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About this guest

For those of you who do not know Stephen,

1. Transformed Dermot Company’s Growth – Stephen orchestrated the strategic transformation of The Dermot Company, growing its assets under management from approximately $1 billion in 2015 to about $4 billion today — managing a vast portfolio of 21 properties and over 6,000 apartments. This impressive expansion marks him as a visionary leader in multifamily real estate.
2. Led Over $8 Billion in Multifamily Investment – With a career spanning decades, Stephen has driven over $8 billion in multifamily investment and development projects across the U.S., demonstrating unparalleled expertise and influence in shaping the country’s rental housing market.
3. Deep Industry Experience & Strategic Insight – Before leading Dermot, Stephen built a strong foundation through roles like founding Meridian Realty Partners, VP of Development at Archstone and Homestead Village, and early work as an analyst at Cushman & Wakefield — giving him a unique perspective that blends ground-up development, value-add strategies, and market-savvy risk management.

About this episode

Join host Adi Soozin as she sits down with Stephenen Benjamin, CEO and Managing Partner of Dermot, a powerhouse in the multifamily real estate space that has skyrocketed from $1 billion assets under management in 2015 to $4 billion today.

With a career spanning decades, Stephen has driven over $8 billion in multifamily investment and development projects across the U.S., demonstrating unparalleled expertise and influence in shaping the country’s rental housing market.

In this episode, Stephen shares his nearly 30-year journey from junior partner to visionary leader, guiding Dermot’s focus on “lifestyle renters” — a thriving demographic fueling the rise of upscale rental living on the East Coast.

Discover how Dermot blends deep market insight, cutting-edge data analytics, and an in-house tech system built on Python to pinpoint prime neighborhoods, evaluate supply and demand, and time investments perfectly. Learn about their signature Ignite program, designed to cultivate vibrant community and premium amenities that keep tenants engaged and loyal.

Stephen breaks down current multifamily market dynamics, including an unprecedented surge in new supply triggered by post-COVID low interest rates — and why he expects a sharp slowdown by 2026. He reveals why Dermot’s strategy of five-year holds is delivering steady, stable returns to investors, backed by meticulous research on income demographics, local job growth, and economic signals.

Whether you’re a real estate investor, developer, or curious about the future of rental housing, this episode delivers insider expertise on the evolving multifamily market, the power of lifestyle-driven design, and how data is transforming property investment for the better.

Tune in and get inspired by Stephen Benjamin’s bold vision shaping the future of upscale rental living!

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Show Notes Generated by Gemini

These show notes were generated by AI

• Introduction of Stephen Benjamin Adi Soozin introduced Stephen Benjamin, the managing partner and CEO of the Dermot company. Adi highlighted Stephen’s success in multifamily investment and development, noting the company’s growth from $1 billion in 2015 to $4 billion today. Adi emphasized Stephen’s unique position in the current multifamily market, where many others are struggling (00:00:00).
• Stephen Benjamin’s Background Stephen Benjamin joined Dermot nearly 30 years ago as a junior partner to the founder, Bill. Bill started the company about 10 years before Stephen joined and built it up after a career in law and finance (00:01:55). Stephen admired Bill’s entrepreneurial spirit and learned the business from them over 15 years (00:02:46). In 2015, Stephen and two long-term colleagues bought the company from Bill, who decided to retire (00:03:38).
• Early Career in Real Estate Before joining Dermot, Stephen Benjamin had a long-standing interest in real estate, enjoying construction and studying architecture in college. They started their career in New York at Kushman and Wakefield, gaining experience in various property types (00:04:25). Stephen then moved to a large multifamily REIT called Archstone, working in different regions before returning to New York in 2001 (00:05:18).
• Preference for the Housing Sector While at Kushman and Wakefield, Stephen Benjamin found all asset classes interesting but was particularly drawn to the living space. They noted the collapse of the office building market in the early 90s, drawing a parallel to the current situation (00:06:06). Adi Soozin agreed, stating that experienced investors often wait for novices to make mistakes before capitalizing on opportunities (00:06:55).
• Dermot’s Focus on Upscale Rental Living Stephen Benjamin explained that Dermot specializes exclusively in apartments and has been vertically integrated with their own management and construction teams. The company focuses on the East Coast, primarily in about nine cities, with New York being their largest market (00:10:29). Their current specialty is “upscale rental living,” targeting the “lifestyle renter” (00:11:24).
• The Rise of the Lifestyle Renter Adi Soozin concurred with the focus on luxury rentals, noting that this segment tends to be more stable than affordable or middle-income housing (00:12:18). Stephen Benjamin pointed out that the changing sentiment of young people, increased home ownership unaffordability, and a preference for experiences over ownership have driven the growth of the upscale rental market (00:13:12). This demographic often prioritizes amenities and flexibility (00:14:06).
• The Importance of Amenities and Community Adi Soozin highlighted the trend of renters, especially young professionals, seeking buildings with high-quality amenities like gyms and health tech (00:14:51). Stephen Benjamin emphasized Dermot’s “Ignite” program, which focuses on programming amenities to build a social component and community for residents (00:19:30). This program includes events and activities tailored to the residents’ profiles, enhancing tenant retention (00:20:25).
• Evaluating Property and Development Opportunities Stephen Benjamin explained that Dermot evaluates opportunities based on their specific demographic, the “lifestyle renter,” and the economic performance of each city. They focus on supply and demand, utilizing various data points and in-house research tools to identify where their target customer will be most intensely focused (00:23:54). Their approach is very micro, focusing on specific neighborhoods rather than large-scale acquisitions (00:24:55).
• Integrating Long-Term Vision with Short-Term Execution Dermot has built a dynamic in-house system using Python to pull live data on desirability, affordability, and supply in their target neighborhoods (00:26:40). They look for areas with high home prices relative to rents and analyze the income levels of their target renter demographic (00:27:30). A critical factor is avoiding areas with excessive new supply in the multifamily market (00:28:22).
• Current Market Conditions and Future Outlook Stephen Benjamin noted the unprecedented amount of new multifamily units being delivered across the US due to low interest rates following COVID. However, they believe the supply will decrease significantly by 2026 in most of their target markets. Dermot’s current strategy focuses on a five-year hold for multifamily purchases, aiming for stable returns for investors (00:29:27).
• Emerging Data Signals and Market Insights Dermot focuses their data analysis on the $100,000+ income level customer, looking at local job information and the sectors important to this demographic (00:31:18). They pay close attention to the timing of job creation and the supply pipeline in specific locations (00:32:22). Stephen Benjamin also mentioned following government spending and local job scene developments as key indicators (00:33:08).

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Transcript

This transcription was generated by Gemini & edited by ChatGPT

Adi Soozin: Hello everyone and welcome to another episode of 9×90. Today we have a very special guest with us — Mr. Stephen Benjamin. I met him through my good friend Sarah Pustilnik and her partner Alex Fair. Stephen is Managing Partner and CEO of the Dermot Company. In a moment, we’ll dive into how he has led over $8 billion in multifamily investment and development across the U.S. throughout his career, which is huge right now.

When I met him, he was modest, saying, “I don’t know if I know that much about the sector.” And I was like, “You’re the only one not hemorrhaging right now in the multifamily asset class.” So, whether or not you realize it, you are like the god of this sector. People need to hear from you because many are terrified — in the multifamily space, people are going belly up, going bankrupt. It’s a bloodbath. And here’s Stephen, sitting on the sidelines saying, “Yeah, our cash flow is a little tighter than usual,” but he’s not in the arena where novices are losing their shirts.

So, ladies and gentlemen, it is my pleasure to introduce the man who took Dermot from $1 billion in 2015 to $4 billion today — Mr. Stephen Benjamin.

Stephen Benjamin: Hey Adi, thanks a lot. It’s great to be here. Thanks for that introduction — however much of it might be true or untrue.

Adi Soozin: It’s all true. I fact-checked it beforehand.

Stephen Benjamin: Mostly true, yeah, mostly true.

Adi Soozin: Alright, let’s back up a bit. Everyone knows if you come on this show, you’re a titan — a gladiator who knows their stuff. What did you do before leading Dermot and taking it from $1 billion to $4 billion? That’s a huge jump, something many young people dream of. What was your path before that?

Stephen Benjamin: I’ll say a few things. I joined Dermot almost 20 years ago as a junior partner to the guy who started the company. I started my multifamily career in 1991, so I’ve been in this business about 30 years. Bill — the founder — was a unique guy, a real entrepreneur, and without his efforts, we wouldn’t have reached the $1 billion stage. He started the company about 10 years before I joined, initially working out of his basement. Before that, he was a lawyer and worked at First Boston for a long time. At 48, he decided to start a real estate company.

Dermot is actually his father’s name — he named the company after him. His father was an Irish immigrant who moved from Ireland to the U.S. and raised Bill and his brothers in the Bronx. It’s a great entrepreneurial story. They came from nothing, and I admire that. We wouldn’t have achieved what we did without Bill. I spent 15 years as his junior partner, not really knowing what would happen next. Unlike some companies, ours didn’t become a family business. In 2014, Bill said, “Stephen, I want to retire. I’m going to start selling assets, or you can buy the company.”

It was a very unusual opportunity in hindsight — these things don’t happen often in real estate. Bill’s daughters were doing their own thing, so it worked out for everyone. Together with two other longtime colleagues, we bought the company from Bill in 2015, much like I originally joined Bill as a junior partner. Over those 15 years, I learned a lot from Bill — having great mentors is critical. Bill showed me how to run the business through trial and error and lots of hard work.

Before that, I was really interested in real estate — I loved construction during summers in high school and college, took architecture classes, and enjoyed traveling to see buildings. I was naturally drawn to real estate as a career. I started in New York working at a brokerage — Cushman & Wakefield.

Adi Soozin: You worked at Cushman & Wakefield?

Stephen Benjamin: Yes, I spent four years there right after school. It was great — I rotated through various roles like appraisal, brokerage, and investment, learning a ton. Then I joined Archstone, which was a major multifamily company at the time. I moved west with that company, spent time in the Southeast, and eventually came back to New York in 2001. So, the ’90s were spent learning the real estate business broadly, and from 1994 to about 1999, I focused entirely on multifamily apartments before joining Bill.

Adi Soozin: At Cushman & Wakefield, what asset classes did you see that you thought, “I would never touch that in a million years”?

Stephen Benjamin: Good question. The good news is I saw everything, and I liked everything. But I was drawn to living space — housing. We did offices too, but office buildings in the early ’90s were in total collapse. When I joined Cushman & Wakefield, you couldn’t fill or finance office buildings. Prices were rock bottom — it’s similar to where we are now.

Adi Soozin: I know! People questioned why I was buying office buildings, but obviously, my mentors saw that industry coming back with a boom. They need office space, and I was buying before others caught on.

Stephen Benjamin: I’m with you all the way. You’re doing the right thing. We’re not in office space, but I believe people will make a lot of money there over the next decade. It’s challenging but full of opportunity.

Adi Soozin: It’s a unique time. Novices are fumbling around, and the old-timers like us sit on the sidelines, watching, waiting to swoop in when mistakes are made. It’s like toddlers running on a soccer field and us seasoned players get to play the game without tripping over them.

Stephen Benjamin: Exactly. Like Warren Buffett said, “When the tide goes out, you see who’s been swimming naked.” I think about that weekly — am I ready, or am I running naked?

Adi Soozin: Obviously, you’re ready. I was shocked at a recent multifamily panel — everyone was bracing for recession, exiting where they can, expecting a bloodbath. Then Sarah told me, “You have to meet Stephen.” I thought, “But he’s in multifamily, and that sector’s getting hammered.” But within ten minutes, you told me, “Our cash flow is down to about 4%,” which isn’t ideal, but you still have cash flow. Most people are losing everything with personal guarantees being called in. And here you are saying, “We’re squeezed a little,” but you’re ahead of everyone else.

People need to hear what you’re doing because you’re playing chess while others are just running around. You’re the calm principal on the playground, seeing the whole board and calling the right moves.

Stephen Benjamin: Thanks, Adi. That means a lot. We don’t consider ourselves titans — there are many I admire in this business — but we do play the long game. It requires care and deep knowledge. Sometimes people call themselves experts but don’t know the details.

Over the last 25 years at Dermot, we’ve done every kind of multifamily deal — we specialize in apartments and don’t do anything else. Occasionally, we’ve had some for-sale product as part of larger projects, but primarily, we’re a multifamily rental company with vertical integration — management, construction, leadership, and investment teams all in-house. It’s an organic process. Capital likes us because of our focus.

We don’t choose many markets — right now, we’re focused on about nine cities on the East Coast, with New York being our biggest market, where we have very deep expertise.

Regarding deals, development has been difficult for the last decade. Some people have made good money during COVID in the Sunbelt, but we missed some of that. Instead, we’ve focused on buying undervalued buildings compared to replacement cost — properties with great bones that we can uplift and improve, especially relative to newer, lower-rent buildings. Value-add has been our specialty for about a decade.

Over 25 years, though, we’ve done affordable housing, development projects, small walk-up buildings, brand new construction, core acquisitions — everything from California to New York and in between. Today, our specialty is upscale rental living.

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Stephen Benjamin: We call it the lifestyle renter. And maybe we can talk a little bit about that, but
Adi Soozin: No, I I think I Okay, you’re preaching to the choir with that because I know a lot of people come in and they want affordable housing. They want low-income housing. And I’m like, do you understand the wear and tear you have there? Do you understand like the headaches you’re going to have there? the tenants don’t behave the same way. They don’t have the sta same cultural standards of conduct. Um my family I don’t know if you got to look at the uh the list of yeah most of the things we’ve done since the 80s
Stephen Benjamin: Yeah.
Adi Soozin: have been luxury
Stephen Benjamin: Yeah.
Adi Soozin: and
Stephen Benjamin: Yeah.
Adi Soozin: we’re like oh luxury is the hardest. No actually luxury is the easiest because in a a recession that that unique group they have everything in place they already have so many sources of income.
Stephen Benjamin: Yeah.
Adi Soozin: They’re they’re just hanging out at one of their vacation houses during COVID and a lot of them were making money because of the stock market during COVID.

Adi Soozin: It’s the it’s the affordable housing and the low income, the middle income that’s the most volatile.
Stephen Benjamin: Yep. Yep. and and you know it’s it’s not it’s not the best part of the you know sort of the American system but those folks in the middle that are at the the lower and middle incomes really get beat up in the very in the changing times and the and the collection issues and the challenges they have and having to move a lot and
Adi Soozin: Yeah.
Stephen Benjamin: you know we say the just getting by part of rental is tough and it’s a very tough it’s a very tough space and um you know it can be a space that’s uh that can make money for folks but we’ve we’ve leaned into this other customer, the one you just talked about and our
Adi Soozin: Yeah.
Stephen Benjamin: we spent a lot of time on the data and the bottom line is with what’s changed, we can talk about some of the points, but w with what’s changed in American sentiment for young people. This is the sort of upscale young person who would be buying homes, right?

Stephen Benjamin: who would have the American dream of buying a home. What’s really changed is home ownership affordability is is dynamically different not just from high interest rates but even before that with everything that happened after the GFC and the cost to build to build new homes just has made it very difficult for people to buy homes. But the truth is today young people a lot of young people don’t even want to own a home. They prefer their money in the stock market.
Adi Soozin: This is so
Stephen Benjamin: They
Adi Soozin: much
Stephen Benjamin: prefer
Adi Soozin: work.
Stephen Benjamin: travel. So lifestyle for us is like we’re choosing to live in a rental building that’s upscale. We could live in a lot of other things. we can live cheaper, we can live further out, we could buy a home potentially. Um, but we’re choosing to live in an upscale rental and that’s what we sort of target. And what’s happened with that demographic, especially in this last five years, is it’s gone up exponentially. The biggest sector is people over $100,000 in rental in rental product. That’s
Adi Soozin: Yeah. No, I I think it’ll continue to go up. I I can’t tell you how many of my friends, like my husband uh built a gym into our house. We built an ice bath, but my friends who aren’t into building things and these weekend projects and renovating all the time, like it’s when when we’re having to travel a lot for work, the house quickly just declines. the garden declines and most people aren’t in this position where they can take time off to to be spending so much time fixing the amenities that they like to have. And so you see a lot of people especially like executives or uh people who are climbing the ranks within consulting firms and um different like services pro professions, business school alumni. They’re flocking to the types of buildings that you’re creating because it allows them to be that Ernston Young consultant who’s working 50 to 70 hours a week, comes home and they have their gym, they have their sauna, their steam room, their and you guys keep up to date on the latest health tech and you’re bringing it in as services.

Adi Soozin: Like there’s this one building um I have another a friend who lives in a building like the ones that you invest in and they put the the red light saunas in.
Stephen Benjamin: Yeah. Yeah. Yeah. Infrared. Yeah. Infrared.
Adi Soozin: Yeah.
Stephen Benjamin: Yeah.
Adi Soozin: Yeah. So
Stephen Benjamin: Yeah.
Adi Soozin: So now everyone’s coming to her building and you have
Stephen Benjamin: So funny because we we we bought a building not far from you in Boon Beach and we bought it maybe in 2022, I think. And at the pool area, the first thing we did is bought one of those kind of very cool redwood iglooy uh infrared saunas. It’s an outdoor sauna, but it’s kind of that big, you know, you’d see it in the woods or the forest somewhere or whatever, and we put it in the amenity right
Adi Soozin: Exactly.
Stephen Benjamin: on the whole deck, and it’s like people are loving the thing, you
Adi Soozin: Yeah.
Stephen Benjamin: know,
Adi Soozin: So, so, so you have like the the 20s to well actually now some people don’t even get married or they’re divorced.

Adi Soozin: What you you have all these you have this entire unique group that they’re health conscious. They like having these health centric amenities, but they don’t have to worry about the upkeep because they’re in your building.
Stephen Benjamin: exactly.
Adi Soozin: And it’s it’s a no-brainer.
Stephen Benjamin: Yeah. And and so what we found like we get asked a lot by our our partners and investors and they do a lot of their own work too and a lot of them are very sophisticated investors like you guys are and you know we get asked a lot about the demographics and the bottom you know how can these rents be so high and the demographics work. How can these people afford these rents? You know and that could be you know the super the super high-end now rents in Palm Beach or down in Miami or it could be in Manhattan where we get asked it a lot. And the bottom line is we our data shows and I think this is almost universal when you get to those higher income rents and those types of buildings that that resident likes you actually get lower rent to income ratios.

Stephen Benjamin: You get more income the ability to pay more rent. They’re actually using less of their annual income on rent than you then as you move into the more middle segment. So, we’re
Adi Soozin: Yeah.
Stephen Benjamin: finding an affluence there and a lot of that is that statistic that I was sort of touching on which I think the average first-time home buyer age moved from 31 to 38 over the last call it two decades, you know,
Adi Soozin: Heat.
Stephen Benjamin: and so we’ve seen a it’s that demographic from 31 to 38 there’s a really interesting dynamic renter, you know, that is upscale. They can do what they want. They’re going all over the world. They’re doing lots of things. They’re very focused on their jobs, families, having kids, getting
Adi Soozin: Yeah.
Stephen Benjamin: married, whatever it is. That’s that customer that we didn’t used to have in multif family, you know. We really didn’t, you know,
Adi Soozin: Yeah. I didn’t even think about that. Well, you also have because you have this uh increase in popularity with women taking more lead business leadership roles and more executive positions.

Adi Soozin: So, but they still want to have that high quality. And I I don’t know if you knew this, but at some consulting firms, if you don’t stay in a specific physical shape, they they don’t allow you to meet with clients. So, I worked at one of the big four um for a very brief time and one of the guys started to put weight on because he was going to all the client dinners at night and drinking and everything. And he came in the one morning and he just he stares at a cup of coffee and it was like, “Jeff, where’s your breakfast?” And he was like, “I have to go on intermittent fasting for the
Stephen Benjamin: Right.
Adi Soozin: next few weeks
Stephen Benjamin: The air
Adi Soozin: because
Stephen Benjamin: diet. Yeah, the air diet. I need the air
Adi Soozin: Yeah.
Stephen Benjamin: diet, too, you know.
Adi Soozin: And and then later one of the other guys explain we went out to dinner, one of the other guys explained to me, we were sitting down and I guess he realized like I was shocked by that because I was new to the company and um he’s like well I’m an engineer and I don’t have to see clients so I can eat whatever I want.

Adi Soozin: So you have this perfect storm that essentially makes it so if they want to be considered for client facing and going higher and higher in these specific companies, they’re having to live either buying those amenities and maintaining them themselves or they’re having to go into a building like yours that has those amenities that can allow them to
Stephen Benjamin: Yeah.
Adi Soozin: not only be working 70 hours a week but look like they spend three hours a day in the gym.
Stephen Benjamin: Yeah. And we have we started this program like about a decade ago. We call it Ignite. People can see it on our website which is the dermac company.com. But um Ignite was our concept of programming the amenities, right? It’s it’s we all of us in multif family you know we we all would build amenities and look at the you know was an arm it was arms race for amenities right to have the most stuff but
Adi Soozin: Yeah.
Stephen Benjamin: programming the amenity is really where the social component is for the residents you know and so our Ignite

Adi Soozin: Yeah.
Stephen Benjamin: program is effectively an in-house group of private catering services right and our team is putting together events that we move through the portfolios uh to offer the same kind of experiences depending on the profile of the building to our residents, you know. So, it might be something more catering to kids if it’s a kid building. If it’s more of like a young professionals building, it might be more mixology class or cooking classes and cool stuff. And like all the gym programming has been around for a while, but the real the real thing that the residents seem to like is joining our club, which we call Ignite, and they pay some extra for that. And then they get the full, you know, the full package of benefits. And it’s been really, really enhancing these buildings a lot. I think we’ve leaned into that as much as anyone in the industry. Certainly at the top of of the industry.
Adi Soozin: Well, and that’s huge because that in increases your tenant uh your
Stephen Benjamin: You

Adi Soozin: tenant
Stephen Benjamin: got it.
Adi Soozin: retention.
Stephen Benjamin: You got it. It’s And it’s all about length of stay. It’s all
Adi Soozin: Yeah. Yeah. And and when you when you put these amenities into the buildings, you ensure that the tenants are connecting with each other over positive things.
Stephen Benjamin: That’s right. Yeah. And because at the end of the day, they want to enjoy their community. they want to be active. You know, we’ve started to hone our social media into, you know, social media and real estate’s got got really fractured out and, you know, we we were managing, you know, 25 sites for 25 buildings and it’s kind of ridiculous. You know, you’d have a couple hundred followers or whatever. And so, we’ve tried to push that all together into sort of what we’re calling this Dur experience, this Ignite experience. And we’re it’s supposed to be fun. So, stuff like this is it’s supposed to be fun for people. And the way you’ve built this program to connect investors and connect people, but it’s also social what you’re doing, you It’s

Adi Soozin: Yeah.
Stephen Benjamin: connecting people, you know.
Adi Soozin: Yeah. Well, yeah. The the nice thing about 9×90 is when I meet someone and I’m like, “Oh, you have to I met this amazing person. you have to hear their story. And then I was, it would be like me trying to knowledge transfer what I learned about someone over an hour. And now I’m able to take episodes like this and send it to people who are like, “Oh, I’m terrified of multif family right now. How did your family do it in the luxury space and this and that and the other thing?” I can just say, “This company is literally doing this right now.” And send them your
Stephen Benjamin: and and it’s all there for us, you know, and that’s that’s what’s cool about it, you know.
Adi Soozin: Yeah. And then the the nice thing about the reason we structure it to be an hour and not just talking about what you’re doing right now, but what you’ve done throughout your past is it allows people to understand that you’re not some impulsive 12-year-old who’s picking a few buildings because you think it looks cool to say you invest in real estate.

Adi Soozin: This is something that you’re passionate about. This is something that you’ve spent time optimizing, figure out figuring out what’s best, what’s the best way to increase not only value for investors but for yourself as well. And you’re also picking things that allow you to sleep at night. I have uh some friends who invest in real estate who I’d never have on the show because they’re literally doing the most unethical like they’re they’re doing like a foreclosure structure. They’re kicking people out of their houses. And I’m like and they like can’t be on social media. They have to be completely blind. They have to hide. And I’m like, you
Stephen Benjamin: Yeah,
Adi Soozin: know, you can invest in real estate where you get to be on social media and people like you, right? Like you
Stephen Benjamin: absolutely.
Adi Soozin: don’t have to do things that make people hate you.
Stephen Benjamin: Yeah, I know exactly what you’re talking about. So yeah, you know, and and for us it’s been, you know, a lot of our partners are institutional big pension funds and insurance companies and as well as high net worths that have have joined us and we’re we’re we’re raising money right now as you know and um you know for us it’s it’s very micro work you know so our work is very micro work.

Stephen Benjamin: It’s very with with investing with us is getting just a very specific group of buildings with a very specific focus with a very you know we’re assuming our investors are choosing all the different things they want to invest in and for us we we’re hopefully giving them something when they want some differentiation within multif family you know and that that’s really the way we built our strategy
Adi Soozin: Yeah. So, so we touched on a few of these questions already. How do you evaluate whether a property or development opportunity is a good fit? You’re looking for things where your specific demographic is located across the East Coast.
Stephen Benjamin: That’s right. And our our thesis with that lifestyle renderer is the is the backbone
Adi Soozin: Yeah.
Stephen Benjamin: economic work is to look and look very carefully at how each city is performing. And we look with some very specific things about supply and demand. That’s what the whole thing is.
Adi Soozin: Yeah.
Stephen Benjamin: And so we draw from a variety of data points and with research that we’ve built in uh in house we have an interesting tool we can talk about a little bit but uh we’re trying to find where we think that customer is going to be um

Adi Soozin: next.
Stephen Benjamin: most intensely focused you know
Adi Soozin: Yeah.
Stephen Benjamin: and that that gives us the ability to say you know maybe Palm Beach Gardens is a little bit better for us than Buon and maybe Puitton’s a little better for us than Deerfield Beach and and why and we’d have reasons for that you know so very it’s like micro neighborhood work for us because we’re not buying this is not the Blackstone structure, the Starwood structure. This is not they’re amazing, but we’re not just buying tons of buildings,
Adi Soozin: I know.
Stephen Benjamin: building a massive, which is also a great business, but for us, we’re we’re probably buying over the next decade, we’re probably buying, you know, couple of buildings a year, three buildings a year, four buildings a
Adi Soozin: Yeah.
Stephen Benjamin: year, you know, um that’s our business. So, we’re trying to choose really carefully. And so I guess the real bottom line is we focus on the cities, we get to the neighborhoods, and we’re looking for differentiators where we believe that building’s going to outperform another building because the pricing differential with this stuff’s not very different.

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Stephen Benjamin: You know, the market’s not very intense about the different like cap rates are very similar no matter what you buy in Florida, let’s say.
Adi Soozin: Yeah.
Stephen Benjamin: They’re very similar, but the assets are going to perform quite differently in multifamily. So what we’ve tried to do is like through trial and error, so through mistakes and through successes, we think we found what can get an outperform. So we think we can get an outperform whether it’s in Manhattan, Brooklyn, Boone, Orlando, the markets we’re in, the Carolinas — we like Raleigh and Charlotte — and we can talk about that, you know, if you’d like to. But so it’s within the market. Can we get an outperform compared to what other people are buying?
Adi Soozin: Yes. So that actually stems into this. We’re—
Stephen Benjamin: Sure.
Adi Soozin: going to skip around on the list of questions a little bit. We have this one here that says, “How does your team integrate long-term vision with short-term operational execution in a market that’s always shifting?”
Stephen Benjamin: Yeah, that’s it. I mean, so for the longest time, I’ll just say it like this. For the longest time, we would get data. Most of us get data from the big national sources and there’s CoStar and there’s AIMetrics and there’s all kinds of research reports and we get all that, but it’s very static. Almost as soon as it prints, the researchers are beginning the next piece.
Adi Soozin: Yeah.
Stephen Benjamin: Do you know what I mean? And we sit on that. So we’ve tried to build a dynamic system. So a woman who joined our company on the investment team, a brilliant woman, started to help us to build an in-house system that’s Python-based. It’s a simple—I think it’s a fairly simple software tool, but we’re pulling data in live.
Adi Soozin: That’s huge.
Stephen Benjamin: So we’re basically scraping, and we’re just scraping publicly available and privately accessible data that we think is the highest quality to measure components of desirability, right? How well does the resident that we’re profiling like this neighborhood?
Adi Soozin: Mhm.
Stephen Benjamin: You know, that’s retail and schools and nightlife and those kinds of things.
Adi Soozin: Yeah.
Stephen Benjamin: Then we’re looking really carefully at affordability. And in our case, we’re looking to see it be very expensive to live there. We’re looking for home prices to be high and relative to rents—
Adi Soozin: Mhm.
Stephen Benjamin: where rents feel good even though rents are high, where you can’t go buy the house next door because it’s very, very expensive.
Adi Soozin: Yeah.
Stephen Benjamin: That’s like in your Florida markets — that’s Wellington, right? That’s Palm Beach Gardens, as I mentioned, where we’ve been working on something — you know, where the home prices are really high. And then we look at this upper renter, which we call the third quartile, and we look to see what their income level really is in that neighborhood, and we’re just pulling zip codes off the census tract stuff and looking at income levels.
Adi Soozin: Okay.
Stephen Benjamin: So it’s the combination of income level, demographic, desirability, and then that last feature which is critical is how much additional supply is there. You know, who else is building there and what are we dealing with? And one of the biggest challenges right now, as you probably know, is we have too much supply of multifamily that was really put in place during the post-COVID boom and now it’s all delivering, and a lot of it’s over at risk, a lot of it’s at costs that are too high and rents aren’t high enough, and everyone’s battling with each other, so it’s kept rents pretty flat. So we’re looking really carefully to avoid pockets where the supply is not in a good spot for a while.
Adi Soozin: But I would say that supply and demand issue, that’s city specific. You’re not seeing that across—
Stephen Benjamin: Absolutely.
Adi Soozin: the whole nation.
Stephen Benjamin: And it’s literally neighborhood specific. Again, we go to the micro because there’s—
Adi Soozin: Yeah.
Stephen Benjamin: a lot of stuff, you know, there’s a lot of stuff in West Palm, but there’s not as much of it when you go to some other pockets, you know, and you can find, you know, so it’s pocket by pocket. And then of course looking at the metro also to see what’s really happening. But the bottom line is we’ve been delivering an unprecedented—across the US, we’ve been delivering an unprecedented amount of new units, and it was caused by the really low interest rates and the excitement in the Sunbelt following COVID to build, you know, and a lot of stuff got going. So we’re working through that, and now you can’t build anything or it’s very difficult to build anything.
Adi Soozin: Are gonna be tomorrow, so—
Stephen Benjamin: Yeah.
Adi Soozin: I would not build right now.
Stephen Benjamin: Yeah. And the way we’re looking at it, to answer your real question, we’re saying in multifamily, we like the five-year hold for multi purchases now.
Adi Soozin: Yeah.
Stephen Benjamin: Because we think that the supply really comes to an end in 2026 — in most markets —
Adi Soozin: Mhm.
Stephen Benjamin: Definitely the ones we track, or it’s already over in some markets like in New York there’s very little supply because New York came out of COVID. Yeah, exactly. So we know the rents will start to move more when there’s not a lot of new competitive supply. That’s just always the way it is. So we really like the sort of five-year horizon, and that’s what we focus on. We focus on a five-year underwrite. You know, we’re not doing office building underwrites to get to 20% returns. Can’t do that in multifamily right now. The returns are lower. It’s definitely more conservative, playing the longer game, so to speak. But for people that are looking for an interesting, stable piece of a portfolio where the net to the investors is 11 to 12% per year over a 5-7 year period, I think it’s a very good business right now. I’m putting my own money into it, and you know, I think it’s a very good business.
Adi Soozin: Full disclosure, I’m an investor in all of these. And I was like, full disclosure, if you were not, I would not look at any of them.
Stephen Benjamin: Exactly.
Adi Soozin: If you’re telling me it’s a good company that you’re not investing in, I’m not touching it.
Stephen Benjamin: Sure.
Adi Soozin: So, let’s see. Here we go. What are some of the emerging data signals that you pay attention to that others might overlook?
Stephen Benjamin: Sure. So we’ve talked about a lot of that. So we’ve tried to skew all our data to this customer. So we’re asking ourselves not so much what’s happening in more affordable rental or what’s happening with wages there, but we’re really looking at what’s happening with that customer that’s at that $100,000-plus income level that we think suits our thesis. And we’ve got to see local job information. So we’ve got to see how job growth is and we’ve got to see the sectors that are important to those kinds of—
Adi Soozin: You just put a building next to every BCG and Ernst & Young office like—
Stephen Benjamin: Yeah, exactly. You know, and so we’re looking a lot at the tech stuff, right? It’s really important where tech has been going and some of the big—the Apple expansion in Raleigh that everyone—
Adi Soozin: Oh.
Stephen Benjamin: talks about. I mean, but if we were, like, we had some stuff in Raleigh and we were all talking about Apple and the brokers would have Apple in the book and, you know, the thing just opened, you know what I mean? You’ve got to actually be when it’s actually going to have those jobs. You can be early, you know, or you can be late. And just talking about it, the construction jobs isn’t when it actually opens up and has those jobs that we’re all focused on. So a lot of it is this timing. And then I think the most important part of the timing is this supply thing. What we have found is if we’re early in the supply and we’re wrong about that, if we’re too aggressive and we’re saying it’s going to be okay, we get flat rent and that just destroys the proforma. You know, so our goal is to be where that rent growth around 3%, 3.5% is viable and that’s what we look—those are the signals we look at a lot. So we’re looking where the governments locally are spending money.
Adi Soozin: I—
Stephen Benjamin: Looking—
Adi Soozin: do—
Stephen Benjamin: Yeah.
Adi Soozin: the same thing. Yeah. I’ll ask my cousins in the middle of a, like, “Tell me where you see a lot of new roads being paved.”
Stephen Benjamin: Yeah.
Adi Soozin: Now.
Stephen Benjamin: Exactly. You know, and that tells you stuff and, you know—
Adi Soozin: Yeah.
Stephen Benjamin: And then we look at just what the local job scene is, who’s building new factories, who’s doing new stuff. I mean, you know, it’d be early to bet on new American manufacturing, for instance. It’s going to probably take a little time, but it’s probably going to change with everything that’s going on in the right markets, you know, but it’s probably not something you should do right away because it’s going to take a few years for things to come together, you know.
Adi Soozin: And even with that, you’re going to have so many robots that are taking over jobs that used to be manual labor—
Stephen Benjamin: Yeah.
Adi Soozin: within American manufacturing. Like, yeah, there are a few robotics companies that I keep tabs on and people who are saying, “Oh yeah, we’re bringing manufacturing back to the US,” and like, you understand you’re not going to be paid to sit in a factory and paint a letter on a thing; there will be robots doing that.
Stephen Benjamin: That job’s gone. Yeah.
Adi Soozin: Yeah. Yeah. That job’s gone. Elon Musk’s Tesla bots are now going to be carrying the packages from one conveyor belt to the other. Like, yeah.
Stephen Benjamin: Right.
Adi Soozin: So that’ll be—I think that’ll be a very interesting one. And that’s one where I’m a little bit more conservative about when they say, “Oh, we’re going to be putting a manufacturing plant in here.” I’m skeptical that they will need a lot of affordable housing around that manufacturing plant. I don’t think we’re going to need as much human capital in the manufacturing plants as we used to.
Stephen Benjamin: Yeah. Yeah. And I think, you know, I agree with that fully, but I do think also we can sometimes get afraid of—my attitude has been I’ve seen more and more that we get afraid about a sector. Let’s take retail, right? And I did the “malls are dead” people, you know, the Amazon factor, and there’s been a lot of changes. But the reality is after COVID, malls have really come back, you know, like real estate and location, all the things that are those fundamentals over all these decades and stuff that we’ve learned about and they’re all real, you know. And so to give up, to paint a different—we’re adapting so quickly as a species and everything and as an American people, it’s phenomenal. And so I’m very optimistic about like I see real estate absolutely being a great business to be in in all kinds of sectors with a lot of focus on whatever it is you’re focused on.
Adi Soozin: Even—
Stephen Benjamin: I mean?
Adi Soozin: with malls, have you seen they’re doing this really cool thing now in a few cities that’s like, I think it’s super exciting like from a very real estate nerdy perspective: they’re converting malls into mixed use. So they’re putting apartment buildings—
Stephen Benjamin: Absolutely.
Adi Soozin: above the mall.
Stephen Benjamin: Yeah.
Adi Soozin: Like, oh my god, the—
Stephen Benjamin: Yeah.
Adi Soozin: everyone in there that like signed a lease and has a store in that mall is like must be ecstatic with what—
Stephen Benjamin: Yeah.
Adi Soozin: the numbers are going to be.
Stephen Benjamin: Yeah. It’s—and then the whole idea where they’re flipping—I call it inside out, but, you know, the mall guys have a different way, but like pushing to have all a lot of access on the outside of these sorts of because what’s always been dull about malls is there’s nothing going on on the outside.
Adi Soozin: Yeah.
Stephen Benjamin: And when they flipped it so that you’re getting some activated outside spaces and then maybe you have an inside where there’s the department stores and some of the inline stores and all, but like you’re adding housing, you’re adding mixed use, maybe an office building is one component of it, a hotel goes up — this is the real stuff, you know. And I think that’s what gets me excited.
Adi Soozin: I have a relative who has jewelry stores and she won’t bother to rent space in a mall if they don’t have an office nearby and has to be class A or class B office because she’s like, you know who my customers are? Lawyers—
Stephen Benjamin: Right.
Adi Soozin: who forgot their wife’s birthday.
Stephen Benjamin: Valentine’s Day on the—
Adi Soozin: Yeah. Yeah. So she’s like, “So I want my jewelry store in the shopping center that is closest to their office.”
Stephen Benjamin: Yeah.
Adi Soozin: And so she’s not the only one. Like what I think we’re seeing with malls nowadays is when they’re near an office magnet, they get the high foot traffic during from those offices. But it has to be—you have to have experiences for people. And I hate when people make—I equate, let’s equate real estate to food for a second. There are all these people who think real estate is ramen noodles. And then when they talk to people like you and me, they realize real estate is a Michelin star—like a three Michelin star restaurant.
Stephen Benjamin: Yeah.
Adi Soozin: And anything less than that isn’t worth touching. So you see the malls that are going out of business, they’re ramen noodle malls. They’re not the Michelin star malls. They’re not the you walk in and it’s an experience and it’s fun to walk around there. We have the Aventura Mall here—
Stephen Benjamin: Yeah, of course.
Adi Soozin: Have you been inside?
Stephen Benjamin: Of course.
Adi Soozin: They have the art displays throughout the mall.
Stephen Benjamin: Yeah. I mean, it’s incredible.
Adi Soozin: Yeah. And then they have a mix of like high-end and mid-tier options in their food court. It’s not like a $2 food court. There isn’t a Subway. There’s a midlevel high-level Israeli restaurant in their food court.
Stephen Benjamin: Yeah, they’re retooling, you know. And that’s the same kind of thing as what we were talking about earlier with, I think, the sort of lifestyle renter. Like, you know, we smart real estate people are adapting to the situations that they’re seeing and they’re—but they’re staying focused on location and focused on the details and they’re adapting, adapting, adapting.

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Stephen Benjamin: We do the value-add on these buildings. We try to buy a building where we think we can change the cosmetic feel without changing the building dramatically. Maybe it’s a little bit older, a little more dated. The prior owner may have had a good run—maybe a great hold—but they’re ready to sell and don’t want to do the value-add.
Adi Soozin: Or—
Stephen Benjamin: We’ll—
Adi Soozin: Even—
Stephen Benjamin: Buy—
Adi Soozin: That—
Stephen Benjamin: It.
Adi Soozin: It’s because they did a syndicate, not a fund model.
Stephen Benjamin: Yeah. And they did great with it.
Adi Soozin: Right. With a syndicate, they’re not going to do everything to maximize it completely because they get their fees when they sell it. So they buy it, do a few things to increase value, and then sell.
Adi Soozin: Whereas with a fund, the thing about a fund is—they’re going to maximize the value of that building 1,000%, every single inch of it.
Stephen Benjamin: Yeah. We’re IRR driven. Our performance is based on the internal rate of return of the whole group of assets. That’s the bottom line. Of course, there are a lot of variables, but we’ve got to raise the NOI. So what do we do? We raise rents, keep expenses as tight as possible—
Adi Soozin: Yeah.
Stephen Benjamin: We work—
Adi Soozin: Raise—
Stephen Benjamin: Every aspect of that. Raise rents and—
Adi Soozin: Perceived value.
Stephen Benjamin: Exactly. So we push a lot. As a multifamily company, we tend to push for revenue growth.
Stephen Benjamin: That means a little less cash flow in the early years because we’re reinvesting it. There is some cash flow, but we’re reinvesting. We’re also calling capital as part of our plan to renovate. We tend to spend 10–15% of our budgets on renovations, which is a fair amount. So we’re going in and doing substantial work to the apartments.
Adi Soozin: But you’re increasing the rent or retention, you’re boosting IRR—you’re doing all these things. So it ends up being more profitable in the end.
Stephen Benjamin: That’s right. That’s the whole thing. With a targeted five-year hold and an exit plan… You can own real estate for generations—it’s a fabulous business, one of the great businesses in the world.
Adi Soozin: Yeah.
Stephen Benjamin: And probably always will be. You can also take the fund approach—a shorter hold with a clear directive. You’re buying and selling at a more rapid pace. That’s the business we’re in on the fund side.
Stephen Benjamin: We do have investments we’ve retained for a long time too.
Adi Soozin: I think it’s good to keep both.
Stephen Benjamin: Yeah, for sure.
Adi Soozin: And doing the fund side keeps your children on their toes.
Stephen Benjamin: Yeah, that’s it.
Adi Soozin: The next generation. An investor asked me the other day, “Why are you so into the real estate market? Why are you grounded compared to the kids you grew up with—all third or fourth generation investors?” And I said, “Because I have to be in the market.” My parents aren’t like, “Sit back, have a martini.” They’re like, “No, no, no. Come run the show.”
Stephen Benjamin: Yeah, for sure. I like that about you.
Adi Soozin: Thank you. So let’s see—we’ve answered a lot of the final questions here.
Adi Soozin: How do you stay ahead of macro trends? We brushed on that already. Just two left and we’ve got six minutes—great timing.
Adi Soozin: Are there any underrated or up-and-coming real estate expos or forums that you think have been valuable to your team?
Stephen Benjamin: Yeah. For us—this is more specific to fundraising and meeting new partners—we’ve been very focused on the European markets.
Adi Soozin: Really?
Stephen Benjamin: Yeah. Traditionally, we’re active in PREA (Pension Real Estate Association) and NMHC (National Multifamily Housing Council). Those are the two we’ve been most active in here in the U.S. But there are several great expos and conferences in Europe. One is called MIPIM—super fun. It’s in Cannes, France every year. It’s really grown a lot. It’s like going to ICSC in Vegas—a very big conference.
There are also smaller ones. One is the USA Conference in Germany—very focused on European investors, especially German investors looking at the U.S. market. Then there’s AFIRE, another great conference that brings together U.S. and European investors. It was formed for Europeans wanting to understand more about U.S. real estate.
Stephen Benjamin: We’re spending a lot of time at institutional conferences. Institutions are the bulk of our investors. And of course, here with 9×90™, we’re hoping to grow our channel to high-net-worth individuals and accredited investors who want a similar approach to institutional partners.
Adi Soozin: Okay, now we’ve covered everything.
Stephen Benjamin: Yeah.
Adi Soozin: There are definitely people who are going to want to get in touch with you and learn more about your fund.
Stephen Benjamin: Yeah.
Adi Soozin: Because you still have a little space in this fund.
Stephen Benjamin: Absolutely. We just launched the fund in July of last year. We’re still raising several hundred million more and are actively seeking new investors.
Stephen Benjamin: The fund is focused on buying buildings and also being a GP partner with other investors. It’s something we’ve done for a long time. The return profile is attractive. The strategy is focused on Florida, the Carolinas, and New York—so it’s a very specific East Coast, 10-city strategy. I believe I uploaded the fund deck earlier.
Adi Soozin: Yes.
Stephen Benjamin: So—
Adi Soozin: We’ll put—
Stephen Benjamin: That’s—
Adi Soozin: It onto the webpage for you.
Stephen Benjamin: Great. I’d be excited for people to check out our deck and learn more based on today’s conversation. You can find us on LinkedIn and Instagram @TheDermotCompany. The website is thedermotcompany.com. All the links are there. We post a lot of updates on our social channels too.
Adi Soozin: What’s the best way for investors to get in touch? They’re probably not just looking to scroll social.
Stephen Benjamin: My name and contact info are in the deck. I’d love to get emails from anyone interested. Should I give it now?
Adi Soozin: Usually we post your assistant’s email.
Stephen Benjamin: It’s all in there—all of our materials.
Adi Soozin: Okay.
Stephen Benjamin: Anyone can reach out through the website. We’re very transparent. My email is sbenjamin@dermotcomp.com.
Adi Soozin: If you guys harass him though, he will block you. Just in case someone wants to scrape every email off the site.
Stephen Benjamin: Exactly.
Adi Soozin: Thank you so much for your time. I appreciate it.
Stephen Benjamin: It’s been great to be with you.
Adi Soozin: I’ll see you in New York or at one of these events.
Stephen Benjamin: Yes—soon. Thanks again.
Adi Soozin: Take care.
Stephen Benjamin: Bye. Have a great day.

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