In this episode of Broker’s Angle, Hal Coopersmith sits down with Ryan Gessin to explore how specializing in New York City’s outer borough office markets helped him build a unique and thriving business. Ryan shares his journey from making cold calls with no market experience to becoming a trusted advisor for landlords, healthcare providers, AI companies, and institutional owners across Brooklyn and Queens. The conversation dives into the evolution of the outer borough office market, the rise of AI-driven leasing demand, and why deep specialization and mentorship are the keys to long-term success in commercial real estate.

Transcript

Hal Coopersmith: You say that you’re one of a few, one of a few brokers doing outer borough landlord leasing.

Ryan Gessin: Yeah, absolutely. And I, I refer to this A lot where in New York City, we have some of the best of the best working in commercial real estate. And if you have a, a beautiful Park Avenue building and you’re looking for someone to advise on lease-up strategies, advise on debt and equity stack, there are hundreds, if not thousands of really quality professionals that you can go to, to give you the best advice as well as significant proprietary information and in the outer boroughs, it’s just not like that.  and you look at markets, we’re talking about, you know, thirty million square feet, thirty-five million square feet of product with only a handful of those that are truly of an institutional background that can represent you as a landlord,  build that business plan, and also speak with real authority on the market.

Hal Coopersmith: So how did you get into outer borough agency side leasing?

Ryan Gessin: Sure. So I, I’ve been at Newmark for about fifteen years, and I originally came to Newmark with this idea that I was going to help build out an outer borough business. At the time, there was a ton of press about residential populations booming throughout Brooklyn and Queens, and there just didn’t seem like a lot of competition. There was a lot of runway. You weren’t hearing about any of the big firms really transacting there. The only problem is, is I had no actual experience, let alone business and leasing experience. I barely knew the neighborhoods and the blocks. but I can sense that there was a real opportunity there, and I literally just started making the calls, doing the outreach in the middle of the bullpen and I was very fortunate to be at Newmark making these calls and,  I think my wife would say I’m, uh, I’m too loud on the phone, which turned out to be a great gift because some senior brokers heard me making these calls. They randomly had an opportunity in Green Point to meet a landlord that had a bunch of assets in Manhattan, but they had this one troubled asset,  in a prime bo-block in Green Point, fully vacant, newly renovated fifty thousand square foot building.

And that senior broker had heard me making these calls, and said, “Hey, let, let, let’s go to a meeting together.” Brought me on this meeting. We were able to secure and win the bas- business based off that senior broker’s relationship, and we went to work. And six months later, we leased half the building to, uh, NYU Langone, the other half of the building to a advertising agency owned by Walmart.

was able to be there for a successful refi of the property. Ownership was thrilled. Had another building in Long Island City of similar size, similar elk. We went on to do that building as well, leased it in another six months, and then I had a calling card.  not only did I have, like, true success to point to, but I had proprietary data of what are the types of tenants in the market? What are they looking for in this particular market? I had hours and hours and hours of true expertise in that particular market that I knew my peers didn’t have. And that really was what catapulted me to begin to acquire more clients and acquire more properties.

Hal Coopersmith: What are tenants looking for in outer boroughs?

Ryan Gessin: I think the market is really separated into three very distinct markets when you’re talking about outer borough leasing. the first one is what we call HUGS tenants, healthcare, university, government, and social services. These tenants generally take very large amounts of space. They’re generally credit and the reason they’re in the outer boroughs is going back to that increasing residential population. If you look at some of the city centers in downtown Brooklyn, in Williamsburg, and DUMBO, the residential populations are exploding, and the services to support those residents are still lagging behind. So everything from, you know, an office of the IRS for the federal government to New York City Public School to, uh, university, college, and healthcare space, those types of tenants are very active in these markets to support the residential population. Another coin to that is those local entrepreneurs that are there, that two thousand square feet to ten thousand square feet that the CEO is living in Cobble Hill, CEO is living in Williamsburg, and they want to be working close to their community.

So we see a lot of, that type of smaller transaction, those Brooklyn-based CEOs that are looking to work and live in the same community, uh, which is I think an incredible opportunity. You know, Williamsburg is absolutely beautiful. If you could spend all seven days a week, you know, near Bedford Avenue or near the water, what a great life. And we’re seeing more and more of that, in the market as a whole. And then the last piece of this is, is what we consider verti-vertical retail. and that is those types of tenants that lease office space, not for their employees. They lease office space to monetize that same residential population. Whether that’s lifetime fet-fitness, whether that’s a children’s play gym, a pickleball club, you know, all of those types of uniquely based tenants that we might consider them to be ground floor tenants. In the outer boroughs, they go vertical, and they’re there to support that residential community.

Hal Coopersmith: So you had this theory that commercial will be expanding to the outer boroughs, kind of chose this niche. How has it played out for you? How did it play out relative to what you thought it would be, and what is it- Yeah what it is now?

Ryan Gessin: So when I first started, the market was going up in that two thousand fifteen, two thousand sixteen era. They started building a lot more commercial office space in Brooklyn. And I carved out this little niche in boutique assets, you know, thirty to sixty thousand square feet in fringe markets, I would say. Not necessarily prime DUMBO, not necessarily prime downtown Brooklyn, but a building in Bushwick, a building in Greenpoint, maybe, uh, building in Williamsburg on the wrong side of the tracks.

And during that increase in market moment I was able to really capture that and do a lot of terrific leasing. in one year, I believe that I leased all my inventory. All six buildings that I represented were leased a hundred percent with brand-new tenants. And that was really exciting, and I, I knew I was going to build on this. There was only one problem then. We ran into a market slowdown, and then we ran into COVID, and had a lot of competition in the market, for a smaller market from the institutional firms. And as the market slowed and there was significant distress in the market, I saw my competition leave. I saw my competition take their eye off the ball, go to the city, go to Manhattan, specifically look at Manhattan assets, or just Really look at expanding their business to other types.

And in, in that moment, I decided to double down on my business. left my actual team that I was with, and I, I went all in on the landlord rep for these particular markets. And the result was I had no more competition, where if there was a real class A building on the market, no one necessarily wanted it or knew what to do with it. Uh, so I was really the last man standing, for these types of these assets. And now that the market is recovering and healing, I get to really have my pick of some of these truly special buildings that were built in the Brooklyn market over the last five years that now are ripe for new representation and to really speak to the types of tenants that are in the market today.

Hal Coopersmith: how did COVID impact some of the commercial assets, particularly for office

Ryan Gessin: For office in general in the outer boroughs, it was an incredibly scary time for a lot of commercial owners. And I would actually say that COVID had a, dual track impact here because what actually helped the Brooklyn market was that so much of the leasing activity was from these HUGS tenants, these healthcare, university, government, and schools.

And specifically from the healthcare sector, we were able to do some of our greatest transactions during the toughest parts of COVID.  we expanded New York City Health and Hospital, for example, in a building in Bushwick on a 30-year leasehold condo with the, wind of our back of, you know, having to expand healthcare associated with COVID. but when it comes to, you know, some of those other areas like Dumbo or Williamsburg that really, really focused on technology tenants and those types of tenants, it was, it was a ghost town, So those types of buildings and those types of opportunities you couldn’t give away. and I really got to take that time to fine-tune my business plan and what I wanted, to move forward and allow me to be really picky in the types of assignments that I was able to take. No longer was I going to take properties that I thought had a low likelihood to succeed just for the ability to say that I represented that building. I was able to really concentrate on what are the attributes of that building that can attract the tenants that actually will lease space in that market, whether it be a school, whether it be a hospital, or whether it be, you know, other types of uses that, you know, feed that residential population, and that really helped, my business moving forward. But the second part of COVID really showed us these lower interest rates, and a lot of these owners refi-ing their properties or acquiring properties at these lower debt levels. And what we’re seeing now is a lot of those buildings are unable to transact, right, because of broken capital stacks related to that era of COVID.

So we had twofold, two different outcomes. One was limited activity and the activity to a very, very specific sector. But then we have lasting effects of these, uh, these healthy, I would call them healthy buildings, broken capital stacks that have really limited some of the availability in the market for quality tenants today.

Hal Coopersmith: You mentioned one type of tenant where the CEO or owner lives in Brooklyn, wants to have an office there, how does that… Obviously there, it’s a growing residential area, but how does that affect the ability to attract talent to Brooklyn as opposed to Manhattan, where if you’re in Manhattan, naturally you’ll get the commuters from Westchester, New Jersey, Long Island, as opposed to Brooklyn?

Ryan Gessin: it’s a great question and something we have to deal with every day in this market. All the time owners are asking me, “Well, why isn’t this advertising agency that’s based in Midtown South, that all their talent is living in Brooklyn or living in the outer boroughs, why aren’t they moving to these areas?

Why aren’t they moving to these incredible buildings that we have in Williamsburg or Dumbo or some of these other areas?” And the answer’s pretty simple. It’s that the public transportation system in Brooklyn was not built to get to one sub-market to another sub-market in Brooklyn. It was built to get to Manhattan. So when you run these commutation analysis, for even people that are living in Brooklyn to get to other sub-markets in Brooklyn, it’s not a pretty picture. So what we’ve seen historically is once a company gets to a certain size, right? So Brooklyn historically is focused on these, these micro tenants, so two to 5,000 square feet. And what we’ve seen historically is once that tenant grows over 5,000 square feet, over 6,000 square feet, they make their way to the Manhattan market for,  recruitment, for growth, and to really, take that next step in their evolution. And that’s what we’ve seen historically for years and years and years, until the AI world has come to, uh, doorstep in Brooklyn.

And AI is coming to take all our jobs, but until then, those employees are living in the office. And we see a lot of these AI companies that are doubling down on the office space. They’re not just– It’s not just an office. They’re basically living in the office, sometimes five days a week, sometimes six days a week, working incredible hours and what we’ve seen, for example, in the Williamsburg waterfront, has been a complete change in the overall makeup of the tenant class, and that’s driven by AI companies. For example, I represent an amazing Class A building at 25 Kent Avenue, five hundred and fifty thousand square feet, and just in the last six months, we’ve leased about a hundred and fifty thousand square feet almost exclusively to AI native companies.

And the difference here is, is because they’re living in the office, they are encouraging and also paying for their employees to live within a walking distance to the office, an incredible amount of money. So to sell your younger employees in a growing AI company that you’re going to work in this incredible Class A asset on the waterfront in Williamsburg and get the chance to actually live in that submarket, that has given added juice to the overall marketplace. We just did a great deal with a, a company called Rilla AI that is moving, three hundred employees, sixty thousand square feet to the penthouse at 25 Kent to really capture that ability to live and work in such an incredible submarket. And that’s something two or three years ago would have been incredibly foreign to, you know, any broker that, that works in these overall submarkets.

Hal Coopersmith: you are very niche in these outer boroughs. People in the office know you as outer market guy. How has that affected, your relationship within the company?

Ryan Gessin: Most people who work at a major company, so I work at Newmark, which is a publicly traded brand, one of, one of the top brands specifically in the city, but also in, in the world. But as most brokers who do what we do, you might work with members of your internal team, but very rarely are you working side by side with other brokers in your office. and I look at my business completely differently. I am an expert and a market lead at my firm, and I am a extra appendage for every broker in my office In a good way … in a good way, right? So I- Not like a bad- Not, not in a bad way, right? So, you know, if someone calls and asks for market data and things like that, uh, it’s my job, I feel like, to, to give them and be open and transparent with them because when they do need an expert in a certain sub-market, they know that they have my knowledge base and ability to win and transact more business.

So people in my office will always see me, you know, going up and down all the floors of Newmark because I believe in face-to-face interaction and I believe in internal brand. when I’m doing a transaction with a, another coworker at Newmark, I’m not calling them on the phone. I’m going to their office. I’m going to their desk. I’m having real conversations. I’m checking in with other members of the organization at all times just so that, I’m part of that overall brand. They know that, reminded that I’m there. They’re reminded that, you know, their relationships could be monetized in a different way by bringing in someone that has a very unique specialization, and that is really what separated myself and my career, but also that separates what I do for a living versus, you know, maybe someone who’s not as specialized.

Hal Coopersmith: How have you been able to potentially be like a satellite office to some of the existing, or help your e- colleagues find a satellite office in Brooklyn for, let’s say, a main tenant in Manhattan?

Ryan Gessin: I think it’s, it’s not necessarily satellite as it is understanding the availability of to be able to be in a different sub-market, right? So sometimes it’s, a vice chairman at Newmark represents a private equity company that just provided significant Series A funding for a growing company that’s currently located in Dumbo. to be able to meet that company where they’re at, and I don’t just mean physically, I mean the whole emotional aspect of where they are in their submarket, but where they are in the streets, right? Like, not just, you know, what their space looks like, but what the ownership is capable of, what does their capital stack look like, or even where their lunch restaurant is, you know, around the corner. And to be able to have those com- those vice chairmen in my office be able to be armed with that type of expertise to go in and service that type of business, that only reflects better on them and the parent company, knowing that they can be a one-stop shop for, you know, anything real estate related, has really, not only helped them and their business, but helped Newmark as a whole.

Hal Coopersmith: Have you also been able to help tenants in Manhattan find an office, a smaller office in Brooklyn that will supplement their main office?

Ryan Gessin: Yeah, absolutely. And There’s also all these incredible tax incentives that whenever you’re working with,  the bureaucratic nature of New York City, some of these things get lost in the shuffle but to be an expert, not just on the real estate, but on the economic side of completing an office lease and moving to the boroughs, is super important. Uh, I’ll give you one example. There’s, uh, something called the REAP benefit, R-E-A-P.  it’s an as of right tax incentive for the EDC, and it’s equivalent to three thousand dollars per job per year for twelve years for a company that moves from Manhattan to the outer boroughs or from Germany to the outer boroughs, it’s such a powerful, powerful incentive, that can equate to fifteen dollars a square foot off of the top line number of anyone’s rent. And when you look at, you know, seeing real estate as such an expensive top-line item for all of these companies, the ability to potentially upgrade your office to brand-new construction, but also lowering your overall footprint and obligation through both rent decreases as well as some of these incentives, proves really valuable to a lot of these companies that are looking to expand, expand locations, open up additional satellite offices, or just move in its entirety.

Hal Coopersmith: You mentioned that, the lower financing coming out of COVID has affected the capital stack. What are you seeing, at least in terms of the capital stack in Brooklyn buildings and outer borough buildings right now?

Ryan Gessin: I’ll give you one example. So the downtown Brooklyn market is about sixteen million square feet, sixteen and a half million square feet with a twenty percent availability rate. So you have three, three and a half million square feet that’s available to lease in that actual market. But when you peel back the onion You look at some of these assets and they are in real financial distress because of the decisions that were made over that COVID time span. So even if there was real demand at this moment for some of these assets, they’re frozen in time. They’re unable to transact and unable to meet the market. And when you are a larger tenant, for example, in downtown Brooklyn, if you’re fifty to a hundred thousand square feet looking for a large floor plate building in downtown Brooklyn, and you say, “Hey, it’s a twenty percent availability rate,” like all of these owners are going to be fighting over our tenancy.

Well, once you really analyze and do a deep dive in that market, maybe there’s two buildings that are financially healthy enough to actually transact at real market numbers today. And I think that’s a huge misconception,  that’s going on in the Brooklyn market when you just look at that statistical page like, “Oh, wow, it’s a tenant market. There’s so much square footage available.” And a part of that is right, but then when you really look at the true availability rate that can actually transact Until the, the, the deck reshuffles and new owners and new basis come into a lot of these properties, you know, there’s, there’s only few that are set up to really meet tenant demand in some of these markets.

Hal Coopersmith: In terms of your business, we talked a lot about the landlord side. How much of your business is tenant side?

Ryan Gessin: So I would say about 40% of my business on the tenant side, 20% being in the outer boroughs and 20% being in Manhattan and nationally. and it’s, uh, been pretty consistent in that world probably for the last decade.

Hal Coopersmith: Do you have a niche in the tenant side like you do on the landlord side?

Ryan Gessin: I definitely believe, in having real expertise in, a specific niche market that allows you to separate yourself from your competition. And, uh, a really pivotal moment in my career, It was probably my second year at Newmark, thirteen, fourteen years ago, my wife was interning at a, dermatology office, uh, located close to where I live on 55th and Lexington. and I set up a meeting with this, this dermatologist who was in three thousand square feet in a Class B building. I went to my senior brokers at the time, really excited. I brought in this meeting. You know, “Let’s go, let’s go win some business. Let’s, let’s make a few dollars together.” I was really excited about it. And, you know, my senior brokers at the time were, were like, “No. We’re not, we’re not going to meet a doctor.” Right? “This is not, uh, a type of real estate that we’re trying to do. You know, come back to me when you have a, you know, a Park Avenue financial services firm ready to take a floor at the lipstick building,” right? so I got to meet this dermatologist. We, we hit it off on this pitch. and he wanted to expand. He wanted to open a downtown office, West Side office, an East Side office.  and he gave me a shot And we went on to do a couple deals, and I built that trust, with that client. I was young enough and hungry enough to treat this smaller tenant like it was the most important thing in my life at the time, and I think that really resonated with, uh, the executive at the time.

So we went on to do three or four deals in that space. I gained a ton of experience, and then, things changed. that company went on to secure a Series A financing to really expand the business. and once that happened, this little doctor’s office became a much bigger part of my overall business. So from two thousand and fourteen to two thousand and sixteen, we did about forty transactions all in the tri-state area, and that experience for me was life-changing because it wasn’t just site selection work, right? Like, there’s a lot of people who can pick the right office space or use demographic data to say we should open up here, or there’s no competitors there but I stayed through that entire process. So every single legal go-call, every construction call, picking out the, the engineers, the HVAC, all the way through open for business, I was intricately involved in every bit of that process. And that not only made me indispensable for that particular client, but just to be able to see the ball go through the hoop for forty or fifty transactions in a two or three-year time span, it exploded my experience, right? Like, I was able to transact at a level now that someone with maybe five to ten years experience would have the same amount of deal, experience under their belt. And I was able to use that experience not just to build on that multi-location healthcare practice, but to also be a great service to all the tenants I worked with, whether it is that financial firm on Park Avenue or that multi-location healthcare company all over the country. That deal experience and that ability to go from site selection to close side by side with all those consultants, really changed my career and also just, that moment, it, it changed everything from having a job to having a career.

Hal Coopersmith: What are some of the technical aspects that a dermatology or medical office needs that are different from a traditional office?

Ryan Gessin: Things that people obviously think about are plumbing, right? So plumbing comes up all the time, right? We need sinks. Okay, well, where does the water come from? Is it core drilled or is it gravity through pumps, right? foot traffic. You know, these are people coming in and out of the building. You know, being able to understand where maybe those patients are coming from and what hours they’re most likely going to be visiting the office and presenting to a landlord in a clear and concise manner, to alleviate some of the concerns of potentially leasing to a healthcare company. the other thing is, is just the build-out cost associated with healthcare is substantially higher than a lot of other, types of, office occupancy out there. So when you’re looking at an overall build-out cost and you’re looking at length of term, understanding, Relocation options, demolition clauses, all these little elements in a legal lease that could come out later or further on in the deal process. To be able to get those all out in the front in the initial, you know, first week or two of really negotiating a deal allows you to be successful and bring these deals to the finish line, where, you know, maybe early in someone’s career or someone less experienced, might not even know which questions to ask in the beginning of that process, to really get to the finish line.

Hal Coopersmith: What about from the legal side? I have an idea, but I wanna hear since you were on the legal calls.

Ryan Gessin: Yeah. So, I mean, the legal call for a lot of my clients with– in, in the healthcare world is almost all of my clients in the healthcare world are private equity backed. and they all are planning for some type of exit, whether that exit is just through recycling of the board and massive acquisitions of competitors or like-minded businesses, or sales to other private equity backed companies, or even more sophisticated sales to hospital systems. So on the legal side, specifically around things like sublet and assignment clauses, specifically around things like,  exclusives in a particular building, having that flexibility, to be able to maximize your future stakeholders instead of minimizing your exit is something that is so incredibly important to these tenants and can be a massive, massive difference in valuation when you’re looking at some of the intricate details of a legal lease for a company that has a hundred locations, a hundred and fifty locations, two hundred locations. Any single purpose entities? How private equity medical tenants are structured are the actual medical entity cannot take private equity financing. So you have a management company that sits above the medical entity. And this is- That holds the license. We both, yeah … and holds the license, right? So the issue that comes up is s- when you deal with inexperienced landlords, this is something that, comes up all the time because they’re really looking for that medi- they think they’re looking for that medical entity, right? They’ve done the doctor deals in the past. They’re like, “No, I want the entity that is seeing patients in the room because, you know, that doctor is making a million dollars a year in revenue. I want, I want that entity.” And to be able to explain upfront very early on the process that you actually want the management entity that is the same entity that’s guaranteeing 100, 200, 300 leases,  despite the fact that they are separate, tied to, but separate from the actual medical entity, is that inside baseball that if you’re not talking about it very early in the process, it creates a huge amount of complications as you get really deep into the legal documents.

Hal Coopersmith: Well, there’s a lot of great knowledge. One of the things we like to talk about is advice that you would have to younger brokers.

Ryan Gessin: Specialization. And specialization doesn’t have to be a specific market. It doesn’t have to be a specific type of industry, but it has to be special. We are in New York City. We are in the capital of the world, and we have some of the most incredible professionals, that do what we do. The people in the corner office at the major firms are the Michael Jordans, the LeBron James of what they do for, for their career. So how do you have that edge, right? And as a younger broker, I would instruct them to drill down. Whether that’s one particular asset, whether it’s a five-block radius, whether it’s what I did, you know, an overall market as a whole that I felt that people weren’t in. Once you’re able to truly specialize and become an expert, you move from being a broker to a true advisor once I became a specialist in a very particular market, I feel, and I believe my clients feel like they are thankful to meet and, and very fortunate to meet someone like me that’s able to speak their language and help them get where they wanna go in a more precise fashion, than any of my competitors can do because I am hyper-focused in one or two areas.

So any advice I would say to a younger broker is, is really specialize. And the second piece is who you partner with early on and who you pick as your mentor. If, the mentor you’re working with, if you wouldn’t be satisfied with their life or what they’re able to do, you have the wrong mentor, right? You want to be able to see what success looks like on a firsthand basis and emulate in your own way some of the characteristics and some of the strategies that they did to get to where they were going.

Hal Coopersmith: Well, Ryan Gessin, that is a wonderful note to end things on. Thank you for being a part of Broker’s Angle.