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Home » From Crushing Debt to Renting Out Billy Joel’s Former Estate—How Ben Chester Turned It All Around
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From Crushing Debt to Renting Out Billy Joel’s Former Estate—How Ben Chester Turned It All Around

Business Circle TeamBy Business Circle TeamJune 4, 2026No Comments3 Mins Read
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From Crushing Debt to Renting Out Billy Joel’s Former Estate—How Ben Chester Turned It All Around
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Identify Ben Chester
Location New York Metropolis
Occupation Tech gross sales and actual property investor
Property Eight properties, three short-term leases (together with Billy Joel’s former Hudson River property)
Funding technique Brief-term leases and home hacking
Financing Standard loans

In 2012, Ben Chester was making $30,000 a yr in New York Metropolis, spending each greenback on lease. Pissed off, he determined to secretly transfer into the sleep clinic the place he labored, subletting his condominium on Craigslist to cowl the lease. 

That hustle finally become a furnished-rental enterprise that attracted enterprise capital, grew shortly, after which collapsed, leaving Ben with $120,000 in personally assured debt. 

Ben received a W-2 job, rented a one-bedroom condominium together with his girlfriend and three roommates to cowl housing prices, and pointed each spare greenback at digging out of debt. Lastly, a couple of years later, he purchased his first co-op in Hell’s Kitchen. 

At the moment, Ben owns eight properties throughout New York, offsets practically all of his W-2 earnings by way of actual property depreciation, and even hosts visitors at Billy Joel’s former Hudson River property. Right here’s how he did it.

You had been $120,000 in debt with no financial savings. How did you get your first deal carried out? 

I mixed a travel-heavy W-2 job with aggressive saving. If you’re on the highway, and the corporate covers motels and meals, your bills mainly disappear. 

I stacked every thing I may towards a down fee, discovered a one-bedroom co-op in Hell’s Kitchen for round $500,000, moved in with my girlfriend and my brother, and saved housing prices to about $750 every. The mortgage principal was roughly the identical quantity, so I used to be basically breaking even whereas constructing fairness. 

That was the entire level: I wasn’t attempting to get wealthy on the primary deal. I simply wanted to lock in a foothold in New York.

How do you make the numbers work in one of the costly markets within the nation? 

The technique that modified every thing was the short-term rental tax loophole. In case you have a W-2 job and also you self-manage your Airbnb, you possibly can apply the property’s losses, together with depreciation and bonus depreciation, instantly towards your W-2 earnings.

I maxed out the $305,000 annual restrict yearly and carried the surplus ahead. On Billy Joel’s home alone, I purchased it for $2 million, put $300,000 into the rehab utilizing 0% intro APR enterprise bank cards, and generated near $1 million in tax financial savings that carry over for years. The tax profit alone made the deal work, unbiased of the money circulation.

What’s the one factor most buyers in costly markets get incorrect? 

They assume the market is the issue. It’s not. Each deal lives in its personal vacuum. If it pencils out, it is smart whatever the ZIP code. 

In New York, you must be inventive. You’re not going to discover a cookie-cutter BRRRR. However you could find a one-bedroom co-op with one thing incorrect with it, home hack it with roommates, and break even whereas constructing fairness in one of the useful actual property markets on the earth.

Cease ready for the right market and begin in search of the deal that works contained in the one you’re already in.

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