BiggerPockets Real Estate Podcast Sleeping at Work to Build an 8-Unit Portfolio in America’s Most Expensive City
19 snips
Nov 17, 2025 Ben Chester, a real estate investor, transformed his life from being $120K in debt to owning eight rental properties, including Billy Joel's former residence. He shares how he ingeniously lived at his sleep clinic job while renting out his apartment to overcome financial struggles. Ben reveals his creative methods for house-hacking one-bedroom apartments into multiple rentals and discusses leveraging tax strategies like bonus depreciation to offset his W-2 income and generate cash flow, proving that investing in New York City's competitive market is possible.
AI Snips
Chapters
Transcript
Episode notes
Sleeping At Work To Survive NYC
- Ben secretly moved into the sleep clinic where he worked to save on rent and got promoted after showing up during Hurricane Sandy.
- He rented out his apartment on Craigslist and later left the business with $120,000 of personally guaranteed debt.
Turning One Bedroom Into Four Rents
- Ben converted a one-bedroom into four rentable spaces with the landlord's help and housed five people to eliminate housing costs.
- He used roommate rent to pay living expenses while directing W-2 income toward debt repayment and savings.
Lock In Housing With House Hacking
- Buy to lock in housing costs with a long-term fixed mortgage if you plan to stay in an expensive city.
- Use house hacking to reduce effective housing expenses and funnel wages into debt repayment or investments.