In this episode of Broker’s Angle, Hal Coopersmith sits down with Jacob Wolkenfeld, Managing Director at Norman Bobrow & Co., to discuss his journey and approach to commercial real estate. Starting as an intern at 21, Jacob built his business from scratch through cold outreach, persistence, and what he calls “mental fortitude.” He shares how focusing solely on tenant representation allows him to align completely with clients’ interests and how consistent activity, strong follow-up systems, and long hours have fueled his success. Jacob discusses the current strength of Manhattan’s office market and the importance of conviction and resilience for new brokers.

Transcript

Hal Coopersmith: Welcome to Brokers Angle. I’m Hal Coopersmith. In this episode, we are speaking to Jacob Feld, managing director at Norman Bobrow. Welcome Jacob.

Jacob Wolkenfeld: Thank you for having me. I appreciate it Hal.

Hal Coopersmith: So. People may or may not be seeing you. You’re a young face. How long have you been in the business for?

Jacob Wolkenfeld: Just over six years now. Yeah. I started when I was 21. Now I’m 27.

Hal Coopersmith: How did you get into the business?

Jacob Wolkenfeld: I mean, I was never like a school guy. I’ll start with that. And then I, at a relatively younger age, I realized I had a little bit of a knack for negotiating sales and then by the time I was in college, I just knew I was going to get my real estate license because that to me was the easiest, quickest way to begin making money, doing sales and negotiating. So when I was in college, I worked on my real estate license. I got my real estate license, and then I started interning for the firm that I’m at now, Norman Bobrow and then I just continued on.

Hal Coopersmith: You say that you had a knack for sales in negotiating. Knew you were going to get your real estate license, what gravitated you towards real estate?

Jacob Wolkenfeld: It just, you know what, that’s what I knew to be the way to make money without being like a super genius at like mathematics and stuff like that. And it’s like, you know, what if I get my real estate license, I’ll start selling homes, leasing apartments or whatever. I never even thought office space and that’s just what was in front of me. I, for a second there, just like everyone probably I want to be a sports agent, and then I realized, shit, I have to go to law school, which no offense, I don’t want to spend four years in law school and then like work in a mail room and then take 10 years to make money. And so then I realized, okay, I’ll start with brokerage and it’s continued ever since, needless to say.

Hal Coopersmith: So you had a gravitation towards real estate. How did you ultimately learn office leasing, what to do?

Jacob Wolkenfeld: I started at Norman, I interned at Norman and then I just continued on. It’s not like I loved office leasing over selling homes. It’s just, that’s where I started. And so that’s where I continued. ’cause that’s the market that I learned. And it, to me, it’s the same game. You sell homes, you lease office space, you lease apartments, all the same game it’s played a little bit differently, but if, if you’re a salesperson, the same skills will apply in all of those areas. Just like I always say this, if I could sell potatoes at the same level as I do lease commercial real estate. I don’t think I would necessarily like one more than the other. Now it’s easy for me to say, oh, I love commercial real estate because I’m in it and I become a pro at it. But otherwise, it’s like really the same game.

Hal Coopersmith: So you started as an intern, you had this knack for sales. What did you do next in terms of, okay. These are clients that I can help. This is how I learn the market and the business.

Jacob Wolkenfeld: So I was interning for a guy in my firm named Charles, and so I was kind of learning on the go with him. And I, I knew I was going full throttle. I knew it, and I knew I was going to do it during school. So I, I was in Yeshiva University, which if you’re not like a super servant Jew, you might take the first few classes every morning as a little bit of a waste of time. It was good. I’m the one that chose to go to that school and all that stuff, and I want to be around those types of people. But from 9:00 AM to 12:00 PM I have classes that I knew I never wanted to learn anything about. So during those three hours, I would be banging out manually a list of all the tenants that I could pull from, Co-star their email addresses so that CEOs, COOs, CFOs, and create my own database. In hindsight, maybe I could have spent $30,000 in India for them to do that for me. But at the time I had no money, so I did it on my own and that’s how I built my database, which I immediately started hitting like with cold emails and outreach and all that stuff to get my foot in the door. And then from there, it’s like you build a little bit of a relationship with that person. You start showing office space and you’re learning a little bit more, and then all of a sudden you’re qualified broker to help that tenant who you may be reached out to in a cold email to help them with their office lease, which could be a multimillion dollar commitment.

Hal Coopersmith: and what’s the advantage of being a tenant rep broker?

Jacob Wolkenfeld: My sell to clients is I get to say I don’t represent that building, that building, that building or any other building, but I’m paid the exact same way and it’s by the landlord. And because I don’t represent those other buildings like those maybe at CBRE or Cushman and Wakefield, Newmark, those big firms that are tough to compete with sometimes. My alliance is 1000% with you. My value comes in doing good for you because if I do one good lease for you today, find you the right space today, you’re going to be more likely to use me in the future, and then you’re going to be more likely to affirm any of your friends.

And all of a sudden that one lease led to maybe 20 leases over the next 50 years of my life, which is the exact same model that someone who takes on a building looks for. They represent a million square feet, but they get to do 20 leases with that building. If I’m strict on tenant rep and I do a good job for tenants, they’re going to refer me business or use me again to where my business and, and you get paid a full commission as a tenant rep broker versus a half commission as a landlord rep broker. But you, you have someone who is 100% aligned with, with what you want. They don’t care if you go to that building, that one or the other. It doesn’t matter, and therefore your interests are 100% aligned, 100%.

Hal Coopersmith: So you mentioned cold emails. You are pretty good at that. How are you doing cold emails and marketing kind of overall?

Jacob Wolkenfeld: Now I’m outsourcing it. For the longest time in the beginning, I would just, like anyone else, I would imagine was just sending out cold emails through their Gmail account. Gmail or Google no longer allows you to do that because they mark you as spam and to their credit, we are spam. We’re sending out a thousand emails a day about office space around the corner from you. You didn’t ask for it. And therefore, those emails no longer end up in people’s inboxes like they once did. And so now, I’m paying people overseas to do this stuff for me. It’s effective, but it is not as effective as it once was coming from my email address. Google just recognizes it as spam and says, I’m not letting this hit. How’s email? Because I’m saying this is a cold spam email.

Hal Coopersmith: What other things are you doing to market yourself?

Jacob Wolkenfeld: So that’s really been the big, like I’m not, I’m from Los Angeles, so I moved to New York. I knew I didn’t have like, relationships that I can bank on. So I, it’s not like my best friend’s father owns a hedge fund with 15,000 square feet I can get in the door with. I knew it was going to all start cold. And once it started cold, it’s like, then you get some introductions because you did a good job for those people. I’m already at the point where I’m doing second or maybe even third leases for some people. As you mentioned before, like I post a little bit on LinkedIn, I get some leads that way. But it’s really, it’s, I have a CRM of all the people I’ve communicated with who have maybe responded to me who I showed space to four years ago, I know the requirement and so I’m on top of it because I know when their lease is coming due. I know what they kind of look for. I know what pain points they might have and that I use to like target them individually and then hopefully like get back in the door and then eventually I’m build the trust that will then get me hired to represent them for their office lease. I’d say that that’s like my main way to get business now. It’s like people who I’ve interacted with before, who I have data on, who I can then now follow up with strategically.

Hal Coopersmith: So you mentioned you do a lot of marketing. It certainly takes a certain mindset to do it, and I think for cold emails, probably some cold calls requires a certain mindset, a lot of rejection that you are working through. How do you navigate that?

Jacob Wolkenfeld: I am blessed in the sense that I naturally have the mindset that allows me to like really persist. I call it mental fortitude, is what I would refer to as because it’s not just persistence, it’s also getting the courage to persist. So you called someone a hundred times, or you called a hundred different people, you got rejected on 99 of those, but it’s the persistence to keep calling that makes sense. But it’s the mental fortitude that gives you the courage to the next day, do the same exact thing over again, and then the day after that to do it again. Then mental fortitude gets applied to when you’re actually working on deals. I’m working with a client who maybe I met 10 months ago. Tough client. They’re not hiring an exclusive broker. They never have. I know that they’ve met with plenty of others, have plenty of deals fall through likely all to their fault. I can kind of tell now, and I’ve been in situations where it’s like I’m getting a ton of heat from these guys and to their credit as they should, they don’t know me from a hole in the wall.

I met them to a cold email, but I provided enough value and they could tell that I’m trustworthy enough. To trust that like when I’m recommending looking at these spaces or moving it forward on this space, that I know what I’m talking about and I’m finding them good space and great deals. But if they don’t have that full trust in you, there will be times where they will lash out. Say, broker, you did this wrong broker, you did this wrong broker. This is why we shouldn’t work with you. And I don’t represent them exclusively, but I’m trying to make their deal and the. Then a deal dies with them and I could say one of two things. I could say, these guys, what a waste of my time up until this point, I don’t want to work with them again. Or I could say, there’s a hundred thousand dollars on the line. Should I really have an ego here or do I have the mental fortitude to overcome all the shit that I just went through with them to now find them a better space and then be the broker that at the end of the lease that they hopefully sign, is the one that they referred to for like the rest of their careers.

Because you have to discount the fact that you met them not from a warm introduction. It started with somewhere cold. And those are the battle scars of meeting people in a cold way and that to me takes mental fortitude like. And that can apply to any business, in my opinion.

Hal Coopersmith: How do you grow that mental fortitude?

Jacob Wolkenfeld: Honestly, the easiest way to do it is to consider the alternative. Okay. The alternative is, screw these guys. I’m not wasting any more time on them. But then I do the math of like, okay, I have six leases out. That would equate to maybe double what that commission would’ve earned me and how much time is it going to take me to now work towards doing an in-depth search for space that is not on the market that they cannot find on their own or that other brokers haven’t presented them with and is enough to get them to trust me again, even though they no longer do because we just had a deal die that they blame me for, and it’s just what’s the alternative is the alternative. Okay. I don’t get the chance at that commission or I do and at the future business. That’s how I like convince myself it’s worth working on something. Let’s say it’s paying a hundred thousand dollars, which is a healthy sum, but if you do the math per hour, does that really make sense over going to pursue these other 15 deals?

It does if there’s future business to be had out of those guys. So if you do a good enough job for them, you persist and you have the mental fortitude, it’s like, all right, you’re really that confident that you can do a good job for us and find us the right space. I feel confident if I’m going to refer you business in the future, because that’s really the game. These one-off deals now don’t matter all that much unless you’re getting their second lease or third least their fifth lease and then all their friends leases.

Hal Coopersmith: So, in sum, look at the kind of goal beyond and look at the long-term gain overcome the short-term pain.

Jacob Wolkenfeld: Correct. And it’s like, do the math. If this is a 1000 square foot tenant, who is, you’re going to make five or 10 grand off of their lease and they’re treating you horribly, it’s not worth the time because that doesn’t make sense because I could spend that time more wisely elsewhere. But if I do the maths, it’s a $100,000 commission. It’s like, okay. Spend the time on this because it’s worth spending the time on, at least for me in my career. Hopefully in 10 years I’ll be talking about a million dollars for that. But, yeah,

Hal Coopersmith: So, you talked about how you are when you have a cold email, the non-exclusive finding, the right space, the right sort of properties for your clients. How do you navigate the market and understand what a client wants and put them into the right building or what a client wants and is not saying or thinks that they may want, but don’t actually want. How do you navigate those sorts of requirements?

Jacob Wolkenfeld: I’d say there are two things, experience and activity of late. So experience, I’m not beating a lot of brokers. I’m 27 years old. I’m competing against people who are in their sixties, who’ve been doing it for 30 years. So they have experience with each and every landlord, each and every building. They’ve seen these spaces that they’ve now leased for a third time to different tenants perhaps. But what they don’t have, or what I take pride in, is recent activity. They’re not doing nearly as many recent deals as I am in all of those buildings and the landlords that they know. So I have the freshest data on where those deals are getting done, and so. What I tell to a client is like, I know the market cold. Based on recent activity that I’ve done and therefore I can maneuver through the buildings and spaces that will not make sense for you, given your requirement and those that will, and then your experience will tell you, okay, a law firm needs space with a lot of windows and is very efficient, so forget about the square footage. Try to fit a number of partner offices in this space for a certain monthly number that in the beginning it’s like, I got a law firm requirement and I’ll send them a space that’s a hundred by a hundred, it’s like the least efficient space for an or a thousand by a thousand. That’s the least efficient space for an attorney as can be.

But after some experience it’s like, all right, now you start to connect the dots and that part I’d argue is very easy to do and then it’s more okay, how do you find the needle in a haystack? It’s, you do research, you’re very active and you take the time to like really look for those spaces, because they’re not out there, that’s for sure.

Hal Coopersmith: So a law firm, I’m a lawyer, I understand what a law firm needs. You mentioned it, partner offices, kind of a bullpen. What are some other industries that you found that they may not know what they want. They have a certain square footage, and it’s actually, this is kind of the right layout for that type of tenant.

Jacob Wolkenfeld: So when you’re talking about layout, you know, who always does know is architects and designers, they always tell you exactly what they want and you know it before they say it. It’s super bright, open, creative, like space, high ceilings helps. But then there, there are the kinds of businesses where it’s. You know, a medical user might not be super familiar, and it might be their second or third lease, but they may not know that a big part of their transaction is just the fact that they’re going to have to invest tons of money into the space because they have an above standard build out. That when you’re looking for a medical space, it’s like if it’s a dentist, you need a lot of rooms and you need a building that is going to, if you have plumbing in place, in a certain space, that’s going to save your client a ton of money if they’re a dentist. You have to explain that to the dentist because they might say, okay, this space with a ton of plumbing in it versus this space with no plumbing in it because it wasn’t a previously a medical space. I like this one more because it’s priced. $5,000 less a month? No, actually this is a worse deal for your business because the infrastructure that exists in this space will save you way more than that 5,000, amortize it over a 15 year lease call, $12,000 a month. All of a sudden, like there’s no, you shouldn’t even be considering that space because of how much you can save with this space. And it’s not costing the landlord anymore money to do that either.

Hal Coopersmith: So you mentioned that you have the freshest data, you’re doing a lot of activity. How are you balancing all those deals all at once? You’re one person.

Jacob Wolkenfeld: So now I’m two. I just recently, as of eight or nine months ago, hired a full-time associate who, who essentially creates a two person in one broker scenario where it’s like. I’m not CBRE, paying them a draw, putting ’em on projects and all that stuff. It’s every deal I do is his deal and every deal he does is my deal. And obviously every deal technically is my deal right now, but there will be a point where his value is so great that his portion of those deals will be greater because he’s working on them. More on his own or completely on his own. But what that allows me to do is like, this is where brokers waste a lot of time. And I did this for way too long. I should not be drafting offers, I should not be preparing lists of spaces. I should be doing the research, coming up with the spaces. But then there should be someone who’s doing that admin stuff. Because that’s a 30 year day. A fourth of your day at worst. And that is a complete waste of a broker’s of a successful broker’s time because that’s not what you signed up for and that’s not where you’re making the money that I now have, which allows me to do more deals. But I was doing 40 last year on my own. So now, if I could do 40 on my own in a year, I better be able to do 60 to 80 the next year with an associate. And it’s not to say that I will, but that allows me to grow my business. But otherwise, our industry is lazy. You just work long hours. If I work a 70 hour week, I’m working probably double most of the brokers who I’m competing against, and therefore I’m banging out lists quicker. I’m learning the market quicker and, and connecting the dots in an easier way.

Hal Coopersmith: And in terms of balancing your time, how are you able to have multiple deals going on at one time and understand, hey, you know, now you have an associate, but before keep track of everything that’s happening.

Jacob Wolkenfeld: Systems, I mean, this stuff should be easy, but it just isn’t super easy. It’s like, I have a sheet of paper on my desk with like the 10 leases that I have out at any given time, let’s say. And I know in the morning I check through those. Where are those? What is the latest on those? Do I have to do something for them? Is it in the tenant’s court? Is it in the landlord’s court? Those I just stay on constantly. But then it’s managing the other 40 prospects who you’re trying to get to that stage that you have to be on top of, and that it’s tough to, it is absolutely tough to manage. And the hardest part is knowing who to spend more time on and who to do it first. Because who’s more real? Who pays more money? Who’s more of a pleasure to hang out with and shop office space with? It’s a combination of a bunch of stuff, but you just. You got to just, you have to have systems in place that just remind you to like, keep on these people and keep on these deals that you’re working on while prospecting. And it’s not easy.

Hal Coopersmith: So you mentioned that you have the freshest data, you’re doing a lot of activity. We’re airing this in October. What is going on in the market right now?

Jacob Wolkenfeld: First time in my career, I can say this, and I don’t like to say it, I’m not a landlord rep broker who wants to be super bullish on the office market and tell everyone people are returning to the market because I represent only tenants, which means I love when the market is soft because I’m negotiating better deals for my clients and finding more spaces for them to choose from. It is as hot as it has ever been in my six, seven-year career, and it isn’t even close. And I’d say this has started in the last six months or so. The market that I work with for the most part, is under 10,000 square feet anywhere in Manhattan. And this applies to everywhere, except for like the Sea Buildings Plaza, Penn Plaza. Call it. At or around Penn Station. So 27th to 40th Street, west of Seventh Avenue. That still remains as soft as ever, but everything else it’s half the time you’re going to see a space nowadays, or at least I’m going to see a space which is frequent. There’s at least an offer in or in the next couple weeks will be an offer in, and I haven’t experienced that yet. So it’s very interesting. How do you express to a tenant who is under the impression that the market is super soft? Because it has been that like, we got to jump on this. If you even want to chance at that space, and by the way, let’s prepare three, four other options because we may very well lose that one. Or we might not get what you’re hoping for with that one from a price perspective.

Hal Coopersmith: And you started in what year?

Jacob Wolkenfeld: My first deal I ever closed was March 15th, 2020, which I classify as the day of COVID. And I started maybe 10 months before that.

Hal Coopersmith: And so how, as a young broker, did you navigate COVID having not done this before, when you say the market’s hot now, it had never been as cold as it was then.

Jacob Wolkenfeld: I saw nothing different. So it’s tough for me to compare to. Listen, when people weren’t leaving their apartments for four months, that was a great time to work on your database, to work on your follow-up and all that. So, so like, it’s a foolish excuse to say. Okay. COVID hit. Now business is bad because of it, because that then allows you the time that you didn’t have before to prepare for the pipeline to come of deals that could possibly come in the future. So for me it was, it happened to be ideal. I can argue because I just started my career. I’m building my database anyway. It would hurt more today if I have $500,000 worth of commissions that are out right now, and the world went on pause and all those deals died, that would hurt a lot more for sure. But it also allowed me three, four months to prepare for, first of all, work with those same clients to prepare for when we do return or work on my pipeline and that’s time that I don’t have to work on, I don’t have time to work on that pipeline today. So I saw it no other way, and it was just, that was like par for the course for me. I knew nothing to compare it to and it was fine. It was, that’s what allowed me the time to now have a huge pipeline of business.

Hal Coopersmith: Well that is a great piece of advice because in a crisis a lot of people don’t necessarily see the opportunity. You mentioned you are working with an associate right now. For this podcast, what would be some advice that you would give to an up and coming broker, someone who is in your shoes or that you work with for your associate?

Jacob Wolkenfeld: So one thing I’ll say is I entered the business with so much conviction that I was going to be great at this. That’s an unfair advantage because that means when you get pushed down or when you don’t make money for the first 10 months, you’re going to be extra motivated to keep pushing because you see the vision so clearly. First advice I would give anyone ever, is find out what you think you have full conviction you’re going to be great at. If it’s brokerage. Push, push, push, push, push, push, push, push, push. Keep going, keep going, keep going, keep going. Don’t make any excuses. There are far greater challenges in this world than someone is saying, fuck you over a cold call. Far greater. Thank the Lord. That’s all you have to deal with. And then just learn and push. Because the more you do, the better you’ll become, the quicker, and then eventually it’ll pay off. And by the way, to this day, I have days where I doubt or I question whether or not this is the business for me. And then I say, holy shit. Remember when I was questioning this five years ago? And then what happened after I continued to push through. That’s the mental fortitude part that it has continues to be the hardest part for me of the business. Nothing to do with learning about numbers or real estate. All that stuff just comes with doing deals. But it’s the mental fortitude piece that’s tough.

Hal Coopersmith: That is a great note to end things on. Jacob Wolkenfeld, thank you for being a part of Broker’s Angle.

Jacob Wolkenfeld: Thank you sir. Thanks for having me.