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Sleeping at Work to Construct an 8-Unit Portfolio in America’s Most Costly Metropolis

EditorialBy EditorialNovember 17, 2025No Comments35 Mins Read

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Ben Chester had no cash. Actually, it was worse—he had $120,000 in debt. He was sleeping at work and renting out his personal rented condominium simply to outlive in America’s costliest market—New York Metropolis.

Now, six years later, he has eight rental properties, is debt-free, and even owns Billy Joel’s former residence (sure, you learn that proper).

In case you’re residing in an costly market and assume it’s unimaginable to speculate, Ben has the components for you. He turned little or no cash right into a one-bedroom condominium empire—shopping for no matter he might in New York Metropolis, understanding it will all be well worth the sacrifice. He’s break up these small flats into a number of leases with as much as 4 tenants, permitting him to make the numbers work even when everybody else says it’s unimaginable.

However that’s not the most effective half. After unlocking a tax “loophole” when shopping for a lake home, Ben is now in a position to offset 100% of his W-2 revenue taxes, that means he typically will get a test again from the federal government yearly, all due to his actual property. Thought it was unimaginable to spend money on markets like New York Metropolis? Ben is about to make it a very engaging possibility.

Dave:
Do you assume residing in an enormous costly market means you’ll be able to’t spend money on actual property? Suppose once more. At this time’s visitor works at demanding journey heavy day job, so he’s constructing a rental property portfolio as a backup plan and he’s doing it in and round New York Metropolis. This isn’t a narrative of an already wealthy particular person shopping for properties in money. It’s about utilizing hustle and persistence to construct in direction of monetary freedom, even in one of many nation’s costliest markets, Ben was even keen to sleep within the workplace he was working in to kickstart his investing profession. And though that kind of sacrifice isn’t for everybody, it’d simply be for you.
Hey everybody, I’m Dave Meyer, housing market analyst and head of actual property investing at BiggerPockets, and in the present day we’re bringing you the story of an investor named Ben Chester and I’m tremendous excited to speak to Ben as a result of he’s one of many only a few individuals I’ve ever met who’s doing fundamental rental property investing in New York Metropolis. Ben isn’t shopping for big condominium buildings for thousands and thousands of {dollars}. He’s additionally not shopping for actually dangerous properties in suspect areas. He’s discovered a solution to purchase one bed room flats that cashflow in a few of America’s costliest zip codes. So on in the present day’s episode, Ben’s going to inform us the precise components he discovered that makes these offers work even when beginning with six figures of debt personally that he had. He’ll inform us the story of how he turned Billy Joel’s home. Sure, truly Billy Joel’s home right into a money flowing funding property, how he can offset virtually all of the taxes from his W2 profession with actual property investments and he’ll give us his recommendation for different traders who need to keep native however reside in hyper costly markets. Let’s welcome Ben. Ben, welcome to the BiggerPockets podcast. Thanks for being right here.

Ben:
Thanks a lot for having me.

Dave:
Alright, properly let’s bounce into your backstory slightly bit. Inform us slightly bit in regards to the circumstances that led to you getting began as an actual property investor.

Ben:
So lots of people I graduated college didn’t get. The most effective job was making $30,000 a yr, which in New York Metropolis is mainly the poverty line and I used to be spending all my time on the workplace, however all my cash was going in direction of hire. So making an attempt to run this experiment the place I truly determined to secretly transfer into my workplace full time. Maintain on. The place have been you working? So I imply once I say workplace, it wasn’t too dangerous. It was truly a sleep clinic. I used to be doing medical analysis for pharmaceutical trials.

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

Ben:
There have been beds and the beds weren’t at all times 100% occupied. So there’s a number of nights the place I truly had a reasonably cozy lodge room in midtown Manhattan.

Dave:
Wait, have been your employers conscious of this experiment?

Ben:
No, they thought I used to be a tough employee. So that is 2012, so shortly after I acquired the job Hurricane Sandy hit and I used to be the one one that really confirmed up on the workplace that day, in order that they thought I used to be an excellent laborious employee. They’re like, oh my god, Ben got here in Armageddon and the hurricane, it seems I used to be simply residing there so I had nowhere else to go, however I acquired promoted and form of moved up fairly fast after that, which was superior.

Dave:
So far as I do know, that’s the first time listening to this on the present. I really feel like that’s one thing you see on TV or in a film the place somebody strikes into the workplace to economize on hire, however you actually did it. Say you gave up your condominium, you want to understand how you pulled this off.

Ben:
I used to be in a lease so I couldn’t truly simply pack up and go away, which it was my unique need to do, however as a result of I used to be on the hook for that hire, I truly put it up on Craigslist and began renting it out. Furnace rental, keep so long as you need. I assumed I wanted to solid a large internet to get somebody within the hire, however there was loopy demand truly for a furnace, versatile housing there

Dave:
I think about.

Ben:
And so I form of hung onto the job so long as I might on the sleep clinic, however that experiment form of ballooned into an precise full-time huge enterprise the place we acquired enterprise capital funding for it and we have been making an attempt to pitch it as a tech firm to get the higher valuation, however what ended up taking place was we have been getting loopy strain to develop tremendous quick and so we have been taking up tons and plenty of stock, however these of you which might be in medium time period leases or any seasonal leases, it’s very ebbs and flows when it comes to demand. So we might develop loopy fast after which have these large troughs of emptiness, which finally killed the enterprise. I truly left that enterprise with over $120,000 value of personally assured debt that I put below that enterprise and it was gone. So I used to be mainly ranging from nothing with, I imply lower than nothing. I had 120 ok of debt that I needed to recuperate from.

Dave:
Oh wow. What a curler coaster. I imply what do you do at that time?

Ben:
Yeah, so I imply it was fairly devastating. Not solely that, it was the debt, but in addition I had spent years of my life constructing this enterprise and it mainly imploded so wanted to mainly work out learn how to survive and I didn’t need to go away New York, which was like my dream was at all times to reside there within the first place. So I positively didn’t need to go away the town, which I feel lots of people find yourself having to do.
And so what I do is I acquired a W2 job. I actually had no different selection. I needed to do it simply to repay this debt over time. After which I additionally acquired an condominium. I had this entire ability set of learn how to hire flats. I knew learn how to work with landlords within the metropolis from that have. So I discovered a one bed room condominium with my girlfriend on the time. We moved right into a one mattress after which we had the owner reconfigure it to mainly flip it into 4. It was like, I’ll name them rooms, however I used

Dave:
Areas in New York

Ben:
After which we rented, we had acquired three roommates, so it was my girlfriend and I after which three roommates and so we now have 5 individuals in a one mattress, one bathtub. However what was nice about that and we did that for a few yr and a half, what was nice is it lined all of our housing bills, so we actually weren’t having to pay to be there, we simply needed to coordinate roommates, which might form of be a ache, however it was value it. After which all my W2 revenue was mainly going in direction of paying off debt and in addition slightly bit in direction of retirement and stuff like that.

Dave:
I grew up within the New York Metropolis space. I perceive what you’re speaking about once you stated a one bed room simply magically turns into 4 bedrooms, however possibly you can clarify that to individuals who aren’t acquainted with that

Ben:
Explicit one. We had truly the tremendous was additionally a contractor and he constructed short-term partitions mainly, so it felt good. It was truly sound privateness and stuff slightly small, however it was livable. After which there’s different conditions the place there’s one the place I actually lived in a walk-in closet with my co-founder. This was previous to that, however once we have been launching the primary enterprise, we lived in a duplex on fifth Avenue, which was wonderful, lovely be place, however we rented the remainder of it out after which we stayed within the walk-in closet collectively. Unbelievable. I like it.

Dave:
Alright, so that you kind of acquired again in your ft doing this technique. It appears like one thing you knew from the enterprise you had began form of replicating that for your self personally. Did you then at any level scale to a conventional actual property portfolio or did you simply hold doing this type of hustle mentality going ahead?

Ben:
Effectively, the objective all alongside was to mainly do that simply to get out of debt and mainly graduate to the following degree, which was going to be possession. And so I saved up a few yr and a half of saving and paying off debt aggressively to get to the down cost. One factor that’s actually useful, once you talked about discovering a job that you could reside in, one model of that lots of people have entry to is a journey job. So when you’re in a job the place you’re getting put up in resorts they usually’re paying your bills, which that was, I used to be in a position to not solely get my hire cowl, but in addition I used to be in a position to get meals and I wasn’t spending loads once I was on the street. So mixture of that, I mainly aggressively put near every thing in direction of saving for an condominium, acquired my first down cost, moved right into a New York Metropolis, which isn’t simple to do, acquired rejected from a couple of as a result of they’d seen my historical past with all these flats I had and the press from having this enterprise.
They’re like, are you going to do that on this condominium? I used to be like, no, no, no. Which wasn’t making an attempt to construct a brand new tech enterprise there and bringing strangers and all that. However what I did do is I discovered a one bed room condominium in and I say one mattress. It was mainly a closet in Hell’s Kitchen. You most likely realize it in one of many grungier areas. In 2019, my girlfriend moved in, additionally my brother transfer in. So we now have three individuals now, which felt like luxurious. We had our personal place. We’re spending most likely $750 every to reside there, which is tremendous low cost for New York. That’s remarkable. The principal cost on each single mortgage was in regards to the 700. So I used to be just about from a internet wealth perspective breaking although I used to be paying into it now, I used to be paying off that mortgage. I used to be not less than impartial on

Dave:
Housing. Everybody, we’ve acquired to take a fast break, however we’ll have extra with Ben proper after this. So I discovered this factor known as the Lennar Investor Market, and truthfully it’s form of genius. It’s constructed by Lennar, one of many high house builders within the nation, and it’s a brand new platform for traders who need turnkey new building properties. These are professionally constructed reinspected and hire prepared. From day one, you’ll be able to browse properties throughout greater than 90 markets. You may see verified rental comps, neighborhood information, and even deal with financing, title and insurance coverage all by means of Lennar’s in-house community. It’s every thing you want to make data-driven funding selections in a single place. Go to biggerpockets.com/lennar and discover the properties out there proper now. Welcome again to the BiggerPockets podcast. Let’s bounce again into my dialog with Ben Chester. I’m curious although, it is a frequent query that I get loads and I feel is fairly frequent in the true property investing group, whether or not it’s New York or LA or San Francisco or any of those fairly costly markets. Why did you select to purchase a house versus say, persevering with to hire and investing in both midterm rental, short-term renters, no matter you need some place else when you wished to get in actual property? What about this strategy made sense to you?

Ben:
I had no thought. I simply knew I simply want to purchase actual property and so first step was I acquired to reside someplace. If I can discover a place I can grasp onto. I additionally seen as each month or yearly landlords are elevating hire. So there’s at all times this type of unsettling feeling. If I need to keep in New York eternally, there’s an opportunity I might get priced out. I gained’t be capable of afford right here if I’m renting. However when you purchase, you’re just about locked in. In fact co-op charges can go up, however it’s not like a landlord elevating hire on you. So if I might simply lock in a spot and have a 30 yr mounted fee and at this level it’s nonetheless beneath 3% too, I knew I’d be set mainly the place I might ensure that at a minimal I’d be capable of afford New York so long as I wished to remain there.

Dave:
Oh, that’s nice. Okay. I like that strategy. And so it appears like that labored for you.

Ben:
It was implausible. Once more, that is 2019, the primary condominium mainly locked in. I seen it as I’m set, I’m going to have the ability to keep in New York it doesn’t matter what after which COVID hits. In the meantime, I’m nonetheless making W2 revenue. I’m nonetheless touring on a regular basis. I didn’t actually care if my residing circumstances have been horrible. I used to be like, so long as I’ve a spot again within the metropolis to remain in, it’s okay. However I began wanting, it was just like the world’s altering proper now rates of interest are nonetheless fairly low at this level. I truly began wanting in Texas and I found that I might save on taxes if I moved to Texas throughout COVID. I additionally might discover a number of actually nice quadplexes and homes there that will mainly cashflow if I purchased the quaint home hack, you progress into one unit, hire the opposite three out, you’ll be able to mainly cowl all bills. However then with the tax financial savings on my W2 revenue, I truly would come out forward even when that property solely broke even. So home hacked with a pal there for a brief time frame throughout COVID. It was like an excellent expertise.

Dave:
Do you know what you wished to purchase? Had been you in search of a duplex or are you continue to simply doing the roommate factor?

Ben:
I had no cash nonetheless every thing was nonetheless going in direction of, I had a few of that debt left and in addition was nonetheless not making any cashflow. So all of the revenue that’s coming in, I used to be saving it for a down cost and at that time I had solely possibly 20, $30,000 saved up and my pal was in an analogous boat, which is sufficient for a down cost. So we ended up utilizing an FHA mortgage, which now you are able to do this with a standard 5% down, which is wonderful. However we use a 3.5 with the next rate of interest FHA mortgage in Dallas. And so we paid, it was like 30 to $40,000 complete to get into this property cashflow from day one with the unit that we have been residing in. And it mainly created this springboard the place the tax financial savings, although it was making a small quantity of cashflow, it was simply we have been saving on taxes. After which on high of that, we have been additionally mainly in a position to begin to construct fairness in there and get the tax advantages and every thing over time.

Dave:
So what was the place? Inform us about

Ben:
It. So it was a quadplex nonetheless have it in the present day. It was 4 models all subsequent to one another, mainly 4 townhouses in a way, all mixed below one roof. So it was tremendous good. It was an space in northwest Dallas that was appreciated a bit after which grew to become a great supply of revenue and in addition for tapping in for fairness for a number of the later purchases that they ended up making.

Dave:
And what occurred after that? You left Texas or what was the following transfer?

Ben:
So now charges are beginning to transfer again up at this level. So I had mainly acquired a pair properties I had with this one in New York that had a rule the place you can hire it out after a sure time frame. So I acquired it as a long-term rental after which I used to be going again to New York and in search of one other place to reside, and so acquired one other co-op by means of an analogous methodology. This time I used to be with my brother who was going to maneuver to New York for residency and in addition one other one who’s an architect, two of them. So we’re all going to mainly reside in a spot that I might discover collectively and form of home hack, which we did. And now the snowballs are actually beginning to take off. And so each couple of years I’m getting a brand new condominium in New York after which I’m additionally beginning to get sufficient money the place I can begin fascinated with down funds outdoors of the town for extra typical leases. You’re pulling off one thing

Dave:
That’s fairly robust, which is by most individuals battle to simply pull off a single acquisition in New York, however you’re pulling off a number of. So once you transfer again from Texas, what’s your monetary scenario? Are you making a number of cashflow off the opposite two leases? Is that serving to you with the down cost or how did you truly finance this third buy?

Ben:
Yeah, so the principle factor I’m at all times in search of is simply I need the property to interrupt even as a result of have in mind, I’m planning to maintain this W2 job, so I find the money for coming from that. If I can break even on the properties with conservative underwriting, I don’t need to anticipate me or kohl or something, however so long as a conservative will break even with the tax advantages of appreciation, I’m blissful. So at this level there’s probably not a lot cashflow spinning off the properties. All the things’s breaking even and there’s sufficient for reserves, so lose a water heater or stuff. I might deal with that with out flinching, however I wasn’t residing off of it in any respect. What was good although is I had this W2 job, so I used to be having sufficient the place I used to be getting slightly little bit of financial savings beginning to go. So there have been some artistic methods I later used to faucet into these retirement funds, however mainly I used to be coming again to New York with sufficient to place down a down cost on one other co-op basically.

Dave:
Do you thoughts sharing us with us the worth level of those new co-ops?

Ben:
Yeah, so at this level I’m nonetheless it about entry degree, so half one million greenback vary, which is entry degree for New York.

Dave:
Okay, that’s not as dangerous as I assumed you have been going to say. I imply that’s near the median house worth within the US proper now. That’s not like loopy New York pricing the place every thing’s $2,000 a sq. foot.

Ben:
That is true. However have in mind these are one bed room flats with one thing improper with them at that time. So in the event that they’re

Dave:
Proper, you’re not getting the luxurious condominium at 500 grand

Ben:
Just like the bathrooms in the lounge. Yeah, precisely. There’s one thing not fairly proper in regards to the place.

Dave:
All proper. So that you’re again in New York, you had your stint in Dallas. Now three properties appears like six models. The place do you go from there? Nonetheless shopping for extra in New York Metropolis,

Ben:
Principally in search of something. So once more, I don’t actually have a kind technique but. I form of dabbled in New York and the multifamily, so I used to be form of wanting in all places to see what would stick. The issue was in New York Metropolis was getting tougher and tougher to search out these models that will make sense. Not unimaginable nonetheless. And I truly did find yourself shopping for one other one we might speak about later, however I used to be nonetheless simply wanting round New York at this level. One factor that occurred too is I acquired my license as a realtor to attempt to mainly stretch the cash additional. I used to be like, if I can receives a commission a fee on the identical time of buying these, it form of offsets the acquisition prices. It could possibly be a great technique. And I began to go searching MLS after which additionally simply on Zillow, in all places round Manhattan, Manhattan wasn’t making a number of sense. And in addition the cashflow, it’s not very attention-grabbing. Even when you might discover one thing that is smart, it’s nonetheless simply breakeven. So I began to develop my search and one hour radius of the town and I discovered a number of actually attention-grabbing waterfront properties, notably the place they’d be identical worth level, half one million greenback homes wanted work. In order that they’re not lovely, able to go homes, however they’re on wonderful items of land.

Dave:
Are these removed from the town or they trip locations? What sort of areas have been you wanting in?

Ben:
So I knew that the property themselves, so long as they’re near the town, I felt like individuals would most likely go so long as the home was a vacation spot in and of itself. So to me, I used to be like my pals and the individuals I do know, they most likely would journey an hour to go to a lake home and it doesn’t essentially matter the place that lake home is, so long as it’s good sufficient and it’s accessible, you’ll most likely get eyeballs there. And it was form of only a intestine factor. There weren’t any comps on the time. There wasn’t actually any kind of clear information that it was a great determination. I used to be similar to, I feel we are able to make this work.

Dave:
And your plan was to renovate them although it sounds such as you hadn’t actually achieved that but at scale, you’ve achieved form of placing up these partitions, however now you’re speaking about taking one thing that’s not very good and turning it right into a vacation spot that’s like a reasonably large

Ben:
Shift. It was huge. It was far more than I anticipated too. And at this level I began listening to BiggerPockets the place it’s at all times about worth add and individuals are coping with contractors and stuff. So I’m like, okay, it appears doable, however oh my god, it’s means tougher than you assume. And in addition I had no thought learn how to worth out properties both like renovations and rehabs, however I did know that this was a lovely lot. I discovered this lake home that was on a double lot on a lake that was inside an hour of the town and it’s similar to, okay, it wants a brand new rest room, most likely wants some updates to normal updates to the skin and a few security stuff, electrical far more than you’ll usually get for a standard home. However it was lendable. I might mainly finance it and I used to be like, what? Worst case state of affairs, now I’ve sufficient W2 revenue coming in that even when it takes longer and it implodes, I can not less than maintain the mortgage on this and have it. Worst case state of affairs, I might simply hire it as a long-term hire.

Dave:
How about financing the furnishing? As a result of that, I joke about this on the present, however I feel the worst underwriting mistake I’ve ever made in actual property is simply completely lacking how a lot it was going to value to furnish

Ben:
Brief-term

Dave:
Rental, particularly if it’s an enormous one that you simply’re making an attempt to make a vacation spot, you bought to spend cash to make it cool. You may’t simply throw Fb market stuff in there. How do you pay for that a part of it?

Ben:
Yeah, so truly that is one other artistic financing that I discovered alongside the best way virtually by chance. I do know you’ve talked about earlier than on earlier reveals, the 0% bank card hack with you may get a 0% intro a PR on a enterprise bank card. Effectively, so I mainly did that and I used to be considering I acquired a 20 ok restrict on the cardboard. So I used to be like, okay, that’s nice. At that time, I had a brand new LLC for each single property that I had acquired. So I had a pair LLCs with playing cards that I by no means used 0% intro on, however they’d credit score traces. And a cool hack that you should utilize, not less than with Amex and Chase is you’ll be able to truly take credit score traces from these different companies and put them onto the 0% card and it’s free. They allow you to do that, you simply name ’em up, it takes like six minutes. So I turbocharge that intro 0% card to mainly fund the complete rehab. And so I didn’t pay any, I feel between 12 and 18 months I didn’t pay something in any respect when it comes to curiosity and I simply paid it off by the top.

Dave:
Alright, time for the disclaimer although. This can be a nice thought. In case you pays this off. Utilizing this type of mortgage is usually a very efficient technique. I hear individuals do that mostly in short-term leases. I feel that is form of a typical strategy to doing this, getting the 0% curiosity. It’s a solution to get just about free financing, however when you don’t have a plan for repaying that again and it’s acquired to be a great plan, this could possibly be actually harmful. So it’s a type of issues the place you form of need to use these once you don’t really want it. In case you are like, I’m banking every thing on utilizing this 0% rate of interest bank card, I wouldn’t do this personally if I have been you. Ben has a W2 job, he has different sources, he has different belongings in order that if one thing goes improper, he can handle that. We speak about this loads on the present, there are completely different sorts of money owed. There’s good debt, there’s dangerous debt. Bank card debt is dangerous debt. In case you’re not paying it off, that’s tremendous costly debt. It might probably actually snowball right into a entice. So that you simply need to watch out with that. However once more, if what you’re doing and also you do it rigorously, it may be a great possibility for you. So how’d this one work out? Massive shift in

Ben:
Technique. So I purchased the property for slightly over 500 Ok, ended up anticipating 30 Ok, 40 Ok complete to place into it. That was a brand new rest room, electrical updates that I didn’t even notice have been that extreme. That ended up being extra sophisticated than I assumed. After which I put in new HVAC system in it ended up costing extra like 150 Ok for all of the rehab plus the holding prices plus additionally the furnishings as a result of I overbuilt it greater than I wanted to. And in addition I most likely did extra work than I actually needed to, however because of this it ended up being, and once more, my objective was simply to interrupt even, however it ended up money flowing a ton and it ended up being a extremely wonderful entry level into the Airbnb market round New York Metropolis.

Dave:
How are you managing it? Did you do all these items your self?

Ben:
Yeah, so I used to be doing it myself simply by default. I used to be like possibly I’ll put a supervisor in ultimately. And I began interviewing property administration corporations, however by means of BiggerPockets I truly stumbled upon this short-term rental loophole and I used to be like, you bought to be kidding me. This could’t be actual. That is unbelievable. And so I learn the books on it. I went by means of three or 4 completely different accounting companies till I discovered one which was like, yeah, properly let’s do that. And so mainly, so long as you’re working a W2 job and also you’re self-managing your Airbnb, you’ll be able to take the losses together with depreciation, together with any bonus depreciation that you simply’re utilizing, which could possibly be substantial. Take all that and apply it as a loss in opposition to your W2 and are available to successfully, you may get near paying no taxes, which is insane. That’s once I was like, oh my God, that is the brand new technique.
It is smart. I’m going to maintain my W2 job. I’m going to amass as many Airbnbs as potential and simply to make it possible for I’m maxing out these losses each single yr on paper so I can mainly offset my taxes. Bear in mind, I’d began out considering, I need to management my housing prices. I assumed that was the most important expense that an individual would have, however actually the most important expense nobody thinks about is definitely the tax aspect. I’m like, it is a sport changer. Not solely am I probably not paying for housing, I might additionally utterly undo my taxes or not must pay them and offset them if I do that the proper means.

Dave:
Stick with us as we take a fast break. We’ll have extra with Ben proper after this. Welcome again to the BiggerPockets podcast. Let’s get again into my dialog with investor Ben Chester. I feel the kind of journey and evolution of philosophy and technique about investing is frequent, that you simply don’t actually begin for the tax advantages, however ultimately you get to a degree the place you notice that when you maximize your tax advantages, it might probably considerably improve your returns. I’m not speaking about 1% or 2%. It might probably make 5 10% distinction in your fee of return annually, which is wonderful. That’s higher than shopping for bonds typically. That could possibly be higher than investing within the inventory market simply from the tax advantages that you simply get.

Ben:
It’s insane. And I give it some thought, my job is fee based mostly largely sub in a tech gross sales job the place I can put extra effort in and get extra pay. And the quantity of effort I put into getting extra pay is means tougher than simply saving on the tax aspect. So you’ll be able to find yourself going loads additional by saving on taxes and having to go get a second job or simply work 40 extra hours per week or one thing like that.

Dave:
Are you able to give us a quantity? How a lot do you assume one among these saves you in taxes per yr?

Ben:
So there’s a restrict. In case you’re single in taxes, you are able to do as much as $305,000 of tax offset per yr. That’s the restrict that you could’t do anymore in that in opposition to your W2. I’ve maxed it out yearly with much more carrying over.

Dave:
Yeah, only for everybody understanding what Ben’s saying is that if your wage, I’m simply going to make this up, Ben, is 250,000, however you had that $305,000 of losses, you’ll be able to carry over $55,000 in losses into the following yr.

Ben:
Precisely.

Dave:
Yeah, it’s fairly wonderful. Yeah, it’s nice.

Ben:
It’s insane. You are able to do that.

Dave:
Yeah. So that you’re basically offsetting your entire W2 revenue?

Ben:
Yeah, basically,

Dave:
Simply so everybody understands, to get 100 grand in depreciation offset, what sort of property do you want to purchase?

Ben:
So it’s truly not that loopy. 100 grand in depreciation offset. Now once more, there’s the tax deduction and there’s precise, with the tax financial savings you’re making, so you actually need to determine your efficient tax fee. Most individuals are most likely between 30, 40% when you’re in that vary. And you should purchase, let’s say one million greenback property with a price segregation research. You bought to separate land, you bought to ensure it’s the proper kind of report that you simply construct. So there’s a complete factor that goes on the place it’s a must to rent an engineer to do it and ensure you have the proper kind of separation of the asset to determine what’s bonus depreciable. Typically, you may get not less than 20, 30% of the acquisition worth again is a straight eligible for bonus depreciation. So when you simply need a hundred Ok, you purchase a 300 Ok property, you’re wanting fairly good at getting 100 Ok write off.

Dave:
And in order that’s supplying you with 100 Ok write off. And in case your tax fee is let’s say 33%, you’re saving $33,000 in taxes by shopping for a property. I’m curious, what’s your learn on short-term leases as a technique proper now as we’re coming into 2026?

Ben:
The issue with short-term leases that you simply don’t get with the long-term stuff is it’s good. You may nonetheless pair in lengthy 30 yr mounted fee debt, which is the one kind of debt I exploit apart from the intro to bank cards and stuff like that. However actually the substantial mortgages, I’m solely 30 yr mounted fee. I feel it de-risks the long-term horizon. However the issue with short-term leases is you’re additionally locked in not simply to regular long-term rents, however you’re actually relying loads on the economic system. Individuals having disposable revenue to journey. The area can change loads, lot extra dynamically than 12 month leases have a tendency to alter. So one factor I have a look at, and that is partly why it makes a number of sense round New York Metropolis, is I need an space that folks will journey to my home, to not the realm.
An excellent instance is the newest buy I made was, that is unbelievable, again to maximizing buy worth and discovering one thing that will make sense inside an hour radius in Manhattan. On Zillow. I child you not Billy Joel’s home was listed on Zillow and it was listed for $2 million. And I’m like, properly, that’s loads. I did the maths. I’m like, that’s a number of bonus depreciation and I might get a number of write offs for that. So I underwrote it, checked out it and dug into the historical past. It seems it was owned by JP Morgan. There’s this large historical past round the home and tremendous attention-grabbing, actually distinctive factor on Hudson River, fairly near Manhattan. And so I purchased it.

Dave:
Wait, you obtain Billy Joel’s home?

Ben:
I purchased Billy Joel’s home. It’s actually up on Airbnb. That’s superior.

Dave:
How did we not get to that scooter on this episode? That’s the good factor I’ve

Ben:
Heard. So that is what it culminated in, which is nice. So I purchased Billy Joel’s home, it’s like up on Airbnb once more. I did a reasonably large rehab mission on it, however I used to be in a position to make use of, once more, intro bank cards. So I used that to ensure I might entrance the rehab on it, purchased it for two million, put about 300 Ok into it. That’s now value about 2.6. That is solely a yr later. And with the tax financial savings that I acquired, it was near one million {dollars} in tax financial savings which might be going to

Dave:
Carry over for a number of years. Oh my God, that’s

Ben:
Unbelievable. That was from final yr. That was nonetheless 60% of the bonus appreciation. So if it was even six months later, it will’ve 100% have been much more. However

Dave:
Wow. That’s unimaginable. Ben, congratulations. You actually discovered a really artistic technique. You’ve clearly gone and brought what you discovered from your small business, which isn’t precisely short-term leases, however I’m certain you discovered loads about simply maximizing area, extracting worth out of properties and utilized it to a extremely cool means of making a living in an space of the nation the place individuals continuously say, you can’t be an actual property investor. And I simply need to commend you for being so artistic and clearly hustling very laborious to determining the proper means to do that.

Ben:
Thanks. I feel every deal is form of in a vacuum. It doesn’t matter the place it essentially is. If it might probably pencil out, it is smart. And I feel New York, you bought to be slightly bit artistic. It’s not at all times one measurement matches all. It’s not going to be a print and repeat kind of a spot, however you’ll be able to positively discover distinctive properties and distinctive offers. And even on the condominium aspect, there’s nonetheless tons of issues yow will discover to restrict down funds, to determine how you should utilize leverage or work with the owner vendor financing. There’s issues you’ll be able to nonetheless do to just remember to’re shopping for into the market you’re excited about.

Dave:
So earlier than we get out of right here, Ben, as we enter 2026, what does your portfolio appear like in the present day?

Ben:
So proper now I’ve about eight properties. Most of these are within the state of New York, three Airbnbs together with Billy Joel’s home, which is the massive one. It’s

Dave:
Superior.

Ben:
It’s the

Dave:
Coolest factor you can say. That’s such a great bragging level.

Ben:
Thanks. And I held on to my W2 jobs, so nonetheless concentrate on that and form of constructing that firm on the identical time. Additionally in search of extra Airbnbs. So

Dave:
Superior

Ben:
Technique out into future years is to maintain maximizing this loophole. It seems to be prefer it’s going to be round for some time longer, so I’ll hold exploiting it so long as I can and simply hold constructing the empire.

Dave:
All proper. Effectively, subsequent time I’m within the northeast to go to family and friends, I need to keep at Billy Joel’s home.

Ben:
You’re welcome. Anytime it’s known as Craig’s.

Dave:
Craig’s an property. Thanks. Superior. All proper. Effectively Ben, thanks a lot for being right here. We admire it.

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

Dave:
And thanks all a lot for listening to this episode of the BiggerPockets podcast. I’m Dave Meyer. We’ll see you subsequent time.

 

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