Episode 13

    Christopher Calabrese on NYC Real Estate, Political Risk, and Building a Full-Service Firm

    Christopher CalabreseFounder, The CS Organization

    24:00
    In this episode of The Wealth Clock with Steven Weinstock, Christopher Jay Calabrese, founder of The CS Organization, discusses the current state of NYC real estate and the political challenges facing landlords. We cover NYC politics and multifamily investment, South Brooklyn and Queens markets, retail vs. rental development, the firm's role in supporting sponsors, out-of-state deals including C-PACE financing, AI adoption in real estate, and advice for new investors looking to break into the business.

    Key Takeaways

    • 1NYC's 2019 rent stabilization laws and COVID crushed multifamily investment further
    • 2If a deal pencils in today's worst regulatory environment, policy improvements make it a home run
    • 3Retail is more resistant to political policy swings than residential multifamily
    • 4C-PACE financing can provide gap funding and non-recourse leverage for creative deals
    • 5Going 150% in networking and learning is essential for new investors

    What This Episode Explains

    • How experienced investors approach risk management and capital protection
    • How real estate syndications and fund structures create investor opportunities
    • How multifamily investments are evaluated, acquired, and managed
    • How real estate operators scale their businesses and portfolios
    • How market conditions and economic cycles affect real estate decisions
    • Insights from Christopher Calabrese's experience as Founder, The CS Organization

    This episode features a conversation with Christopher Calabrese on The Wealth Clock with Steven Weinstock.

    Frequently Asked Questions

    How did New York's 2019 rent stabilization law affect multifamily investment?
    Christopher Calabrese explains that the 2019 rent stabilization laws, combined with COVID, further suppressed multifamily investment in the city, in some cases leaving units sitting vacant because the cost to renovate them, sometimes $20,000 to $60,000, exceeds what the rent-capped unit can ever recoup.
    Why does Christopher Calabrese consider retail more resistant to political risk than residential in NYC?
    Retail real estate isn't subject to the same rent stabilization and tenant protection laws that constrain residential multifamily in New York, making it comparatively more insulated from the city's shifting political and regulatory environment.

    Episode Sponsors

    WE Capital Mortgage Fund logo

    WE Capital Mortgage Fund invests in fully vetted, first-lien bridge loans backed by real estate collateral, with a focus on capital protection and consistent income.

    CableNOI logo

    CableNOI helps apartment owners unlock hidden NOI by renegotiating, restructuring, or replacing bulk cable and internet agreements. The result is higher property income with zero tenant disruption.

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    Full Episode Transcript

    Steven Weinstock: 0:01 Hi everybody, and welcome to the Wealth Clock with Steven Weinstock. I've been investing in real estate for 20 years, over 20 years, from single family homes to multi-family properties, and recently launching my own real estate investment fund. This podcast is brought to you by WE Capital and the Goethals Capital Fund, where we buy properties in cash, lock in deep discounts, eliminate the mortgage risk in year one and refinance later on in order to scale. The show is not about me, it's about operators, founders, closers, who are building real results in real time. Today I'm excited to have Christopher Jay Calabrese with me. Christopher began his career in Brooklyn back in 2013, quickly found his passion for the many different sides of the business in 2016. He founded the CS organization, which now spans four major verticals: boutique brokerage, capital advisory, management and development. Christopher, thank you so much for coming. Christopher Calabrese: 1:28 Thank you for having me, Steven. Steven Weinstock: 1:29 We are both New Yorkers. We're both in Brooklyn. We recently had an election for New York City Mayor. Now, this was a primary, and typically whoever wins the Democrat primary typically becomes the New York City mayor. Recently that person who won, last name is Mamdani, seems to not be a fan of landlords. He wants the city to own it all. What's your opinion on the biggest shift that we're gonna see in real estate over the next two or three years in New York City? Christopher Calabrese: 2:21 I think that first of all, not to get too political on policy itself, I think that his policies are very extreme. Some would say socialist. It's a little scary. We're in a very delicate position in real estate and also in business in New York City as it is from COVID and the rent stabilization law in 2019, and all the other effects of just everything. His policies, I think, a hundred percent will crush landlords and crush residential investment as far as multifamily further than it's already been crushed. Steven Weinstock: 3:16 We have lots of vacant apartments here in New York City. And typically a regular landlord would renovate the apartment and get as much rent as he can. And because of certain policies we have here in New York, we have units that are sitting vacant because the cost to renovate the unit is $20,000 or $60,000, you can't raise the rent above $1,200 or $1,400 or $1,900. It almost pays not to renovate that unit. So you're creating a housing shortage based on policy. How did you first get into real estate? Christopher Calabrese: 4:23 My family's been in real estate for about 50 years. Started real estate at 18 as a broker, my family's business. I quickly loved it and started my company three years after getting into the business while I was in college. Steven Weinstock: 6:08 Talk to us about some national deals. Are we talking development? Are we talking investment sales? Christopher Calabrese: 6:15 On the capital advisory side is where I have a national presence. The farthest deal that I did out was in Colorado. We did a deal for a boutique sponsor who did a conversion to a boutique hotel. He approached us with financing requests. We came in with C-PACE. He had a senior piece in place. He needed gap funding. C-PACE gave him an extension of leverage and also a level of non-recourse leverage. Steven Weinstock: 13:03 Any specific asset classes that you're bullish on? Christopher Calabrese: 13:19 I think that retail's gonna continue to do well specifically in North Brooklyn and in Manhattan. Retail's pretty resistant to these swings in politics. Steven Weinstock: 19:10 If you were advising somebody new today, what advice would you give them? Christopher Calabrese: 19:15 The biggest advice is you gotta go 150% in every aspect. Whether it's meeting people, going to networking events, understanding the vocabulary of the business, understanding who are the players. One of the things that helped me a lot is I went to so many events when I was a kid. I was 19 years old, I look like a little baby. And I would just be everywhere, every month, no matter what.

    About Christopher Calabrese

    Christopher Jay Calabrese began his career in Brooklyn in 2013 and founded The CS Organization in 2016. The company now spans four major verticals: boutique brokerage, capital advisory, management, and development. His family has been in real estate for about 50 years.

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