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November 18.2025

2 Minutes Read

Investing in Real Estate in the NYC Market: Ben Chester’s Inspiring Journey

Investing in Real Estate in the NYC Market visual with success story text and NYC backdrop.

Can You Invest in Real Estate in Big Markets? Absolutely!

If you believe that investing in real estate is impossible in a pricey market, think again! Ben Chester, a passionate investor in the bustling New York City area, flipped this notion on its head with his remarkable journey. Unlike individuals born into wealth, Ben's story is one of hard work, creativity, and determination.

We came across 'I Was Sleeping at Work to Save, Now I Own 8 Rentals,' which covers investing in real estate in expensive markets, and it raised some compelling points that we’re expanding on in this article.

The Hustle Behind the Success

Initially, Ben faced a daunting challenge: he graduated with a low-paying job while living in one of the most expensive cities in America. Facing an oppressive rent burden, he came up with a radical solution—he secretly decided to live in his office! Working at a sleep clinic — equipped with beds — made his unusual living arrangement plausible. Instead of using all his money to pay rent, Ben cleverly rented out his apartment on Craigslist, which brought in additional income.

Turning Challenges into Opportunities

Overcoming personal and financial hurdles taught Ben the skills necessary for an investment career. With a goal of buying real estate without being driven out of New York, he adopted a strategy of living frugally while saving aggressively. This enabled him to purchase his first co-op with multiple roommates sharing rent expenses. Cash flow was positive—all while he was paying off substantial debt from his previous business venture.

Building a Real Estate Portfolio—Even in NYC

Ben’s journey went from a single co-op to a portfolio that includes eight properties, among them a renovated house once owned by the legendary Billy Joel! By combining his real estate knowledge with smart financial strategies, Ben took advantage of the rental market and tax benefits available to him. His unusual approach speaks volumes about how innovative thinking and determination can lead to financial stability, even in high-cost areas.

So, could you create your own investment story amidst soaring prices? With the right mindset, like Ben's, anything is possible!

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Investing in Real Estate in the NYC Market: Ben Chester’s Inspiring Journey

Can You Invest in Real Estate in Big Markets? Absolutely!

The Hustle Behind the Success

Turning Challenges into Opportunities

Building a Real Estate Portfolio—Even in NYC

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