Nearing Financial Independence with Just ONE “Luxury” Rental

Seeing investors with hundreds of rental units can be intimidating, but you DON’T need a massive real estate portfolioHey rookies, we often showcase investors rapidly building their portfolios, but today we’re focusing on something even more important, getting that first property that transforms your financial future.And look, while one property won’t make you an overnight millionaire, it can dramatically accelerate your path to financial freedom. And our guest today proves this perfectly. He switched from only investing in the stock market to house hacking a duplex, and the results changed everything. He did it all on a state employee salary. So today he’s going to share how he found his ideal property, how he mastered being a landlord with literally zero prior experience and how he used AI to simplify sourcing deals.This is the Real Estate Rookie podcast. And I’m Ashley Kehr.And I’m Tony j Robinson. And give a warm, warm welcome to Ronnie. Ronnie. Thank you for joining us today, brother.Thanks for having me. Really excited to be here.Yeah. Ronnie, can you walk us through your journey from just traditional investing to discovering what you call luxury house hacking? What made you pivot from your original retirement investment strategy to getting into exploring real estateGrowing up? No one in my family really ever talked about finance or investing at all. I wouldn’t call us poor growing up, but certainly there was financial stress and it was evident to me even as a young child. So having financial security has always been something that’s been really, really important to me. And growing up everywhere that people talked about, Hey, get a job that you get from college, get that education, and then from there you’ll get a career where you’re going to be financially stable, you won’t have to worry about bills. So I did that, and while I was in college, I just remember being in the library one day and looking around and I was like, man, I’m not particularly enjoying this. And then I was like, well, that’s okay. I am going to bang this out real quick and I’m going to jump into the workforce and things will be so much better at that point.
And then I started really looking and I was like, all right, well, what’s that path going to look like? And the traditional path would be you spent your entire life up to this point going to college, educating yourself to then go into the workforce and work 40 years and then eventually retire and enjoy 15 to 20 years. And sounds really bleak, but that’s kind of the way I was looking at it and I was just like, man, this does not sound fun. So then I kept looking for alternative solutions and found Mr. Money mustache. When I found that blog, I really just dove in head first, but then slowly I started to realize that even though I had a great savings rate at the time, once housing came into play, then at that point my savings rate would slow down and it really was going to slow down my path towards financial independence. So that’s where real estate came in, and I started looking at house hacking. Didn’t know it was called house hacking, but that’s really what got me started.So Ronnie, this rent by the room house hacking, or was this looking at multifamily units and renting out the other units?I guess the main driver for me was always like, all right, I’m just going to invest in the stock market. So I didn’t want to jump into something that was really too complicated. I figured, all right, I’m just going to get a duplex. I’m live in one side, rents out the other, just need to subsidize my housing in order to continue to invest into the stock market. But then I just went into it thinking, all right, I’d be fine living here and it’s going to subsidize my housing to the point where I’ll be able to maintain a very, very high savings rate and go from there. But then once I bought this home, I realized, wait, I really have to figure out what I’m doing here. I kind of just jumped in head first. No one that I knew was doing anything like this. Then from there, I found BiggerPockets and really just started educating myself and I realized, oh my God, this could be something that’s actually scalable, because I thought, Hey, it took me seven years to get here. There’s no way I’m going to continue to be able to buy multiple properties. But through this podcast and the real estate one really just started learning that this could be scalable and that there was a lot of benefits to real estate and kind of just have been moving on forward from there, continuing to educate myself and trying to find another deal. So this property is a side-by-side duplex. At one point, it must’ve been a single family home and throughout the years it’s a very old home. Throughout the years got converted into a duplexAs a side-by-side one. Usually you can see the upstairs and downstairs, but I don’t think I’ve ever seen a side-by-side.Yeah, and that’s what really drew me to this home is that you look at it from the outside, it does not look like a multifamily home at all. It looks really, really nice too, and it’s in a great neighborhood. So I walk the property and I actually went into this property thinking, all right, I’m going to, because it’s kind of like a lopsided duplex. It’s not evenly split. So my initial plan was, all right, I’m going to purchase this property live on the smaller side and rent out the bigger side. However, it came with a tenant already in place, thankfully they’ve been great and they’re actually still here. So we just renewed the lease and now this is three years into owning it, or this is the third year, just past two years haven’t actually moved to the smaller side. So now I am getting a roommate next month to take up one of the spare rooms over here. And actually it ends up being a slightly better deal financially because between the room rental and renting out the other side, I end up making more money than if I lived on the other side and rented out this one.And I think that’s why house hacking is so cool because you can blend it in a few different ways. And Rhonda, you just said you can rent out one side, make revenue from that side, but then you can also rent out the rooms on your side to generate even more cash. So I really do think that for a lot of people in 2025 who from I think from lifestyle perspective can swing it, house hacking is one of the best and easiest ways to get started in real estate investing. The cost to require the property is typically lower. You get the experience of not having too much to manage on your first deal, usually just a couple of tenants that you’ll be working with, and it’s just a great way to get started. So you said that your initial goal, Ronnie, was to help subsidize the cost of your living expenses. So maybe walk us through the numbers on this deal once you get this roommate in place, how do you think things will shake out on this property?Yeah, so purchased the home for 400,000. It was probably one of the more expensive homes at the time that were multifamily duplexes. There were obviously three family and four family homes that were a bit more, but the other side rents for 1725 and the roommate will be paying 700. Between that, it’s going to more than cover the, it’s going to cover the mortgage, and if this property were paid off just from the other side being rented out, I’d be able to cover my living expenses. That’s kind of one of the things that I’ve been kind of struggling with or not struggling with, but more debating is do I continue to try to scale a portfolio or do I pay this home off? And then from there, I guess it’s one of the things that I’ve heard Scott Trench mentioned a few times where you play defense a lot and then once you play defense enough to build a solid foundation, you could really start playing offense very aggressively. So one of the things that I’ve been debating is if I pay off this home, then my cost of living is covered. And then from there I can job hop and really try to grow my salary to then from there, be able to scale my portfolio even faster.Well, I love getting this insight from Scott Trench as to how you are making some of your financial decisions. We are going to take a quick ad break, but when we come back, we are going to hear more from Ronnie on how he’s successfully raising his unit’s rent and has leveraged AI to find his next deal. We’ll be right back. Okay, now let’s get back into the show. So you’ve been able to increase rent over time. Please tell us about what your strategy has been to actually implement this.Yeah, so on one of the episodes of this podcast, I actually heard about the binder strategy and I decided, you know what? I feel like that’s probably the best thing that I can do because similar to you, Ashley, I do not confrontation or difficult conversations like that. So I figured, all right, this would probably be the easiest way to kind of express my desire to raise the rents, but also say like, Hey, you’re also getting a pretty good deal here. So what I did was I went to BiggerPockets and got the kind of a rent estimate for my property. Then from there went to apartments.com and Zillow and did the same thing. All of them were pretty much in the same ballpark. From there, I looked at the neighborhoods that the other properties were in and compared them to mine and also the square footage and bathroom account as well, and of course bedroom count.
So once I had all this information, it was a pretty evident that the unit was well under market, and once I presented it to them and kind of just laid it all out there, I said, Hey, you’re getting a pretty good deal here. I do have to increase the rent, but I don’t even want to bring it all the way up. Can you just work with me here to move it a little bit further? And we went back and forth and landed on roughly the halfway point, met pretty much right in the middle and raised up the rents. And that’s what I did the first time. The second time is we just signed a new lease, actually mentioned to them, I think it was a few months before the lease was going to end, Hey, are you still thinking about continuing to rent here? And if you are, let me know and we could try to work on the numbers again. And they pretty much knew exactly what I was going to say and present before I actually did. So they actually came to me with a number that made sense to them, and it was actually spot on to the dollar of what I was going to propose. So it kind of just worked out great. And Brightside is I ended up avoiding any awkward conversations, so that was great.It looks like the binder strategy has impacted a lot of people in the rookie audience. And Dion McNeely I think was one of the first people to mention that strategy, and we’ve interviewed him a couple of times, but I think his most recent episode was 463. So for all of our rookies that are out there, check episode 463 to give more about the binder strategy that influenced Ronnie here. Now, Ronnie, you’ve increased your rents, you’ve been able to build up your reserves, and now I get that you’re looking for your next property. You’ve also got a really, I think, unique strategy here that I want to get into because you’re leveraging artificial intelligence. The buzzword ever since chat, GPT became publicly available and now everyone’s kind of lost our minds of what artificial intelligence can do. And I feel like we probably haven’t talked about it enough on the rookie podcast about how to leverage AI as a tool to make us more efficient, to save us time, to make lives easier as real estate investors. So how were you using AI to help you find your next deal?Yeah, so again, another podcast episode that I had listened to, I think it was Ariel might’ve been the name of the person, and they had a very sophisticated way of looking at properties, and I believe on the episode they mentioned a website called Browse ai. So I figured they mentioned that this was very easy way to get in, kind of dip your toe into the waters of AI and try to see, all right, how can I use this? And I actually went back and did it again yesterday. I have it set up now so that it just goes into Zillow. It takes all the properties that are listed there and just gives me basic information on them. So it uploads it to a Google sheet, and from there it’ll tell me the address, the bedroom, bath count, the square footage, price, a picture of the property, and then also a link to the actual listing.
So once I see that, then from there I kind of just create an average and a median of the square footage and if anything kind of sticks out or is an outlier, then from there I kind of go look at it. And also I can see the exact same thing for rental properties. So when I went to go raise my rent as well, I looked and had a similar report sent out, and basically what it does is it tells you everything that’s listed for rent right now, and then it’ll update it every couple of weeks or so and tell you which ones are not listed there anymore. So then I know what’s actually been rented or what’s just sitting on the market so that I have a better idea of what’s the real going rent in the area, because oftentimes I’ll see that there’ll be some outlier property that’s 500 bucks above asking or above typical market. So that kind of throws off the averages, so I make sure to use it in both aspects.I love that approach. And I also love that you mentioned Ariel and I was looking at her episode, so she was episode 429, so episode 4, 2 9, if you want to go back and listen to Ariel’s episode, but very similar to what Ronnie just broke down, where you, you’re looking within the data to kind of find some of those hidden gym properties that maybe other investors are overlooking. And she was doing it in a much more complicated way. I think she was like an engineer by background and she had a bunch of scripts that were running. And it sounds like you’ve maybe found a moreRookie friendly,A rookie friendly way to get to the same result. It’sVery rookie friendly. Again, I actually tested it out yesterday and I think it was something like 10, maybe 15 clicks of the mouse and you’re good to go. And it really just walks you through step-by-step exactly how to do it. And also it’s just free. You can pay more to have it run more often, but I do it, I believe it’s once a month for each report and then it keeps updating automatically and again free. So why not also use chat GBT for my listings and everything like that as well, and to make standard operating procedures. So AI a little bit of everywhere.So Ronnie, what exactly is your buy box? What are you having the AI look for in these properties?Yeah, if I see anything with higher square footage, I’ll look at that and I really have narrowed it down to my town because that’s the area that I’m most familiar with. So people can use this at scale and find a whole bunch more properties that they could potentially buy, but I really narrowed it down to my town and within my town, certain neighborhoods. So there is a dump in town, so I try to make sure that I’m within a few miles away from that just to avoid that particular area. Then there’s a few neighborhoods as well that I know can be a little less desirable. So I try to filter out those two areas. And then from there, anything that falls outside of those, I filter through those and figure out, all right, well, what’s the asking price? What’s the potential revenue based off the bedroom count?
And then if there’s any that have a bit more square footage, I go to those as well. So one example was actually a few weeks ago, saw one come up and it had much more square footage than it should have had, I guess, for a two bedroom. So I went and saw it and turns out that for some reason a third of each unit, it was an up down duplex listed as two bedrooms, one bath in each one, and a third of each unit was the living room. So it just was a very weird layout. The bedrooms were kind of tiny and squished. And then there was also, while I was there, I noticed, all right, well there’s this huge living room area that could be closed off, made smaller, and then you can add another bedroom if you wanted. But while I was there, I realized that there was an unfinished attic that could also be finished and then add another bedroom, maybe even two up there because it was very big.
So a lot of people weren’t very interested in the property. I think from what we saw with my real estate agent, there was only a handful of showings, but once we went there and saw that, we knew that there was some potential there didn’t actually end up getting the property because there ended up being a few other issues that came up, ended up passing on it. But it’s just an example of one time where I’ve seen a property that has really had some hidden potential, and I feel like I probably come across them maybe once a month within my very small buy box. So I’m sure if you expand this out, you’d get much more hits.Yeah, our friend James Dard from on the market talks a lot about creating the right business plan for each property and identifying the opportunities that a lot of other investors overlook. And I love that you’re leveraging technology to help make that task easier for you. Ashley, again, we don’t talk a lot about AI on the podcast, but it is something that’s so important. Have you dabbled at all? Are there any use cases of AI in your business that you found that are like, Hey, this is something I leveraged regularly yetFor tenant communication? For example, just the other day in this one village, you can’t have an unlicensed vehicle sitting in the driveway. It has to be parked in a garage or something like that. And I had a tenant that had the plates off their car. I got a notice, so I just pop it into ai, can you write a letter to my tenant that they need to remove their car here? And I sent a link to the actual code language that was in the village and the link, the building inspector’s information and stuff like that. It just popped out this nice little letter for me to go ahead and send. So that’s probably the most common way is that I’m using it to draft different letters and documents and templates even, I would say. But then also within our property management software there, there’s a bunch of AI integration there, automatic things that are set up to respond to tenants that way too. So tenant communication, I would say the big thing for me,And I feel like for a lot of investors, that’s kind of where we’re starting because it’s probably the easiest way. I know our PMS on the short-term rental side has similar functionality where somehow it gets to know your properties based on whatever information you plug into it and it can kind of respond on your behalf. But some other just one-off use cases, this is actually one I just found out about a couple days ago, but when I am analyzing a property location obviously matters in real estate, but sometimes it can matter a lot, especially in the short term rental industry. And if you’re a couple blocks in one direction, revenue could be really, really different. So I’m able to export the coordinates for all of the properties in a market, and I can plug that into chat GPT and say, put this into a heap map for me.
Let me see where the highest and lowest performing properties are. And then, hey, here’s my subject property. Show me where this is in relation to this heat map. I can see, am I in the hot zone or am in the cold zone with this property? It did it so quickly and I was really, really impressed with how quickly it sipped it through that data. Anyway, I think there are a lot of different ways that we can start leveraging ai. And Ronnie, thank you for giving us, I think the insight into how Ricky can do without having to code like Ariel did. And what was the name of the tool that you were using? Again, I’m sorry, if you can repeat it,Browse AI and chat EBT as well for making listings for my rental and creating standard operating procedures, and both of them incredibly user-friendly. Again, the browse AI one was maybe like 10, 15 clicks and started getting reports right away and chat GBC, obviously you just type in whatever you need and it’ll do it for you. So I use that a lot to create standard operating procedures for different things. So for instance, before my tenant mentioned that they were going to be renewing the lease, I started trying to create a procedure for how to do a showing and any steps that I might need. And then when someone moves in, what should I do in order to make sure that that transition goes as smoothly as possible? And I don’t just copy and paste it. I of course use that as a template and try to build off of that, but it gives me a really good foundation to build off of. And then from there, I’ve noticed a handful of times where there’s some things that it’ll mention and I’m like, wow, I forgot about that one. All right, let me add that in here and kind of just build off of it from there.Now, Ronnie, you’ve built a relationship with AI to help you run your business, but what about other investors in your network? How have you been able to build those relationships and make those connections throughout your real estate journey?Yeah, so one of the things that I always hear you saying is just try to take action and put yourself out there, mention to anyone that you are involved in real estate. So I started following a few investors locally here that had been on the podcast. One of them is Andres Bruna. He was one of the first guest on the podcast, I forget what episode, but saw that he was a local CT investor. And I figured, you know what? Why not let me follow him on Instagram? And from there saw that he was going to a local meetup and I decided, you know what? Let’s just go and try to be as extroverted as possible. Make sure that you try to offer some sort of value there. And being a financial analyst by day, I figured, all right, you know what? I am not afraid to go out and take action, whether it be they need someone to do a showing for a rental or if they need some landscaping or if they need someone to run numbers for them, I figured I’d go there and just try to offer as much value as I could.
And I guess I must’ve done something right because after a week or two, him and his partner, they ended up reaching out to me and there was a property that they were going to go walk through for a potential flip, and they said, Hey, do you want to just shadow us for a bit? And I said, sure, why not? And I did that two or three times and then after a while they kind of just brought me onto the team. And then from there, it kind of just continues to snowball. You start meeting more and more people and start seeing what other successful investors are doing, and you try to replicate that because if it isn’t broke, then why fix it? So kind of just have tried to gather as much information over these last two years and really just try to learn as much as I can so that I don’t repeat as many mistakes as other people have. I’m sure I’m going to make plenty of mistakes, but I just want to minimize the risk as much as possible.Well, we have to take the final ad break, but we’ll be right back after this while we are gone, make sure you are subscribed to the Real Estate Rookie YouTube. Okay. Welcome back from our break. So Ronnie, we wanted to touch on the big decision you’re currently making because I think a lot of rookies will relate to this. Do you first pay off your current duplex or do you invest in a second property? So let’s talk about each of these paths that you are thinking of tanking and kind of give us the pros and cons of each.I guess on paper, the smart decision would be your mortgage is slightly less than what you would be able to make on another rental property or even in the stock market. So definitely don’t pay that off. But there I think is an argument to be made for paying off the mortgage free up some cash flow so that you can take bigger risks that might potentially pay off in the long run and have a higher impact on your wellbeing. Because the way I see it, if my property were paid off, I feel like at that point there’d be much less worry or stress on my end to job hop and see like, Hey, do I like this other position that can get me a pay increase? And then from there now it’s easier to get the down payment for the next property. Can I maybe try to start my own business?
Things like that. So I think it’s a little more nuanced than people often give it credit for. And then on the flip side, if I invest in another property, then you can always have great results with that as well, especially if I try to maybe go up to three or four family homes. So I think there’s an argument to be made on each side, but I also don’t want to end up biting off more than I can chew because I’m not exactly raking in the big dollars right now. So I want to make sure that I take things slowly because I think Warren Buffet once said, maybe it was Charlie Munger, number one rule is don’t lose money. So really trying to make sure I don’t do that one. ILove that concept of not just looking at the numbers, that there’s other nuances to take into an account. And I think one of the other things to add to that is being able to sleep at night, your primary mortgage is going to be the best interest rate in most cases. If you’re going to get financing from a bank, you could get seller financing at great terms and interest rate, but your primary residence will be one of the best mortgage rates that you can get because it’s your primary. But sometimes sleeping at night is better and knowing that the home that you live in is paid off, where if you have rental properties with debt, the tenants are paying those and you don’t have a personal responsibility to paying your own mortgage anymore. And it’s just that thought, that mindset that you have a paid off home, which I think is something to take to factor in when actually looking at these two decisions and not just solely looking at the numbers.Yeah, I think there’s another argument to be made too in favor of paying it off is that sure, you could potentially go out and earn a higher return than what you’re paying on your mortgage interest, but you’re also adding another property, which is more management, and it’s like at the end of the day, what actually helps you get to the lifestyle that you want? Is it three paid off properties or is it 12 properties with mortgages? And it’s like, which one of those is actually going to get you to where you want to go and allow you to live the lifestyle that you want to live? Because for most of us, we’re doing this because we want some sort of financial independence, but we also want time freedom. That’s why a lot of us do this because we want the ability to say yes and say no to certain things, but if you’re bound by the whims of all your tenants or your guests, are you really getting the lifestyle that you want to? So Coach Carson talked about the small and mighty portfolio. DL McNeely talked about the strength in his small portfolio and sometimes paying it off can get you there, even if not, maybe the most effective way can get you there in a way that gets you the lifestyle that you want.Yeah, and that’s definitely something that every time that I, because I go back and forth on this a million times every day, but every time that I’m thinking about it, I always kind of go back to that as what am I optimizing for? Am I optimizing for maximum returns or am I optimizing for freedom? And at the end of the day, I think I am optimizing for freedom. So that’s why I tend to lean more towards paying off the property and then from there, every rental going forward can have a mortgage on it, and then I’ll scale that way. But kind of like you said, actually paying off that primary residence does have that kind of psychological factor to it as well, which I think can really help you in so many ways from a mental health standpoint, but also just freeing up cashflow. So I think there’s a lot to be set for that as well.
Obviously there’s plenty of people who are going to do it completely different, but that’s their path. And I’ll take mine, but I think Coach Carson said a small and mighty portfolio really is really impactful. So even if I just had, like you said, two or three properties that are paid off at that point, it’s going to be such a game changer and it’s going to really impact my life and then my future family’s life as well, because having that freedom would allow me to go on and do things with them that my parents unfortunately weren’t able to do with me because they were working so much. I think it’s definitely something that I always struggle with, but the optimizer in me, the perfectionist in me always wants to be like, no, just maximize returns. And then the other part of me is like, no, no, no, come on. We’re just doing this for freedom.And that is such a big part of it too, as to like, okay, if you want to accumulate a lot of properties, that’s going to take a lot of work. You’re going to have to put in the work to do the acquisitions, to get the deals, to find the deals, to get them under contract, then to put in some kind of operations for them. Even if you’re outsourcing property management, there’s still asset management that you need to do. So it’s also like, do you have the time or do you even want to spend the time building this large portfolio, or do you want to have that small and mighty portfolio? So that’s a big thing to think about too. It’s not only the return piece, the money piece, but it’s also the time and effort that’s going to go into creating that too. I know that I don’t want to build this huge, massive empire and work every single day to build it, vacate it.Yeah, no, absolutely. And that’s kind of one of the reasons why I tend to investing in the stock market a little more is because you just said it and forget it. But at the same time, every time that I do these calculations, because I created this calculator for rental properties that I’ve been using for myself, and anytime that I look at that versus the stock market, typically the rule in the stock market is the 4% rule where you can live off of 4% of the size of your portfolio, but typically what I’ve seen in real estate is that that number could be six, 7% sometimes depending on the property, even higher. It’s just a much quicker way to optimize for financial independence. So that’s why I tend to be looking more at the real estate market now as opposed to the stock market because you can just get to financial independence so much quicker, especially if you’re house hacking.
It really is like a huge game changer because that’s easily the number one expense for most people. Once you have that covered one, maybe two other properties can get most people covered after that. And this is something that I feel like most people can do regardless what your salary is, because a lot of people, including myself when I first started, didn’t know that you could get into a property with just 5% down every time I’d look on Zillow before that, I would think like, oh man, how am I going to get 20% down for these incredible properties? There’s no way I’d be able to do it. But for the average, Joe, you’re, you’re able to get in with 5% and right there you just reduce the cost of living for yourself. And it’s just a really big benefit that I think everyone should probably do at least one house hack. Even if you don’t plan on being in real estate long-term, just do at least one to get the ball rolling and really create some sort of freedom for yourself and some passive income. That way you’re not incredibly reliant on your W2 because you never know when that could go away as well.I think the big takeaway here is that you have this dilemma, but this is such a great opportunity either way. This is a great decision to have to make either way, no matter which way you choose, one option is not the wrong option. Yes, there may be a difference in how it impacts your life and what your return on investment is, but these are two very good options to have. So anybody else in this predicament, just remember that no matter which way you choose, there is benefits to both of these options, and it’s a really good decision. It’s really good situation to be in. So congratulations, Ronnie, for being at this crossroads.No, yeah, thank you. I mean, it wasn’t a short journey. I started investing back in 2015, so about 10 years now to get to this point, but it’s definitely been worth it. And I think, again, anyone can really do it as long as they’re disciplined and have strong work ethic, whether it’s in the stock market or in real estate, you can do it. I would say real estate could get you there a little quicker, probably 10 towards doing that, but anyone can definitely do that. I think the other argument to be made is a middle ground that I have been debating as well is maybe potentially recasting my mortgage to at least drop the payment down a little bit, and then from there, using the excess funds to try to scale the portfolio. So it’d be a little bit of both, but that one I’m not entirely sure just yet, which of the three is the right path to take.Well, Ronnie, thank you so much for joining us today. Can you let everyone know where they can find out more information about you and how they can reach out to you?Yeah, I think the best way to reach out to me would be on Instagram, it’s just Ronnie Reia is R-O-N-N-Y-H-E-R-E-D-I-A. And yeah, just send me a message on there and would be happy to chat with anyone.Hey, well thank you guys so much for joining us for this episode of Real Estate Rookie. I’m Ashley. And he’s Tony, and we’ll be back soon with another episode.