He slept his way into a NYC portfolio

Ben Chester came to the Big Apple as a penniless grad student, then quietly built a portfolio of eight properties—three in NYC, and even Billy Joel’s upstate house. Here’s the sneaky way he pulled it off, with his advice on how to size up a co-op board and more.

Average home price: $832,934 (up 3.5% YoY, per Zillow)
Homes that sell over list price: 21.3%
Homes that sell under list price: 66.4%
Average rent: $4,170/month (up 5.5% YoY)

How he got started: Chester’s first “investment” was more a loophole than a purchase: Working at a sleep clinic, he realized nobody would question why he was always there—so he moved in and listed his apartment on Craigslist in 2012. “I was blown away by the demand,” he says. He bunked at the office for two years while expanding his sublet scheme to hundreds of apartments. In 2019, he bought a one-bedroom co-op in Hell’s Kitchen for $480,000, which he split with his girlfriend and brother, adding a loft bed and pullout couch to make the tight space work.

His market’s pros: Everyone just keeps coming to NYC. “There’s an insatiable appetite for apartments,” he says. Even with today’s high mortgage rates and even if the day-one numbers look ugly, rents tend to catch up to mortgage payments in a year or two. “New York City is a safe place to store money.”

The cons: Chester doesn’t sugarcoat it. “It’s much easier to invest in just about any other city in the country,” he warns. In his experience, the math in NYC works only if you plan to live there yourself and house hack, designing “pods” where you cram in every friend you can stand as a roommate. In addition to sky-high prices and a ban on short-term rentals, about 70% of NYC’s housing stock is co-ops, which require buyer interviews and can refuse an application—no explanation required. Although condos typically lack these restrictions, you’ll pay around 10% more. Chester chose co-ops requiring just two years as a resident; after that, he moved out, rented out his unit, then rinsed and repeated his way to three properties.

His advice: Even if a co-op board says it allows rentals, scrutinize board minutes to see how they really feel. “It will give you a sense of how annoying they’re going to be,” Chester explains, adding that restrictions on pets are often a sign they’ll micromanage other aspects of a property. If renting out your co-op is a priority, don’t just check house rules; be upfront about it during your board interview, too. “It can be an uncomfortable question, but it’s better than getting stuck,” he points out. He also encourages investors to get creative when carving up a small space. “I once moved into a walk-in closet—with a roommate,” Chester admits. “That allowed us to rent out the main living area so we were basically able to live there for free. Once that first place is paid down, buying can accelerate.”

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