In this episode of Listening with Leaders, host Doug Noll interviews Paul Montelongo, founder and CEO of Montelongo Capital, about his evolution from buying his first single‑family home at 17 to managing over $100 million in real‑estate assets through syndication. Paul explains his focus on value‑add multifamily, storage, land development, and student housing, emphasizing that he buys "businesses"—the existing tenant base, branding, and operational systems—rather than just bricks and mortar. He describes the current market environment in 2025‑26, noting a stabilization of capital markets and a persistent housing shortage of roughly 4.5 million units, which creates opportunities for investors who can act quickly. The conversation delves into his rigorous deal‑sourcing process, where his team evaluates 250‑400 potential deals annually to select only two that meet strict return criteria. Typical hold periods are five years, with an average 2× equity return, 7‑9 % cash‑on‑cash during ownership, and 18‑20 % annualized IRR on exit. Investor acquisition relies heavily on omnipresent networking, social media, and personal relationships with business owners, physicians, and tradespeople, with revenue generated from management fees and a general partnership stake. Paul shares his personal motivation—goal‑driven persistence, competitive spirit, and a disciplined work ethic—rooted in early entrepreneurial experiences and a family influence. A substantial portion of the dialogue focuses on the art of listening: paying attention to what is unsaid, validating others, and using curiosity to uncover hidden information, which he ties to both deal success and leadership effectiveness. He also reveals a deep, non‑sectarian interest in theology and the psychology of religion. The episode concludes with calls to action for listeners to share the podcast and for potential guests to apply.
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Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Paul Montalbano, welcome to Listening with Leaders. You are the founder and CEO of a company called Montalbano Capital, and you're in the real estate business. And so we're going to spend a little bit of time today learning about how you went from zero to 100 to become an extraordinarily successful real estate investor and help other people do the same thing. Let me start off by just asking you to share your backstory with us a little bit.
Sure. Good to be here, Doug. Okay. Backstory. Yes. I run a company called Montelago Capital. We invest in a number of asset classes, multifamily, storage, land development, student housing. Those kinds of asset classes. But I haven't always done that. I've only done that for about the last 11 and a half years. Prior to that, I just did small investments, single-family residences, and did many of those. I bought my first property when I was 17 years old, a couple of years ago.
Okay.
Yeah. And I've had several businesses— construction, insurance, restoration, new building, retail building, a marketing company, the, those kinds of things. And before entering into this space of commercial real estate, all of my businesses and real estate was self-funded myself. Once I entered into the bigger space, then it took on another dimension called— we call syndication. So essentially that's putting together a group of investors, managing the property for them on their behalf, doing the day-to-day operations, and then paying them a return on their investment. Quarterly returns, annual returns, and then of course, uh, equity returns. And then we just, we rinse and repeat and do that. So currently we have on the books under management a little over $100 million and we're adding. So it's become a, a model that we know. And the other big thing is that I'm, I'm really optimistic about the real estate market in '25 and '26. For those people who know how to operate and those people who know how to do real estate.
Well, tell me more about that.
We, we're, we saw a dip, we saw some stagnation in the real estate market over the last 2 to 3 years and 2 and a half years. And now we see it stabilized out or at least reached a, a place of levelness where we now understand what we're dealing with. The capital markets went crazy the last couple of years.
You—
it was hard to, to count on capital, hard to count on debt, and at a price that, that made the deal worth it. But now that seems to level out. And then there were a tremendous amount of loans that were made on a floating basis that are coming due, have been coming due late '24, '25, '26. And so that provides an opportunity for people who are active in the, the real estate market as buyers like I am. We're sellers too, but we're not selling. We're just buying.
Yeah. I look at— Trump was inaugurated today, and regardless of what the politics are, I think the potential for economic turbulence is out there. And so I'm a stock market investor myself. And so it's— we're going to be in a really interesting time. And when we think about commercial— when I think about commercial real estate, I'm thinking about the office buildings that are vacant in all the big cities because of the pandemic and how difficult it's been for building owners to keep tenancy rates up and that sort of thing. But I don't think you— that— I don't think that's where you focus. You focus—
No, we're in housing.
Yeah.
So the demand for housing in this country is underserved.
That's true.
Depending on the statistic you look at, but some 4.5 million residences are needed currently. And apartments and homes and build-to-rents, those kinds of projects or products are still in demand.
And are, are the projects that you're involved in, those new construction? So you put—
so we buy existing properties so that, uh, day one we can have cash flow. Ah, uh, we don't have to wait for it to be built. We step into an asset, an operating asset. And then what we do is we put our footprint on it. We put our business personality on it. These, by the way, so here's your first salient point, if you will. I don't really buy bi— I don't really buy real estate. I buy businesses.
Okay.
So if you own an apartment complex, you own 200 units and I'm buying the dirt and I'm buying the doors, but what I'm really buying from you is your marketing, your website, your personnel, your customers. We call 'em tenants. I'm buying your good Google reviews. I'm buying your crappy Google reviews. I'm buying the whole thing. And then we go in and we turn it around and put our own personality on it so that we can increase its value in the marketplace. And. Offer it for sale at its optimal price.
So you're looking for properties that have been undermanaged or—
Undermanaged, under— rents are low, market awareness is poor. There could even be some delinquencies on it. Just all kinds of little— we're not looking for troubled properties per se, but they just, they need some TLC. Maybe the owner was— is tired, fed up, right? Has had it too long. Mom and pop. But yeah, I'm just, you know, not— and there is a market for people like myself to go out and buy highly distressed properties. That's not us, right? We buy what's called value-add properties, something where we can force the appreciation.
How do you find these properties?
Mostly brokers, word of mouth, network. There are a group of sites and pages and such that we scour. Last year we looked in 2024, I think we evaluated 255 or 260 deals to find 2. The year before we evaluated 400 deals to find 2. So wow. We, you know, we evaluate a lot of deals. We make the decision based on the return that would be offered to our investors. And of course then the exit return that would be offered to our investors and ourselves.
So how long do you typically hold onto a property before?
5 years.
Already.
The business plan is 5 years. The business plan is 5 years. If our average exit timeframe is about 37, 38 months, but the business plan is 5 years.
So you can turn around a property, take a property that's undervalued, undermanaged, and turn it around in 3, 4 years.
If you buy it right and you start forcing the appreciation, putting in the value-add components, then it can increase in equity and it can increase in value fairly soon, fairly quickly.
What kind of returns are you getting on average?
On average, we're getting a 2x return. Oh, so yeah, which is pretty healthy. Now that 2x comes in at year 5, but along the way we typically pay somewhere between 7 and 9% cash-on-cash return. And then on the exit, we do the profits, divide those back out, and they are typically coming in around 18 to 20. per year on average.
That's pretty good. And how do you find your investors?
Networking like crazy. As you likely know, we're very omnipresent on social media, so that helps. We network like crazy. We go to every event that we can possibly get our hands on, and not just in the real estate space, but in other spaces. We have a lot of business owners that invest with us. We have physicians, we have plumbing company owners, roofing company owners, those kinds of things. These are people that have their own businesses already. They're making a good living at their business, but they have investable money and they want— they know and they want to put it into real estate. They just don't want to go through all the challenges of operations. And so that's where we come in and it's a done-for-you model.
And then you do— you make your money off, I'm sure, management fees and take a small piece of the action.
They're, they're management fees and we take a general partnership position and yeah.
Excellent. So you've been doing this for a while and you've had a lot of business experience before that. What is it that keeps you going every day. They get you up and get you excited.
You said every day. Does that— some days not.
All right.
I think at some point when I entered a business, I set a goal, I set a mark. And so every day I wake up and I'm going to go get that mark. I'm going to go get that goal. Every day it feels like I've got to be making a step forward or step toward that goal. And so the only way that I know how to get that goal is to continue taking that step, which makes me wake up every day and look forward to it. So, so I'm, I'm being facetious. I would say 98% of the time I look forward to it.
So it sounds like you're motivated by just seeing things happen and making things happen and watching stuff grow and making money for people.
And yes, I would say that's a fair assessment. I've done these personality assessments, I've done dozens of them, and they all reveal the same thing as they're all very similar in their results, and that is a self self-starter, driven by the goal, driven by the endgame, driven by the process. Not so much interested in awards or plaques or trophies. I don't really. So there's an internal drive, and I don't know if we're born with it. I don't know if we developed it. I'm fortunate that my, my father was a driver of sorts, and I'm sure I saw that as an influence, and, and that, that helped. But I— but it's a self-motivation. Sometimes you have to create the self-motivation. You have to create the thing that's going to motivate you. So try not to get too wrapped up in my ego, and— but, but I do find that I'm very competitive. And so if there's something out there for me to compete against, or someone for me to compete against, that is a motivator to me as well.
Yeah, I remember my trial lawyer days, having to motivate myself to do the— people have no idea how tedious it is to be a trial lawyer. Being in the courtroom is fun, but that's about 1% of the work. And, uh, you know, walking into a, a room, a client's space with 5,000 boxes of documents and having to read every single one of those documents every, at least 5 times before I understood what was going on.
Sure.
Taking months to do that.
That's funny you say that because right now I'm reading everything there is to know about the, about bonds and issuance of bonds and municipal bonds. Oh, really? We have a project that, that we have this going on with, right? And I'm just— I'm absorbing everything, just dozens and dozens of pages. And my team, they always kid me because like when we get into a new deal, there's a large package of SEC-regulated documents that come to us and I just go grab a cup of coffee and I sit down and I just start reading. I enjoy it like a good book. So I get what you're saying about the preparation. Yeah. And it's all that preparation just for that little game time.
That's right. And it— it pays off.
Oh yeah. Oh yeah.
And if you can't, if you can't stand the preparation and the tedium of preparation, then it's going to be difficult to be successful.
And I think I've, I think I've been fortunate to find out for the most part what I enjoy.
Oh, that's good. Yeah.
And so as long as I stay in that realm of doing the things that I enjoy, the pursuit, the deal, the making the transaction, the negotiating, seeing the thing come to fruition. That's where my enjoyment is. And that's why I have really good people wrapped around me that do the day-to-day, actual day-to-day, you know, taking of rents and service calls and accounting and those kinds of things so that I can go out and do what I like, what I feel like I'm fairly good at and what makes the most progress. And so when you have that, it helps with the motivation.
Right. Yeah, especially if you're sufficiently self-aware to recognize that, you know, details are important, but there are a lot of details that you can delegate to other people. Sure. And trust them to do the right job so that you can really focus on what you're really good at. So as you look back over your career, Paul, what do you think is unique about you that has set you apart from other people? There are a lot of people in real estate, a lot of people. What is it about you that's made this project so successful?
That's a great question because I continue to ask myself that. Continue to search for that, right? Continue to try to convince myself of something. But I think I like the pursuit. Okay? I think by nature, look, if we weren't here in 2025 and you and I were here a thousand years ago, I'm sure that I would see you out in the forest on a hunt.
Right, exactly.
And so it's that, but I think there's a certain stick-to-itiveness that I've been blessed with. Sometimes it's called stubbornness. Persistence. Yeah, I like to call it persistence and discipline. And yes, I think I've been blessed with a, a certain level of discipline. Also, I think that I've been blessed with the ability to collaborate and put people together and help them see how they're real contributors to the team and how they're helping me and how I can help them. And so I think there's a teamwork element involved there that I probably picked up from playing sports through my, through my life, and that helped. So I think those few things there. And the other thing is I, I, I like a variety of things. If I really listed for you all the things that I've done professionally, there's The only common thread really is that they were new ventures at the time I entered them. And then you learn, you ask questions, you wrap yourself around people that know, you take risk, and then you just, you jump into the swimming pool and you learn how to swim.
And that leads into my next question. You're— how do you learn how to listen? That's a key part of what you do.
Oh my, I mean, I haven't always had that ability.
Most people don't. It's a skill that has to be learned in math.
But many years ago, I just learned that I had to listen more. So the thing that I— the thing that I try to do is I try to listen for what's not said. And also, when someone tells you who they are, like if they say, I'm such and such, you should really believe them until they prove otherwise.
Right.
Like, I, I'm not a person who follows through on things, but by golly, I'll be on your team. And great. Their first thing they said was they're not a person who follows through. That's the thing you should believe unless they prove you differently. So that's a listening skill. And I have a real interest in people's backgrounds. So if you go to my library over here, I've got hundreds and hundreds of books, and I would say the majority of them are biographies or autobiographies.
Interesting.
Like, I want to know people's journey. And so that requires paying attention.
Curious. Curiosity.
And being curious.
Wanting to, and also wanting to learn.
And wanting to learn.
Continue.
So that's my strategy. It's just, I'm just curious and I, I'm just, you know, interested in knowing things.
And so, so I take it you, you just apply that to every deal. You get curious about a property. Sure, it piques your curiosity, and now you start digging into the property and looking at it and studying it and thinking about it and talking to people about it and listening to what people have to say, and probably most importantly, what they're not saying about it, because there's a lot more information in what's not said than there is in what is said.
Precisely, precisely. And something about when you listen, it gives you credibility, it creates authority. Now we could talk for 45 minutes, and not you specifically, but another person. You could talk for 40 and I could talk for 5, and I'm listening the other 40. And the sense, the feeling that you will get when you walk away is, man, that was a great conversation with that guy. Although I had 1/9 of the words come out of my, my face.
That's right. And, and, and that's because We all have a deep need to be heard.
Sure.
And the experience of being heard is very rare. And so most people will end up talking about themselves. And if you can listen to that and validate their experience, they feel like, wow, that was really an amazing conversation, even though they did all the talking. Yeah, exactly. When my wife and I walk away from a social function, I said, anybody ask who you were? Nope. Anybody? She said, how about you? I said, nobody asked a word about me. All I did is listen.
Yeah. And you walk away feeling like, wow, nobody really cared.
I don't feel that way because it's really hard for me to, it's hard for both of us to explain who we are and what we do. So we're happy not having to talk much, but we're both really good listeners and it's gratifying to see people feel validated and heard at a deep level. Oh man, you really get me. And sure. That's a really powerful experience to give to somebody else.
Yeah. I had an experience over the weekend with a gentleman. We were supposed to have a meeting today. We've got bad weather here, so he called and he goes like, we're gonna, we're gonna move the meeting. And this weekend I'm celebrating the 10-year anniversary of my heart transplant, and we're gonna move the meeting because there's ice. And then we'll talk about next Thursday, and then we gotta work on this. He went through this list of things. I'm like, whoa, you did what 10 years ago?
Heart transplant.
Heart. I did not know this about you, sir. And so we went off on this tangent about his health when, mm-hmm, how he feels tremendous now. And it was obviously a life-altering event, But threw in that one little thing, and my every— everything about me just peaked up. I got to know more about that. The meeting can wait. I got to know more about that.
Wow. Yeah, that's really cool. And you never know when you listen that you're going to find out stuff like that. Sure. That just opens you up and people in a completely different way.
Absolutely. Never know until you listen.
So one more question, Paul, before I let you go. What's, what's one thing about yourself that we would never know about? Unless you revealed it to us.
If I reveal it to you, then you'll know about it. Let's see, what would I know? What would you know? That I have a deep interest in things theological.
Really?
No association to a religion, but I have a deep, deep, deep interest in all things theological and have studied most, if not all, I'm sure, but most of the major religions and philosophies. I've studied them in depth, and I'm just— I'm interested in theology and the psychology of theology.
So that's absolutely fascinating. I could spend hours talking to you, but we don't have hours. We got to wrap it up. Paul, thank you so much for your time today. I really appreciate it and enjoyed the conversation.
Glad to help. You're welcome.
Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show and mean a lot to me and my team.
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