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

BiggerPockets Real Estate Podcast

BiggerPockets

Education, Business, Investing

4.8 • 16.5K Ratings

🗓️ 17 November 2025

⏱️ 34 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 sacrifice. He’s split these small apartments into multiple rentals with up to four tenants, allowing him to make the numbers work even when everyone else says it’s impossible. But that’s not the best part. After unlocking a tax “loophole” when buying a lake house, Ben is now able to offset 100% of his W-2 income taxes, meaning he often gets a check back from the government every year, all thanks to his real estate. Thought it was impossible to invest in markets like New York City? Ben is about to make it a very attractive option. In This Episode We Cover Turning a one-bedroom apartment into four living spaces with multiple roommates The astonishing price Ben is paying for these tiny rentals (and why they’re worth it) The tax “loophole” that regular real estate investors can use to offset all of their income Buying (and renovating) Billy Joel’s house! Yes, Ben actually did that How to finance your home renovation when you don’t have the cash (0% interest) And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/real-estate-1201 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Do you think living in a big, expensive market means you can't invest in real estate?
0:04.8	Think again.
0:05.8	Today's guest works at demanding travel-heavy day job.
0:09.5	So he's building a rental property portfolio as a backup plan, and he's doing it in and around
0:15.7	New York City.
0:17.1	This is not a story of an already rich person buying properties in cash.
0:22.6	It's about using hustle and persistence to build towards financial freedom even in one of the country's most expensive markets.
0:30.9	Ben was even willing to sleep in the office he was working in to kickstart his investing career.
0:37.0	And although that type of sacrifice
0:38.6	isn't for everyone, it might just be for you.
0:46.2	Hey everyone, I'm Dave Meyer, housing market analyst and head of real estate investing in bigger
0:50.8	pockets. Today we're bringing you the story of an investor named Ben Chester.
0:55.9	And I'm super excited to talk to Ben because he's one of the very few people I've ever met
1:02.1	who's doing basic rental property investing in New York City.
1:06.8	And Ben isn't buying giant apartment buildings for millions of dollars.
1:10.7	He's also not buying really risky properties in suspect areas.
1:15.9	He's found a way to acquire one-bedroom apartments that cash flow in some of America's most
1:21.3	expensive zip codes.
1:23.5	So on today's episode, Ben's going to tell us the exact formula he found that makes these
1:29.2	deals work even when starting with six figures of debt personally that he had.
1:34.3	He'll tell us the story of how he turned Billy Joel's house, yes, actually Billy Joel's
1:38.8	house into a cash flowing investment property, how he can offset almost all the taxes from his W2 career
	...

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