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

Podcast: BiggerPockets Real Estate Podcast
Host: Dave Meyer
Guest: Ben Chester
Date: November 17, 2025

Overview

In this episode, Dave Meyer interviews Ben Chester—a real estate investor who managed to build an 8-unit portfolio across the New York City region, one of the country’s most expensive markets. Ben did it starting from six figures of debt, while working a demanding W2 job, and using a combination of creative strategies, unconventional sacrifices (including living at his workplace and sharing cramped spaces), and maximizing tax loopholes. This episode is a masterclass in relentless hustle, practical problem-solving, and the power of leveraging both high-cost markets and tax laws to your advantage.

Key Discussion Points & Insights

1. Humble Beginnings & Extreme Sacrifice (00:00–06:39)

• Ben began his career making $30,000/year in NYC—barely above the poverty line in such an expensive city.
• To save on rent, Ben secretly lived at his workplace—a sleep clinic—utilizing empty beds at night.
  • Quote: “They thought I was a hard worker… Turns out I was just living there, so I had nowhere else to go.” (02:46, Ben)
• During Hurricane Sandy, being the only employee to show up got him noticed and promoted.
• Ben’s first hustle: subletting his own apartment on Craigslist, sparking the idea for a flexible rental venture that ballooned—with the help of venture capital—before collapsing, leaving him with $120,000 of personal debt.

2. Climbing Out of Debt Through House Hacking (04:27–08:03)

• Post-business failure, Ben focused on basic survival and staying in NYC—taking a W2 job and aggressively house hacking.
• Rented a one-bedroom, legally and physically reconfigured into four rooms, and brought in three roommates (plus his girlfriend), resulting in zero net housing costs.
  • Quote: “We have five people in a one bed, one bath. But… it covered all our housing expenses.” (05:11, Ben)
• This strategy allowed him to channel all income into debt repayment and savings, plus gather experience with landlords and rental management.

3. Scaling to Ownership: From NYC to Texas & Back (06:39–15:10)

• After a year and a half, Ben saved enough for a down payment. He moved into a New York City co-op (not without rejections due to his history).
• In 2019, locked in low-cost housing by purchasing, splitting with roommates/family, and covering the mortgage through shared living.
• COVID-19: Used a job with frequent travel to minimize personal expenses even further, then seized an opportunity to invest in Texas for better cash flow and tax advantages.
  • Utilized FHA low-down-payment loans to buy a Dallas quadplex, house hacking on-site.
  • The Texas property became a springboard for future acquisitions via equity and tax benefits.

4. Creative Strategies for Acquisition in High-Cost Markets (15:10–20:20)

• Each deal focused on breaking even (not necessarily cash flowing in the high-cost NYC market), relying on W2 income for reserves and down payments.
  • Entry-level NYC co-ops at ~$500k, typically “one-bedrooms with something wrong with them.”
• Ben got his realtor’s license to capture commission on his own deals and expanded his search to properties within an hour of Manhattan.
• Identified undervalued, fixer-upper waterfront properties and vacation homes that could attract city dwellers as destination Airbnbs.

5. The Leap into Value-Add & Short-Term Rentals (19:31–24:34)

• Moved into more complex value-add deals: bought, renovated, and furnished a lake house as a luxury short-term rental (Airbnb).
• Employed creative financing—notably leveraging 0% APR business credit cards both for furnishings and renovations, maximizing cash flow runway.
  • Quote: “I turbocharged that intro 0% card to basically fund the entire rehab… just paid it off by the end.” (21:26, Ben)
• Caution was advised: this works only if you can repay before the promotional period ends.

6. Tax Optimization: The Short-Term Rental Loophole (23:20–29:31)

• Ben discovered and capitalized on the “Short-Term Rental Loophole,” allowing him as a W2 employee to use depreciation and bonus depreciation from self-managed STRs to offset W2 income.
  • Quote: “You can take all that and apply it as a loss against your W2 income… you can get close to paying no taxes, which is insane.” (23:23, Ben)
• With proper cost segregation, 20–30% of a property’s price could be bonus depreciated, yielding massive paper losses and thus huge real tax savings.
• Maximum offset: up to $305,000/year against W2 income, with excess losses carried forward.
  • Quote: “I've maxed it out every year with a lot more carrying over.” (29:02, Ben)

7. Billy Joel’s House & The Power of Unique Properties (30:42–33:10)

• Ben’s biggest move: purchased Billy Joel’s former house (within an hour of Manhattan) for $2 million—using his learnings around tax savings, destination properties, and value-add renovations.
• Rehabbed with $300k, jacking up the property’s value to $2.6 million in a year, and unlocked nearly $1 million in tax savings (write-offs to be carried over several years).
  • Quote: “Billy Joel’s house was listed on Zillow… I bought it.” (31:56, Ben)

8. Mindset, Flexibility, and Market Myths (33:10–End)

• Ben emphasizes that deals must “pencil out” regardless of market, and that creative approaches are key—especially in expensive locales.
• Encourages finding unique angles: limiting down payments, leveraging seller financing, and being open to unorthodox strategies.
• Portfolio Snapshot (2026): Eight properties (mostly NY), including three Airbnbs—with Billy Joel’s house as the marquee asset. Maintains W2 job and plans to keep maximizing the STR tax loophole as long as possible.
  • Quote: “Next time I’m in the Northeast… I want to stay at Billy Joel’s house.” (34:14, Dave)
  • Quote: “You’re welcome anytime. It’s called Craggs Craigs and Estate.” (34:19, Ben)

Notable Quotes & Memorable Moments

• Sacrifice:
  “No, they thought I was a hard worker… Turns out I was just living there, so I had nowhere else to go.” (02:46, Ben)

• Creative House Hacking:
  “We have five people in a one bed, one bath. But… it covered all our housing expenses.” (05:11, Ben)

• Resilient Mindset:
  “I didn't want to leave New York, which was like my dream… So what I do is I got a W2 job… to pay off this debt over time.” (04:23, Ben)

• Tax Strategy:
  “As long as you're working a W2 job and you're self managing your Airbnb, you can take the losses… and apply it as a loss against your W2 income.” (23:23, Ben)

  “I've maxed it out every year with a lot more carrying over.” (29:02, Ben)

• On Buying Billy Joel’s House:
  “Back to maximizing purchase price… Billy Joel's house was listed on Zillow… I bought it. It's literally up.” (31:56–32:01, Ben)

• On Mindset in High-Cost Markets:
  “Each deal is kind of like in a vacuum. Doesn’t matter where it necessarily is. If it can pencil out, you know, it makes sense.” (33:10, Ben)

Timestamps for Key Segments

• 00:00–03:06: Ben’s start and living at work to save rent
• 04:23–06:39: Surviving business failure, debt, and house hacking
• 06:39–14:52: First property purchases in NYC, house hacking, and branching to Texas
• 19:31–23:09: Moving into value-add projects and hands-on renovations
• 23:09–24:34: Self-managing STRs and exploiting the tax loophole
• 29:45–31:54: Understanding the scale and limitations of STR tax savings
• 31:54–33:10: The Billy Joel’s house acquisition and its financial impact
• 33:37–34:14: Ben’s current eight-unit portfolio, future plans, and mindset for success in expensive markets

Takeaways for Aspiring Investors

• Financial Freedom is Possible Anywhere: Your market's high prices don’t have to stop you—Ben succeeded through adaptability, sacrifice, and creative financing.
• Leverage Your Unique Situation: Whether it’s living at work, house hacking, or converting “problem” properties, there are always creative strategies.
• Tax Knowledge is Power: Understand (and leverage) all tax advantages—especially if you’re still working a W2.
• Don’t Fear Unconventional Deals: Unique, value-add opportunities—like historic homes or properties with great land—can offer upside others overlook.
• Stay Resilient: Ben’s journey through failed businesses, debt, and tough living situations proves that persistence is paramount.

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