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Show Summary
In this episode of the Real Estate Pros podcast, host Q Edmonds speaks with Jack Cohen, a seasoned business therapist with 45 years of experience in commercial real estate finance. Jack shares his journey, emphasizing the importance of learning from mistakes and the value of having a therapeutic approach in business. He discusses strategies for personal and professional growth, the significance of context in decision-making, and the need for critical thinking. The conversation also touches on overcoming adversity and setting personal goals for peace of mind.
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Jack Cohen (00:00)
that I either learned, made up or stole. And I curated it as kind of a workbook for people for self-management of their career. In it are frameworks I use to manage me, to manage others, manage teams, to manage businesses. And in it, I say that the most important, most valuable asset you’ll ever learnyou’ll ever own is yourself and your own capacity to earn money. On that basis, there’s only three keys to success, but you have to do it daily. Acquire skills, accumulate experiences, develop relationships. So this has always been my mantra every day. Did I learn something new? Did I meet somebody new? Did I get a new experience that I can learn from?
Quentin (02:25)
Hello, everyone. Welcome to the Real Estate Pros podcast. I am your host, Q Edmonds. And you know what I like to say, I’m excited to be here today. And I’m excited because I always have a fantastic guest. I always have somebody that comes with a unique perspective, always giving me something to think about, always shifting my mind. And this guy has put two words together that I’ve never heard before, business therapist. That’s right.business therapist. This gentleman has 45 years of experience. Listen, I just cannot wait for you guys to get how his brain works, the way his perspective worked and actually what he does and what he brings to the people that he serves. And so I am excited to introduce you guys to Mr. Jack Cohen. Mr. Jack, how you doing today, Sir?
Jack Cohen (03:15)
Quentin, thank you for the very nice introduction. I’m doing great and I’m happy to be here. I’m looking forward to our chit chat.Quentin (03:22)
Absolutely, yeah, man, I try to make sure I put some sauce on it, but I also try to not embellish too much. I try to keep it what it is, man. And so I think people are going to see, you’re going to live up to the introduction. so Mr. Jack, what I really want you to do is just, I want you to take us into your world. I want you to tell us what you’re mainly focused on these days. If you want to give us a little origin story, we love origin stories, the hero’s journey, we love hearing about that. And then if you want to tell us what part of the world you’re in as well, we would love to know that too.So Mr. Jack, the floor is yours, man
Jack Cohen (03:54)
That’s very kind of you. That’s a big playing field. Where to start? I think, again, those, you can see I have gray hair. If I stand up, you can see I have a pot belly. And so with age comes gray hair, pot belly, and maybe some wisdom. And I would say wisdom born out of experience. And I have…I’ve been in the commercial real estate finance business as a principal and agent and an advisor for almost 45 years. I really do believe in all humility that I have made every mistake one can make in business and still survive and prosper.
And the end result of that is I have been an owner operator as well as a hired gun. And today I find myself in a rare position where I get to play business therapist. I’m on retainer with three different firms in the finance business and I have different roles and responsibilities with them. And I have side projects with other customers and clients who need
help. You know when as an entrepreneur, when I was running and growing a business, I had a finance business. I ran it for 35 years. When I started as I didn’t start the business, it was a family business. My dad started it. We did we originated debt for commercial real estate and we service the debt like property management for loans.
And when I stepped in, we did about 200 million of annual volume and 200 million of servicing. By the time I left, we were six billion in origination, 35 billion in servicing. And I recapitalized that business six times over 15 years.
It’s those kind of experiences that are kind of locked in into my head where I’m having an opportunity to quote, share those experiences with others. I’ll call it a la carte. When I was running those businesses, I always had a board of advisors. I don’t know what it is about entrepreneurs maybe because they want to dominate.
Quentin (06:50)
Mm.Jack Cohen (07:00)
the domain of their design and they don’t want to have advisors. But I have always advocated other people in business have advisors, have quarterly meetings with them and have them from outside your business, maybe even outside your industry. Entrepreneurs don’t really want to do that. So I play business advisor, business therapist as a board of one. And, you know, on a regular basis, they’ll say, hey,Joel Simmons is driving me crazy today. What do I do about that? Hey, Quentin came in with a long-term incentive comp plan. How have you handled this? How do you think about goals and objectives? What do you do for planning? These are all things that an experienced professional has been through. And I’m kind of hoping that I can optimize your journey by sharing with you what I know didn’t work.
Quentin (07:58)
I love that Mr. Jack, you want to optimize their journey. I mean, I absolutely love that. And you want to do that with your wisdom. Like I call it the overflowing of abundance, right? Like you’ve poured so much in you. It’s overflowing now and I’m going to optimize your life based on really what’s overflowing out of me. And so I absolutely love that. I want to pick your brain on some strategies. So I’m going to ask this question and I would love for you to answer it two ways if you’re okay. I would love to know some.professional strategies that you use for yourself, but also some personal strategies that you use. When I say personal strategies, you know, some people they do cold plunging or some people, you know, they do meditation. Like, do you have any personal strategies that help you along the way as far as professional strategies as well?
Jack Cohen (08:44)
Okay, so cool question. So in a shameless selling attempt, about a year and a half ago, I published a book called Freedom Frameworks. and and so here you can see. So Freedom Frameworks. And what it is, is a collection of frameworks, habits, tips, tools,Quentin (08:58)
Wait, there we go, Yep, got it.Jack Cohen (09:10)
that I either learned, made up or stole. And I curated it as kind of a workbook for people for self-management of their career. In it are frameworks I use to manage me, to manage others, manage teams, to manage businesses. And in it, I say that the most important, most valuable asset you’ll ever learnyou’ll ever own is yourself and your own capacity to earn money. On that basis, there’s only three keys to success, but you have to do it daily. Acquire skills, accumulate experiences, develop relationships. So this has always been my mantra every day. Did I learn something new? Did I meet somebody new? Did I get a new experience that I can learn from?
And so
A lot of, one of the things I learned the hard way, divorce, I’m happily married for 25 years, second time, last time. But what I’ve learned is everything, nothing at business works at home. Everything at home works at business. And so a lot of the personal strategies I have framed for business.
Quentin (10:45)
Mmm.Jack Cohen (11:06)
And one of the things I talk about is why, what, how And content gives context gives meaning to content. So Quentin, if you and I at the end of this and you say, Jack, this was amazing, bow, I would know to bend at the waist. But if you and I were having cocktails on the beach,And the sunset was coming down and you said, look over there at the bow. I wouldn’t bow at the bend at the waist. I would look at the front of the boat. So context gives meaning and content. And the mother of all context is the question answered why. So why am I doing something? What is my purpose? And I talk about this in the context of unintended future.
Quentin (11:39)
youJack Cohen (12:02)
Can you fantasize about a point in time in your future that when you put yourself there, you can inventory the elements of that fantasy? And that begins the process that I use for corporate strategy, for corporate planning, for annual planning, for sizing up a real estate deal. What outcome do I seek? Because I begin with the end in mind.And then I assess my current reality by the tyranny of my present. Right? We all day to day are burdened by all this shit that’s coming at us and people can’t see straight. That’s why we have confirmation bias. It’s why we make the same mistake over and over again. And whether it’s in business or at home, it’s the same thing. So getting outside of yourself, creating pull energy,
If you remember Alice in Wonderland, Alice is running across the chessboard and the rabbit stops her and says, where are you going? And she says, I don’t know. And the rabbit says to Alice, if you don’t know where you’re going, any path will get you there. You would never go home and say to your family, all right, everyone, empty everything in the house, in the car, we’re going on vacation. Right? But that’s how we run our businesses.
Instead, what you would say is, company meeting, all right, family, we’re going to go on vacation. How long? Warm or cold? Near or far? Once we know that, we will decide our mode of transportation and what assets we need to bring with. Isn’t business the same way? If I want to develop a property, buy a property, build a portfolio, lend money, invest in others,
Quentin (13:30)
YouMmm.
Jack Cohen (14:00)
I have to begin with the end in mind.Quentin (14:45)
Yeah. I’m going tell you, Mr. Jack, this is exciting. I’m going tell you what excites me. He and you used to frame the phrase business therapist. Because I have a saying that I say to people, everybody may not have a therapist, but everybody needs therapy. Everybody needs to do something therapeutic. And I never quite thought about it. Business, even in business, you need therapeutic moments. Because me going through therapy, this is what I’ve learned, is thatI am paying somebody for the years of experience that they have done. They have done schooling, they have done research, and I am paying them years of experience to get my, to get me unstuck out of my own head. Like just to talk, like to talk things through, like to reason things through. And it never dawned on me until you just said it, how much business people need therapy within their business. They need therapeutic methods to get them unstuck.
Jack Cohen (15:30)
Right.Quentin (15:43)
And so here comes somebody like you with 45 years of experience. Like you said, I’ve been through the ups and downs. You are paying me to walk you through the stuff that you can’t walk through yourself. And that applies to business. Therapeutic methods apply to business as well. Because therapy in itself just means to be made whole. That’s what therapy means. And that’s what you want to be in business. You want to be made whole. Nobody want to be in the red, right? And so I love everything that you’re saying. And I love the idea.the name of your book, I think, you know, are you on Amazon? I know we’re going to get to that later, but yeah, we’ll get to that because I love the idea. One of my favorite books is Atomic Habits. And so as you talk, like, I’m like, yeah, yep. Come on. Exactly. Exactly. One of my favorite books. So your book is going to be on my list for sure, man. And so listen, I love the way you think. And I know you said yourself,
you’ve made some mistakes and you’ve made enough mistakes in this business where you can see if somebody is hitting down that road. And so I just would love for you to take us and walk us through maybe one adversity, right? So that the people that’s listening, that’s stuck at various journeys will know, okay, this is how we can overcome this adversity. So can you take us through how you came through an adversity?
Jack Cohen (17:05)
Well, persistence, grit. Angela Duckworth wrote a book called Grit. I survived the great financial crisis. And this is just kind of a story. And then I’ll give you my advice that I got from somebody that was a learning moment.I, in 2006, I had a business that was about $65 million of gross revenue and about $7 million of profit. The great financial crisis started to happen. I was an early adopter. I saw what was happening in the summer of 2007, and I tried to shrink my business. I couldn’t shrink.
fast enough and my business went from $65 million to $5 million gross. I was not working on a 95 % margin. And so I ended up consolidating, letting some people go, going to the bank, signing personally, putting money in the business, investing in the business. And yes, in the end, I survived and prospered. But if…
You asked me, I don’t know if it was out of adversity, I was trying to buy a business once and a guy said to me, didn’t get the buy. And the guy said to me, Jack, do you want what you want or do you want to be right? And I had no idea what he was talking about.
And Quentin, I will tell you, it was 10, maybe 15 years later that I finally realized that I had this acquisition. I was going to buy this guy’s business and roll him into mine. But I offended him because I wanted him to agree that my business vision, my business model was better than his.
So did I want his approval or did I want his business? And so I have the number of times I can look back in my life where I oversold. How many salespeople do you know who had the sale at Hello and essentially managed to themselves out of the sale? It’s because it, do you want what you want or do you want to be right?
Quentin (19:28)
This is so interesting because I don’t necessarily pick models. I’m trying to see how to say this. I kind of let. So OK, I just got to say it like this. I do have a biblical worldview, right? So I, you know, I pray, I listen to God and I never go out to look for a New Year’s resolution. I kind of let it come to me. And my New Year resolution, like my dying moment for this year is.for me to stop looking to be right and looking to just be obedient. Stop looking for the need to be right. And I’m going synthesize that this way, especially with someone like you. I am learning to stop pushing against people that know better than me. Stop trying to be right. Stop trying to prove what I know and actually listen to somebody that knows better than me. That’s where I’m at in 2026. It’s like listening to
people that know or not even people that because trust you got to trust the person. So I’m just not saying listen to random people. But when you when you have somebody who is vested time in you, who you know, care about what you’re trying to do or somebody that even that you’re paid to board in, listen to what they saying. So I’m trying to think, you know, everything is seeking to be right. At least that’s where I’m at for right now for 2026 is that I’m dying to the fact that I have to be right and open to the fact just listen and be obedient.
That’s where I’m at. Does that resonate? How does that sit with you, Jack?
Jack Cohen (21:00)
I think I think it’s great. again you use the word obedient and you set the context that you were biblical and following God and God coming to you. What troubled me about the word obedient is I think one of the most important skills any of us could have is critical thinking.Quentin (21:23)
Absolutely.Jack Cohen (21:25)
Can you listen to different people’s perspectives, hear what they’re saying and assess it for yourself? Right? So, so Quentin, somebody said to me recently, are you comfortable who you are or are you too busy trying to be what you aspire to be?And I go back and forth with that, right? Because I think aspirations are fantastic. I used to say to my kids, we define, when they were little, we define right and wrong based on a standard of excellence we aspire to, not what we can get away with. And you know as children, one of them got it, and the other was a sneak until he kind of got it.
Quentin (22:04)
Yeah.Jack Cohen (22:15)
And it took him longer than his older brother to figure that out. But I think I’m reading a book now by a guy named Robert Rosencrantz. It’s called The Stoic Capitalist. And he’s a billionaire and it’s his story, but he talks about how obedient his parents were and the world he grew up in. He grew up in New York. He was poor.He didn’t know anyone who was educated, et cetera. And his story is getting out of that ghetto, if you will. And he’s always been a believer in kind of assimilating to the cultures around you. And he follows the stoic thinking and applies it to how he made money. But I think his punchline was too many people listen to the gospel of
Quentin (22:49)
Gotcha.Jack Cohen (23:09)
others and they’re not really progressive enough to be critical in their thinking and make decisions for themselves. So I love what you’re saying as long as your obedience is not to follow blind faith and be who you are to be what you want to be.Quentin (23:11)
Got you.Yeah, no, and thank you so much for synthesizing that thought and bringing even more context to it. Because I totally agree. We ain’t talking about no blind faith. We’re not just talking about just obeying anybody or just, and I don’t know, obey is kind of like an antiquated word anyway, right? And you know, it really is. But you said it best, you know, and I’m thinking about, you you being a higher gun, people bring you in. I’m going try to wrap it up like this, like,
Why would they bring you in if they’re not going to trust what it is that you’re seeing? Right. Why would they waste time, waste your time? I know you’re grateful for the money. Like, you’re going to pay me fine. But really, if you want to be better, why would you bring me in and not trust or even put, implement what it is that I’m telling you? And so that’s kind of more of synthesizing what I mean. Like, if you found somebody you can trust, if you found somebody who you would
Jack Cohen (24:07)
⁓ yeah.Quentin (24:31)
led to or that you were referenced to or someone you’ve seen it work. Like you said, you got to be critical. I like to say chew on the meat, spit out the bones. you know, you may, yeah, right. You know, you may can’t digest everything. Everything may not be good for your system, but what’s good for your system, run that system, run that play so that you can get what you need to get. Does that make sense? Yeah, yeah, absolutely. Yeah, yeah.Jack Cohen (24:41)
Yes, that’s right.Very much so, very much so.
Quentin (24:58)
Listen, Mr. Jack, let me ask you, what’s the next goal for you, sir? there anything that you’re shooting for, anything you’re looking to solve, scale, figure out, like, what’s the next goal for you?Jack Cohen (25:09)
Quentin, since it’s just you and me and we’re having a vulnerable moment, I would like, I’ve had this goal every year I fail, I’d like to develop a peace of mind to know that I did my very best. My wife says I’m an acquired taste, but I have a cadence problem.My resting RPM seems to redline most people’s active RPM. And so I have a lot of energy. I have a lot of thoughts. I’m particularly articulate and I have an, because of it, an unsettled mind. So for me, for 2026, I want to exude more grace, more patience.
more humility in order for me to get this piece of mind, a regulated cadence and more mental health because of it.
Quentin (26:17)
I love talking to you, Every morning, I tell myself I’m going to, and I’m going to paraphrase it. I’m not going give you my exact quote, but I say every morning that I am going to practice humility, neatness, patience, kindness. Like when I present myself with whatever I’m doing, I’m going do it in being humble, being patient, being kind.with humility. I talk, actually it’s the prayer I really pray. And I said prayer, I was trying to kind of diverge from that, but it’s really what I do so that I can present myself to my wife every morning. Like when I deal with my wife, I want to be patient. I want to be humble. I want to have humility. Like these are the things that I want to do. And then when I come to the business, this is what I say to define my piece. I say, I’m going to be cheerful, courageous, confident, certain and undaunted.
Jack Cohen (26:58)
That’s great.Quentin (27:14)
I’m going to be cheerful, courageous, confident, certain and undaunted. So when me and Mr. Jack talk, I’m going to be cheerful. I’m going to be courageous. I’m going be certain. I’m going to be confident and I’m going be undaunted. We’re going to have an incredible conversation. I’m going be happy about it. I’m going to be confident about what I’m talking about. I’m going to be certain what I’m to talk about. This is going to be an amazing vibe. And I believe that’s what it is. And that centers me and calms me down and bring peace to any situation I’m about to go into. So I hear you, sir. I hear you, man. I hear you,Jack Cohen (27:40)
That’s great. That’s great. That’s great.Quentin (27:45)
Listen, Mr. Jack, this has been an amazing conversation. Time has been well spent. If someone wanted to reach out to you, connect with you, learn more about what you’re doing, how can they get in contact with you,Jack Cohen (27:59)
So I guess the two easiest ways is I’m on LinkedIn, Jack Cohen, and I mentioned Dark Knight Ventures, but Aramark Partners. And I have a website. My website is darkknightlikebatman, two Ks, ventures, plural, because there’s more than one, .net. So on my website, you can see.blogs that I’ve written, podcasts that I’ve been on, as well as some of the clients I’ve done business with. I’m easily, Mike can reach me by phone or by email through either of those.
Quentin (28:34)
Absolutely. Mr. Jack, I literally, I can talk to you probably for another half an hour. Easy, easy. But I have other obligations. But I just want to say that this has been a pleasure. I thank you for your time. I thank you for putting that without persistence. But I’m glad we persisted. And I’m glad you’re here, right? Because this was an incredible episode. And I know our viewers are going to get a ton of value. So I appreciate you, sir.Jack Cohen (28:40)
Very nice.Well, thank you very much. enjoyed it very much, Quentin. And I wish you the best of luck and tell your wife that I think she’s very, very lucky that every morning you focus on how you’re going to present yourself to her. Really good.
Quentin (29:14)
Iappreciate that. Well, brother, we shared something. I’ve been married for 15 years and divorced, and now I’m remarried to my best friend and my purpose partner. So yeah, this one, I’m going make sure I attack the right way. So I appreciate you saying that, Absolutely. Well, listen, y’all heard Mr. Jack. You’ve got the value. Definitely go get his book, The Freedom Frameworks. You got to go get it. I’m going to get my copy. So support Mr. Jack. But you…
Jack Cohen (29:29)
Good for you.Quentin (29:43)
better make sure you are subscribed here. You’ve got to come back because we’re going to continue to bring up amazing people just like Mr. Jack. So again, I thank you, sir. And to everyone else, we will see you on the next time.
