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

Summary

---

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

Podcast: BiggerPockets Real Estate Podcast
Host: Dave Meyer
Guest: Ben Chester
Date: November 17, 2025

---

Overview

In this episode, Dave Meyer interviews Ben Chester—a real estate investor who managed to build an 8-unit portfolio across the New York City region, one of the country’s most expensive markets. Ben did it starting from six figures of debt, while working a demanding W2 job, and using a combination of creative strategies, unconventional sacrifices (including living at his workplace and sharing cramped spaces), and maximizing tax loopholes. This episode is a masterclass in relentless hustle, practical problem-solving, and the power of leveraging both high-cost markets and tax laws to your advantage.

---

Key Discussion Points & Insights

1. Humble Beginnings & Extreme Sacrifice (00:00–06:39)

• Ben began his career making $30,000/year in NYC—barely above the poverty line in such an expensive city.
• To save on rent, Ben secretly lived at his workplace—a sleep clinic—utilizing empty beds at night.
  • Quote: “They thought I was a hard worker… Turns out I was just living there, so I had nowhere else to go.” (02:46, Ben)
• During Hurricane Sandy, being the only employee to show up got him noticed and promoted.
• Ben’s first hustle: subletting his own apartment on Craigslist, sparking the idea for a flexible rental venture that ballooned—with the help of venture capital—before collapsing, leaving him with $120,000 of personal debt.

2. Climbing Out of Debt Through House Hacking (04:27–08:03)

• Post-business failure, Ben focused on basic survival and staying in NYC—taking a W2 job and aggressively house hacking.
• Rented a one-bedroom, legally and physically reconfigured into four rooms, and brought in three roommates (plus his girlfriend), resulting in zero net housing costs.
  • Quote: “We have five people in a one bed, one bath. But… it covered all our housing expenses.” (05:11, Ben)
• This strategy allowed him to channel all income into debt repayment and savings, plus gather experience with landlords and rental management.

3. Scaling to Ownership: From NYC to Texas & Back (06:39–15:10)

• After a year and a half, Ben saved enough for a down payment. He moved into a New York City co-op (not without rejections due to his history).
• In 2019, locked in low-cost housing by purchasing, splitting with roommates/family, and covering the mortgage through shared living.
• COVID-19: Used a job with frequent travel to minimize personal expenses even further, then seized an opportunity to invest in Texas for better cash flow and tax advantages.
  • Utilized FHA low-down-payment loans to buy a Dallas quadplex, house hacking on-site.
  • The Texas property became a springboard for future acquisitions via equity and tax benefits.

4. Creative Strategies for Acquisition in High-Cost Markets (15:10–20:20)

• Each deal focused on breaking even (not necessarily cash flowing in the high-cost NYC market), relying on W2 income for reserves and down payments.
  • Entry-level NYC co-ops at ~$500k, typically “one-bedrooms with something wrong with them.”
• Ben got his realtor’s license to capture commission on his own deals and expanded his search to properties within an hour of Manhattan.
• Identified undervalued, fixer-upper waterfront properties and vacation homes that could attract city dwellers as destination Airbnbs.

5. The Leap into Value-Add & Short-Term Rentals (19:31–24:34)

• Moved into more complex value-add deals: bought, renovated, and furnished a lake house as a luxury short-term rental (Airbnb).
• Employed creative financing—notably leveraging 0% APR business credit cards both for furnishings and renovations, maximizing cash flow runway.
  • Quote: “I turbocharged that intro 0% card to basically fund the entire rehab… just paid it off by the end.” (21:26, Ben)
• Caution was advised: this works only if you can repay before the promotional period ends.

6. Tax Optimization: The Short-Term Rental Loophole (23:20–29:31)

• Ben discovered and capitalized on the “Short-Term Rental Loophole,” allowing him as a W2 employee to use depreciation and bonus depreciation from self-managed STRs to offset W2 income.
  • Quote: “You can take all that and apply it as a loss against your W2 income… you can get close to paying no taxes, which is insane.” (23:23, Ben)
• With proper cost segregation, 20–30% of a property’s price could be bonus depreciated, yielding massive paper losses and thus huge real tax savings.
• Maximum offset: up to $305,000/year against W2 income, with excess losses carried forward.
  • Quote: “I've maxed it out every year with a lot more carrying over.” (29:02, Ben)

7. Billy Joel’s House & The Power of Unique Properties (30:42–33:10)

• Ben’s biggest move: purchased Billy Joel’s former house (within an hour of Manhattan) for $2 million—using his learnings around tax savings, destination properties, and value-add renovations.
• Rehabbed with $300k, jacking up the property’s value to $2.6 million in a year, and unlocked nearly $1 million in tax savings (write-offs to be carried over several years).
  • Quote: “Billy Joel’s house was listed on Zillow… I bought it.” (31:56, Ben)

8. Mindset, Flexibility, and Market Myths (33:10–End)

• Ben emphasizes that deals must “pencil out” regardless of market, and that creative approaches are key—especially in expensive locales.
• Encourages finding unique angles: limiting down payments, leveraging seller financing, and being open to unorthodox strategies.
• Portfolio Snapshot (2026): Eight properties (mostly NY), including three Airbnbs—with Billy Joel’s house as the marquee asset. Maintains W2 job and plans to keep maximizing the STR tax loophole as long as possible.
  • Quote: “Next time I’m in the Northeast… I want to stay at Billy Joel’s house.” (34:14, Dave)
  • Quote: “You’re welcome anytime. It’s called Craggs Craigs and Estate.” (34:19, Ben)

---

Notable Quotes & Memorable Moments

• Sacrifice:
  “No, they thought I was a hard worker… Turns out I was just living there, so I had nowhere else to go.” (02:46, Ben)

• Creative House Hacking:
  “We have five people in a one bed, one bath. But… it covered all our housing expenses.” (05:11, Ben)

• Resilient Mindset:
  “I didn't want to leave New York, which was like my dream… So what I do is I got a W2 job… to pay off this debt over time.” (04:23, Ben)

• Tax Strategy:
  “As long as you're working a W2 job and you're self managing your Airbnb, you can take the losses… and apply it as a loss against your W2 income.” (23:23, Ben)

  “I've maxed it out every year with a lot more carrying over.” (29:02, Ben)

• On Buying Billy Joel’s House:
  “Back to maximizing purchase price… Billy Joel's house was listed on Zillow… I bought it. It's literally up.” (31:56–32:01, Ben)

• On Mindset in High-Cost Markets:
  “Each deal is kind of like in a vacuum. Doesn’t matter where it necessarily is. If it can pencil out, you know, it makes sense.” (33:10, Ben)

---

Timestamps for Key Segments

• 00:00–03:06: Ben’s start and living at work to save rent
• 04:23–06:39: Surviving business failure, debt, and house hacking
• 06:39–14:52: First property purchases in NYC, house hacking, and branching to Texas
• 19:31–23:09: Moving into value-add projects and hands-on renovations
• 23:09–24:34: Self-managing STRs and exploiting the tax loophole
• 29:45–31:54: Understanding the scale and limitations of STR tax savings
• 31:54–33:10: The Billy Joel’s house acquisition and its financial impact
• 33:37–34:14: Ben’s current eight-unit portfolio, future plans, and mindset for success in expensive markets

---

Takeaways for Aspiring Investors

• Financial Freedom is Possible Anywhere: Your market's high prices don’t have to stop you—Ben succeeded through adaptability, sacrifice, and creative financing.
• Leverage Your Unique Situation: Whether it’s living at work, house hacking, or converting “problem” properties, there are always creative strategies.
• Tax Knowledge is Power: Understand (and leverage) all tax advantages—especially if you’re still working a W2.
• Don’t Fear Unconventional Deals: Unique, value-add opportunities—like historic homes or properties with great land—can offer upside others overlook.
• Stay Resilient: Ben’s journey through failed businesses, debt, and tough living situations proves that persistence is paramount.

---

For more information and inspiration, check out BiggerPockets' guides and community forums.

---

Transcript

[A]

Do you think living in a big expensive market means you can't invest in real estate? Think again. Today's guest works a 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.

[B]

Ben was even willing to sleep in.

[A]

The office he was working in to kickstart his investing career.

[B]

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.

[A]

And today we're bringing you the story of an investor named Ben Chester. And I'm sorry, 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. And Ben isn't buying giant apartment buildings for millions of dollars.

[B]

He's also not buying really risky properties in suspect areas. He's found a way to acquire one.

[A]

Bedroom apartments that cash flow 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.

[B]

That makes these deals work even when.

[A]

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 who wanna stay local but live in hyper expensive markets. Let's welcome Ben.

[B]

Ben, welcome to the BiggerPockets podcast.

[A]

Thanks for being here.

[C]

Thanks so much for having me.

[B]

All right, well, let's jump into your.

[A]

Backstory a little bit. Tell us a little bit about the circumstances that led to you getting started as a real estate investor.

[C]

Yeah, so like 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, you know, 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.

[A]

Where were you working?

[C]

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.

[A]

Oh, okay. So there were beds.

[C]

There were beds, yeah. And, you know, the beds were not always 100% occupied, so there's a lot of nights where I actually had a pretty cozy hotel room in like, midtown Manhattan.

[A]

Wait, were your employers aware of this experiment?

[C]

No, they thought I was a hard worker. So this is 2012. So, you know, 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. Like, oh my God, Ben came in. Despite, like Armageddon, the hurricane. 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.

[A]

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 like, moves into the office to save money on rent. But you, you really did it.

[B]

You.

[A]

So you gave up your apartment. Like, you need to know how you pulled this off.

[C]

I was in a lease, so I couldn't actually just like, pack up and leave, which was my original, like, 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, you know, stay as long as you want because I thought I needed to cast a wide net to get, to get someone interested in, to rent it. But there was like crazy demand actually for, for a furnished flexible housing there, I would imagine. 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, like full time massive business where we venture capital investment for it and we're 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're taking on lots and lots of inventory. But those of you who are in medium term rentals or any seasonal rentals, it's like 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 the, like, less than Nothing. I had 120k of debt that I had to recover from.

[A]

Oh, wow, what a rollercoaster. I mean, what do you do at that point?

[C]

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 because I really had no other choice. I had to do it just to pay off his debt over time. And then I also got an apartment because I had this whole skill set of like, you know, how to rent apartments. I knew how to kind of 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, you know, I'll call them rooms, but spaces in New York. Yeah, yeah.

[A]

Yes.

[C]

And then we rented. We got three roommates. So as 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, 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. You know, I grew up in the.

[A]

New York City area. I understand what you're talking about. When you said a one bedroom just magically turns into four bedrooms. Maybe you could explain that to people who aren't familiar with that.

[C]

That particular one we had actually the super was a. Was also a contractor and he like built like temporary walls basically. So it was actually, it felt nice. Like it was actually, you know, sound privacy and stuff. A little small, but, you know, it was livable. And then there's other situations where like there's one where I literally lived in a walk in closet with my co founder. This. This was prior to that. But when we were launching the first business, we lived in a duplex on fifth Avenue, which was like amazing, beautiful, beautiful place. But we rented the rest of it out and then we stayed in the walk in closet together.

[A]

Unbelievable. I love it. All right, so you sort of got back on your feet doing this strategy. It sounds like something you knew from the business you had started, like 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?

[C]

Well, the goal all along was to basically do this just to get out of debt and basically like 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 co op, which is not easy to do. Got rejected from a few because they had seen my history with like all these apartments I had. And the press from like having this business, they're like, are you going to do this in this apartment? I was like, no, no, no. But. Which I wasn't. I wasn't trying to build like a new tech business there and like, you know, bring in strangers and all that. But. 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. It's, you know, in one of the grungier areas. In 2019, my girlfriend moved in, also my brother move in. So we had three people now, which was felt like luxury. We had our own place. We're spending like probably $750 each to live there, which is super cheap for New York. Like, that's unheard of. The principal payment on every single, like, mortgage was about the 700. So, like, I was pretty much like from a net wealth perspective, like breaking even. Even though I was paying into it now, I was paying off that mortgage. I was like, at least neutral on housing.

[B]

Okay, everyone, we got to take a.

[A]

Quick break, but we'll have more with.

[B]

Ben right after this.

[A]

So I found this thing called the Lennar Investor Marketplace, and honestly, it's kind of genius.

[B]

It's built by Lennar, one of the.

[A]

Top home builders in the country and.

[B]

It'S a new platform for investors who.

[A]

Want turnkey new construction homes. These are professionally built, pre inspected and.

[B]

Rent ready from day one. You can browse properties across more than 90 markets.

[A]

You can see verified rental comps, neighborhood.

[B]

Data, and even handle financing, title and.

[A]

Insurance all through Lennar's In House network.

[B]

It's everything you need to make data driven investment decisions in one place. Go to biggerpockets.com Lennar and explore the.

[A]

Homes available right now.

[D]

Aaron the ad guy here. You know if your tax prep involves digging through emails and bank statements from like eight months ago, I've been there. We've all been there. Baselane, though completely saved me from that chaos. It's a landlord banking platform that organizes every transaction as it happens. Rent, expenses, everything is tagged by property and just a disclaimer. It's not technically a bank, but Threadbank does the banking part and they're a member of fdic. That said, the way Baselane organizes everything is super helpful. Now I can actually see how my rentals are performing. Try it for [e-mail] BP and get a $100 bonus.

[A]

I'm usually the guy who thinks smart.

[B]

Technology just means expensive way to complicate simple things.

[A]

But then Simplisafe showed me security cameras.

[B]

That actually yell at burglars for me and suddenly I'm living in the future. I didn't know I wanted to here's what I personally love about Simplisafe Traditional security systems wait until someone's already broken in to alert you. But Simplisafe's Active Guard Outdoor Protection actually stops crimes before they start. I also like that their AI powered cameras detect threats while intruders are still outside your home and alert live security agents. Those agents then confront the person through the camera telling them they're being watched, that police are on the way, and they can even sound sirens and trigger spotlights. I truly trust Simplisafe to not only protect my home, but also my wallet. There are no long term contracts and no hidden fees and they've been named Best Home security system by U.S. news and World Report five years running. Plus there's a 60 day money back guarantee. Right now you get exclusive early access to the biggest Black Friday sale of the year. That's 60% off for any new system. This is their best deal ever. So if you've been thinking about real security for your home, now's the time. Go to simplisafe.com pockets that's simplisafe.com pockets.

[E]

If you're serious about scaling your portfolio, you need two good data and good deals. Lennar's Investor Marketplace gives you both. It's full of new rent ready homes in markets across the country. Each property comes with verified rental comps and local insights. You can see potential returns, compare markets and make offers, all without leaving your desk. It's like finally having the homes, the data and the financing all in one place. Head to biggerpockets.com Lennar and see what's live right now. That's biggerpockets.com Lenar L E N N.

[A]

A R if you own a short.

[B]

Term rental, here's something worth knowing. Not all landlord policies are built for your type of property. And with holiday bookings, chilly weather and higher guest turnover, having the right coverage is more important than ever. Steadily offers insurance designed specifically for short term rentals, covering property damage, liability, lost rental income and even unexpected issues like bed bugs. Steadily works exclusively with real estate investors so they understand the details that make short term rentals unique and they coverage to match it. A quick review of your rates and coverage every year can help you protect your property and your cash flow. Get a quote in [e-mail] landlord insurance steadily rental Property Insurance for the Modern Investor welcome Back to the BiggerPockets podcast.

[A]

Let's jump back into my conversation with Ben Chester. I'm curious though, because 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?

[C]

I had no idea. I just knew like I just need to buy real estate. And so the first step was I got to live somewhere. Like if, if I can find a place I can hang on to. I also viewed as like every month or every year, you know, landlords are raising rents. So there was always this kind of like unsettling feeling. If I want to stay in New York forever, there's a chance that I could get priced out. Like I won't be able to afford here if I'm renting. But if you buy, you're pretty much locked in. Like of course like co op fees can go up, but it's not, 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. 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.

[A]

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

[C]

So it was fantastic because so this is again, this is 2019, the first apartment basically locked in. I viewed it as like I'm set, like I'm going to be able to stay in New York no matter what. And then Covid hits. So meanwhile I'm like still making W2 income. I'm still traveling all the time. So I didn't really care if my living conditions were terrible. Like I was like, as long as I have a place back in the city to stay in, it's okay. But I started looking, I was like, you know, the world's changing right now. Things interest rates are still pretty low at this point. I actually started looking in Texas and I discovered that like 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 cash flow. If I bought, you know, the old fashioned house hack, you move into one unit, rent the other three out, you could basically cover all expenses. But then with the tax savings on my W2 income, I actually, you know, would. 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.

[A]

Did you know what you wanted to buy? Like were you looking for a duplex or you still just doing the roommate thing?

[C]

I had no money still because everything was still going towards. I had some of that debt left and also is still like not making any cash flow. So all the income that's coming in, I was saving it for a down payment. And at that point I had like only maybe like 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 30 to $40,000 total to get into this property. Cash flow 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 cash flow, 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.

[A]

So what was the place like? Tell us about it.

[C]

So it was a quadplex, still have it today. It was four units all next to each other, basically like 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 Inc. And also for tapping in for equity for some of the later purchases that I ended up making.

[A]

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

[C]

Yeah, so now rates are starting to move back up at this point. And so I had basically acquired a couple properties. I had 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 it was with my brother who was moving to New York for residency and also another one who was an architect to 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 snowball 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 like more conventional rentals.

[A]

You're pulling off something that's pretty tough, which is buying. Most people struggle to just pull off a single acquisition in New York. Yeah, but you're pulling off multiple. So when you move back from Texas, what is your financial situation like? Are you making a lot of cash flow off the other two rentals? Is that helping you with the down payment or how did you actually finance this third purchase?

[C]

Yes. So the main, the main thing I'm always looking for is just like I want the property to break even because keep in mind, like 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, like, you know, don't want to expect miracles or anything. But as long as a conservative will break even with the tax benefits appreciation, I'm happy. So at this point there's not really much cash flow spinning off the properties, everything's breaking even and there's enough like for reserves. So like you know, lose a water heater stuff like you could, I could handle that without flinching, but I wasn't like, you know, 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 you can later use to tap into those retirement funds. But basically I was, I was coming back to New York with enough to put down a down payment on another co op essentially.

[A]

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

[C]

Yeah, so at this point I'm still looking at it at entry level. So like half a million dollar range, which is entry level for New York.

[A]

That's not as bad as I thought you were going to say because 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.

[C]

This is true. But keep in mind these are one bedroom apartments with like something wrong with them at that point. Like setting up their right.

[A]

You're not getting the luxury apartment, 500 grand.

[C]

Like the toilets in the living room. Yeah, exactly. Like, you know, like there's, there's something like not quite right about the place.

[A]

All right, so you're, you're back in New York, you had your stint in Dallas and now three properties. Sounds like six units.

[B]

Where do you go from there?

[A]

Still buying more in New York City.

[C]

Basically looking for anything. So again, I don't really have a form strategy yet. I kind of dabble in like New York and multifamily. So I was kind of looking everywhere to see what would stick to. The problem was in New York City was getting harder and harder to find those units that would, that would make sense, not impossible. There's 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 cash flow. It's not very interesting. Even if you could find something that makes sense, it's still just break even. So I started to expand my search in one hour radius of the city and I found a lot of really interesting waterfront properties, particularly where they'd be like, you know, same price point, half a million dollar houses needed work, right? They're not like, you know, beautiful ready to go houses, but they're on amazing pieces of land.

[A]

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

[C]

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, you know, my friends and the people I know, like they probably would travel an hour to go to like a lake house. And it doesn't necessarily matter where that lake house is, as long as it's nice enough and it's like 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.

[A]

And your plan was to renovate them though, because it sounds like you hadn't really done that yet. Like at scale, like you've done kind of like 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 shift.

[C]

It was massive. It was, it was way more than I expected to. And at this point I started listening to bigger pockets where it's always about like value add and people are dealing with contractors and stuff. So I'm like, okay, like, you know, it seems doable, but oh my God, it's like way harder than you think. And also, I know I didn't price out properties either, like renovations and rehabs, so. But I, I, I did know that this was a beautiful lot. I found this lake house that was on like 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 like, you know, general updates, the outside and like some safety stuff, electrical, like, you know, way more than you normally like get for a normal house. But like, it was lendable, I could, I could basically finance it. And, 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, like I can at least sustain the mortgage on this and have it like worst case scenario, like I could just rent it as a long term rent.

[A]

How about financing the furnishing? Because that I joke about this on the show, but like, I think the worst underwriting mistake I've ever made in real estate is just like totally missing how much it was going to cost to furnish short term rental. Especially if it's like a big one that you're trying to make a destination because 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?

[C]

Yeah, so actually this is another creative financing trick that I found along the way almost by accident. Like I know you've mentioned before on previous shows, like the 0% credit card hack with like you can get a 0% intro APR on a business credit card. Well, so I basically did that and I was thinking like, you know, I got like a 20k 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 them up. It takes like six minutes. So I turbocharged 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. I just paid it off by the end.

[A]

All right, time for the disclaimer though. This is a great idea. If you can pay this off. Like 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 can 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 free credit card, I wouldn't do that personally. If I were you, like, 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 strategy.

[C]

Yeah. So I bought, I bought the property for a little over 500k, ended up expecting 30k, 40k total to put into it. That was a new bathroom. Electrical updates I didn't even realize were that severe. That ended up being more complicated than I thought. And then I put like new h vac system in. It ended up costing more like 150k for like all the rehab plus the, plus the holding costs, plus also the furnishings because I overbuilt it more than I needed to. And also, like I did, I probably did more work than I really had to.

[A]

Okay.

[C]

But as a result, it ended up being, and again, my goal is just to break even, but it ended up cash flowing a ton and it ended up being like a really amazing, like, entry point into the Airbnb market around New York City.

[A]

How are you managing it? Did you do all the stuff yourself?

[C]

Yeah, so I was doing it myself just by default because, like, maybe I'll put a manager. And eventually, and I started like interviewing property management companies, but through bigger pockets. I actually stumbled upon the short term rental loophole and I was like, you gotta be kidding me. This can't be real. This is unbelievable. Yeah. 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, 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 income 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, I'm maxing out those losses every single year on paper so I can basically offset my taxes. And remember, I started out thinking I want to control my housing costs because I thought that was the basic biggest expense that 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.

[B]

Stay with us as we take a quick break.

[A]

We'll have more with Ben right after this.

[D]

Aaron, the ad guy here. If you're a landlord, you've probably done this. You approve a repair, it's done, life moves on. Then three months later you're like, wait, did that water heater really cost that much? Baselane keeps track of all of that for you. It's free banking for landlords that automatically tags every transaction to the right property. And just as a side note, Baselane itself technically isn't a bank. Thread bank does that part and they're a member of fdic. But regardless, rent comes in, expenses go out, and you can finally see how each unit's actually doing. So go to baselane.com bp and grab your $100 sign up bonus.

[A]

I'm usually the guy who thinks smart.

[B]

Technology just means expensive way to complicate simple things.

[A]

But then Simplisafe showed me security cameras.

[B]

That actually yell at burglars for me and suddenly I'm living in the future I didn't know I wanted. Here's what I personally love about Simplisafe. Traditional security systems wait until someone's already broken in to alert you. But Simplisafe's active Guard outdoor protection actually stops crimes before they start. I also like that their AI powered cameras detect things threats while intruders are still outside your home and alert live security agents. Those agents then confront the person through the camera telling them they're being watched, that police are on the way, and they can even sound sirens and trigger spotlights. I truly trust Simplisafe to not only protect my home, but also my wallet. There are no long term contracts and no hidden fees. And they've been named best home security system by U.S. news and World Report five years running. Plus there's a 60 day money back guarantee. Right now you get exclusive early access to the biggest Black Friday sale of the year. That's 60% off for any new system. This is their best deal ever. So if you've been thinking about real security for your home, now's the time. Go to simplisafe.com pockets that's simplisafe.com pockets.

[E]

Most investors say real estate is about location, but in reality it's about information. That's why I like what Lennar is doing with their investor Marketplace. It's a platform that gives you everything up front. Real rental comps, local growth trends, scores, even neighborhood data before you ever click, submit offer. And every property is new construction built and inspected by Lennar, which is one of the biggest names in home building. So you're always making data backed decisions. If you want to make smarter buys, not just more buys, check out biggerpockets.com Lennar that's biggerpockets.com Le N N A.

[D]

R.

[B]

Most investors spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning to steadily they focus exclusively on landlords. Whether it's a single family rental, a Brrrr Builders risk policy or midterm holiday guests, you get fast quotes, flexible coverage and protection for property damage, liability and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in [e-mail] landlordinsurance steadily landlord insurance designed for the modern Investor welcome back to the BiggerPockets podcast. Let's get back into my conversation with investors.

[A]

Esther Ben Chester I think this 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 like 1% or 2%. Like it can make 5, 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.

[C]

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

[A]

Can you give us a number? Like how much do you think one of these saves you in taxes per year?

[C]

So there's a limit. If you're, 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 any more than that against your W2. I've maxed it out every year with a lot more carrying over. Yeah.

[A]

Just for everyone understanding what Ben 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.

[C]

Exactly.

[A]

Yeah. That's pretty amazing. Yeah, it's great.

[C]

It's insane. Yeah.

[A]

Yeah. So you're essentially offsetting all of your W2 income.

[C]

Yeah, essentially.

[A]

Just so everyone understands, to get 100 grand in depreciation offset, what kind of property do you need to buy?

[C]

So it's actually not that crazy. 100 grand in depreciation offset. Now again, there's the tax deduction and there's actual like what's the tax savings you're making? So you really need to figure out your effective tax rate if you're, you know, most people are probably between 30, 40% if you're in that range, you know, and you can buy let's say a half 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, you know, report that you build. So there's like 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 appreciable. 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 100k, you buy a 300k property, you're looking pretty good at getting 100k write off.

[A]

And so that's giving you 100k 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.

[C]

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 fixed, 30 year fixed rate debt, which is the only type of deb use other than like the, you know, the intro to credit cards and stuff like that. But really like the substantial mortgages, I'm only looking at 30 year fixed rate because I think it de risks the long, long term horizon. But the problem with short term rentals is you're also locked in not just a 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, a 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 like New York City is I want an area that people will travel to my house, not to the area. Like a good example is the most recent purchase I made was this is unbelievable. Back to like maximizing purchase price and finding something that would make sense within an hour radius of 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 of. 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 like owned by JP Morgan. There's like this huge history around the house and like super interesting, like really unique thing on Hudson river, like you know, pretty close to Manhattan. And so I bought it.

[A]

Wait, you bought Billy Joel's house?

[C]

I bought Billy Joel's house. It's literally up.

[A]

How did we not get to that.

[C]

Scooter in this episode?

[A]

That's the coolest thing ever.

[C]

Yeah, so this is like what it culminated in, which is great. So I bought Billy Joel's house. It's like up on Airbnb again. I did like 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 300k into it. It'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.

[B]

To carry over multiple years.

[A]

That's unbelievable.

[C]

That was from last year. That was still 60% of the bonus appreciation. Wow. So if it was even like six months later with that, 100% had been even more.

[A]

But 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, for being so creative and obviously hustling very hard to figuring out the right way to do this.

[C]

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

[A]

So before we get out of here, Ben, what is. As we enter 2026, what does your portfolio look like today?

[C]

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.

[A]

It's awesome. It's the coolest thing you could say. That's such a good bragging point.

[C]

Thank you. Yeah, and I hung onto my W2 job, so still, you know, still focus on that and kind of building that company at the same time. Also looking for more Airbnb. So awesome strategy out into future years is to keep maximizing this loophole. Looks like it's gonna be around for a while longer, so I'll keep exploiting it as long as I can. And yeah, just keep building the empire.

[A]

All right, well, next time I'm in the Northeast to visit friends and family, I want to stay at Billy Joel's house.

[C]

You're welcome anytime. It's called Craggs Craigs and Estate.

[A]

Thank you. Awesome.

[E]

All right.

[A]

Well, Ben, thanks so much for being here. We appreciate it.

[C]

Thanks so much for having me. It's been a dream to be here.

[A]

And thank you all so much for listening to this episode of the BiggerPockets podcast.

[B]

I'm Dave Meyer.

[A]

I'll see you next time.

[B]

I've had my home security system for quite some time now, and the best part? Half the time I forget it's even there. It's just quietly doing its job, keeping my place safe while I get on with life. If you're wondering what I use, it's Simplisafe, and it has been solid from day one. What makes it different is how proactive it is. Most systems only react after someone breaks in. That's like opening an umbrella after the rain stops. Simplisafe helps stop trouble before it starts. Its AI Cameras can spot a potential threat outside, and real live agents jump in, talking through the camera, letting the person know they're on video, that the police are on the way, or even flipping on a siren or spotlight if needed. It's protection that actually prevents problems instead of cleaning up after them. That's why I've stuck with it all these years. It just works quietly and confidently, like the world's most polite bodyguard. And right now is a great time to get started. 50% off any new system. For a limited time, go to simplisafe.com host again, that's simplisafe.com host because there's no safe like SimpliSafe, most investors spend more time chasing deals than reviewing their insurance. But a quick coverage check can be fast, easy, and one of the smartest ways to protect and even improve your property's cash flow. As the months get colder, frozen pipes, icy walkways, and seasonal wear and tear can increase the likelihood of claims. And traditional insurance companies aren't always built to handle these claims quickly or smoothly. That's why more real estate investors are turning to steadily. They focus exclusively on landlords. Whether it's a single family rental, a Brrr Builders risk policy, or midterm holiday guests, you get fast quotes, flexible coverage, and protection for property damage, liability and even loss of rental income. Now is the perfect time to review your rates and coverage. Get a quote in [e-mail] landlordinsurance steadily landlord insurance designed for the modern investor.