He slept in his office for years. He now owns Billy Joel’s house

Sleeping in your office might sound like a Severance-style nightmare, but Ben Chester turned it into an opportunity—by renting out his empty New York City apartment. Check out how this wild scheme led to a portfolio of eight rentals, including Billy Joel’s old digs in upstate New York.

Q: How did you begin investing in real estate in New York City, of all places? “I simply wanted to live here and have enough money not just to put everything toward rent. At the time, I had a job at a sleep clinic. I was like, ‘I could probably secretly live here, and nobody would stop me because they’d assume I’m working.’ So in 2012, I posted my room on Craigslist and was blown away by offers over asking. So I moved into my office for two years.”

Q: Did anyone find out? “There were a couple of close calls. One time, pest control came in and saw stacks of clothes under my desk. They told the CFO, who was like, ‘What’s going on? Are you a hoarder?’ He didn’t even consider the possibility that I was living there. I had a friend who was living in his office; he and I teamed up and got more apartments and rented them out. We eventually moved in together into a walk-in closet in one apartment.”

Q: Did landlords know you were subletting? “The first ones were under the radar. But by a certain point, because we were renting multiple units from the same landlords, we told them. They were like, ‘If you guarantee the rent, fine.’ We then scaled to 700 renters in around 300 units, but went through huge swings with massive demand in the summer and vacancies in the winter. The company went under. I had personally guaranteed the company credit card and ended up on the hook for $120,000.”

Q: Wow. So what next? “I found a one-bedroom apartment, got three roommates, house hacked to cover my expenses, and eventually had enough to buy a co-op. I bought co-ops in 2019, 2021, and 2023—each time living in them for two years, then renting them out. Over the span of five years, I bought eight properties, including Billy Joel’s lake house.”

Q: Tell me more. “I started shopping outside the city, and a house popped up in Highland Falls that needed updates for under $2 million, with an infinity pool and Hudson River views. I saw buried in the listing that it was originally JP Morgan’s summer home, and that Billy Joel rented the place. He wrote Turnstiles there, including ‘New York State of Mind’ literally on his way to the house. I turned it into a bed-and-breakfast called Cragston.”

Q: What’s your advice for investing in an expensive market like NYC? “I think it’s easy to look back and say that there’s a grand strategy. But I think what I did is just take it one step at a time and think, ‘Where am I willing to make sacrifices?’ Then you just take one slightly larger step and build a mini empire.”