Sleeping at Work to Build an 8-Unit Portfolio in America’s Most Expensive City

Dave:Do you think living in a big expensive market means you can’t invest in real estate? Think again. Today’s guest works at demanding travel heavy day job, so he’s building a rental property portfolio as a backup plan and he’s doing it in and around New York City. This is not a story of an already rich person buying properties in cash. It’s about using hustle and persistence to build towards financial freedom, even in one of the country’s most expensive markets, Ben was even willing to sleep in the office he was working in to kickstart his investing career. And although that type of sacrifice isn’t for everyone, it might just be for you.Hey everyone, I’m Dave Meyer, housing market analyst and head of real estate investing at BiggerPockets, and today we’re bringing you the story of an investor named Ben Chester and I’m super excited to talk to Ben because he’s one of the very few people I’ve ever met who’s doing basic rental property investing in New York City. Ben isn’t buying giant apartment buildings for millions of dollars. He’s also not buying really risky properties in suspect areas. He’s found a way to acquire one bedroom apartments that cashflow in some of America’s most expensive zip codes. So on today’s episode, Ben’s going to tell us the exact formula he found that makes these deals work even when starting with six figures of debt personally that he had. He’ll tell us the story of how he turned Billy Joel’s house. Yes, actually Billy Joel’s house into a cash flowing investment property, how he can offset almost all the taxes from his W2 career with real estate investments and he’ll give us his advice for other investors who want to stay local but live in hyper expensive markets. Let’s welcome Ben. Ben, welcome to the BiggerPockets podcast. Thanks for being here.

Ben:Thanks so much for having me.

Dave:Alright, well let’s jump into your backstory a little bit. Tell us a little bit about the circumstances that led to you getting started as a real estate investor.

Ben:So a lot of people I graduated school didn’t get. The best job was making $30,000 a year, which in New York City is basically the poverty line and I was spending all my time at the office, but all my money was going towards rent. So trying to run this experiment where I actually decided to secretly move into my office full time. Hold on. Where were you working? So I mean when I say office, it wasn’t too bad. It was actually a sleep clinic. I was doing medical research for pharmaceutical trials.

Dave:Oh, okay. So there were beds in these?

Ben:There were beds and the beds were not always a hundred percent occupied. So there’s a lot of nights where I actually had a pretty cozy hotel room in midtown Manhattan.

Dave:Wait, were your employers aware of this experiment?

Ben:No, they thought I was a hard worker. So this is 2012, so shortly after I got the job Hurricane Sandy hit and I was the only one that actually showed up at the office that day, so they thought I was a super hard worker. They’re like, oh my god, Ben came in Armageddon and the hurricane, it turns out I was just living there so I had nowhere else to go, but I got promoted and kind of moved up pretty quick after that, which was awesome.

Dave:As far as I know, that is the first time hearing this on the show. I feel like that’s something you see on TV or in a movie where someone moves into the office to save money on rent, but you really did it. Say you gave up your apartment, you need to know how you pulled this off.

Ben:I was in a lease so I couldn’t actually just pack up and leave, which it was my original desire to do, but because I was on the hook for that rent, I actually put it up on Craigslist and started renting it out. Furnace rental, stay as long as you want. I thought I needed to cast a wide net to get someone interested in the rent, but there was crazy demand actually for a furnace, flexible housing there

Dave:I imagine.

Ben:And so I kind of hung onto the job as long as I could at the sleep clinic, but that experiment kind of ballooned into an actual full-time massive business where we got venture capital investment for it and we were trying to pitch it as a tech company to get the better valuation, but what ended up happening was we were getting crazy pressure to grow super fast and so we were taking on lots and lots of inventory, but those of you that are in medium term rentals or any seasonal rentals, it’s very ebbs and flows in terms of demand. So we would grow crazy quick and then have these big troughs of vacancy, which ultimately killed the business. I actually left that business with over $120,000 worth of personally guaranteed debt that I put under that business and it was gone. So I was basically starting from nothing with, I mean less than nothing. I had 120 k of debt that I had to recover from.

Dave:Oh wow. What a roller coaster. I mean what do you do at that point?

Ben:Yeah, so I mean it was pretty devastating. Not only that, it was the debt, but also I had spent years of my life building this business and it basically imploded so needed to basically figure out how to survive and I didn’t want to leave New York, which was like my dream was always to live there in the first place. So I definitely didn’t want to leave the city, which I think a lot of people end up having to do.And so what I do is I got a W2 job. I really had no other choice. I had to do it just to pay off this debt over time. And then I also got an apartment. I had this whole skill set of how to rent apartments. I knew how to work with landlords in the city from that experience. So I found a one bedroom apartment with my girlfriend at the time. We moved into a one bed and then we had the landlord reconfigure it to basically turn it into four. It was like, I’ll call them rooms, but I used

Dave:Spaces in New York

Ben:And then we rented, we had got three roommates, so it was my girlfriend and I and then three roommates and so we have five people in a one bed, one bath. But what was great about that and we did that for about a year and a half, what was great is it covered all of our housing expenses, so we literally weren’t having to pay to be there, we just had to coordinate roommates, which can kind of be a pain, but it was worth it. And then all my W2 income was basically going towards paying off debt and also a little bit towards retirement and stuff like that.

Dave:I grew up in the New York City area. I understand what you’re talking about when you said a one bedroom just magically turns into four bedrooms, but maybe you could explain that to people who aren’t familiar with that

Ben:Particular one. We had actually the super was also a contractor and he built temporary walls basically, so it felt nice. It was actually sound privacy and stuff a little small, but it was livable. And then there’s other situations where there’s one where I literally lived in a walk-in closet with my co-founder. This was prior to that, but when we were launching the first business, we lived in a duplex on fifth Avenue, which was amazing, beautiful be place, but we rented the rest of it out and then we stayed in the walk-in closet together. Unbelievable. I love it.

Dave:Alright, so you sort of got back on your feet doing this strategy. It sounds like something you knew from the business you had started kind of replicating that for yourself personally. Did you then at any point scale to a traditional real estate portfolio or did you just keep doing this kind of hustle mentality going forward?

Ben:Well, the goal all along was to basically do this just to get out of debt and basically graduate to the next level, which was going to be ownership. And so I saved up about a year and a half of saving and paying off debt aggressively to get to the down payment. One thing that’s really helpful, when you mentioned finding a job that you can live in, one version of that a lot of people have access to is a travel job. So if you’re in a job where you’re getting put up in hotels and they’re paying your expenses, which that was, I was able to not only get my rent cover, but also I was able to get food and I wasn’t spending a lot when I was on the road. So combination of that, I basically aggressively put close to everything towards saving for an apartment, got my first down payment, moved into a New York City, which is not easy to do, got rejected from a few because they had seen my history with all these apartments I had and the press from having this business.They’re like, are you going to do this in this apartment? I was like, no, no, no. Which wasn’t trying to build a new tech business there and bringing strangers and all that. But what I did do is I found a one bedroom apartment in and I say one bed. It was basically a closet in Hell’s Kitchen. You probably know it in one of the grungier areas. In 2019, my girlfriend moved in, also my brother move in. So we have three people now, which felt like luxury. We had our own place. We’re spending probably $750 each to live there, which is super cheap for New York. That’s unheard of. The principal payment on every single mortgage was about the 700. So I was pretty much from a net wealth perspective breaking even though I was paying into it now, I was paying off that mortgage. I was at least neutral on

Dave:Housing. Everyone, we’ve got to take a quick break, but we’ll have more with Ben right after this. So I found this thing called the Lennar Investor Marketplace, and honestly it’s kind of genius. It’s built by Lennar, one of the top home builders in the country, and it’s a new platform for investors who want turnkey new construction homes. These are professionally built reinspected and rent ready. From day one, you can browse properties across more than 90 markets. You can see verified rental comps, neighborhood data, and even handle financing, title and insurance all through Lennar’s in-house network. It’s everything you need to make data-driven investment decisions in one place. Go to biggerpockets.com/lennar and explore the homes available right now. Welcome back to the BiggerPockets podcast. Let’s jump back into my conversation with Ben Chester. I’m curious though, this is a common question that I get a lot and I think is pretty common in the real estate investing community, whether it’s New York or LA or San Francisco or any of these pretty expensive markets. Why did you choose to buy a home versus say, continuing to rent and investing in either midterm rental, short-term renters, whatever you want somewhere else if you wanted to get in real estate? What about this approach made sense to you?

Ben:I had no idea. I just knew I just need to buy real estate and so first step was I got to live somewhere. If I can find a place I can hang onto. I also viewed as every month or every year landlords are raising rent. So there’s always this kind of unsettling feeling. If I want to stay in New York forever, there’s a chance I could get priced out. I won’t be able to afford here if I’m renting. But if you buy, you’re pretty much locked in. Of course co-op fees can go up, but it’s not like a landlord raising rent on you. So if I could just lock in a place and have a 30 year fixed rate and at this point it’s still below 3% too, I knew I’d be set basically where I could make sure at a minimum I’d be able to afford New York as long as I wanted to stay there.

Dave:Oh, that’s great. Okay. I like that approach. And so it sounds like that worked for you.

Ben:It was fantastic. Again, this is 2019, the first apartment basically locked in. I viewed it as I’m set, I’m going to be able to stay in New York no matter what and then COVID hits. Meanwhile, I’m still making W2 income. I’m still traveling all the time. I didn’t really care if my living conditions were terrible. I was like, as long as I have a place back in the city to stay in, it’s okay. But I started looking, it was like the world’s changing right now interest rates are still pretty low at this point. I actually started looking in Texas and I discovered that I would save on taxes if I moved to Texas during COVID. I also could find a lot of really great quadplexes and houses there that would basically cashflow if I bought the old fashioned house hack, you move into one unit, rent the other three out, you can basically cover all expenses. But then with the tax savings on my W2 income, I actually would come out ahead even if that property only broke even. So house hacked with a friend there for a short period of time during COVID. It was like a great experience.

Dave:Did you know what you wanted to buy? Were you looking for a duplex or are you still just doing the roommate thing?

Ben:I had no money still everything was still going towards, I had some of that debt left and also was still not making any cashflow. So all the income that’s coming in, I was saving it for a down payment and at that point I had only maybe 20, $30,000 saved up and my friend was in a similar boat, which is enough for a down payment. So we ended up using an FHA loan, which now you can do this with a conventional 5% down, which is amazing. But we use a 3.5 with a higher interest rate FHA loan in Dallas. And so we paid, it was like 30 to $40,000 total to get into this property cashflow from day one with the unit that we were living in. And it basically created this springboard where the tax savings, even though it was making a small amount of cashflow, it was just we were saving on taxes. And then on top of that, we were also basically able to start to build equity in there and get the tax benefits and everything over time.

Dave:So what was the place? Tell us about

Ben:It. So it was a quadplex still have it today. It was four units all next to each other, basically four townhouses in a sense, all combined under one roof. So it was super nice. It was an area in northwest Dallas that was appreciated a bit and then became a good source of income and also for tapping in for equity for some of the later purchases that they ended up making.

Dave:And what happened after that? You left Texas or what was the next move?

Ben:So now rates are starting to move back up at this point. So I had basically acquired a couple properties I had with this one in New York that had a rule where you could rent it out after a certain period of time. So I got it as a long-term rental and then I was going back to New York and looking for another place to live, and so acquired another co-op through a similar method. This time I was with my brother who was going to move to New York for residency and also another one who’s an architect, two of them. So we’re all going to basically live in a place that I could find together and kind of house hack, which we did. And now the snowballs are really starting to take off. And so every couple of years I’m getting a new apartment in New York and then I’m also starting to get enough cash where I can start thinking about down payments outside of the city for more conventional rentals. You’re pulling off something

Dave:That’s pretty tough, which is by most people struggle to just pull off a single acquisition in New York, but you’re pulling off multiple. So when you move back from Texas, what is your financial situation? Are you making a lot of cashflow off the other two rentals? Is that helping you with the down payment or how did you actually finance this third purchase?

Ben:Yeah, so the main thing I’m always looking for is just I want the property to break even because keep in mind, I’m planning to keep this W2 job, so I have enough money coming from that. If I can break even on the properties with conservative underwriting, I don’t want to expect me or kohl or anything, but as long as a conservative will break even with the tax benefits of appreciation, I’m happy. So at this point there’s not really much cashflow spinning off the properties. Everything’s breaking even and there’s enough for reserves, so lose a water heater or stuff. I could handle that without flinching, but I wasn’t living off of it at all. What was good though is I had this W2 job, so I was having enough where I was getting a little bit of savings starting to go. So there were some creative strategies I later used to tap into those retirement funds, but basically I was coming back to New York with enough to put down a down payment on another co-op essentially.

Dave:Do you mind sharing us with us the price point of these new co-ops?

Ben:Yeah, so at this point I’m still looking at it about entry level, so half a million dollar range, which is entry level for New York.

Dave:Okay, that’s not as bad as I thought you were going to say. I mean that’s close to the median home price in the US right now. That’s not like crazy New York pricing where everything’s $2,000 a square foot.

Ben:This is true. But keep in mind these are one bedroom apartments with something wrong with them at that point. So if they’re

Dave:Right, you’re not getting the luxury apartment at 500 grand

Ben:Like the toilets in the living room. Yeah, exactly. There’s something not quite right about the place.

Dave:All right. So you’re back in New York, you had your stint in Dallas. Now three properties sounds like six units. Where do you go from there? Still buying more in New York City,

Ben:Basically looking for anything. So again, I don’t really have a form strategy yet. I kind of dabbled in New York and the multifamily, so I was kind of looking everywhere to see what would stick. The problem was in New York City was getting harder and harder to find those units that would make sense. Not impossible still. And I actually did end up buying another one we could talk about later, but I was still just looking around New York at this point. One thing that happened too is I got my license as a realtor to try to basically stretch the money further. I was like, if I can get paid a commission at the same time of acquiring these, it kind of offsets the acquisition costs. It could be a good strategy. And I started to look around MLS and then also just on Zillow, everywhere around Manhattan, Manhattan wasn’t making a lot of sense. And also the cashflow, it’s not very interesting. Even if you could find something that makes sense, it’s still just breakeven. So I started to expand my search and one hour radius of the city and I found a lot of really interesting waterfront properties, particularly where they’d be same price point, half a million dollar houses needed work. So they’re not beautiful, ready to go houses, but they’re on amazing pieces of land.

Dave:Are these far from the city or they vacation destinations? What kind of locations were you looking in?

Ben:So I knew that the property themselves, as long as they’re close to the city, I felt like people would probably go as long as the house was a destination in and of itself. So to me, I was like my friends and the people I know, they probably would travel an hour to go to a lake house and it doesn’t necessarily matter where that lake house is, as long as it’s nice enough and it’s accessible, you’ll probably get eyeballs there. And it was kind of just a gut thing. There weren’t any comps at the time. There wasn’t really any sort of clear data that it was a good decision. I was just like, I think we can make this work.

Dave:And your plan was to renovate them though it sounds like you hadn’t really done that yet at scale, you’ve done kind of putting up these walls, but now you’re talking about taking something that’s not very nice and turning it into a destination that’s like a pretty big

Ben:Shift. It was massive. It was way more than I expected too. And at this point I started listening to BiggerPockets where it’s always about value add and people are dealing with contractors and stuff. So I’m like, okay, it seems doable, but oh my god, it’s way harder than you think. And also I had no idea how to price out properties either like renovations and rehabs, but I did know that this was a beautiful lot. I found this lake house that was on a double lot on a lake that was within an hour of the city and it’s just like, okay, it needs a new bathroom, probably needs some updates to general updates to the outside and some safety stuff, electrical way more than you would normally get for a normal house. But it was lendable. I could basically finance it and I was like, you know what? Worst case scenario, now I have enough W2 income coming in that even if it takes longer and it implodes, I can at least sustain the mortgage on this and have it. Worst case scenario, I could just rent it as a long-term rent.

Dave:How about financing the furnishing? Because that, I joke about this on the show, but I think the worst underwriting mistake I’ve ever made in real estate is just totally missing how much it was going to cost to furnish

Ben:Short-term

Dave:Rental, especially if it’s a big one that you’re trying to make a destination, you got to spend money to make it cool. You can’t just throw Facebook marketplace stuff in there. How do you pay for that part of it?

Ben:Yeah, so actually this is another creative financing that I found along the way almost by accident. I know you’ve mentioned before on previous shows, the 0% credit card hack with you can get a 0% intro a PR on a business credit card. Well, so I basically did that and I was thinking I got a 20 k limit on the card. So I was like, okay, that’s great. At that point, I had a new LLC for every single property that I had acquired. So I had a couple LLCs with cards that I never used 0% intro on, but they had credit lines. And a cool hack that you can use, at least with Amex and Chase is you can actually take credit lines from those other businesses and put them onto the 0% card and it’s free. They let you do this, you just call ’em up, it takes like six minutes. So I turbocharge that intro 0% card to basically fund the entire rehab. And so I didn’t pay any, I think between 12 and 18 months I didn’t pay anything at all in terms of interest and I just paid it off by the end.

Dave:Alright, time for the disclaimer though. This is a great idea. If you can pay this off. Using this kind of loan can be a very effective strategy. I hear people do this most commonly in short-term rentals. I think this is kind of a common approach to doing this, getting the 0% interest. It’s a way to get pretty much free financing, but if you don’t have a plan for repaying that back and it’s got to be a good plan, this could be really dangerous. So it is one of those things where you kind of want to use these when you don’t really need it. If you are like, I’m banking everything on using this 0% interest rate credit card, I wouldn’t do that personally if I were you. Ben has a W2 job, he has other resources, he has other assets so that if something goes wrong, he can take care of that. We talk about this a lot on the show, there are different kinds of debts. There’s good debt, there’s bad debt. Credit card debt is bad debt. If you’re not paying it off, that is super expensive debt. It can really snowball into a trap. So you just want to be careful with that. But again, if you know what you’re doing and you do it carefully, it can be a good option for you. So how’d this one work out? Big shift in

Ben:Strategy. So I bought the property for a little over 500 K, ended up expecting 30 K, 40 K total to put into it. That was a new bathroom, electrical updates that I didn’t even realize were that severe. That ended up being more complicated than I thought. And then I put in new HVAC system in it ended up costing more like 150 K for all the rehab plus the holding costs plus also the furnishings because I overbuilt it more than I needed to. And also I probably did more work than I really had to, but as a result it ended up being, and again, my goal was just to break even, but it ended up cash flowing a ton and it ended up being a really amazing entry point into the Airbnb market around New York City.

Dave:How are you managing it? Did you do all this stuff yourself?

Ben:Yeah, so I was doing it myself just by default. I was like maybe I’ll put a manager in eventually. And I started interviewing property management companies, but through BiggerPockets I actually stumbled upon this short-term rental loophole and I was like, you got to be kidding me. This can’t be real. This is unbelievable. And so I read the books on it. I went through three or four different accounting firms until I found one that was like, yeah, well let’s do this. And so basically, as long as you’re working a W2 job and you’re self-managing your Airbnb, you can take the losses including depreciation, including any bonus depreciation that you’re using, which could be substantial. Take all that and apply it as a loss against your W2 and come to effectively, you can get close to paying no taxes, which is insane. That’s when I was like, oh my God, this is the new strategy.It makes sense. I’m going to keep my W2 job. I’m going to acquire as many Airbnbs as possible and just to make sure that I’m maxing out those losses every single year on paper so I can basically offset my taxes. Remember, I’d started out thinking, I want to control my housing costs. I thought that was the biggest expense that a person would have, but really the biggest expense no one thinks about is actually the tax side. I’m like, this is a game changer. Not only am I not really paying for housing, I could also completely undo my taxes or not have to pay them and offset them if I do this the right way.

Dave:Stay with us as we take a quick break. We’ll have more with Ben right after this. Welcome back to the BiggerPockets podcast. Let’s get back into my conversation with investor Ben Chester. I think the sort of journey and evolution of philosophy and strategy about investing is common, that you don’t really start for the tax benefits, but eventually you get to a point where you realize that if you maximize your tax benefits, it can significantly increase your returns. I’m not talking about 1% or 2%. It can make five 10% difference in your rate of return each year, which is amazing. That’s better than buying bonds sometimes. That could be better than investing in the stock market just from the tax benefits that you get.

Ben:It is insane. And I think about it, my job is commission based largely sub in a tech sales job where I can put more effort in and get more pay. And the amount of effort I put into getting more pay is way harder than just saving on the tax side. So you can end up going a lot further by saving on taxes and having to go get a second job or just work 40 more hours a week or something like that.

Dave:Can you give us a number? How much do you think one of these saves you in taxes per year?

Ben:So there’s a limit. If you’re single in taxes, you can do up to $305,000 of tax offset per year. That’s the limit that you can’t do anymore in that against your W2. I’ve maxed it out every year with a lot more carrying over.

Dave:Yeah, just for everyone understanding what Ben’s saying is if your salary, I’m just going to make this up, Ben, is 250,000, but you had that $305,000 of losses, you can carry over $55,000 in losses into the next year.

Ben:Exactly.

Dave:Yeah, it’s pretty amazing. Yeah, it’s great.

Ben:It’s insane. You can do that.

Dave:Yeah. So you’re essentially offsetting all of your W2 income?

Ben:Yeah, essentially,

Dave:Just so everyone understands, to get a hundred grand in depreciation offset, what kind of property do you need to buy?

Ben:So it’s actually not that crazy. A hundred grand in depreciation offset. Now again, there’s the tax deduction and there’s actual, with the tax savings you’re making, so you really need to figure out your effective tax rate. Most people are probably between 30, 40% if you’re in that range. And you can buy, let’s say a million dollar property with a cost segregation study. You got to separate land, you got to make sure it’s the right type of report that you build. So there’s a whole thing that goes on where you have to hire an engineer to do it and make sure you have the right type of separation of the asset to figure out what’s bonus depreciable. Generally, you can get at least 20, 30% of the purchase price back is a straight eligible for bonus depreciation. So if you just want a hundred K, you buy a 300 K property, you’re looking pretty good at getting a hundred K write off.

Dave:And so that’s giving you a hundred K write off. And if your tax rate is let’s say 33%, you’re saving $33,000 in taxes by buying a property. I’m curious, what’s your read on short-term rentals as a strategy right now as we’re entering 2026?

Ben:The problem with short-term rentals that you don’t get with the long-term stuff is it’s nice. You can still pair in long 30 year fixed rate debt, which is the only type of debt I use other than the intro to credit cards and stuff like that. But really the substantial mortgages, I’m only looking at 30 year fixed rate. I think it de-risks the long-term horizon. But the problem with short-term rentals is you’re also locked in not just to steady long-term rents, but you’re really relying a lot on the economy. People having disposable income to travel. The region can change a lot, lot more dynamically than 12 month leases tend to change. So one thing I look at, and this is partly why it makes a lot of sense around New York City, is I want an area that people will travel to my house, not to the area.A good example is the most recent purchase I made was, this is unbelievable, back to maximizing purchase price and finding something that would make sense within an hour radius in Manhattan. On Zillow. I kid you not Billy Joel’s house was listed on Zillow and it was listed for $2 million. And I’m like, well, that’s a lot. I did the math. I’m like, that’s a lot of bonus depreciation and I could get a lot of write offs for that. So I underwrote it, looked at it and dug into the history. It turns out it was owned by JP Morgan. There’s this huge history around the house and super interesting, really unique thing on Hudson River, pretty close to Manhattan. And so I bought it.

Dave:Wait, you bought Billy Joel’s house?

Ben:I bought Billy Joel’s house. It’s literally up on Airbnb. That’s awesome.

Dave:How did we not get to that scooter in this episode? That’s the coolest thing I’ve

Ben:Heard. So this is what it culminated in, which is great. So I bought Billy Joel’s house, it’s like up on Airbnb again. I did a pretty big rehab project on it, but I was able to use, again, intro credit cards. So I used that to make sure I could front the rehab on it, bought it for 2 million, put about 300 K into it. That’s now worth about 2.6. This is only a year later. And with the tax savings that I got, it was close to a million dollars in tax savings that are going to

Dave:Carry over for multiple years. Oh my God, that’s

Ben:Unbelievable. That was from last year. That was still 60% of the bonus appreciation. So if it was even six months later, it would’ve a hundred percent have been even more. But

Dave:Wow. That’s incredible. Ben, congratulations. You really figured out a very creative strategy. You’ve obviously gone and taken what you learned from your business, which isn’t exactly short-term rentals, but I’m sure you learned a lot about just maximizing space, extracting value out of properties and applied it to a really cool way of making money in an area of the country where people constantly say, you cannot be a real estate investor. And I just want to commend you for being so creative and obviously hustling very hard to figuring out the right way to do this.

Ben:Thank you. I think each deal is kind of in a vacuum. It doesn’t matter where it necessarily is. If it can pencil out, it makes sense. And I think New York, you got to be a little bit creative. It’s not always one size fits all. It’s not going to be a print and repeat type of a place, but you can definitely find unique properties and unique deals. And even on the apartment side, there’s still tons of things you can find to limit down payments, to figure out how you can use leverage or work with the landlord seller financing. There’s things you can still do to make sure that you’re buying into the market you’re interested in.

Dave:So before we get out of here, Ben, as we enter 2026, what does your portfolio look like today?

Ben:So right now I have about eight properties. Most of those are in the state of New York, three Airbnbs including Billy Joel’s house, which is the big one. It’s

Dave:Awesome.

Ben:It’s the

Dave:Coolest thing you could say. That’s such a good bragging point.

Ben:Thank you. And I hung on to my W2 jobs, so still focus on that and kind of building that company at the same time. Also looking for more Airbnbs. So

Dave:Awesome

Ben:Strategy out into future years is to keep maximizing this loophole. It looks like it’s going to be around for a while longer, so I’ll keep exploiting it as long as I can and just keep building the empire.

Dave:All right. Well, next time I’m in the northeast to visit friends and family, I want to stay at Billy Joel’s house.

Ben:You’re welcome. Anytime it’s called Craig’s.

Dave:Craig’s an estate. Thank you. Awesome. All right. Well Ben, thanks so much for being here. We appreciate it.

Ben:Thanks so much for having me. It’s been a dream to be here.

Dave:And thank you all so much for listening to this episode of the BiggerPockets podcast. I’m Dave Meyer. We’ll see you next time.