My grandfather had a few rules. One of them is always know where the exit is. That could be physically. I think you can use that as a metaphor for, your job or an investment. And so I tend to always think about that from a safety perspective.
Ed MathewsIf you're within three feet of me, we're probably talking about real estate, much to my family's chagrin. But here's the thing, most people see 7% rates and freeze. I see opportunity. They're waiting for the perfect deal, and well, I've analyzed thousands of them, and perfect just doesn't exist. So I talk to operators across every asset class, flippers, multifamily syndicators, note investors, and whatever else is working. No sales pitches allowed, just real lessons from people actually doing it. I'm Ed Mathews, and this is Real Estate Underground. Greetings and salutations real estate undergrounders. It is Ed Mathews again with the Real Estate Underground. Thank you so much for making us a part of your day. I'm grateful for the opportunity. Today we have Dr. Jordan Romano from a place that I absolutely love, Boston the Boston area. And he is a real estate investor, but, the interesting thing about his approach is f- first the thing that jumped out at me is how he finds deals, which I'm fascinated by, and we're gonna talk a lot about that. And there's a whole bunch of other things we're gonna be talking about, but that's where we're gonna start. Jordan, welcome to the show, and thanks for your time today.
Dr. Jordan RomanoThanks for having me.
Ed MathewsYeah, my pleasure, truly. One of the things th- that I'm always interested in is how people got into the business. So why don't we start with who you are, what you do, and how you got in, how you got into this industry?
Dr. Jordan RomanoSure. I'm, my name's Jordan Romano. I'm a, I was born in the suburbs of Jersey and grew up in outside of Philly. I'm a physician. I've lived in the Boston area now for about 15 years. I trained in New Hampshire. How did I get into real estate? My mother was in real estate. I had just finished Actually, my first real estate deal was terrible timing-wise. I bought a hou- I didn't want to rent during my residency, my medical residency. I was on a rural rotation, and my mother traveled up to New Hampshire, she was in real estate, and was sending me pictures. This is before smartphones. She was sending me pictures, and they would they would have to load on your camera. I don't You probably remember those days. It's like- And one by one, the pictures were coming through, and I bought a single family home. I bought it, I bought in 2000 It was 2006 right? I bought like literally at the peak. And then I sold it and I had to bring money to the table and sold like right as things were, in 2011, end of 2011. Yeah. So it was, that was bad timing. But how did I get into real estate thereafter? I had come down to Boston after being in New Hampshire for five years. So I was, I came down here in 2011, 2012. I think around that time it was our current president's first term and he was in real estate and my fam- my mother had been in real estate and it was like this, the thesis, one thesis of investing is invest in what you know, and that, that was always around me. When I'd come home... The story I like to tell is, I don't know if they still do them. Do they still do broker opens for res- for residential? If they,
Ed Mathewsif... I'm sure they do. I don't-
Dr. Jordan RomanoYeah I
Ed Mathewsdon't attend them, but-
Dr. Jordan RomanoSo when I, yeah, so back in, this is call it 2000, when I was in college, I'd come home and to spend time with my mom, she'd go and be doing brokers opens, and I'd go with her and I loved it 'cause it was like free food and the spreads were usually good. And she would always let me pick like one, McMansion or like giant farm property. She wasn't into selling those. We'd go see the little condos and then we would go see a couple like aspirational properties. So I would say that was my first taste into real estate. And so then once I started having some money, this is call it 2012, 2013, the, the thesis that I like is invest in what you know, and real estate was around me and I said, "You know what? I know..." And my mother had retired up to where I did my training, and so I said, maybe I'm gonna invest in some real estate up here."
Ed MathewsYeah. Yeah and, one of the things that I learned about you getting ready for this conversation is you tend to be hyperlocal with your investments. You're not a long distance investor at all. Yeah,
Dr. Jordan RomanoStan Druckenmiller says "Put all your eggs in one basket, just watch the basket really well," something along those lines. Something like that. I don't immediately stick all my eggs in one basket. I don't think he does either. I think that's a would be a, a, a so- a, a quick take on what he was saying. Basically, you do put out some feelers, and once your thesis is proven out some- what is, what's the saying? It's not about It's about how much you've bet when you were right and how much you've bet when you were wrong. It's not really about being right and wrong. Spread. It's how right are you when you're right and how wrong are you when you're wrong. And I've had a good thesis. Ev- you can't invest in hindsight, but my thesis has played out nicely. And obviously I think a lot of your listeners and investors in real estate are realizing what made sense even a few years ago maybe is not making sense moving forward.
Ed MathewsCouldn't agree more. Yeah. And you and I tend to follow a similar investment thesis in that I, I invest almost exclusively es- especially when I'm the operator in Middlesex County, Connecticut, basically. So I'm, half an hour north, half an hour south, half an hour east, west. And that's a target rich environment for me. It's a more rural market than you probably work in. But s- similar idea in that I wanna know, I wanna be able to lay hands on a property if I need to. And the other part of it that really helps is I know all the brokers, I know all the contractors. They're friends, it's, they're not acquaintances. And it's it... You learn living in, whether that's professionally or actually living in your market, you learn a whole lot about the dynamics of what's going on. I know what the inventory is in Middlesex County. It's something I, I grab at least once a week from one of the realtors in the area and I'm able to track it. And that helps me make decisions in terms of where we're gonna deploy capital.
Dr. Jordan RomanoYeah, I just here's a perfect example. I was just chatting with somebody about listing some land for me and she said, "Oh I can't show it on Saturday." And, "How about Monday morning?" "Oh, wait-" I'm showing the the big cat cafe. And I was just like, "That's for sale?" And she was like, "I'll see you at 11 o'clock." And I'm like, "Oh." So I like, I... She didn't mean to- she didn't- it's an off-market showing, but that's not what it's called. I changed the name on purpose. But she, by being hyper-local and by knowing those folks, and just by... I, w- I like going, I go with my mom. I go to the local diner. There's a couple of them. One is in, by the college town, and then there's another couple diners that I like to go that are, but being in those greasy spoons, you bump into people. 100%. You b- and you're like, "How's it going? What business is going on?" "Oh, I'm doing this big job here." And and maybe, I think the other thing to keep in mind, too, is a lot of people think in too small of timeframes. You can look on Zillow right now and see what's on the market. But to your point, if you are talking to these folks the, the likelihood that over 20 years it could lead to some business. And that's not the only reason to do it. It's for the love of the game, if you will. But you'll bump into somebody and something will click, right? You'll have some detailed information that may inform you on whether or not you should sell or buy or how you're going to shift your investments.
Ed MathewsYep. So in the introduction of this show which you'll hear after we record is is that if you're within three feet of me, we're probably talking about real estate at some point during the conversation. Just I drive my wife and girls crazy with it. I'll be standing in line at the grocery store and, "Hey, how's it going, Ed?" "Hey, pretty good. I was looking at this property the other day," and ba. And pretty soon it's, "Oh, my aunt's selling," or, "My uncle's selling," or, this or that. And I can't tell you how many deals I've found that way. You have an interesting way of finding deals yourself talking about the zoning. Why don't you walk us through that strategy in terms of how you create deal flow?
Dr. Jordan RomanoSome of it I would say is the w- the word I would use is just curiosity and that curiosity, w- what does that actually mean? It means most people should realize, and this is the benefit of being hyperlocal, is that there are planning and zoning boards and that a lot of jurisdictions around the, the country they're not even... E- even the ones that you would think are not that terribly sophisticated have a lot of data and information. And I'm not even talking Zillow. I'm talking like, Meeting notes,
Ed Mathewsminutes.
Dr. Jordan RomanoYeah, exact- meeting notes- and minutes, and you can lis- you can listen to them and you can k- see where the puck is moving. You can see, oh, they approved this big storage unit. Wait a minute. One of the biggest developers, this is something I'm picking up on and it's by s- even saying it out loud. I'm refreshing a thought right now just by saying this. One of the biggest developers in the area, who I know o- owns a couple hundred units, just went back to the planning board to expand his storage space. Now, he could be wrong, right? But this is a guy who, through his family, through multiple generations, has been building and expanding his portfolio in the area, and he is doubling down because he wants to expand his storage business space. Now, maybe he's doing that because he wants to flip it, and it needs to be a certain size to attract outside money to f- there are all kinds of... But to me, it's signal, right? It's like why is he doing that? Oh, that's v- that's very interesting. The, the one deal that I have done recently, and I just talked about listing some land. I drive... I'm going up again this weekend for the holiday weekend. I'll be driving around the town. I had passed this... It was listed on this property I purchased, was listed on Zillow for, I don't know, six months or so. And I happened to be driving in the car with my mother, and I happened to say, "Oh, that's a lot of land." And I just paused and I was like, "That's a lot of land." And I knew where I was in the town. It was n- there's a big hospital and then there's a smaller hospital, and this is like a block away from the smaller hospital. So nice location, public water and sewer. It's .9 of an acre, and the house sat to one end of the lot line. And I happened to look to my mom and I said, "Could we subdivide that? Do you think the town would allow it?" And I'm like, "What price would I have to buy the house where I could flip the house back onto the market if I needed to and not lose a lot of money to play out this thesis?" Sure enough, I go to the planning board and with the, I get it surveyed. I'm, whatever, 10 grand, I have it surveyed. I go to the planning board with the... And this is a local surveyor who comes with you. They do a great job. And they approved it. Two s- they, the town wants small lots for, what they call workforce housing, where people can put, a $400,000, $500,000 home, which is a starter home, maybe with an ADU, maybe not. And now I have three lots. One has the existing home and two vacant lots that are buildable on town water and sewer. And what's the, I don't know who, I don't know who to attribute this to, but it's you don't find a deal, you make a deal. Yeah. So there are deals, right? That on Zillow where you're like, it just makes sense and you're see... I like the game. I probably like you. I like seeing-- I like the arbitrage and I like seeing what other people don't see, and I like cre- almost like I watch my little boys building and watching you know, cre- that, and the little boy in me of building something and creating something. And I'm helping the town and I'm create- and I created something that wasn't there before. And so it would've been a perfectly, and still is, a perfectly fine single family home. But now we can put a couple more homes there. They're not entirely cramped. It's a third of an acre. And now a nurse that works at the hospital is gonna be able to build a home. And I have a re- a, a retired couple that's interested that wanted to build their own home that can now do that. So- Yeah that- Yeah, and it's- So I would say it's, going back to your original question, it's curiosity and I stare at the same town map. And by the way, you're gonna miss deals. You're gonna miss deals in the neighboring towns. There's all kinds of things. You're like, "Oh, that would've been interesting." And I miss things. But that builder who owns 200 units has now come to me to buy those two p- He also is interested in those two pieces of land. He lives a couple blocks away. He drove by this, this thing daily. And so that's what I would say is also don't underestimate just because somebody else hasn't done it. One of the loops in my brain is what am I missing? But am I wrong, right? Because this big time builder drove past this, 700 times a year going to work and coming back, maybe more, call it 1,000 times, and he didn't think to buy it. So what-- and I realized the real risk is, okay, if they don't approve the subdivision. And so I, sharpened my pencil and I'm like, "I think this'll work." And sure enough, now this guy is gonna buy from me something that's... How do you think he feels? It's two blocks away from where he lives.
Ed MathewsYeah, no, it's, and it, A, the relationships are are a fundamental piece to success, right? Absolutely. And but the other part of it is that, you've got to be able to look at properties. We bought something similar. We bought, So funny story. I think the listeners have heard me tell this story 37 times, but I'll tell you anyway. I- is that the we bought a 58-acre farm locally here in, in Haddam, where I live. And the, the initial conversation was about the 1,300 square foot house. And he called me back and he, w- we agreed on the house and the five acres around it. He called me back like 20 minutes later and he's "What do you want to do about the land?" "What land?" I get in my car and drive back. I'm like, "Holy, there's 58 acres back here." And we worked it out and he got a fair shake and I got a good deal, and he didn't have to pay a tax bill he didn't want to pay anymore. And I I'm ultimately gonna end up building seven to 10 houses back there. So same deal.
Dr. Jordan RomanoYeah I like those sort of deals. I like the idea of at least in New England, in, in this small town, there's a cyclical nature. I think, again- Very the big piece that I would-- And I suspect you're-- I suspect people do this, but they don't pay attention to their curiosity. It's when you're in... I really scrutinize photos when I'm in- looking in Zillow. They're like, "Okay, kitchen, this and that," and you're like, "There's no dishes in the cabinets. Nobody's home. Somebody's carrying this tax bill, and it's coming to winter, and do you know what oil-- Oh, it's an oil... They're, they heat by oil? And you can't have the pipes freeze. They're g- And they just did a price reduction. If this is still on the market in the fall, they're taking... I can come with cash and really get a good deal on this." Sure. And that's what happened with that with that single family home that I subdivided. It was a end of the fall. Do you really wanna carry this to the busy spring season? You're, it's six of one, half a dozen of another. You might get 20,000 more dollars, but with heating costs and taxes and waiting time, and it's a maybe in the spring. Yeah. It's not a guaranteed. Or do you wanna take my- It's a couple thousand a month. What's that?
Ed MathewsIt's a couple thousand a month.
Dr. Jordan RomanoThat's right. For, for the chance to maybe get the price that maybe you'll get maybe, right? And or you can just take my deal now, and they said, bird in the hand. And that's how you make deals like that. And it's, Yeah and it's a win for everybody.
Ed MathewsYeah. So you talk about curiosity and one of the things that my team had kinda pointed out was relentless curiosity, and that that's a couple more levels above, right? And so y- you're a busy physician. I know you do other things as well. And the-- So when do you spend the time? You mentioned you also have a family. So when do you spend the time? Do you require sleep or how are you generating, how are you generating deals on a consistent basis?
Dr. Jordan RomanoI think what some of it is you rotate crops, right? To, to your point. It's if you have ongoing relationships, then that's something that comes due every now and again. I think that I look at, I look at the maps, it's on my bookmarks. It's on... if you load up my computer right now, it's one of the tabs that au- automatically opens up. So I would say it's mo- it's moments. Am I definitely-- Am I getting beaten by people who do this day in and day out? Certainly. But look, I got, I still found that deal where the guy working on the bigger deals missed this little deal and now wants the land to keep his builders busy. I would say it's in... The medical term is in the interstitium. It's like in the in between. It's in the in between. It's half an hour a day before I go to bed, or it's not terribly regimented. And then I have weekends. I, I think at the end of the day, it's I've made a concerted effort that it is a large part of my investment portfolio, and it's also a large part of my sort of mission because it is fixing up a town. It is investing in this town specifically where I trained for medicine. And that is a little bit of my, my mission. I feel like I'm giving back and I truly believe that everybody wins. Like, when I do that subdivision, there's more tax that the town gets because somebody's gonna build a home, but then somebody gets a home, and then I've made some money as well, and then the builders and plumbers and... It's just the ripple effects of encouraging investment. I, I'm a... Capitalism has become a dirty word, but to me, that is just a, a virtuous type of capitalism where these small towns can truly benefit. And I think everybody, that somebody's gonna, somebody's gonna mow the lawn, right? The- I c- the- I can't tell you- People are gonna spend money and the, and more people are gonna be living in the town to spend money at the grocery stores and at the restaurants and at the coffee shops. And it just, I'm not saying that's all me. There, there's a team that has helped facilitate that, and I think that's, when you have a deal not go through like I just did it's that's hard to deal with because- Yeah you have a vision and not everyone is always going to,
Ed Mathewsbuy in.
Dr. Jordan RomanoUnderstand.
Ed MathewsYeah.
Dr. Jordan RomanoYeah, exactly.
Ed MathewsOne of the things, it's interesting you frame it like that because one of the things that I tend to do when we acquire, particularly with the single-family properties, is I go door to door. I go across the street. I go n- next door neighbor to the right, next door neighbor to the left, introduce myself, give them my contact information. A, if we're ever making noise at too early or too late, I want to know about it. But also, B I want to know-- I want them to know that we're gonna take y- we're gonna be good stewards of that property, and we're gonna clean it up. We're gonna fix it up. We're gonna sell it to a nice family, which is going to inc- not only inc- y- remove any potential blight that is happening around that property, but it's also gonna raise the values of their properties as well. Everybody wins when you do these kind of deals.
Dr. Jordan RomanoYeah, I'm a fan of you need to be reminded more than you need to be taught. And so- coming on this podcast and hearing that is that was a tough lesson that I had to be reminded of. I've-- I had a, a lot of things go well. I'm coming off of a strikeout that was painful where a lot of neighbors rallied against one of my projects. And I I've gotten away from the door... I've, I've-- I have a lot of relationships locally. I got away from the door-knocking in anticipation of presenting to the zoning board before this deal. And th- and what you just said to me is a, at-- when I go up this weekend, it is gonna be hat in hand, and it's going to be speaking to a lot of these neighbors about that project and almost apologizing that I couldn't convey to-- that I didn't come approach them beforehand with, it was a deal that I I needed a zoning variance because it was-- the box was too big for the piece of land that it sat on for it to qualify for four units. So I needed a variance from the town to say, "Yes." The, the box was huge. It's the largest two-family in the downtown area. It's meant to be four units. It should be four units. And a neighbor, i- this is his right. I don't have any hard-- Well, I don't have any... I understand why he felt the way he felt, but he pitched a, an effort to bring a lot of people to the meeting, and I think the zoning board as being as objective as they could it is hard to ignore the literally the full room that they said- Vox populi has not been that full in, I think they said a couple years, just to oppose my deal. And so I... what you just said to me is a, a great reminder of, to put on my to-do list, is that when I'm up there this weekend is to go chat again with all the neighbors because... And it's not, it is not for self-serving, it's more to be in service, of the town. And from my perspective, it's to apologize that I didn't bring them into sort of even the planning of why I think the four units would actually benefit all of them, and it's not going to be a drawback. So that's sharing a little sort of vulnerable moment where I don't always win, no, of course not. Like the, but it's also helpful because you never know what you're gonna come across. It's funny for all the people who got up to speak against my project, I stayed after to chat with all of them. I said, "I wanna... i'm gonna stay here." I was there till 11:00 PM. And one of the people even, she came up to me and she goes, "Oh, you should buy the one next to that. The people who run that one are terrible, and the, and it's, we have so many problems with them." And I'm like, "Here you were saying I'm this evil person, and yet now you want me to be a partner to help fix up the neighborhood." So it's- Right I guess it cuts both ways. It does. But thank you for that reminder, 'cause that is- Yeah, sure I think that's a, an important piece that not a lot of people do. And it's because it's hard to do, to knock on somebody's door and say, "Hey, I'm that evil investor developer that, that has a... I'm not nameless or faceless. Here I am,"
Ed Mathewsyeah. And I think the key phrase that you used before is really important, and that is to be in service, right? Be of service. And, a- and I think in a lot of cases where there's disputes like the one you're describing, and I've been in my fair share of those as well, is that in a lot of cases, those folks just wanna be heard, right? They wanna be heard and, in many way, in many cases, a solution can be found. Not necessarily on the debate floor of a planning and zoning meeting, but over a cup of coffee or a beer, you know- Definitely usually you can figure that out, right? Not usually. A lot of times you can figure that out. And sometimes you can't, and so be it. But and then you go to plan B and plan C and plan D until you find something that you can make work. But the the interesting thing that I find is that, like I said earlier I think in a lot of cases, folks just wanna be heard.
Dr. Jordan RomanoYeah, and I think that's wh- where what I would say is for being hyperlocal and doing my deals and sourcing that way, I-- when I went to the zoning board, and some of that is how do I do it all? Obviously I missed some things, right? As being a phys- a physician and being busy, I had been working a few different types of deals, I guess this is my excuse, and it didn't make my list. It just didn't make my list of like- Yeah I didn't-- on my what's this saying? On my bingo card of things that would come up, it would be- Right that a neighbor would rally 20 other single family owners in the surrounding blocks to come, so I didn't think I would need to have a counterforce of people to speak in my favor. Could I have done that? Yeah, of course. I know all those other builders and things like that who would have come. In fact the head of the zoning board w- is one of those folks who owns a lot of units, and he almost, convinced the board. Not because he's trying to help me out, but because- it benefits the neighborhood he understands what I'm doing.
Ed MathewsAnd so- A rising tide floats all boats, right?
Dr. Jordan RomanoThat's- And they-- yeah, exactly. A- and he understands what the city wants, and he was, I think the difficult... I think I could have fought the decision. I think ultimately I decided to back out of the deal. That has had some reverberations. I think there's some folks that are... It's a small town. They're not used to seeing deals break up, and I think that's been something I'm probably gonna have to deal with for some time, but that's part of doing business, it's
Ed Mathewspart of it, yeah. One of the things that I'm always... let's move on to the final five. Yes sir. So one of the things I'm always fascinated by, and, someone like you who, you have a successful medical career. You have, other things that you do that are quite successful. You are a renowned expert, and you are investing in real estate above and beyond. The things, the basic things are taken care of, right? You're not really sweating paying the mortgage. You're not... Car payments are handled. Saving for tuition's probably in pretty good shape. And nevertheless, you get up and go to work on Monday morning. And f- to me, I've learned over the years that is purpose, right? That it's ab- something above earning, right? It's well above that. And, I'm curious what your purpose is. What gets you out of bed on Monday morning?
Dr. Jordan RomanoI think by my nature, I'm a curious person. I like finding and seeing things that maybe other people don't and I like that, and that translates into a lot of different arenas. You alluded to the fact I do some medical expert witness work, and so I've really enjoyed operating in that space as well. And same with the real estate. I like I like having an impact, and I think that, it's-- I'm not I can only speak to like sort of my lived experience. What I can say is a lot of people maybe feel disenfranchised. I don't watch too much of the news. Enough for it to be I think informed. But I think that's the cool thing about being hyper-local is you can have an impact on a small town. I don't take anybody's-- I don't take outside money. I don't even take family money. This is me just investing my own money. Now, I have family members that say I should have taken a lot of money. I would've owned many hundreds of units and that sort of thing. But you can have an impact. You can have an impact in these, in, in America. And America is made up of a lot of these small municipalities. It doesn't take... it's been a decade, and I feel like I have an impact. People know me. I, I am-- I help, build the other, and support other people's businesses. The, the lawn care guys, the plumbers, the handymen, the, the guy, the, the college kids who wanna paint in the summers. Like these are... maybe you have fond memories of that when you were a kid. Like you, I'm, I... You can help support an economy and have a positive impact and it, and you don't-- It has nothing to do with Washington. It has nothing to do with international affairs. And I think to me that's important. And it, and there is a piece of giving back that I would say that's I have had a lot of extraordinary opportunities in my life. A lot of them I've found on my own. But I've been supported by a community, and to me a lot of people say thank you and you move on. I don't I don't think that's a wrong way of looking at things. I just have felt that this community where I did my medical training was such an important part of my life that supporting the individuals that, and the town and the housing where people who work at the hospital live has been my way of giving back.
Ed MathewsAwesome. Awesome. I'm curious about the mentors you've had along the way and, So I'm curious, what's the best advice you ever got and who gave it to you?
Dr. Jordan RomanoOof. I would say dep- it depends. I would say just general life advice. My grandfather had a few rules. One of them is always know where the exit is. That could be physically. I think you can use that as a metaphor for, your job or an investment. And so I tend to always think about that from a safety perspective. He had to leave the country that he grew up in and then came to the came to the United States. And so knowing where the exit was T- and being able to, I can't imagine having a, somebody knock on your door and say you have to leave within 24 hours, and then having to sell items and things of that nature to leave. But I think that's an important piece is always knowing where the exit is, having flexibility and optionality. Living in y- in the United States I think we have a lot of that just geographically. You're-- There's a lot of flexibility that other people in other countries may not have that ability. I would say for real estate, I tend to favor Sam Zell. He he has a or had a-- I think he passed away this past year. He was a bit cantankerous, but I liked his advice. He wrote a book "Am I Being Too Subtle?" I think it's... You can just listen to him on the podcast if you don't wanna read it, but I like that book. He would say, I remember in an interview somebody was saying to him like what do you think of the market?" And he's like, "I don't care about the market. Show me the deal, 'cause there are good deals in bad markets and bad deals in good markets. So I'm more interested in what deal you're doing, not necessarily..." Now, is it harder to do deals depending on interest rates and where money is flowing and, job markets and... Yeah, of course. But you can still do good deals in, in, in air quotes, "bad markets." I think those are the best, best-
Ed MathewsYeah, that was e- excellent advice. I'm gonna, I'm gonna s- I'm gonna borrow your grandfather's advice for sure, always know where the exit is. I'm gonna, I'm gonna marry that with my grandfather's advice, which was always present a moving target. I- in terms of, looking back and, I think you've been very vulnerable, and I appreciate it in terms of what's worked and what hasn't over the years. When you look back on your professional career, let's talk specifically about investing, right? What's a decision that you look back on and think, "Oh man, I would love to have that one back"? And how did you manage your way through it?
Dr. Jordan RomanoIt's-- When we're done, I'll probably think of another one, but the, off the top of my head, a rising tide floats all boats. I didn't think that the economy would continue to go the way it's going. I've had, because of my hyperlocal kind of off-market strategy and conversations, I could have realistically, probably a couple hundred units at this point, pretty close to it. I passed on a big deal that would've gotten me a bulk of that. A family that owned-- They were going to sell me their entire portfolio. It was, At the time, I did not have a property manager. I did not have-- It was-- And I'm not drawing judgments of the tenants or anything along those lines, but it was like C-minus class. It was really rough product. Tenants I probably would not have wanted to deal with myself. And I didn't do the deal because I wasn't thinking large enough. And in hindsight, I could've-- It would've ca- it would've been very capital intensive to buy it, to bring it up to B, 'cause I like-- My whole thesis is I like to be in B, 'cause in good times C is moving to B, in bad times A is moving to B. Make B product, stay in B product, charge B mo- product rents, and you'll always do fine. And I've-- That has served me very well. You miss out some on the upside, but on the downside you're covered.
Ed MathewsAnd over
Dr. Jordan Romanothe long term- But yeah, that deal I passed on it, and one of the other local guys, big guys, got wind of it and it was gone like the faster... When I hesitated and I said, "I'm not sure," it was gone. And these guys, they're fast. They write a check, it was done. So-- And that's that was a pathway to a hundred units. But you know what? The-- I, I'm, I guess I'm old enough to know that there are levels to, to every game you play, but it's also It can never get good enough. Like there's always more. And so I think the deals that, that haven't happened, here's another one that I've shared before, but I like this one as well. There's a big highway, the big highway and Dartmouth's hospital is off this highway. It's the confluence of two of the biggest roadways probably in New Hampshire and Vermont. Off to the side, I noticed there was for sale some land, a janky puzzle piece of land right off the highway. And it was owned by five brothers. And I'm like, "Why hasn't this deal gotten done?" This was over COVID. And it was a, a tear down house on four acres of the whole area was probably 10 acres, and they owned about four acres of it. But you couldn't get the f- the five brothers to the table, and somebody was always holding out because he had more back taxes or some, a lien on his hou- other house, and it was... But what I-- And this is the problem with dealing, doing deals and not moving fast in a small town. I got them under contract. I had spoken to the guy who owned another two acres, who turns out he owns a, he had a large commercial garage on one, on this parcel as well, that he had a landscaping business. He was gonna sell the landscaping business. I'm trying to figure that out. Then there was maybe three or four single family homes there I could have put this together. It's currently listed... just because you miss out on a deal doesn't necessarily mean it's a bad thing. It's currently listed, I think it's down to $5 million. But I could have bought in most of the land and then bought off the single-family homes one by one by overpaying for them, and been in for, call it, I think my numbers were like 1.75 or call it $2 million. I didn't have the cash, but I could have figured it out. It's now-- It was listed for six and a half. It's now come down. I think it's now under f- it's now I think listed for four and a half. But the person who came in it took-- Once I passed on and I didn't go to closing on that single-family home with the brothers, that's all it took. I t- because I brought in my contractor, and once he knew, he wanted to respect me, but once he knew I was not moving forward, it was gone. Yeah. The next person who liv- who came in and played out my thesis and cleared all, l-leveled everything, and it's a perfect place for a small corporate park or something like that. And it is one of the busiest intersections in the state, in, in that mid part of New Hampshire. And I saw that. And so I think that's the thing, is you gotta be able to let things go. I think that's that's the one lesson is like y- they're gonna be de- there's always another deal. I guess that's the, th- that is tomorrow's another day, there's always another deal, and just let it go. A lesson learned. It just, it showed that my intuition's good. I'm good at seeing the future and seeing value in places.
Ed MathewsYeah.
Dr. Jordan RomanoAnd let it go.
Ed MathewsIt's a healthy thing because it'll make you crazy, right? So I also it parallel to learning to let things go like that I also for every property I've sold, I never drive by them ever again if I can avoid it. I just, I don't wanna know. I hope they, I hope the folks that bought it do well and love the place and all that but I go out of my way... there's one property that I have to drive because it's literally on the road between my home and my office, so I drive by it every day. And actually I drove by it every day for about 10 years and thought, "When that comes for sale, I'm buying it," 'cause I'm sick and tired of looking. It was a mess, and now it's beautiful. And the folks that live there are taking excellent care of it and it's still beautiful, and I'm happy for them and, But other than that, of, all the other properties that I've bought and sold, multifamily, single family, whatever, I never ever go back. So I'm curious about how you take in information What's the book on your nightstand these days, virtual or otherwise?
Dr. Jordan RomanoGoing back to something I said before, you need to be reminded more than y- you need to be taught. I tend to read books... He actually, I think in this segment in the book talks about how he reads books, which is skipping around. That's how I've always read books. I'm not a page one to page, 250. It's The Almanac of Naval Ravikant. He's like a philosopher thinker with a, a tech binge tech, angle to him. I think that he has a lot of interesting ways of looking at life and and he's older than, I am by call it 10 or 15 years, so I think that's helpful from a perspective, I'm just trying to think of what else. There's a book, I'm blanking on the name of it. It's by her... I think her name's Annie Duke or Dukes. She was a poke- a female poker player. Oh,
Ed MathewsYeah.
Dr. Jordan RomanoAnd she wrote- I know the book. I haven't read it she wrote a couple books. Yeah, she wrote a couple books. She did consulting, probably still does, for- Yeah, she still does Like hedge funds and VC firms about taking risk. And so she wrote books. I think it's even called something like that. It's like Calculating Risk or something along those lines. It's a re- a book with a red cover. That's in my stack. I tend to drive everybody who comes over to my house nuts 'cause I just have... I'm that guy- Yeah who has stacks of books. I, it does not take me much to- Th- Thinking in Bets, by
Ed Mathewsthe way, is the book you're thinking of.
Dr. Jordan RomanoWhat's that? Thinking in Bets. Thinking in Bets. Yeah. That's it. Yes. It's a good book. And but I don't... I tend not to put all my money on one book, s- Speaking of Bets. I take a little bit. All it takes for me, and that's why I will consume lots of books very quickly and then revisit them, because to me it only takes one line or a couple lines, and I tend to do- my books have the dog, dog tag, are dog-eared or m- bookmarked for, so when I revisit them, those lessons I come to very quickly. Because i- again, I think it's important that sometimes when you revisit... I'm sure we're all human. I feel like this will resonate. Sometimes if you hear something when you're not ready, it doesn't mean as much. But if you read something at the right time, you're... it's gonna click, and it's gonna... You're like, "Oh, th- this, I get it." And so there are things in Sam Zell book that I will come back to about how he arbitraged X, Y, or Z, and it, and it just, it helps me to revisit those. Right now, actually on my nightstand is The Almanac of Naval Ravikant. It's a white book. Yeah. It's... Yeah. It's taken from podcasts and tweets and goes over... It's like tech philosophy, but it's something I enjoy.
Ed MathewsAnd very applicable to our business as well. I've read it, and it's absolute genius. So yeah, and in fact, I'm a notorious re-reader of books. And, a- and, it's similar how our brains... It's funny how our brains work similarly, because if you ever borrow a book from me, you're gonna get it and it's gonna be highlighted and dog-eared and notes in the margin. I'm a very active- That's right reader. It's the only way I can re- make sure I retain the stuff that I wanna y- I wanna learn from these books. 'Cause, I look at a book as if, some human being is boiling down 10, 12, 15 years of their life in 250 pages, and I'm gonna try and suck the marrow out of that bone as best I can, right? It's it's 'cause y- it's a rare opportunity to get that kind of view into somebody's brain, so I'm curious, the last question in the lightning round, and then we'll we'll start to land the plane. How do you define success in your life?
Dr. Jordan RomanoI would say de- It-- Right now, right now it's optionality and flexibility. I... It's something that I had been, and I technically still am, but at at n- not in a full-time capacity worked f- in a kind of corporate academic medical environment for pretty much my whole career. And now I do that in not full-time, and that allows some flexibility and optionality. The world's a big place, and I think when you nose, when you're nose down in a book or in, in your job, I think there's nothing wrong with that. That's how you become a, you become very good at something. I think the difficulty is there's a lot going on in the world that you're gonna miss. And so I'm enjoying taking a step back from that and having the optionality to do what I want and work from where I want when I want. I think that a lot of Americans are looking at the world that way, maybe in a... You say post-COVID, but we're well beyond COVID now. But I think a lot of people still think that way. And so to me, success is waking up, doing what I want, when I want, with who I want very soon after I think of doing it. Meaning there isn't a big time delay and I don't have to say, "Oh, I, I have to delay doing that for, I can't do that for six or eight or 10 months." And listen I'm fortunate enough to be in a position to do that and I'm just trying to, use my success to bring others, under under the tent and help other people if they define success that way. 'Cause to a lot of people, they wouldn't even see that. They'd find that some of what I do may be too risky and not enjoyable. But to me I have honed a skill that I feel like it's hard for me to lose. And it certainly doesn't benefit me to think that I could lose. So I tend to think about in a... A younger me wouldn't have thought in such an optimistic way, but I'm, I tend to be very optimistic in how I approach what I'm doing and I'm really, I'm just like, if I present whatever it is that is a win and as much people win as possible that's a great way to to have a day.
Ed MathewsAwesome. Awesome. Yeah. It's I try to do the same thing, right? Is, I'm looking at the world and realizing that it's, there, there are certainly opportunities out there. And anyway. So when you're not talking about real estate, what do you like to do?
Dr. Jordan RomanoThat's a good que- it's interesting. Like you, when I'm doing something else, I'm probably, it probably comes up- Talking about real estate. Yeah, I'm, it's me it probably comes up as well. Because I think it's interesting that, it's something I wanna share with-- I do share with, with buddies of mine who weren't involved in it and now they are. And I have a buddy l- he, maybe he'll listen to this too, but e- every time we speak, he's like, "You don't understand. Thank you." He was paying a ton in tax, and now he has... He's very I think faith is a big part of his life, and I think that, giving back to his community in a similar way that I am with where I trained I think that he's really enjoying that and has brought it into his family as well as-- And so I think that he enjoys that. So I would say what am I doing? I don't know. I do, it, I think it's, I'm going to the places... I'm spending, realistically right now, my parents are older. I'm spending time with my parents- Yeah with where they are. They, my parents are divorced, but between Long Island and up in New Hampshire, I spend a decent amount of my off time. And it's just enjoying time because It's easy to forget that what we're doing is we're all headed to the same place. Finite. And I don't mean to be terribly morbid, but it's easy to, we're playing to, to the, playing the, the going to the poker thing with Annie Duke's, it's like all our chips are going back in the middle eventually. Okay, fine. Maybe you can play some games and the chips get divided a little differently. But I, I, to me, I'm just trying to make sure that I'm enjoying what I'm doing. And a lot of what I'm doing is just spending time with family, knowing that some people probably have less time around physically with us than we, we may like. But that's part of the game that we're playing.
Ed MathewsYeah. Between Bryan Johnson and Kara Swisher, I think those are the only two folks that have i- have figured out im- immortality. The rest of us we're we're gonna, what's the term? Shuffle off our mortal coil at some point.
Dr. Jordan RomanoSomebody was like, the, the jokes about Bryan Johnson are like, what if he does all this and he gets hit by a bus? And then I don't know. If you enjoy it and it makes you enjoy life more I think there's also, what's the qua- I'm sure there's some, pithy saying you, it'll pop up on my phone on Instagram I'm sure when we're done about like getting the most out of life. It's not the, it's not the, it's not the longevity. It's like how much you're meaning and you're getting out of out of each day rather than how many years how many years you're living. I, I think that that's another conversation. I think- So- when you hit those levels of wealth, that's the one thing you want, that I see a lot of people chasing. And just from my med- this isn't a medical opinion, but a lot of, they're on the... Sometimes when you're that far out on the curve of healthcare it, it advances, You're an N of one and it's probably not having the impact that... I don't doubt that you might, it might tweak some numbers and you might feel better, but the likelihood I don't think it's as simple as everybody makes it out to be. We're programmed to die. It is hard to rewire that program. I'm sure there are people working on it. Yeah.
Ed MathewsNot in our lifetime, my friend. But we'll see. You never know. Somebody'll figure out how to manage, what's it, what are they called? Telomeres or whatever, and, it'll, That's a big part of it. That's a big
Dr. Jordan Romanopart of it
Ed Mathewsyeah. We'll see. You'd know better than I. I was an English
Dr. Jordan Romanomajor. And the simple thing is we have a wick, and the wick is burning- and when the wick burns down, your, the candle goes out. Y-
Ed MathewsIt's interesting. You made me think of my grandfather who was a a World War II era Marine, and he would swim a mile or two every day. Every day, religiously. And he was also a really funny guy, and had a very good self-deprecating sense of humor. And I, I... One, one year I bought him a T-shirt. I had a T-shirt made for him that said on the front it said "Eat right, exercise daily," and on the back it said, "Die anyway." And he wore that proudly for years until he stopped until he stopped swimming. But... And lived, 20 years after I gave him that T-shirt,
Dr. Jordan Romanoyeah, they were, they were built different. My grandfather sounds almost identical. He swam, that was his thing. He swam two miles every day- Yep at the community center, and he was he was a World War II era guy. He was in the second front on, in North Africa. Yeah, and just l- lived well into his 90s. Smoked a pipe, you know- Same just lived a, a harder life. But he, But he l- but he really lived his life. Yeah. And it was, Yeah I'm glad I'm glad for you that you had a, what sounds like a similar role model in your life. They don't ma- when they say they don't make them like they used to I think- That is that is definitely true.
Ed Mathews100% true. So Jordan, I've really enjoyed this conversation. Thank you again for joining us today. So h- if people wanna get to know you or learn more about your business, what's the best way for them to get in touch?
Dr. Jordan RomanoYeah I do... Like I said, I'm a physician but on the side I do medical expert witness work. The entity that I interact with and engage with folks through is medicalexpertwitness.com. If you just wanna chat about other stuff too, it's a good way to get access to my calendar. If you go to medicalexpertwitness.com, you can, there's a part that says I think it's book time with Jordan. You have although my assistant says I should probably not do that so much 'cause it, my ti- free time does get booked up. But I enjoy, I meet people all over the country. I love chatting with folks. Feel free to reach out. I, it's part of life is meeting new people.
Ed MathewsYeah, right on. Jordan Jordan Romano, thank you so much for joining us today. Continued good fortune and hopefully we, since we're basically neighbors, I hope we get to meet each other in person someday soon.
Dr. Jordan RomanoFantastic. Thanks for having me.