The Off Market Mindset

Welcome back to Off Market Mindset! In this laid-back yet power-packed episode, Michael Riordan sits down with Joseph Doherty—a Northern New England commercial real estate specialist and capital-finder who’s redefining how deals get done. Based in Greater Boston, Joe’s expertise spans anything over four units, and he’s built a reputation as the go-to guy for investors and family offices seeking bigger opportunities.

You’ll hear Joe’s journey from collegiate hockey player to door-to-door cell-phone salesman, enterprise sales leader at Oracle, and eventually a savvy real estate operator. Along the way, he’ll share how lessons from the rink and the sales floor taught him to engineer win-win outcomes—helping communities, preserving relationships, and still hitting impressive cash-on-cash returns.

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Creators and Guests

Guest
Joe Doherty

What is The Off Market Mindset?

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your front-row seat to the real-world playbook of creative real estate investing. Each week, host Michael Riordan sits down with deal-makers who thrive outside the conventional mortgage box—think subject-to specialists, seller-finance pros, lease-option architects, note investors, master-lease tacticians, and more.

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We dive into real transactions alongside investors who are knee-deep in the action, using creative financing to solve homeowners’ toughest challenges. Together we unpack every tactic—how they sourced the lead, structured the terms, and navigated the roadblocks—so you can see exactly what it takes to move a deal from problem to payoff.

Speaker 1:

You're now tuned in to the off market mindset. Who?

Speaker 2:

Where real estate gets real. Hey, guys. Welcome to the off market mindset. My name is Michael Reardon. I'm the host of the podcast, and we're here with Joe Dougherty.

Speaker 2:

He's in the Greater Boston area. He actually likes to invest in the what is it? New England area? Yeah. Northern New England.

Speaker 2:

So for buy and hold, you know, we'll do states that

Speaker 3:

are neighboring Massachusetts. So you got Maine, Vermont, New Hampshire.

Speaker 2:

Nice. Okay. And then, you know, he is focused on commercial real estate. So anything over four units, that's your man to talk to in the area. And you are not just a investor, but you're also a lender as well.

Speaker 2:

Is that correct?

Speaker 3:

Yeah. So more so of a capital finder. Luckily for us, we've had some opportunities where projects went well and the word got out and we've helped other people with larger projects sort of tap into investors that were looking for bigger opportunities. And then some of the actually, family office type investors as well through some of the commercial lenders that we have partners with down here in Boston. You know, again, just trying to make people who are looking for capital aware that there's, you know, multiple sources.

Speaker 3:

At the same time, when a good developer has something that's, you know, able to provide good cash on cash return, always willing to make those introductions for people's behalf.

Speaker 2:

Awesome, man. Yeah. Which I'm I'm actually excited to talk about some of that, especially from your notes and stuff like that that you had sent me before we connected. You've got some really cool things going on. So but before we get into things, just go ahead and I'm sure there's a lot more behind, your introduction that I completely missed.

Speaker 2:

Right? So, for people to get a a better picture of who you are and what you do and stuff, do you wanna kinda add to anything or

Speaker 3:

Yeah. I mean, I I think I'll I'll just say I'm very humble to the point where I've been in some big rooms and the best and most talented are always learning. So I wanna be sort of seen that way as well. I like to ask good questions. I've definitely found that when you go alone, you don't go as far.

Speaker 3:

So, you know, my my sort of background comes from being an athlete. I was a ice hockey player, throughout my life and, you know, played a little bit in college. But really, it just all comes down to a team. So hockey players, you know, they they get knocked down a lot and they get back up. So, you know, that's no better preparation for life than getting knocked down and getting back up all the time.

Speaker 3:

The only caveat to that I'll I'll say is, you know, I I would say, you know, sales is one of the best things that ever happened to me. After school, not really having a ton of direction. I I I started selling cell phones door to door. I actually went and knocked on a few doors and that sort of opened up, no pun intended, another door to get into corporate sales. I worked at a

Speaker 2:

You planned that out, didn't you? Yeah,

Speaker 3:

no. So I knocked on the door and it was actually somebody that I knew from my playing days And we had coffee later on and he worked in insurance. So that led to a career in financial services for a little while when I was in my 20s. Then that was right around where tech was getting big and Oracle was actually opening up multiple offices in the Burlington area, which is a suburb of Massachusetts. So I rode that way for nine years in enterprise sales, was a manager, was a national manager, had the chance to, you know, work with companies like HBO and Bain Capital and Fanatics.

Speaker 3:

So again, a lot of good experience that I didn't know at the time would prepare me for today, but I can tell you when you try to think about solutions and value, always good things happen.

Speaker 2:

Yeah, 100% you could look at a problem in one way or another. It's, I have a problem and I can't do this, or I have a problem, how do I figure it out and fix it, you know?

Speaker 3:

Right.

Speaker 2:

But And

Speaker 3:

if people take the time to so again, we all wanna make money. Right? But if you just take the time to do what, you know, pay says, try to find find the bunnies. Right? Or if you try to do things to sort of be in a service sort of kind of position, it it it always sounds corny, but it's really just about just taking time and and using the so the information that's available, whether it's through the the people on the other side of the desk, if you will, or vice versa?

Speaker 2:

Oh, yeah. I mean, the thing about sales, right, I mean, you have door to door sales or, like, phone sales, things like that is completely different because it's not just somebody going in the store to buy a, you know, a new shirt or groceries or something. When we're talking to people in a position like that, it's there's always something more behind it, right? Don't have to ask somebody, oh, why are you buying this shirt? You know?

Speaker 2:

But if somebody comes to you and, you know, as an example, we're in real estate and they're like, oh, I need help. I'm in foreclosure. You know, it takes a human being to say, okay, well, what's going on? Tell me more about it so I can help you out. You know?

Speaker 2:

So a 100%, if you look at everything as a transaction in sales, you're never gonna get far. Right. You have to look at it like, how can I help this person? And even more important, even though there's always going to be something in it for us, we can't look at it that way. Because, like as an example, say someone's going through a foreclosure but we can't purchase their property, there's still things that we can do and responsibilities that we have to better our communities.

Speaker 2:

You know, so they may not be able to be a good fit for us as far as like a property per se, but maybe we can connect them with counselors or, you know, food services or, maybe help them with moving, things of that nature as well.

Speaker 3:

So Absolutely, man. You know? And and that's what's really drawn me to this the whole time is, you know, it doesn't end when when a transaction sort of isn't a fit. Right?

Speaker 2:

Mhmm.

Speaker 3:

There's always that opportunity to sort of make the most out of it and have that, be a mutually beneficial sort of outcome. And, you know, there's nothing wrong with walking away feeling like you helped somebody.

Speaker 2:

Yeah. I mean, not every sale, involves financials. Right? Like, at the end of the day, you could look at a sale in two ways. Right?

Speaker 2:

So, oh, I you know, got this property and, you know, I sold them on the idea to let me purchase their property from them, and I helped them out. Or you can also, you know, sell yourself. Right? Like

Speaker 3:

Definitely.

Speaker 2:

I helped this person. That's a you know, that's still a commission in your in my eyes. And I know from what you're saying, it sounds like you as well. So now you had mentioned something earlier, obviously. Like, you said with your sales career, like, that was, like, one of the biggest things for you.

Speaker 2:

Like, if you look back to where you were in the past and, I guess, where you are right now, how how did you mean by, like, sales? Like, you're you're glad you got into that. That was, like, one of the biggest things for you. Like, I forget what you said exactly. But

Speaker 3:

Yeah. It's just one of the one of the the best things that ever happened to me. Right? So, you know, again, I think I went to a Catholic high school and it was really just about sports. And when you kind of grow out of that and it's time to sort of hit the real world, there's a little bit of trying to figure things out.

Speaker 3:

And unlike anybody else had some sort of good opportunities come our way and some not so good. But when it came to me sort of saying why sales was so important, I'll give you a couple of reasons. Number one, it allowed me to sort of find something that I was good at and sort of tap into mental multiple sort of mental components. So I I like solving problems, and I and I like sort of winning. So, again, it just spoke to that.

Speaker 3:

But the the other thing I'll tell you is I had to get a securities license in in order to sell mutual funds. Whereas one of my in one of my roles, I worked in the Financial District in Boston. And that studying requirement put me in the library during my partying days. So all the guys would be at the apartment having a great weekend. I'd have to be waking up or sort of going to make sure I could make it to the library to study.

Speaker 3:

I actually met my wife in the library because she was studying for the same test. She she had the same exact book. You know, normally, I wouldn't have been so bold to hit somebody up in the in in the library, and this is before, you know, the apps in in dating. But long story short, she had the same struck struck up a conversation. Was just right place at the right time.

Speaker 2:

That's really cool. Yeah. That was the ultimate sale right there. There you go.

Speaker 3:

That's it. You know? I I you know, like I said, you know, I'm I'm very, very humble and blessed because, you know, I've been fortunate enough to be able to travel, been fortunate enough to to to meet some very amazing people, people I still consider friends in in in in my network, people who I've raised capital with. And, you know, I'm gotta take my my family to Disney World after doing certain real estate transactions, and, you know, sales helped me build my my the the home that we live in.

Speaker 2:

Nice, man. Yeah. No. A 100% I can, you relate to that. I've been in sales for a very long time as well.

Speaker 2:

And I think, you know, in the very beginning, everyone starts out, Oh, I want to make more money.

Speaker 3:

Yeah.

Speaker 2:

But then as you're progressing and it's like, Okay, well, I'm making money, but it's like you get to a point where it's kind of like stale. It's like, what else is there? You know, what else can I do? And, you know, when you listen to some of these sales gurus and, you know, they're teaching you to close hard, right? Like, Like there's always that aspect that's important, right?

Speaker 2:

Because when it comes to people, you got to get them out of their own way sometimes.

Speaker 3:

Yeah.

Speaker 2:

Right? But if you're always trying to close them, you're doing them a disservice because you're not allowing them to realize it for themself.

Speaker 3:

Right.

Speaker 2:

Right? So I think one of the most important aspects in bringing that human touch into it is not just talking about yourself, your product, your service, and everything else, but like you said, figuring out the deeper level, like what is it that they need? Can we even help them in the first place? Also getting them to explore more about their situation for them. You shouldn't have to sell them.

Speaker 3:

Right.

Speaker 2:

Right. It's just by asking the right questions and being curious about them, like genuinely curious, you can actually get them to realize their own situation. So that way when you present the solution, you're presenting them with something that they actually feel is going to help them. Yeah. And then it's not about closing them, but getting them out of their own way and helping them overcome themself.

Speaker 3:

Yeah.

Speaker 2:

Right? Because at the end of the day, it's not overcoming objections. It's overcoming the person. So, I mean, I don't know your sales background, but, like, for me, I sold timeshare, and when I was looking at it from a money aspect, I eventually started feeling like bad. Like, oh, I'm selling these people something and, you know, maybe they don't need it or blah blah blah, and these things go through your mind.

Speaker 2:

But then when I started approaching it better, I would tell people, you know, I don't think this is going to benefit you. Whereas when you're in that closer mentality, it's, oh, it's going to benefit them regardless. Like, you're going for the sale versus, you know, selling to help. So great. But how do you feel like that has maybe affected the way that you do things now with your real estate business?

Speaker 3:

Yeah. And I I appreciate that. And and, you know, I think we've all been there, right? Like, you know, there's there's that's the beauty of sort of life. Right?

Speaker 3:

We get to sort of have different experiences that lead us to better ones. And then, you know, sort of coming through that journey. You know, I I know when I was young, I I definitely you know, I had a hammer and everything around me was a nail. Know?

Speaker 2:

So I

Speaker 3:

was just trying to hit everything. And, you know, you know, happy to say that, you know, I I learned, you know, a lot of lessons. And I I I feel like, you know, the evolution of sort of really kinda understanding that having a diverse tool set, whether it's, you know, like, human to human, ability to sort of listen first for two ears, but the ability to sort of engineer the right outcome and always learning that a win win is always gonna be the prime example where two people walk away, maybe they lost a little bit, but they both feel good about the the the overall sort of decision. Mhmm. That's really kinda what what what I'll I'll I'll sort of, like, leave that at.

Speaker 3:

I've been on the end of transactions where maybe it was one-sided, and you don't feel good about it. So it's kinda echoing what you were saying. Right? Yeah. I've been in this situation where it was like your boiler room sales sort of culture.

Speaker 3:

You know what I mean? Hammering the phones, trying to beat the guy next to you for, you know you know, club performance or getting sort of MVP of the quarter. All that stuff works. You know, it's crazy, you know, what I would do just for some extra pizza. You know what mean?

Speaker 2:

Yeah.

Speaker 3:

I would say, you know, again, back to being able to say that I I I've really been fortunate enough to to be around talented people. And one thing that I'll always say is people who are usually the best, you know, usually have very sort of low egos, and they also are humble where they're they're always trying to get better. I definitely feel like I started off with that, you know, you know, need to try to prove myself, and I would maybe overlook learning opportunities or look overlook the ability to sort of maybe network or sort of, you know, connect with somebody that I, you know, maybe that was the opposite. And because they were the opposite, I didn't value that opportunity. Now it's so much different.

Speaker 3:

My kids help me all the time. Explain different terminologies or I just see how being a coach to a seven year old or an 11 year old, how that actually is applicable when you talk to adults, right? People don't want to feel outsmarted. They don't want to feel that they're not following. You know what I mean?

Speaker 3:

And they're in a position where they have to you know, potentially pretend. Right? So for me in in in in the real estate space for the last few years where I've been, I say one thing all the time in every conversation. I know nothing. I don't know.

Speaker 3:

So I'm not gonna go in with a preconceived notion. And I and I'm gonna back it up. You know, our first flip, great neighborhood, totally, you know, well known for its school system. So instantly thought that that house was gonna be sold to a family looking to get in before the school year. So we were pressuring

Speaker 2:

the one you divided?

Speaker 3:

No. No. This is this is our first one. So, you know, just, you know, same town that we're that that, you know, we live in. The property, like I said, was a block from one of the better elementary schools.

Speaker 3:

There's a handful of them. This one's sort of just known for its campus and teachers and they've got special programs out of that particular facility. So it turned up two people with mobile mobility issues, know, wheelchairs, people with, you know, bad sort of, you know, hips and things like that. There was a bidding war, three people that I never would have ever expected to be the ones who drove the price of it. Yeah.

Speaker 3:

Again, mobility issues. The reason why it was such an attractive property is because it had no stairs.

Speaker 2:

Okay.

Speaker 3:

That was that was it wasn't us. It wasn't how we priced it. You know, we we we put in a brand new kitchen. We thought it, you know, that was gonna be the draw to the family. But because it was stairs, it was a home run hit.

Speaker 3:

And, you know, again, goes back to me saying, I know nothing. You know? And that sort of just takes me into every sort of time I'm having a conversation. I wanna know what the drivers are. You know, if there's distress, let me try to figure out how that can be utilized to sort of get that win win engineered.

Speaker 3:

You know, again, that's the the sort of the the mindset going into everything.

Speaker 2:

Oh, yeah, for sure. I just wanna address something. So everyone just watched me trip in a chair. That was crazy. I literally just tripped in my own chair.

Speaker 2:

But, dude, exactly what you're saying. It's kinda crazy because I have a deal that's it's closing next month on the eighteenth, and it was a novation, and I listed it as a realtor. So I'm a realtor and I'm an investor. And the people that listed it, they listed it with the seller, and they were looking to get a specific price. For people that don't know what an Ovation is, it's basically you go under contract for one price, and then you just work on selling the property for the owners.

Speaker 2:

So they had it listed zero action. I don't think I maybe had like three showings on it in almost three months that it was listed.

Speaker 3:

Yeah.

Speaker 2:

And the only action that we had was from open houses. So long story short, we had an offer. They backed out. Everyone that came to the open houses, they didn't like the property because of the layout. Right?

Speaker 2:

So just going back to what you were saying, the layout is what made your property sell. Right? Yep. The reason this didn't sell was the layout was awkward. Now the homeowner, the contract expired for the novation, and they decided they wanted to delist their property.

Speaker 2:

So I reached out to the investor that hired me, and I told him, listen, would it be okay if I reached out to the homeowner and tried to see if I can get this listing back? So he's like, yeah, sure. Well, the funny thing happens that a family came through the property right after it was delisted, and they loved the property so much because it was a split property, and they had an older child that lived with them still. And what people didn't like about the property made it super attractive to them because it had split AC units, one side had the master, you know, a really nice little area underneath, and it was a beautiful property.

Speaker 3:

Yeah.

Speaker 2:

So it was that exact thing that made that property end up selling. And the cool thing

Speaker 3:

is just wanna throw yeah. Well, you know, I just wanna make sure you give yourself some flowers, man. Like, the action steps you took to, you know, get the list, go to the effort, earn the credibility, and then earn the right to go and ask for the listing again, that's, you know, that's the grit. That's the sort of the the action taking into that, you know, you earned that through and through, and that's a that's an awesome sort of, you know, ending. So congrats on that.

Speaker 2:

Yeah. I I I appreciate it, man. And, honestly, it's like what you said. It's just the rooms that you're in. If I wasn't in the rooms that I'm in right now surrounded by the people that I'm surrounded by, number one, I wouldn't have got the listing.

Speaker 2:

It was a sub two student. He posted in a group that he was looking for someone to list the property in the area, and I just happened to be a realtor in the area. Just being in that room got me that listing. And then with the listing, I mean, worked hard. I'm not one of the realtors that just throws it on the MLS.

Speaker 2:

I spent almost a thousand dollars on photos, marketing, email blasts, weekly showings. I mean, you name it. I did everything that I could to sell this property. But the unique thing about it too is going back to what we were talking about being human, because when I reached out to him, he was not happy. Right?

Speaker 2:

And I kinda look at this as selling a timeshare to someone that hates their timeshare. And you have to be a special, you know, person to be able to do that. And not talking myself up, but a lot of times I would educate people so well on their own timeshares and teach them how to use their timeshare, I wouldn't even worry about selling them the timeshare that I was selling. And I would go over their program, I knew my competitors so well that I showed them they had a great timeshare, they had a great program. And then what I would do after that, and they understood their timeshare was good, they just didn't understand how to use it, I would go back and I would say, Okay, well, you know, that's that timeshare.

Speaker 2:

If you like your timeshare and the benefits that you have from it, this is what ours offers, and this is why I feel like you guys should add a little bit more as a complement to what you have, because you have a great timeshare, you just don't have enough. Right? So then I used to sell people like that all the time, And I truly believe in it. I own a timeshare myself. So for people that are talking, maybe listening to this, and they're like, oh, you're a scammer, you're a piece of crap, whatever.

Speaker 2:

No. I own one, so, you know, what can you say about that? But I did the same thing with him. So when I called him, I was like, hey, Daniel. I just wanted to give you a call.

Speaker 2:

This is the agent that listed the property. You know, I'm not gonna say their names, but, so and so told me you wanted to delist. I just wanted to find out, you know, what was going on, because I know you were trying to sell because of like health issues and stuff like that, and you know, so I just asked him questions, figured things out. He wanted a specific price There was a price he wouldn't go below. Right?

Speaker 2:

So it just so turned out that that same day that I got a offer on the property from that family. It took some negotiating with the seller as well as negotiating with the buyers, but I actually got the buyers to come up from $6.80 to 700. So and that's 700 k. Or no. $6.60.

Speaker 2:

They had a original offer at $6.60. I got them all the way up to 700,000 because I knew his number that he wanted, and in order for him to pay the agent and pay me and get his net that he wanted, we couldn't go below that 7 mark. So 100%, and I'm not I didn't bring that up to, you know, pat myself on the back, even though I will. Thank But it really goes to show exactly what you just said, how important all of that is.

Speaker 3:

Right. And, you know, it's a financial exercise. Right? And everybody has sort of their own drivers behind it. And the fact you took the time and the effort, and now you have that sort of lowest watermark that you can't go below.

Speaker 3:

Now you sort of you're armed and you didn't have that information prior on on the first go round. So, you know, the way things can turn and I always feel that it's a collaborative effort. You know, I I work with a lot of agents, so, you know, I can touch on it, but the the the property in Stoneham, that was the subdivision. I went in through a showing, and I let her know that I was an investor, and I would go and be there unrepresented throughout the process. So luckily, that sort of opened up the sort of the dialogue, and I just sat It's

Speaker 2:

not a real Zoom meeting unless you have problems. So

Speaker 3:

Yeah. But the point I was gonna make is, you know, the the agent that I was talking to in in the process, I think in the beginning, they had been sort of getting such low offers. Nobody took the time to understand that there was a lot going on behind the scenes. Like I said, health issues, death, probate, all these sort of other items. Then because I was able to really sort of switch roles and be, I would say, a solution to the problem, then there was four heirs the family.

Speaker 3:

And I wasn't trying to get them to be lowered on the price. Then, you know, it's so it came up in the conversation that the backyard had a special permit that they were going for for a variance. So 10,000 square feet is the the the typical lot size. This one was 5,000. The attorney that helped them there was a family friend that helped them.

Speaker 3:

Very high profile attorney in the town. Yeah. He was he was able to get that special variance approved in the extension. The biggest piece to that is, you know, I was working with the seller's attorney, the seller's agent, and our team all at once trying to help get something across the line that several other developers weren't able to do. And we got a lot, a buildable lot come out of it.

Speaker 3:

And just a story about, I would say some adversity, right? We had a builder come in with a great offer for us, but the amount of time it took because of that land court. So in Massachusetts, certain types of properties, if you have to go through land court because the land is registered, you have to sign up for longer processing times. Anyways, developer that we had expressed stress and we didn't wanna keep him handcuffed with his deposit. We gave it back and and and we took a risk that we were you know, we might have to maybe take less, but, you know, we were very fortunate enough.

Speaker 3:

And and I I just think that karma is a is a real thing. You do right by people. So when when we we broke the original developer out of the deal, he actually offered to sell us the drawings. We didn't even know that he had drawings all ready to go out for the property. Oh, So we had drawings and we were gonna get sort of a fast track permit.

Speaker 3:

So when we sold the plans with the land, we are gonna actually get the same price that we got originally. And again, just a win win win all around. Just good people trying to, you know, do right by the sellers. And, you know, again, it it it it wasn't easy, but it paid off.

Speaker 2:

Yeah. Is that the one that you put in your notes, the one where you divided it?

Speaker 3:

Yes. Yes.

Speaker 2:

Okay. Let's you know, for people listening, obviously, I mean, we're talking about, oh, be human. And, oh, when you bring the human aspect in, like If you can explain it a little better, like, what what do you feel like actually made them want to do the deal with you? Like, when you say, like, you asked them, you found out about the heirs and you found out about the property and everything, what kind of questions were you asking in order to get a response like that?

Speaker 3:

Yeah. The conversation of openers are really there's nothing special to them. Literally use the same ones all the time, such as how come you're selling it, you know, at the price you're you're you're asking for? How come you've had to lower the price? And, you know, then that opens up the the the dialogue, you know, that you get a lot of info from, you know, why they decided to and what sort of causing it.

Speaker 3:

You know, there's a lot of scenarios where, you know, they were given an offer and, you know, whoever it was, you know, sometimes it's a wholesaler. Know, You they'll they'll they'll they'll not be able to lock it up and and get the back out. And then, you know, those folks are sort of kinda holding the the property, you know, for longer than they expected. And now they're in a in a situation where it's a little bit of desperation.

Speaker 2:

Yeah. And

Speaker 3:

it's never an option for us to come in and pounce on that. You know, like, there's, a blood in the water situation. That doesn't really help us because this is our community. Our kids go to school here. They play sports here.

Speaker 3:

I coach, so do my partners. It has to be a situation where we're 100% transparent and the reputation is intact because we don't wanna be walking down the street and somebody says, hey, there they go and they they took advantage of our grandmother. You know what I mean?

Speaker 2:

Yeah. So instead of being the shark, you wanna be the rescue boat.

Speaker 3:

That's right. You know? And then just, you know, back to back to that human part of it's really something, like, you know, you mentioned in the beginning. I go through options. Like, I don't I don't I don't lead with, you know, a creative opportunity because this started off as seller financing for from a transaction standpoint.

Speaker 3:

But we were in that conversation, you know, I I asked, you know, why couldn't they get a loan? Why couldn't they borrow the money from somebody? Why you know, there there was one of the family members that, you know, had a faster time horizon because they wanted to relocate. You know, how come, you know, we we can't find a way to just, you know, get her supported? You know, all these things just started coming out.

Speaker 3:

And, you know, one of the the the brothers was actually in real estate as well. So he kinda came he came on the phone at one point with us, and I think we sorta kind of got his support and that helped because then after that, the attorney came on and he was known as sort of like the tough guy in in the town, you know, where you don't wanna mess with the. So to get him on our side and then sort of be supportive of what we were pitching, which was seller finance. Because, again, there was two heirs that needed money faster than the others. So we're gonna cut the the asking price in half, which is, you know you know, just under a million.

Speaker 3:

And we were gonna pay off, you know, two of of of the errors. And then we also wanted the the lot to come in unencumbered, which was a sort of a a move by my attorney. They didn't sort of love that in in the beginning, but, know, again, we earned the right to sort of let them know that, you know, we had a process, that they were gonna be protected. And, you know, it's a part of the offer that we feel most comfortable with. We got there.

Speaker 3:

Seller financing ended up falling through because in Massachusetts, one of the heirs was on MassHealth, which is a subsidized sort of healthcare. And can't be seen as having a rental stream or sorry, an income stream while you're on that.

Speaker 2:

Oh, those are benefits. Yeah.

Speaker 3:

Yeah. So fortunately or unfortunately, they had to lower the price by another $100,000. So, you know, we we came up with the cash and figured out figured a way to do that, but our lenders and our money partners were willing to be participants because, again, we did a double close at closing for the lot. We already had a buyer lined up. So, you know, people's equity exposure, you know, was dramatically improved when they knew we had a buyer for 360 350 k for the for the vacant lot.

Speaker 2:

Mhmm. That's cool, man. And then one thing I'd like to talk about is your other deals as well. So what really intrigues me is the fact that, you know, you're not this super investor. You've been doing it forever and stuff like that.

Speaker 2:

Like, you're just coming into the game, and you've already gotten a 100 unit deal. You have this split that you made over $300,000 on. And then the other deal was you converted a, was it an office building into, how many rooms was it? Like 40 rooms, something like that?

Speaker 3:

No, no. So it was 8,500 square foot office building and we converted that into seven rental units with

Speaker 2:

Seven units, okay.

Speaker 3:

Potential for more because basement's not done over yet. But that was an interesting project. It was right in the the beginning of our career. We made some mistakes. You know, we we we leveraged investors and, you know, again, luckily, the building is performing.

Speaker 3:

You know, it's a it's a 10% return on on the cash. But it's a situation where we are navigating, we end up signing a ten year covenant with the state of Vermont for the funds for the renovation. Coupled that with an actual seller financing for the acquisition. We've got 4% at a forty year term. So, you know, some good things for sure, but, you know, construction went way over.

Speaker 3:

You know, we managed it from afar, do a lot of trips back and forth. So, you know, I'll say that for a bunch of rookie mistakes that we made where we we still have hopes that this is gonna be a home run-in the end. It might be a home run for our grandkids, but, you know, but it it's it it does have, you know, some some some bright spots. You know, again, we we think that we could pay down the covenant and really sort of increase the performance of the building and opportunities will open up from there. You know, high interest rate environments are tough for refinancing buildings that, you know, use a lot of capital to sort of renovate it and taking the building in the middle of Downtown Rutland, Vermont near the ski resorts and sort of weatherizing it, bringing it up to code.

Speaker 3:

There's things we didn't know, like you had to have the ADA disability act, you know, accounted for, right?

Speaker 2:

Oh, yeah.

Speaker 3:

Sprinklers, you know, like we, you know, there when we bought the building, there was a path where we didn't have to use them because there was, you know, plenty of egress. But, you know, seven units is not a small amount of space, it's not a small amount of people. So you really got to do the right thing from an insurance standpoint. And we didn't have that experience. We thought one of our investors was someone that would be a little more hands on, but they could have helped guide us because he had more of that background.

Speaker 3:

But hey, we're all in this together.

Speaker 2:

Yeah. The fact that he's in it the way he is, if he's partnered with you, he should be worried about his own investment. But, you know, that's pretty cool now. How did you actually, like, come about getting into this deal? Like, especially being, like, new to the game and being a rookie, as you had mentioned, that's pretty big investment to get into just right off the bat.

Speaker 2:

I mean, why not start with a single family like everybody else?

Speaker 3:

Yeah, so this was our third building, our third project. So we had the very first home with the mobility sort of bidding war, right? With the people who were fighting over the home because there was no stairs. Did a condo. And then we were just having challenges because it was a slow.

Speaker 3:

It was a low rate environment and then 2020 and you know people were just coming in with cash offers outbidding us in our local market. So if anybody's familiar with you know the Boston market, it's it's very unique. You know the you know the school systems, the the the the economy is it it and then the lack of supply. It just leads to, you know, a lot of high equity and then a lot of homes and getting people to sort of take care their cuts and everything like that. It's it's just not as easy and it's also not our business model.

Speaker 3:

So with that being said, we decided to expand our network and we were definitely flying high with confidence, right? Hey, we just had two successes. We're gonna buy things on creative to sort of shelter our growing pains along the way.

Speaker 2:

Yeah.

Speaker 3:

Then when we found out that there was grant programs in the area and it was near a ski resort, it just seemed a little more if I'm being honest, think we were selling ourselves pretty good Yeah. On on why we should do it. You know, shout out to some some people in the community who who, you know, helped with, you know, giving some advice, you know, pointing out that it's you know, not all is lost because, again, it it is still performing. You know, we took

Speaker 2:

Who was it that helped you? When you say shout out, let's shout them out.

Speaker 3:

Well, yeah. So the the guys from Vetted, Kyle, Colin, and James on their team, you know, they they they've always been a resource. And and Justin Tumiowski also did a great job of sort of giving some, you know, background and some insight.

Speaker 2:

Oh, nice. Yeah. Justin is a great guy.

Speaker 3:

Yeah. Yeah. I'm I'm lucky to have him in in in the in the new new new new community. And, you know, his team, everybody, including CJ, you know, they're they're they're they're always a phone call away. And, you know, again, I I I haven't done any deals with him yet, but, like, you know, I'm always thinking of them, and I know it's just one of those things be a go giver.

Speaker 3:

And, you know, it it it it's I I definitely believe in that. But for for this particular deal in in Vermont, you know, again, it's it's something that we took we took literally dilapidated building, and now it's producing a $120,000 a year. So Yes. We're proud of it because we survived. And, you

Speaker 2:

know Is that gross or net?

Speaker 3:

That's gross. Yep. Gross. No. Nice.

Speaker 3:

Yeah. And then, you know, when we pay down the the covenant, we can increase those rents, you know, by another 20 k. So, you know, the sorry. Yeah. The the annual income by another 20 k.

Speaker 3:

So it'll go from $1.20 to $1.40 pretty quick. That's, again, something to be proud of.

Speaker 2:

I that's great. Yeah.

Speaker 3:

That's amazing. To answer your question like how and sort of like, you know, again, coming from technology sales, right? You don't wanna sell the feature, right? You wanna sell the solution to the problem. And when I think of sort of why somebody would wanna do a deal, I always think of, you know, what's the sort of the net financial sort of components to a deal like that.

Speaker 3:

And when you come in and you're talking about, you know, trying to help save people time, you know, understand what type of distress is involved, You know, could be family. It could be disaster relief. It could, you know, I I see, you know, I see homes that with like water or fire damage as as gold mines, right? You know? And again, it's one of those things.

Speaker 3:

It's one of the four D's, right? And when you start to look at and gravitate toward those problems where everybody else kinda runs away and they're looking for turnkey, it it helps sort of reduce competition, and then it kind of puts the discussion on a sort of playing field of, you know, how do we solve a problem together? Right? And then just the other thing I'll say that's was which was a big factor and and you'll see a theme here is we work with the agent. So we actually paid the commission for both the agents in on the Vermont deal.

Speaker 3:

So getting the 4% seller finance and getting the sort of the grants that come into play, we knew that in order to sort of help sort of sell it to the to to the the to sellers. We we needed to get them to sort of see, you know, that it was a win win. And the the the realtor the realtors didn't have a lot of experience, but what they did do was they sort of they dug their heels in, and they ended up sort of doing a good job at helping us get get over the finish line.

Speaker 2:

Yeah. No. That's great, man. I mean, kinda the same thing with the deal I just told you about. The agent, it was actually a broker, and he's never done a deal like this.

Speaker 2:

And he even told me, he was like, I'll be honest, I've never done anything like this. It's, you know, super strange, but I mean, I'm always open to, you know, learning something new and taking away from it, which is huge when it comes to real estate. I mean, there's so many realtors and I say this all the time and, you know, people that watch my videos have heard me, but so many realtors-

Speaker 3:

Let me ask you a question, you know.

Speaker 2:

Yeah, go ahead.

Speaker 3:

Role does the concept and the topic of protection sort of, like how do you use that as instead of like a negative in a conversation, how do you try to use it to sort of help facilitate?

Speaker 2:

How do you mean? Could you ask that a different way?

Speaker 3:

Yeah, sure. So, you know, when I hear people say, I've never done this before, and you hear attorneys or realtors say, like, you know, it doesn't feel or sound right, you know, I've learned that it's really just that we're not doing a good enough job sort of outlining the layers of protection that are available. But every time you put protection at the forefront and you sort of wear it as, a badge of honor, think that just increases the probability. So I'm sure you've come across that as well. I always like to hear how people sort of kind of position, you know, what we try to do to sort of make people feel protected.

Speaker 2:

Yeah, of course. Well, one of the big things is just looking at the situation. Right? So in this situation, even though he's never done a deal like this before, it's still kind of like your typical on market deal. So for him, his big thing was he's never gone from having a property that was on market to making an offer on the property and all of a sudden it's off market.

Speaker 2:

Right? So the whole time I made sure that I kept them in a loop and was honest. Right? That's the most important thing is honesty because, I told them, listen, it's a strange situation. I'm actually not the home seller's client.

Speaker 2:

So I was the client of an investor that they put a contract on the property and were selling it for the homeowner. So right there, that could be a red flag for anybody, but by telling him what the situation was and why it went off market and why he's still accepting an offer, it gave him the understanding. And he was educated enough to say, okay, well, I can see that, right? Then I went even further with it. So what I did is I told him, listen, you know, I was going to use for the closing agent somebody in our area just because, you know, it's what I'm comfortable with.

Speaker 2:

But you're from the area, so who do you use?

Speaker 3:

I gotcha.

Speaker 2:

And he was like, oh, well, I use such and such title company. I was like, okay, great. Would you actually refer them to me? I would like to use them just because they're local, to make this a lot easier.

Speaker 3:

So

Speaker 2:

that brought in so much credibility because one of the biggest things people may think is, oh, well, this could be a scam, right? And then it's like, okay, even further, they want to use their own closing. So now we're using his title company, right? He's a broker, so I've got him doing all the paperwork. I just got the signatures and stuff for him.

Speaker 2:

And then on top of that, we're all going to meet in person. So I reassured him, I said, listen, the sellers are going to be at the closing in person. That's why I would like it to be local, and then I'll be there as well, as well as you and your buyers. Know? So another thing that I made sure to do since he was a broker, that could have been a super unethical transaction if I was the client of the buyer of the seller, right?

Speaker 2:

So one of the other things that I made sure to do is make it clear I was never the seller's client.

Speaker 3:

Yeah.

Speaker 2:

Because if I was a seller's client, he canceled the listing. It was already, you know, in my brokerage. So they're due that commission. Right. But what I made sure to do was tell him, and just to be sure, man, and and I know you're a broker, I just wanna make sure you're comfortable with this transaction before moving forward.

Speaker 2:

Remember how I told you I was, you know, hired by the investor? I just want you to know I was never a client of the homeowner. The homeowner had a contract with the investor, and I listed the property under the investment company. So I just want to make sure that you understand that everything is legal and it's also ethical, so that way there's no violations to NAR because National Association of Realtors is like the mafia.

Speaker 3:

Yeah. Well, impressive, though. You know, you're you're you're you're a professional. You know? And and and people, they don't realize how much can be saved by just doing a little bit upfront, a little work like that upfront.

Speaker 3:

That's awesome. Congrats.

Speaker 2:

Yeah. And so I guess just, you know, being open, being honest and really just knowing what I'm talking about, like you said, just being professional about it is, you know, the most important factor. But, you know, speaking about professional, I mean, I saw that you also, you know, closed on a 100 unit deal. That's amazing, right? So how did that transpire?

Speaker 3:

Yeah. So it's it was it's a 100 unit doors and we closed on the capital raising relationship. So the Vermont project sort of helped open up a lot of doors. I actually really believe in raising capital all the time. So letting people know what what we're working on, what, know, what we're doing and what we're trying to find.

Speaker 3:

There's there's no better sort of time like the present and before you actually need capital. One of the people that were that I actually played college hockey with ended up becoming a wealth manager out of New York. I just let him know that, you know, there's some good things happening in and around the the New England areas, especially in the vacation destinations. And again, you know, some some great resorts within an hour to two hours from from from Boston. So people like to escape.

Speaker 3:

Right? And, you know, I six months went by, never heard from him. He calls me. He said, I don't have any money for you, but I have two clients that are looking for money. Yeah.

Speaker 3:

And he's got a new role and they do projects in New York. They've got two projects in Connecticut, one in New Haven and one in Norwalk. So, you know, I just kicked into action and, you know, I I I said to him right out of the gate, this is not something that I focus on, but I'm gonna, you know, make every effort.

Speaker 2:

I just developed the dude.

Speaker 3:

I developed a list of people that I thought could help, and I did ask them. And the the fact was we were willing to enable to figure figure out, you know, what was best for for my friend's clients. We developed a relationship from doing so, and someone in our network actually connected us to JLL's family office. And then, you know, that conversations opened up doors with some other big well known, you know, CPRE, Cushman Wakefield. And, you know, they're looking for a very particular type of opportunity.

Speaker 3:

Right? It's gotta be high on the cash on cash return. The developer has to have the right experience and and right track record. And, you know, when you find those together and you sort of offer to those offices, they they have no problem with putting in front of the right people that could fund those projects. And I learned a lot about the capital stack.

Speaker 3:

Right? You know, debt versus equity, you know, joint ventures at that level. So again, I'm very, very happy to say that we've got, you know, written agreements on two projects in Connecticut, and we're looking to double down in 2025 and 2026 to sort of, you know, make that be a, you know, a big component of what we do.

Speaker 2:

Awesome, dude. Well, I mean, obviously, you're a resourceful person, and not only are you resourceful, but that brought you into a lot of really great rooms. And, you know, one of the most important things that's happened for me within, my investment career is just the, you know, relationships that I was able to build. And it sounds like you're the, you know, type of person that anybody should wanna build a relationship with. So, you definitely know, looking forward to continuing ours.

Speaker 2:

But if people want to reach out to you and, you know, be able to, you know, network with you, where would they be able to do that?

Speaker 3:

Yeah. No. I'm I'm always on Instagram, you know, checking messages and Facebook as well. You know, if if if it's within the community, you know, the you know, I'm I'm trying to learn and be as comfortable with Discord as well now. But, you know, I'm happy to also, you know, you know, give you my my my email address and my my cell phone number if if anybody ever wants to sort of reach reach out to me that way.

Speaker 3:

But, yeah, you know, I I I go back to what we've been talking about. I feel like I'm learning and I'm humble enough to say that there's other people out there that I can learn from. And you know, one of the things that I I I don't have going into any conversations is ego. I do think that you know when you have some of these opportunities to connect within the community and ask for help with other people, you want to make it count, right? You also want to be prepared to sort of offer value or be useful, right?

Speaker 3:

And at the same time, I want to let everybody know that if I ask a dumb question or by, know, there's something that I find out that I shouldn't know going into it, I'll make I won't make the mistake in not being prepared with that in the future. But again, it's one of those things where you don't learn unless you, you know, don't take action.

Speaker 2:

No. A 100%, man. Well, if if people wanna reach out to you, you know, do you have, like, an Instagram handle or, like, Facebook handle? Yes. Or do you wanna give your number email here?

Speaker 3:

Yeah. Sure. So upside underscore r e for real estate underscore dev, which is short for development. So upside underscore r e underscore dev. And then my email address is Joe d, so first name and last initial, at upside hyphen r e hyphen development dot com.

Speaker 3:

Kinda long, but that was the only the web domain that was available.

Speaker 2:

No worries, man. Well, I am gonna be posting all your socials in the description for the podcast episode. I'll also be posting mine as well. So if you guys wanna reach out to either me or Joe, remember Joe is a developer. He's in commercial real estate as well as capital raising.

Speaker 2:

And for me, I am buying properties in the Central Florida area and all over the state of Florida, but I also can help to move properties anywhere around the country. So if you need somebody to help you dispo, I've got a lot of international, national buyers as well. So but, yeah. I dude, I appreciate you. I think this is a a great episode.

Speaker 3:

Long overdue. I'm I'm I'm glad that we're, you know, we're we're, you know, in each other's sort of circles now. So by all means, I look forward to, you know, continue to work with you.

Speaker 2:

Oh, yeah. Well, this is one of my ways to network. And is there anything that you wanna leave anybody with?

Speaker 3:

No. I'll just say that, you know, again, it it really it's it's a team sport. And at the end of the day, you know, the the the one thing that we're doing is we're providing some type of a service to someone. I just feel like we can save a lot of people a lot of time, whether it's investors who are really good at what they do, helping them find opportunities that that are, you know, vetted and, you know, are good fit. It's something that's a service that's useful to people with with with capital.

Speaker 3:

And at the same time too, it's it's a situation where, you know, we are really providing a great sort of service. Right? Developers are very good at what they do. Sometimes raising capital is not a strength at at at the moment for all developers. So don't be surprised if you're in the gated community, if you're in any type of other sort of capital raising network, some your best investors might be people that are coming from that sort of lower tier that are looking to try to break into that next level and working with them early enough in their careers or or that journey can really open up a lot of doors in the future.

Speaker 2:

For sure. Well, awesome, man. Appreciate you. Like I said, we're gonna put all your information in the description so that way anybody can reach out. But, you know, everybody, thank you so much for watching.

Speaker 2:

If you enjoyed the video, make sure to like, subscribe, share, comment, and do everything that you do with social media. If you feel like there's things that you want us to talk about in future episodes, leave comments below for that. And if there's any room for improvement as well, you know, I'm sure me or Joe, we were perfect with taking criticism. We're very open and humble. So, leave that as well, and let us know how we can do better for you in the future.

Speaker 2:

Alright, guys. Take care.