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.”…