The Wealth Clock With Steven Weinstock
The Wealth Clock with Steven Weinstock is where top operators, founders, and closers share what really works in real estate, business, and life. Hosted by real estate investor and fund manager Steven Weinstock, each episode dives into practical strategies, raw lessons, and behind-the-scenes stories from people who are building and scaling in the real world. Whether you're raising capital, growing a company, or trying to level up your investing game, this podcast is your no-fluff source for honest conversations and actionable insight.
The Wealth Clock With Steven Weinstock
Christopher Calabrese on NYC Real Estate, Political Risk, and Building a Full-Service Firm - EP13
Christopher Jay Calabrese started brokering deals in Brooklyn at 18 and never looked back. Today, he's the founder of The CS Organization, a full-service real estate firm with verticals spanning brokerage, capital advisory, development, and property management.
In this episode of The Wealth Clock, we cover:
- How NYC politics are reshaping the future of multifamily investment
- What he’s seeing in South Brooklyn, Queens, and beyond
- Why he’s bullish on retail and cautious on rental development
- How his firm helps sponsors fill gaps like capital, CO-GPs, and track record
- The structure of out-of-state deals, including creative financing with C-PACE
- Why AI adoption is slow in real estate and how he uses tech in his own workflow
- Advice for new investors and the power of aggressive networking
Christopher also shares stories from his early career, how he built CS from scratch, and his take on the biggest challenges facing real estate operators in 2025.
📍 Guest: Christopher Jay Calabrese
Founder, The CS Organization
Website: https://thecsorganization.com
Instagram: @ChristopherJCalabrese
LinkedIn: Christopher Jay Calabrese
🎙 Brought to you by WE Capital and the Goethals Capital Fund
Send The Host, Steven Weinstock, a comment
🎙 About Steven Weinstock
Steven Weinstock is a real estate investor and founder of WeCapital and the Goethals Capital Fund. Since 2001, he has built a diverse portfolio of residential and multifamily assets while helping investors access passive income through strategic real estate opportunities. On this podcast, he shares real-world insights on investing, capital raising, and what it really takes to build and scale in today’s market.
📩 Want to invest or get in touch?
Visit: www.WeCapitalX.com
📱 Connect with Steven:
LinkedIn: www.linkedin.com/in/stevenweinstock1
Instagram: https://www.instagram.com/wecapitalx/
YouTube: https://www.youtube.com/@TheWealthClockPodcast
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. Over his career, he's arranged the sale and financing of numerous properties that has been actively involved in transactions across the us. On top of that, he's a frequent speaker contributor on real estate topics, and I'm happy to have him join. Christopher, thank you so much for coming.
Christopher Calabrese:Thank you for having me, Steven.
Steven Weinstock:Pleasure. All right. Quick question. We're gonna jump right into it. Let's start with something timely. We are both New Yorkers. We're both in Brooklyn. It seems that everything that happens in New York seems to make national news. 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. His first name, I think it's Zorhan seems to not be a fan of landlords. He wants real estate. He, but he wants the city to own it all. What's your opinion or the biggest shift that we're gonna see in real estate? Over the next two or three years in New York City? As far as residential?
Christopher Calabrese:Yeah. I think that first of all, not to get too political, on, 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 all the other, rent stabilization law in 2019, and all the other effects of just everything. So I, we're in a kind of a spot where we need to be able to lift up, not be, broken down further. So that's my first thought. My second thought is his policies. I think we'll either, excuse me. A hundred percent we'll crush landlords and crush residential investment as far as multifamily further than it's already been crushed, I would say.
Steven Weinstock:Yeah. And we've had some regulation hit New York City. You mentioned 2019. 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 and because the cost to renovate the unit is 20,000 or 60,000. You can't raise the rent above, 1200 or 1400 or 1900, it almost pays not to renovate that unit. So you're creating a housing shortage based on policy and in general, I'm a free market guy, let the market determine. But this policy in New York, it really makes it very tough for landlords. You're from New York. Let's rewind a little. How did you first get into real estate? Yeah. You mentioned you're from New York, you're from Brooklyn. How'd you get into real estate?
Christopher Calabrese:My family's been in real estate for about 50 years. Started real estate at 18 as a broker, my family's business. And quickly, I quickly loved it and started my company three years after getting into the business while I was in college.
Steven Weinstock:How many generations did he go back here in Brooklyn?
Christopher Calabrese:Just my father. He came from Italy. He came from Sicily, started in real estate when he was 18 and never looked back.
Steven Weinstock:Okay. Yeah. A true Brooklyn native. I like that very much. What were you doing before you launched the CS organization? What was your typical day like? You're in real estate but you didn't create your own company just yet.
Christopher Calabrese:I was brokering deals focusing on multifamily and development sites In Brooklyn. Couple, a couple deals in Manhattan that, we took a few runs at with some clients, but mostly in Brooklyn.
Steven Weinstock:Your firm the CS organization covers, different verticals as they call it. How do you balance all these pieces under one roof capital advisory, management, development brokerage? It's a lot of moving pieces.
Christopher Calabrese:Yes. And I'm pretty much in all of the. Operation of every single one of those every day. And the reality is that it's so complimentary. Removing from the management and the development aspect, the capital advisory and the brokerage, they really go hand in, so a lot of the clients we help service in both capacities.
Steven Weinstock:Talk to us about some national deals. Or out or deals that you did outside of New York? Are we talking development? Are we talking investment sales? Talk to me about outside of New York.
Christopher Calabrese:Absolutely. On the capital advisory side is where I'm have a national presence. We are in the middle of a few deals from the Midwest to the southeast. I did a deal. I would say the farthest deal that I did out was in Colorado. We did a deal for a boutique sponsor based in Colorado, who did a conversion to a boutique hotel. It was like adaptive reuse, did a phenomenal job, knocked it out of the park. He approached us with financing requests. We came in with C pace. He had a senior piece in place. He needed a little bit of, like a gap funding in a sense. Came in with a c pace to get like a extension of leverage. Blend down the blend down the cost of capital across the stack, but also it gives him a level of non-recourse leverage as well. So we did that back in 2022.
Steven Weinstock:Got it. What kind of sponsors are you typically dealing with? Are these institutional, are these. Mom and pops are these just are some of them new sponsors and they're bringing on a team to give them a little gravitas. What's your typical client like when it comes to this?
Christopher Calabrese:I would say from a beginner in the real estate business, I do a lot of construction work, a lot of construction financing, bridge transitionary type of debt. So a lot of them are new developers or they are seasoned. They're doing maybe things differently just because of the environment and I'm able to bring 'em into different, capital structures.. Steven Weinstock: Are you finding a lot investing further and further away? In other states, obviously Florida, Texas, we have a lot of New Yorkers who are buying in those areas. Is that because, they're afraid of New York? Is there just no more opportunity in New York? Were they forced to start looking at other locations? What's your opinion on that? I think that the true New Yorkers. Are always gonna own New York real estate. I think that 2019 made a lot of multifamily operators have a change of heart and I think that 2020 COVID really solidified that for them. I was looking in Florida in 20 18, 20 19. And the, new Yorker was like, still very rare that, oh, you're a New Yorker, it's not as common now you go down over there, you're in New York. Oh, there's a hundred of you because it's like everybody that you talk to said, no I'm shifting to the Southeast and the Sunbelt, et cetera.
Steven Weinstock:Yeah. I myself I started over 20 years ago. I couldn't touch New York when I first started. But at the time it was more of just, the price and, the amount to get involved. I started buying about 45 minutes away in central Jersey. And spent a lot of time there. I did dabble in New York for a while. I disliked being a landlord in New York. I owned some property some multifamily, I did well with the sale. I did well on appreciation. But being a landlord, managing the property was tough. And this is, 20 years ago, this is pre 2019. There's just no room for the landlord to, to ever really I don't wanna say not to win because you have tons of, billionaires with New York real estate. But if you have a tenant that is not paying. You're dealing with, c class property or even a d class property and you're not getting paid, that could cost you two years worth of rent sometimes with the way the court system is. Sure. I wasn't even involved in COVID in New York, but I saw it out of state. I also own in Kentucky and I own in parts of Ohio. And for the most part, these are red states. The court system is. Pretty fair. I do see little by little there are things that are making it tougher for the landlord. But for the most part it's, it's a few months and, the eviction gets filed and processed and, no games, there's no there's no back and forth. It's one court appearance and you're done. And in New York it was multiple a lot of lawyers helping out the tenants. I guess it, it was just very tough. And at the same time I speak to people here in New York that are buying in New York. I know this guy who's buying, 20, 30 unit buildings in Queens and in the Bronx. And he's telling me that if he can make it pencil in today. At today's horrible political climate. If he could get it penciled in today, then if anything changes, all of a sudden it becomes a home run. And that's really what he is banking on. Obviously he's getting good deals, he's established he has banks coming to him offering him properties that are on their books. But I'm not sure if there's room for a new investor to buy a New York development may be. You tell me is there room for a new investor to just buy a 25 unit property in Queens or are they getting screwed?
Christopher Calabrese:Lemme just address the first thing you said. You said that he's banking on what if it changes, right? He is buying on a good basis, let's say. A lot of the trades we seeing over here rent stabilized. They're like seven caps, seven and a half cap. So yeah, we see we definitely see some of that happening in certain submarkets. We see, we still seeing crazy cap rate trades because of just either emotional transaction or neighborhood, whatever they're, certain neighborhoods have different type of motives, with these type of things. So I don't know how they get away with the value they create or don't create, or how they make a pencil, but they. They do. We have sub, sub five cap trades in Bensonhurst which is just wild. But nevertheless, I think that the development market is, the pipeline is very weak. I don't, I think the 45 x doesn't help the smaller developers. That's why you're seeing a lot of condo deals. I don't think rental deals pencil today for the most part, unless you got a incredible basis on the land. We won't even look at any rentals really, just because of the way that the environment is, the way the costs are, the way that, you know, even though the rents are sky high, the taxes are crazy and the utilities and just expenses are outta whack. And I will tell you this to address the original question. We are seeing a lot of inventory. In in, in Queens, but also in, in the submarkets that we operate in Brooklyn. Like a lot in South Brooklyn, there's a lot of entry, there's a lot of entry for 10, 20, 30 unit buildings right now.
Steven Weinstock:Any specific asset classes that you're bullish on? You just mentioned a part of Brooklyn 10, 12, 20 unit buildings. Any other asset classes anywhere else in New York that you're excited about?
Christopher Calabrese:I think that retail's gonna continue to do well specifically in North Brooklyn and in Manhattan. Certain certain pockets, of course. I think that retail's pretty. Resistant to these swings in politics. But you know what it is it really comes down to what happens with this election. This election's gonna impact business more than it's gonna impact just real estate. Hey, what do you think? It's your opinion.
Steven Weinstock:I used to think that New York is very resilient and no matter what happens because of the population growth. As you have people leaving you always have more people coming. You had a lot of people who left New York and the people who leave New York are typically the ones with extra dollars. They could afford to leave. So if people are gonna leave because of the political climate, the people who are staying. Either they could be billionaires too and they just don't care. If milk is, $3 or $12, it doesn't affect them. So they could stay and they could live, in their mega mansions or mega apartments. But if regular, and regular is a rough word, but if upper middle class people are leaving because they don't like the tax climate or the crime climate, and you're leaving people who are less well off. You are shifting the balance of the city and the makeup of the city, and in every country in the world every, even a third world country, you always have the ultra rich and you have the mega poor. And a lot of these countries have nobody in between. You have the oligarch so to speak, and government bureaucrats on top or billionaires, and then the rest of the people are just broke. And the strength of a country. And the reason why America is great is because we have such a large middle class, we have tons of people. Making anywhere from, $50,000 a year to 400,000 a year. So you're not talking about the mega rich and we're not talking about the broke. And the more you shift the balance of New York to take away, from the top or the top middle class, then you're leaving the lower and it will affect New York.
Christopher Calabrese:Sure will. New York is is heavily reliant on, especially in Manhattan. F and b and entertainment. So if that goes away and you have less of a consumer base, and we have so many restaurants, so many, how are they gonna make it? It's it's a problem.
Steven Weinstock:Everybody's talking about AI and tech. I was recently on a panel where, they were asking why real estate companies are five years five, 10 years behind on the technology curve. You're in the real estate business you're dealing with, different aspects of it. How are you using technology or specifically ai throughout your day?
Christopher Calabrese:We basically do a lot of prospecting. So I use technology. For prospecting besides the old fashioned cold calls, which we do a hell of a lot of, but as far as AI specific, I'm not bringing too much into it yet into my business. I use it for certain applications as the typical templates. Things you just wanna, or reorganize, descriptions and different things. But generally speaking it is really still manual for me. And maybe it's because I'm just a little old fashioned, I like control over.
Steven Weinstock:Yeah.
Christopher Calabrese:I also mentioned that using it as a super human calculator is pretty effective, but, we use it for. Different calculations on the debt side, and it's mind boggling.
Steven Weinstock:Yeah, I agree.
, Christopher Calabrese:People just don't know what it really could do and can't do. They just don't spend the time to get educated.
Steven Weinstock:Yeah. I saw this I saw this stack that chat. GPT gets I think it's 123 million visitors a day, or maybe it's a month or whatever it is, but 123 million and only like 10% of those people are using it for. Work, meaning they're mostly using it for, to like, not play games, but for meaningless stuff. And it's because of what you said, they don't know what you're able to do with it. And I think though, as people use it more and more it, it should do more and more.
Christopher Calabrese:Yeah. It's amazing.
Steven Weinstock:What's been one of the biggest challenges you had as a business owner? In the last I don't know, five years or so?
Christopher Calabrese:Challenge. I think that I think building a business is one of the most challenging, exciting, and, a sense of accomplishment, right? You get a sense of accomplishment. I think that the process is the fun part. And I think that one of the biggest challenges that me personally is just, going through the motions. When I started, I started when I was like, when I was a kid almost, and I'm still pretty young. I'm 30. I started young and I didn't realize that when I started how hard it would be and I was teaching like myself a lot of the stuff too, even though my family's, extremely real estate diverse, but, I wanted to learn on my own and fail on my own. So that, that was very challenging. But it really made me more positioned for today and the whole process really brought me into being me. I grew up into the business,
Steven Weinstock:if you were advising somebody new today, you met somebody, you have a relative not somebody they could bring into your business. But if you were advising somebody today they want to start being involved in real estate as an owner, as an investor, what advice would you give them knowing what you know?
Christopher Calabrese:The biggest advice that I would give them is you gotta go 150%. In every aspect, whether it's meeting people like yourself, doing things like this, going to networking events, understanding the vocabulary of the business, understanding who's the players in the business, understanding the business itself how to get business, how to keep business. It just never ends. One of the things that I really think that. It helped me a lot is I went to so many events when I was a kid. I used to be like 19 years old. I look like a little baby. And I would be there really, I didn't know too much about anything really. And I would just, I'm Chris, I'm pretty, I would everywhere, every month, no matter what. And I was, I, and I'm pretty shy person, but I, with business I put on my big boy pants and I went out there and that's what I think it, matters.
Steven Weinstock:If you're looking at a deal and the sponsor is good, you've worked with them before, but you're seeing, maybe a hole in the deal where you feel it's not gonna work out, what kind of conversation do you have with this, sponsor who, they might have spent some good money on the due diligence already. And, how do you tell them other than just telling them that you can't help them, oh, you can't get them a loan, or whatever it is. How do you let them know that, maybe, this deal is a bad deal and does that ever affect relationships?
Christopher Calabrese:It happens often. I'm very happy you asked that question because it's one of the things that we pride ourselves as CS in doing, because we're on the principal side as well. The resources that we have as a brokerage is very different than a typical brokerage. I put myself in the shoes and I have relationships deep rooted. In, in, in a number of markets that I could tap into to help bring resources to that hole. So if the hole is a CO-GP, if the hole is a track record, I have people that at least I could at least attempt to put them with. Doesn't mean it's gonna work every time, but I make those efforts and I have those relationships.
Steven Weinstock:What are you doing to stay on top of your game? Meaning, and I'm, and I'll ask like this. What how are you educating yourself about what's happening? Are you listening to podcasts? Are you reading books? Is it networking? What are some of the tools that have helped you over these last couple of years?
Christopher Calabrese:I listen to one to two podcasts per morning. Typically when I'm doing my morning routine. I love listening to people like yourself and listening to people like us talk about real estate. I could go on and on with all these podcasts that I could name off, but I also, one of the things that I'm talking to the best people in the business every day. I'm working with the best people. I'm also constantly at events. I'm constantly with, associating with the top that, that I could aspire to be there and also to learn what their opinion is and what their pain points are in today's market.
Steven Weinstock:Okay Christopher, I had a great time. I usually like to keep these short.
Christopher Calabrese:Nice.
Steven Weinstock:But let the audience know how could they reach you? I'll put it in the show notes, but whatever you want. Phone number, email, social security number, whatever you wanna share.
Christopher Calabrese:Yeah, it can reach you on Instagram. Christopher j Calabrese and on LinkedIn. Christopher j Calabrese. My website is thecsorganization.com.
Steven Weinstock:All right, Chris. Thank you very much. I really appreciate it. We're both from Brooklyn. I am sitting in Brooklyn right now in the, I guess you could say the Sheephead Bay area. And I live in the Marine Park section. But I'm born and bred born and raised in the, in Brooklyn. You sound more like a Brooklyn native than I do. But when I travel and I go to Kentucky often, I always, people always tell me, Hey, you have an accent. They call me Yankee. They're this, they're that. But, I always think I have no accent, but you sound like a, like a Brooklyn guy. So I'm happy to have you on. Thank you very much everyone for watching or listening to this episode. You could watch us on YouTube and you could see Christopher on the screen alongside me, or you can download us on any of the major podcast platforms. And see you on the next episode. Thank you.
