Ben Chester

Real estate investor who built an eight-property portfolio while working a W-2 job, using creative house-hacking, short-term rentals and tax strategies (including bonus depreciation) to offset income and scale his business; owner of a renovated Airbnb that was formerly Billy Joel's residence.

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Nov 17, 2025 • 32min

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

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.

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