure out how to do deals with none of my own money because I was all out. I was very ⁓ house heavy at the time and low on cash and that’s how I stumbled into ⁓ this seller finance type niche where I realized, well, I’m able to do a lot of good doing this work. I’m able to meet my investors’ marks for their returns.

which still permitted me to make money doing what I was doing and provide a home for someone to move into and live in that they could afford while hitting all those other metrics. took some pain along the way, took some life lessons, ⁓ adversity, some struggle, belong along the way, a willingness to say yes and create some opportunities that not a whole lot of other people, there weren’t podcasts about this at the time.

There was just some folks that I talked to in my network that had figured some of these things out and I put it all together and started doing it at scale.

Quentin (09:51)
Thank you, man. Thank you for that reflective answer. Thank you for that, that just transparent answer. I really, really appreciate that.

And as you was talking, you know, a thought came to mind that I heard and it talks about pain often provides passion, right? Often the things that we go through, the experiences of failure, struggle, it actually fuels the passion that we have now. And so I love, man, I love the fact.

that you’ve been through some adversities, know, 2017 with this home. But now you use that to passion, to power, to provide you with the passion that you have now with affordable housing and making sure that triple, like you said, the triple thing, I can’t even say it like you said, but the triple income, right, is working for you, is helping your investors, the community, and also providing you for the life that you want to live. And so.

I appreciate it, man. And I would love to know what’s next on the list. What is your next goal? What is your next? What do you like to solve a scale next? What’s next for you, Mr. J?

Jay Chekansky (11:31)
Yeah, honestly, it’s going to be just improving what I’m doing right now, adding more deals, more opportunities, helping more of my investors, creating more home ownership.

with a little, how do I say this, bringing on a few team members to help me out because I’ve been carrying most of this load for a number of years. There are some things that I can delegate to improve how I spend my time.

Quentin (12:10)
Yeah, man, that’s the type of stuff ⁓ I love hearing because there’s a why, right? Like when we know who we are, we know what to do, right? And one of the things that you have mentioned and it sounds like one of your whys is your family, is your kid. And so one of the reasons I know why you do what you do and who you are, I’m a family man. And so I love the fact that you realize you’ve been carrying the load. Now it’s time to get some of that load off of you so that you can get your time back.

So you can make the option of what you want to do with your day. My wife, she has a saying where she says, my presence is a present. Like me being available, me being there for her is a present in itself. And so I love that, man. I love the different things that I’m hearing from you, I ⁓ would love to know, man. I ask you this and I love to get people’s perspective on it, especially people like you who’s running a business, talking to investors, improving the community.

When you hear the word relationship, what comes to mind? Relationship within business and just relationships in general. When you hear that word, what comes to mind for you?

Jay Chekansky (13:16)
It actually brings back a lot of opportunities that came about primarily based on relationships. ⁓ A couple business partnerships formed. I had two competitors in my market that I became friends with that we started collaborating with and now we’re doing deals together.

Quentin (13:44)
Mmm.

Jay Chekansky (13:46)
All relationship based. lot of, ⁓ you know, with the private money that I put to work for my investors, 95 % of that relationship based.

Quentin (14:04)
Yeah, man, think relationships are everything in this space. I think we are better when we are in healthy relationships. I actually use the word community a lot, that we’re better when we’re in a community of people that can support us. I always say community is common unity. It’s people who are doing different things but with the same goal in mind. So when you have people, know, peers, when you have people who you can bounce ideas off of.

It just makes the ecosystem better because you have somebody that you can lean on, that you can run ideas by. And I always say, you know, the better your community, the healthier things would be. And healthier just means like just making things whole. Right. So when you have a good community, your mindset is better. You can think better. You have ideas. You can run by people that affects the money that affects your health. That affects being less stress. That leads to more time with your family. Like, I just feel like the relationship aspect is so important.

Because again, it just makes your whole ecosystem more healthier. And so, yeah, I think relationships are very, important. Mr. J, let me ask you this. Is there any topic that I have not brought up that you would like to talk about? Is there any words of inspiration, education, motivation? Like, if you came in here with something on your mind that you feel like our viewers should know, I kind of just want to open up the floor that way you can deliver that message.

Jay Chekansky (16:09)
Yeah, sure. Happy to. I think that walking through how I’m able to structure these seller finance sales might help ⁓ shed some light or spark some interest in your listeners and seeing how they could apply some of the same strategies in their community. ⁓ as I ran through very quickly earlier, ⁓ I will find single family homes. ⁓ Maybe they’re in distress.

You know, there’s a reason, right? We’re still buying at a discount. We’re adding value by improving these homes to make them safe, to make them clean, to make them move in ready for whoever is going to buy these houses. We’re putting our investor capital to work. ⁓ We’re keeping them secured at a maximum 75 % loan to retail value. And that ensures that…

you know, their capital, is secured, you know, with a mortgage and firstly in position is going to remain secured with a strong loan to value. And then on the other side of that, we’re reselling these properties and those monthly payments, you know, when we’re structuring these deals, we want those monthly payments to be within about a hundred to hundred fifty dollars per month of what the area rents are. And that’s going to ensure that

know, someone that is looking at being a first time home buyer is going to be able to afford those monthly payments. We’re ensuring that they have at least a 10 % down payment when they’re they’re buying the home from us. And what that proves to us is that they are a good steward with their own finances, that they’re going to be a trustworthy borrower, that they have adequate skin in the game. And that not only are you going to be a good steward of their loan, but a good steward of their property and a good steward of the community.

Quentin (18:04)
I love it. Mr. J, man, I appreciate you coming on. I appreciate you sharing your story, your strategies. Listen, if someone wanted to reach out to you, connect with you, collaborate with you, learn more about what you’re doing, how can they get in contact with you,

Jay Chekansky (18:20)
Yeah, absolutely. So more than happy to help anyone out with some, you know, some questions to understand the strategy a little better. And I do do some one on one coaching with other folks that want to get started in this business. The easiest way to find me is going to be on Facebook, Instagram or Twitter. And it’s just simply Jay Chekansky and all of those platforms. You reach out to me with a direct message there and more than happy to help you out.

Quentin (18:45)
Yeah.

Absolutely. ⁓ Man, let me say three things to you, Mr. Jay, First, mean, thank you for your time. We talked about time. You know, I’m taking time away from you, from your son, from your kids. So thank you for your time, sir. I appreciate you being here. Secondly, thank you for your story. Thank you for just being authentic and transparent. I believe stories have a way that can literally course correct somebody’s life. So I think the nuggets that you gave today may spark ideas for people to think about things differently. So thank you so much.

Lastly, thank you for your perspective, for your mindset and bringing that mindset to this platform. I appreciate you coming on Mr. Absolutely. But listen, y’all heard Mr. Jay, his information is in the show notes. Get in contact with him, but definitely make sure you are subscribed here because I promise you, we’re going to continue to bring up amazing people just like Mr. Jay, so sir, I say thank you again and everyone else. Y’all have a fantastic day.

Jay Chekansky (19:25)
All right, sounds good. Thank you very much.