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

BiggerPockets Real Estate Podcast · Nov 17, 2025 · 31m

Ben Chester had no money. In fact, it was worse—he had $120,000 in debt. He was sleeping at work and renting out his own rented apartment just to survive in America’s most expensive market—New York City.

Now, six years later, he has eight rental properties, is debt-free, and even owns Billy Joel’s former residence (yes, you read that right).

If you’re living in an expensive market and think it’s impossible to invest, Ben has the formula for you. He turned very little money into a one-bedroom apartment empire—buying whatever he could in New York City, knowing it would all be worth the…