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Michael S. Leibowitz
I was fearless at 21. I grew up in Staten island. Very modest beginnings. So I grew up always wanting to kind of get out of that. Doing that at 21 was tough, but I never afraid of it.
Scott Clary
Michael S. Leibowitz is the President and CEO of Douglas Element Inc. With over 25 years of experience leading companies in.
Michael S. Leibowitz
Insurance, finance and real estate.
Scott Clary
He's the founder of Harbor Group Consulting and has redeveloped iconic properties like the.
Michael S. Leibowitz
Mondrian South Beach Hotel. When I came into Douglas Elliman, number one reason that I took this role, Douglas Elliman brand, best brand in residential real estate by far. As a 10 year old I always saw myself as Captain Kerr. I thought like the only way I was really ever going to be the CEO was I had to become it myself. Just started selling insurance and then created a business out of we handle the insurance on the World Trade center before 9 11. That business after 911 went through the roof. A seasoned entrepreneur and investor, Michael also.
Scott Clary
Supports causes like Make a Wish and the Bascom Palmer Eye Institute.
Michael S. Leibowitz
In this episode we dive into his.
Scott Clary
Journey of building, leading and scaling high impact ventures.
Michael S. Leibowitz
The successes in the failures. I think it's hard for people to really like believe that you can't do a good deal with a bad guy and you can't do a bad deal with a good guy. If you do everything that you need to do, the result is your stock will go up. Don't worry. Worrying is the worst thing you can do.
Scott Clary
Welcome to Success Story. I'm your host, Scott Clary. The Success Story podcast is part of the HubSpot Podcast network. Now, HubSpot doesn't just have great podcasts. They also have great tools for entrepreneurs. Let me tell you a story. I'm sure you've all heard of the Angel City Football Club. Well, you don't just become the world's most valuable women's sports franchise by accident. Angel City Football Club did it. The little help from HubSpot. When they started, data was housed across multiple systems and HubSpot unified their website, their email marketing and fan experience in one platform. This allowed their small team of three to build an entire website in just three days. The results were nearly 350 new fan signups a week and a 300% database growth in just two years. Sure, you can be a great team in the arena, but if you truly want to build a legacy, a franchise and a dynasty, you have to build a community outside of the arena. And HubSpot helped Angel City Football Club do just that. If you want to learn about how HubSpot can help your business. Visit HubSpot.com there's some other great case studies and you'll learn how HubSpot can help your business grow better. And one quick ask before we dive into today's episode, I need your help with something important. I've just launched a quick survey to better understand what you guys want from the show. And your feedback is going to directly shape our upcoming content. It's only going to take a few minutes of your time and I made it super easy to find. Just head over to scottdclary.com survey and as a thank you for helping me out, I'm giving away a free gift card to one lucky respondent chosen at random once we hit 100 responses. So not only will your feedback help make this show even better, you might score something cool just for sharing your thought. I really appreciate your help with this one, Michael. Let's do this. Okay, so you built your First Empire at 21. You sold a company for a very big number. What made you hungry enough to take on Douglas elements crisis?
Michael S. Leibowitz
Well, it was, it didn't become an empire until later on, right? At 21. It started modestly. Douglas Elliman is, it's not a crisis. And I think that, you know, when you're that age, you're fearless. And I was fearless at 21. I grew up in Staten island, you know, very modest beginnings. You know, my dad was a New York City cab driver for 25 years. He ended up getting out of that for a little bit of time and did, you know, did some more things in his life. But, you know, so I grew up really always wanting to kind of get out of that and be successful. And he had some friends that were, you know, from some interesting backgrounds and were really good influences on me that always stressed legitimate business and education. And when I say legitimate business, obviously you can understand what they were doing and, but they had a profound effect on, you know, on who I am and my motivation. And, you know, doing that at 21 was, was tough, but I never, I was never afraid of it. And coming into the Douglas Elliman, you know, business is, again, I, you know, listen, I would call it challenges, right? The residential real estate business has a lot of challenges to it. Douglas Elliman, you know, had a longtime leader and, you know, I had to fill that role, which was, you know, a big act to follow. And I looked at it as a challenge. I didn't look at it in any other, any other way.
Scott Clary
So if you think about, so just to walk through Your entrepreneurial career. You. You built. You're an operator.
Michael S. Leibowitz
You.
Scott Clary
You can build from scratch. And maybe crisis isn't the right word, the opportunity, but still, it's a pivot from what you've been doing your whole life at this point, right? You are not building from scratch. You're stepping in to an existing framework, existing organization. I have no doubt you could have built after exits. You could have built something from scratch. So I guess the question is, even for people trying to navigate their career, how did you think through the opportunity? If you have the capability to build from scratch, why would you go into an opportunity that's already molded and there's like rigid structure in place? Because sometimes entrepreneurs have a tough time in existing structures.
Michael S. Leibowitz
Yeah, I mean, that's a really great question, the way you pose that. Because I did. I built, you know, the business from scratch. I was the first employee, you know, in the business. And that is really hard. Right. And ultimately I built a brand within that business. And I always used to say, you know, to myself that, you know, can you imagine if I had. I usually used to use Aeon Aeon, which is the number, probably two, largest insurance business in the world. I always used to say, could you imagine how much I could sell if I had Aon's banner above my head? You know, that I had to create my own banner. And when I came into Douglas Elliman, I will tell you, the number one reason that I took this role was that the Douglas Ellman brand was a built brand, already internationally known, as far as I'm concerned, synonymous with luxury real estate and the best brand in residential real estate by far. By far. And it was like the first opportunity for me as a person that had to build a brand from scratch, that I almost felt like, this is going to be easy. I already have the brand. All I need to do is take the brand from A to B. So it's great. Interesting that you asked that question because that was the exact thinking in my mind when I took this role. I thought of how hard it was to start from the beginning on my own, build my own brand within an industry that was very institutionalized. Insurance. Right. I mean, there's not a lot of big players in the insurance distribution consulting advisory space. And so I always would say to myself, my God, can you imagine how to brand? Like, to me, that was like starting on third base, you know, so.
Scott Clary
But it's. It's interesting. It's an interesting conversation because there's so many ways to, quote, unquote, be successful in Life. And I think that it's sort of like the 21 year old you. So you built this insurance empire. I don't think you had any money at the beginning when you first started building that, correct? It was.
Michael S. Leibowitz
I had no money. And honestly like there was some jobs available at that time to like go work in. You know, obviously they were, you know, beginning jobs, you know, starter jobs. But also in my mind I never really thought, I always thought I had to kind of create my own job. Like, I never thought, I never like would have. You know, I went to CW Post, which was like, you know, school in Long Island. It wasn't really, you know, I didn't go to Yale, I didn't go to Harvard, I didn't go to an Ivy League school and I couldn't, I didn't think I could go to Goldman Sachs or JP Morgan and get them to hire me at that age. And I was thinking like that. I just thought I had to do. I didn't think I had a choice. I thought like the only way I was really ever going to be the CEO was I had to become it myself. You know, and I always saw myself, I was a big Star Trek fan right as a kid and I always, as a 10 year old, I always saw myself as Captain Kirk. I didn't see myself as Spock or Scotty the engineer. I was always Captain Kirk. In my own crazy mind as a little kid, I thought I looked like him a little bit, you know. So I always wanted to be the CEO. So to me, starting my own business right out of the gate was the only option for me.
Scott Clary
So the first business you started, was the first version of it successful or did it go through multiple. Because I'm talking about people that go through, you know, a hundred different ideas that don't work before one does.
Michael S. Leibowitz
Yeah, it's interesting because it was, I mean my first thing that I did was I actually took some shared. It was funny because we work became wework, but I actually took a desk in shared space that was near where I lived. And I remember I called the business msl. Those are my initials, MSL Associates. I made myself little business cards. I had an office, I went to the office and I had a couple of relationships that I had and I sold them some insurance. And that's how it got started. And it was as simple as through.
Scott Clary
100 different types of business and have 100 different ideas, you hustle them.
Michael S. Leibowitz
I'll give you an example. I sold this one business multiple times and in the last sale There was some doc. There was some crazy tax rule that one of the lawyers found that, like, could have, like, made me pay a certain amount of tax. I don't remember what the story was, but we had to find our original incorporation documents to find that. It was like a 30 year rule or something. And we had to find our original incorporation documents back to when I started the company. And we ended up finding them as crazy as it was. But, like, that was the original business. So there was no. I didn't have a. Oh, I started this business. I failed. I had to start it again. No, I just started selling insurance. And then I sold more and I sold more. And then I ran into another opportunity by accident that I created a business out of that ultimately became a business that was. I sold multiple times. The last time I sold in 2018 was for, you know, a real number. And no, it was from the beginning. That was it. I didn't. I didn't have a business that failed.
Scott Clary
I love it. I think that that's. I don't think that's very common. I think a lot of people just go through multiple iterations of trying something, but I also think that people give up too soon as well. Like, it just sounds like you just grinded it out and figured, I grind.
Michael S. Leibowitz
I'm still grinding it out. Okay, I'm still. Today I'm grinding it out. But the funny part about that is, is that I also look at the people that go through. I actually spoke to an insurance. An insurance. A real estate agent a few days ago about coming to Douglas Ellman, and he was a guy that had multiple business failures in the residential real estate business. And he was going through with me the issues that he had. Like, they were a problem. And I said to him, I love the fact that you went through all of this in your life. And he goes, what do you mean? I said, because, you know, the, you know, the successes, you know, the mistakes, you know, the things that you have to do, you know, the fact that you've been through it all, you're more valuable to me, okay? Because you've been through it. Because you've bounced back because you kept going. You know, the successes are in the failures, right? So, like, I think it's hard for people to really, like, believe that, but the truth of the matter is, is. And again, listen, my overall businesses were successes, but within those successes, we had things that, you know, we didn't do as well as we thought we could have done. That we fixed and we went back and tried again. And that's what it's all about. You know, this, my dad used to say to me is the reason they put erases on pencils, okay? Because we don't have pencils anymore, okay? But people make mistakes. It's okay.
Scott Clary
You know something that's interesting, because you bought back your business and then resold it and bought it. So I'm curious about how that happened. But, you know, reading between the lines, when that happens, that usually means the person who bought it didn't do that well with it, and then there was an opportunity for you to reacquire. And I see this happen more often than not. So I'm curious if you pinpointed, like, the personality traits of an entrepreneur that allows them to be successful when someone else with a lot of resources and capital still can't be.
Michael S. Leibowitz
Yeah, well, listen, I think that there are people that come to this country that don't know a single person. They don't know the language, right? And you hear this story that they drove a cab for a year and then they became a billionaire, right? I mean, there's a lot of those stories out there, you know? And at the end of the day, the one common denominator between the people that are incredibly successful and aren't is work ethic. You do not have to be the. I don't think I'm the smartest guy in the room, okay? I think there are plenty of people that'll go and take a math test or a reading comprehension test and will get a better score than me. But you are not going to overwork, outwork me, okay? And the people that I'm around now, I don't think are used to the level of work that I do. The people that I had a big team that worked with me in my previous businesses, and we all ran at the same pace. I used to joke around, people would say to me, how did you get such an amazing team? And I would say, I created them in my basement like I created those people. And what I mean by that really is I'm joking. But, you know, success breeds success. The people that are with you learn your habits, and the people that can live in that environment are the ones that are going to be the successful ones and keep going and stay with you and all that. And I thought this element right now, I'm in that phase of finding and discovering the people within the organization that could run at this pace, okay? And that are totally committed 24 7. I gave my life, to my career, and. And that's what it takes and if anybody thinks, you know, people talk about work life balance. Yeah, you can have work life balance. I, I play sports, I do things and all that, but you really have to be willing to dedicate all of it if you really want to be truly successful. Unless you can invent a vaccine or something, you know, And I'm sure that would take 24, 7 too. But if you're in like the block and tackling business of sales and brokerage, you know, or advisory, or even if you're a lawyer or you're creating another, a business, whatever that may be, it is a life commitment.
Scott Clary
Yeah. I think that. I also think that there's seasons to your life. Like what people get wrong about balance is they want balance their entire life. I think that it's okay. Where's the point where if you do want to spend more time with your family, that's okay, but know that's going to take away from your ability to put hours into your work. So when you're 20, 30, maybe even, you know, late 30s, you put all of yourself into your work to build this foundation that's going to let you, on the back half of your life, take a little bit of a break if you want it. I think that the issue is that people want this easy, soft life from right out of university or high school, and they're never going to get the life they want if they think like that. Yeah.
Michael S. Leibowitz
Well, it's funny, one of my college roommates, dad, when we graduated college, I remember he said it to us at graduation and he looked at both of us and he goes, pay now, fly later.
Scott Clary
I like that.
Michael S. Leibowitz
Right. I'll never forget. There's so many. You know, I've been lucky that this. I've had so many sort of mentors or people that have said things to me, and I really, really take it in and it's the truth. But like, that's what people say to me, the same thing now. It's like, why aren't you, you know, sitting back and relaxing and all that?
Scott Clary
You know, you could, but you've done so much. You could if you wanted to.
Michael S. Leibowitz
I can never work. I could promise you that I can. I never have to work again. I'm not doing this for any of it. But I was never really in it for. I was never in it for the dollars.
Scott Clary
Never talk to me about as much as you want to share about the selling, rebuying it back, selling it again. It's very strategic. I don't think many people have experienced that, but it's an interesting concept. So that obviously worked out. It paid off very well. I don't think it was planned probably from the first time, but shit happens. So what was the.
Michael S. Leibowitz
What was.
Scott Clary
You built this company, you sold it. The first time I walked through, it was a private equity strategic. And then what happened?
Michael S. Leibowitz
Yeah, what happened was I had started multiple companies, but. And I end up selling all of them to this. I ended up merging them into a company called National Financial Partners that was created by Apollo, the investment fund. So like I said, I was 21, I'm now 28 years old. And a partner of mine calls me and says, hey, Apollo is looking to do a. What they called a roll up back then. Nobody likes the word now, but it was, it was a roll.
Scott Clary
Is that a bad word now?
Michael S. Leibowitz
Yeah, people would always say that a roll ups a bad word because all it is is really putting companies together. It's not really creating anything.
Scott Clary
There's not enough value. Just.
Michael S. Leibowitz
It's just a financial kind of, you know, thing. Right. So they came to me, I was 28. And they said, you know, we're putting these companies together. There's five or six people we put together. We'd like you to do with us and roll your businesses into this business and you'll take back stock in a private company. You're going to make a lot less money than you were making. And, you know, I was 28. I had already. I was already making a lot of money for someone 28. And. But I had to take all these steps back. And I said, well, I don't really need to be doing this the rest of my life. And I really didn't want to be in. I had one foot out the door always. I was always looking for the next kind of thing in my mind. I always thought there was a bigger frontier for me than insurance. So I agreed to do it. And we created this company called National Financial Partners that ultimately went public. This was in 1998. We went public in 2003. I ended up buying back three businesses from them. I left one of them there in 2000. During the financial crisis in 2010. Our stock, we had a $55 stock. It went to like 80 or 90 cents. All of my subsidiaries that I was the CEO of were still making a lot of money. I said to the management team, guys, you know, you paid me already. We've all made a lot of money. I don't need to do this anymore. I think I'm leaving. I'm going to go do something else. And they were like, well, what the hell are we going to do with these businesses if you leave?
Scott Clary
How old are you?
Michael S. Leibowitz
This was 2010, 2009. So I was like 30. How old was. I was like 40.
Scott Clary
Okay, so you put some time.
Michael S. Leibowitz
I was there for 11 years.
Scott Clary
Yeah, okay.
Michael S. Leibowitz
I was there for 11 years and amazing people. I still speak to all of them. Amazing, amazing people. So. But I said to them in an honest way, like, guys like, you know, you're kind of blowing the place up, our stock is, you know, whatever. And there were things that I had said to do that I thought that they didn't listen to, but it was all, it was in an amicable way. And they're like, well, what are we gonna do with these businesses if you're not here? So they were like, why don't we sell you back? Let's, let's figure out a deal where you take back three of the businesses. One of them, which was a property and casualty business, which was their largest subsidiary at the time we left there in that. We left it at the company. I didn't buy that one back. I bought them all back. So the market really changed on them. It was the financial crisis. And that's how I got the business back. I got back three of them. One of them I still own today, which is a pension administration business. The other was a program insurance program business for New York condos and co op buildings. And the other was an advisory consulting business called Harbor Group, which was the one that really was the, you know, the blowout business that did, you know incredibly well that I had created from nothing. I was doing a favor for someone in 1994 and I saw a business in it and I ultimately created the business. Fact I had a guy that worked for me that was a really smart guy that I wanted him to really spearhead that and he thought there was nothing in it. And I'm like, all right, if you don't want to do it, I'll do it. And he really didn't see it. And it ultimately became a very large insurance advisory and consulting business. We had every major, we were basically insurance diligence to lenders in the CMBS commercial mortgage backed securities world. And it became a very big business. We had every major client from Goldman Sachs to JP Morgan to UBS to bank of America. We did business internationally. Matter of fact, we handle the insurance on the World Trade center really for 9 11. And that business after 911 went through the roof. I testified in both World Trade center trials. Matter of fact, before, you know, there's a really interesting story behind it where I wanted them to insure the buildings for the full value. And Larry Silverstein, who was the guy that was buying it, thought I was. They thought I was crazy and it was going to raise their insurance premium through the roof and it was going to kill the deal. And they yelled and screamed at me. I was 29 years old at the time and, and they were pissed. And I con. I wanted them to ensure the building contemplating both buildings going down. And we were at a meeting before 911 and they said to me, what, what do you think is going to do? You know, yelling at me almost what do you think is going to happen that these buildings come down? I said, well, what happens if a 747 hits the building? And they pulled out some engineering report that they had that said you'd have a $600 million loss. And I go, I don't really care about a maximal probable loss study, which is what they showed me. And when I was, when I was questioned in the deposition after it happened for the trial, David Boyes, I think it was, maybe it was David Boyes. I remember they were boys or somebody else who, you know, was a big time and we had the biggest lawyers in the world on this case said to me, are you the one that said that a 720, if a 727 hit the build building? I go no, no. I said 747. To me that was the only thing that could have brought those buildings down. So the result of my work on that really just that business just went from a business that was making a few hundred thousand dollars a year to a business that was dropping 20, 30 million dollars a year to the bottom line. And within instantaneously, every lender started calling me, saying hey, we need GMAC was my first client in that business. They were the ones that financed the World Trade Center. They were the most unbelievable client. I never lost that client up until I sold the bill. I sold the business. I didn't lose them as a client. I did every single piece of business for them. I advise them on every single deal. Goldman Sachs, I mean every lender we had, we did all of their work. And banks like that don't hire one anyone. But we were so good at what we did and so specialized that we work for exclusively for these major banks. And it always, you know, it started before 9 11, but once 911 happened, you know, I ended up getting incredible notoriety from it. And we really took that business to the next level.
Scott Clary
How did you at even 29. Get in the rooms so that you can negotiate a deal on like the World Trade Center. That's still young. That's wild.
Michael S. Leibowitz
Yeah. You know what was interesting about it? There was a woman who we got the business from. So I got the business because somebody. I was doing somebody was a brokerage client of mine when I was like 24, 25, was selling loans to Smith Barney back then. He remembers Smith Barney. This is a long time ago. It's only I really exist anymore. Okay. Was selling loans to Smith Barney and he left and he went to work at gmac. And he asked me to do him a favor and he says, listen, can you review this for me? I'm like, I don't really do that. But I was a young, aggressive guy. I'm like, I'll do it for nothing. Don't worry, you don't have to pay me. And I did it for him. And I did one, then I did two. He's like, no, no, let's pay you. I'm like, no, no, it's fine. I was just so happy to have their brokerage business at the time. And he's like, I'll pay you. And he paid me 200 bucks to do it. And I was like, okay, fine. So then I started charging for it. He leaves that firm, small firm, and goes to work at GMAC in Horsham, Pennsylvania. They were just. It was the birth of CMBS Securitized Lending at that time. The birth. Nobody was really doing it other than Nomura and them. I get a call to go down there and I meet with this woman who was a Catholic school teacher before she was a banker. And she said. She walks in and she sits down with me. She asked me a million questions. She gives me a test to take home. I end up sending it back and I do. I send back like a 40 pager, okay? Of stuff, okay? She calls me back and makes me drive back down to Horseman's living in New York. Time. I say with. She goes, you know, you did. I put you up against two other firms. You sent back the best report by far. She goes, but we're General Motors. We don't hire one, anybody. And I'm not allowed to ask you how old you are, okay? But I know you're young. But I'm not going to hold it against you. And I'm going to hire all three of you, okay? After two or three months, I was so all over this thing because I'm now this 24, 25 year old kid with general Motors. Acceptance Corporation as my client. I can't even, I can't even believe I'm in the room that I even have this opportunity. And again we were getting a few hundred bucks to do. I think I was charging them 400 at the time. After a few months they got rid of the other two. None of the bankers wanted to deal with these older guys and they gave it to me. I ended up getting all of it. I got the whole account. It started becoming a business. They were my big client. And then when World Trade center came along, I was their guy. Okay. And this was the biggest CMBS loan at the time was $833 million. Was the loan give you the exact amount? And they gave it to me. Who else? They didn't use anybody else. And I will Never forget after 911 they called me so, you know, grateful for that. I was all. I mean I just give you a snippet of what went on and why we got those built. We got, we made them insure the buildings for $3.6 billion which ensured both built buildings at full replacement cost. Okay. And that's why the World Trade center got rebuilt. If we would have not done that and did the loan amount, 833 million that Silverstein wanted, that would have been the only coverage you would have had. Okay. So I went to a meeting at Silverstein's office four days after 911 and the CFO of his company walked in. He goes, I hated you until 911 because I made their premium go from 5 million bucks to like 15 million. And the World Trade center got rebuilt because we had $3.6 billion of coverage. And then the only reason that there was the trial was they tried to sue and say we should get 7.2 billion because it was two airplanes that hit the building, meaning that it's two occurrences and we should be paid twice. That was their logic behind the whole thing. It ultimately ended up being settled in a negotiation and there were two trials. But it's a fascinating story. The whole. I mean I could talk about this.
Scott Clary
This is one thing a while for.
Michael S. Leibowitz
Two hours about all the intricacies of how it went down, but it really put my insurance career on the map. And I ended up becoming the go to insurance advisor to every major bank in the world with that by far and with like literally 90% market share.
Scott Clary
That's absolutely wild. That is, I mean I. There's not, there's not too many. I guess the lesson out of that is you just put yourself in rooms and you didn't Give a shit about the money. You just put yourself out there. And that's the. The downline effects of that were 90% market share.
Michael S. Leibowitz
Yeah. And from there we did. We literally did every. I mean, the largest finance real estate transaction we did was a $40 billion transaction with Equity Office Properties in the middle of the financial crisis. You know, Harris, the hotel company, I mean, the Venetian Casino. I mean, every single transaction, major transaction. We handled every one of them, everyone. So it was a really amazing business. And at the same time, I also had my other business. I had my other insurance brokerage services business. Yeah. So they're all going at the same time. They're all ripping at the same time. Yeah.
Scott Clary
So you never had an issue. I mean, I'm sure in the moment it was a little bit stressful for like a 20 some year old to deal with some of this. I mean, that's not.
Michael S. Leibowitz
I didn't sleep the 9 at 911 because I was really worried that, like, oh my God, did I. Did I miss something?
Scott Clary
Did you do it right?
Michael S. Leibowitz
Yeah, I don't know if I missed something. I'll never forget driving into the city I lived in Long island On, you know, September 14th, I think it was three days later. There wasn't a car on the road. There wasn't a person in New York City. It was a barren place. But I will tell you, the night of that, I was. I did not sleep that night. I was going through all my files, rechecking it, you know, so concerned. And then there was obviously litigation. You know, GMAC gave me the lawyer. They paid for it. They were the most unbelievably loyal. And listen, I did my job and all that, but you know how things go.
Scott Clary
Yeah.
Michael S. Leibowitz
Naturally start pointing a finger.
Scott Clary
Like when Seven Points.
Michael S. Leibowitz
They were loyal. They never questioned the thing they were loyal to. They were so loyal. You have no idea what amazing people. I still know. A lot of them, I mean, I still speak to. They're now called Brickadia. It's owned by a joint venture of Jeffries in Brickadia. It's called Brickadia. But I, you know, I didn't sleep that night. I was worried about it. It was very stressful. Testifying in the World Trade center trial. You know, the best lawyers in the world are on that case. And I was a young guy. Okay. Like I said, I. When I did the deal, I was like 29. When the trials happened, I was 31, 32. It was. It was tough. It was tough.
Scott Clary
You know, so now, I mean, after that, stress is all very Subjective like that. Stress taking on big opportunity. It's all very subject compared to that. Yeah, I mean, that was a big one. I think that's. I think that's probably more than most people deal with in their life. I don't think many people have to deal with that kind of money at that age. Okay, so fast forward a little bit. That's the story of how you really got. That's, that was like the thing that gave you all the momentum. And then, you know, it's, it's, it's all history after that. You bought and sold the company multiple times. The, the last time that you bought and sold it, what was the last transaction before you were like, I'm done with this. I'm moving on to a different part of my life.
Michael S. Leibowitz
2018, I had, like I said, I had three businesses. Actually, four I sold in 2018. I sold two of them to a very large insurance business, like a $20 billion company. And that was in 2018 and 2019. I sold that other one, the program business, and then I stayed with them for a while, you know, in transitioning the business and all that. I created a family office. Actually, I created the family office before the sale because I was already doing things like that, but I created a family office. I bought a hotel in Miami in 2019. I was investing, you know, looking at, very busy. I mean, I'm looking at deals, investing in things. You know, I was never not busy. So I was doing that. I was on the board of, of another company, a financial company. Then I actually did a spac. I did one of those.
Scott Clary
Those are popular for a minute.
Michael S. Leibowitz
Those are popular for about three minutes. Yeah. And then. And I was on the board then. When Douglas Elliman became public In January of 22, I went on that board as well. And always doing, you know, entrepreneurial things, you know, within that time.
Scott Clary
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Michael S. Leibowitz
Yeah. I mean, I think there's so many things you have to do. Right. And I also think that, you know, I don't want to say luck. I don't want to use that word. But there is a level of karma that you've got to have, and that usually is a result of all of the hard work that you're putting in. You know, the luckier. You know, the harder I work, the luckier I get. Is true. And there's a lot more to that simple little cliche. But I think that. And the other thing I would say is you gotta be around the right people. It's so important in every aspect of your life, in your. In your personal life, in your business life, the people that are on your team. And I never say someone that works for me. I always say with. It's a team effort.
Scott Clary
Right.
Michael S. Leibowitz
Every aspect of it. There were people along the way that, you know, I said earlier and, you know, we were talking is that somebody said this or that to me, and I really remembered it, and it really stuck to me. There's all of that. And you gotta do business the right way. You gotta be honest in every aspect of your life. Because if it's a stranger, who are they you have to lie to. Right. If it's something you care about, you're just gonna ruin it with a lie if you lie. So being straightforward, being honest, being direct, working really hard, making sure the people around you are good. Your lawyers are good, your accountants are good. The people on your team, the people you're bringing in. And the other thing I would say is you have to be a motivator. You got to. You have to make people want to be on your team. You know, you got to be the leader that people want to follow, you know, because you can't do it alone. And one of the biggest. I was in a thing when I earned my early twenties called Y E. O. Y O. Yeah. Which is. Yeah. And we used to have all these things, and they gave me this book in YO called the E Myth. And, you know, it kind of talks about entrepreneurialism and scaling, being able to scale businesses and how you do it. And Listen, I scaled an insurance consulting business. It doesn't get much harder than trying to scale an insurance consulting business because our competitors in that space were companies with five or eight employees and we had 100 and ultimately 130, 140, 150. I forget the final number. But it's very hard to scale professional services businesses, right? Because it's so people oriented, you know, and you got to manage the margins, you got to manage what the product that the people are putting out, which is themselves. Right. You have to have your training, you've got to have quality control. I mean there's so much that goes into, you know, like that's where like sometimes is the entrepreneur, there's the operator, there's the business getter. Right. There are multiple things you have to be to be an entrepreneur. And it's very unusual to see an entrepreneur that's an operator. Right. The entrepreneur is usually the idea guy, the business guy, the rainmaker or girl or person. Right. And I had a lot of women in my businesses. So, you know, when I say guy, I, I'm the opposite of that.
Scott Clary
How do you define. And actually that's a really good point though because I've always defined operator as somebody who actually builds the business.
Michael S. Leibowitz
Not really, no.
Scott Clary
How do you define.
Michael S. Leibowitz
It's not, if you really think about it, right? Someone's got to come out with the idea. Someone's got to be the guy or the, or the girl that says, oh, this is the business we're going to go into. This is what we're going to create. They've got to be that visionary, right. They're usually the, the, you know, the insane person, right, that's got all the ideas and whatever. Then you get down to the operator. You got to hire people, you got to deal with the HR of them, right. You got to know who the right people are to put in what positions. Then you got to get your financials. Right, Right. So operations is a whole other animal than creating what you're going to be doing. And it's very rare to find the entrepreneur that also can be the operator. Very rare.
Scott Clary
What happens when somebody's too visionary though?
Michael S. Leibowitz
Oh, I can get in the way in a big way. Because a lot of times, yeah, a lot of times they're not realistic. Right. And a lot of, a lot of visions don't translate into list. Like I said, I have a family office. I have been investing in things for 30 years, okay. People have brought me so many business plans. I get so much unbelievable vision and Then I ask the question is, well, how does this make money? How does this tie into a real business plan? You know, I see so many deals that people go and they raise money and people buy into that person's vision because they're very believable. But unless you look at the other side of that and say, all right, well, how is this going to make money? That's a whole other story. And I will tell you, the majority don't make money. Okay? 90% of the deals you look at never make any money. And you gotta be the no guy. You gotta say no over and over and over again and be brave enough to say no, not buy into that vision. And the other thing I would say is the. One of the most important things in business, whether you're an entrepreneur, whether you're an operator or anything, is discipline. You have to be disciplined. Most people do deals because they want to do a deal. They get emotionally into it. They want to, yeah, we're going to do this. It's going to be great. It's going to be this. It's going to be that. They don't look at the reality. Everything I always look at, I always want to know what my downside is first. Always. I don't care what it is. I want to know the downside.
Scott Clary
Worst possible scenario, what's the downside?
Michael S. Leibowitz
Don't tell me about all of the things. Right. Because in all the things, you also have to execute. Yeah, right. Think of how many things go into creating something that's successful. How hard it is.
Scott Clary
No, it's very hard. Well, that's why. I mean, so when your family office. I'm assuming your family office does, like, early stage, you're not doing, like.
Michael S. Leibowitz
No, no. I'll give you an example. We were just looking at a business. Now, it's been around for 30 years. It's an operating business. It makes a machine, okay? And one of my big questions to the guy that's evaluating it is, well, what happens if someone invents something that makes this machine obsolete? We're one trick pony business, right? So there's like, so many things you have to look at, and then. Listen, there's analysis paralysis. You don't want to overdo it, too. And you're in business to take risk. So there's like.
Scott Clary
Well, this is the thing, right? So one thing that I find interesting is when somebody's been a great entrepreneur and they built a business and it's been acquired and then they have a whole bunch of money that they're sitting on, they make a lot of investing mistakes because a good entrepreneur doesn't always mean a good investor. And now you've been doing it for 30 years, you're not new to this. But for somebody that looks at businesses, I think there's lessons in this for an entrepreneur who's building and also an investor who's looking at putting their, you know, money into the right business and betting on the right person. What, what should an entrepreneur be thinking about? What should an investor be looking for that you've seen sort of is a good signal for success?
Michael S. Leibowitz
Well, the number one thing is the person you're betting on. Everything is a jockey bet everything, right? I mean, you, you better know that the person that you are as leading that business has the attributes that I mentioned, right? They're entrepreneurial, they've got a great idea, it's incredible. They know how to execute it. And if they don't know how to execute, that's okay. But hire people that can execute, right? Make sure you put the right team in place that's going to do it and you want to meet that team. But it's all a jockey. But like when, when Meta, right, was falling apart and the stock went from, if you remember, from 300 to $88, I bought more. I bought more for one reason. I'm going to tell you this. I think Mark Zuckerberg is an absolutely brilliant genius. It was a jockey bet for me. And the fact that he changed the company's name from Facebook to Meta at the top. He was at the top and he thought he needed to change the name to bring that business into the future. How many entrepreneurs or CEOs of a company that are at the top have a trillion dollar business and feel the need to change the name of the company to bring it into the next century, as you would call it? And I said to myself, wow, to me, that told me everything about what that guy's thinking. And it told me is he's not going anywhere, right? That's another guy that, like, he's a CEO. He created, this is his whole life. He's not going there because if he's out of there, I don't want to own that stock, okay? And so at the end of the day, when I look at businesses, I'm always looking at this. Who's the CEO that's running that company? That's the bet you're making. That's where you see some businesses where somebody takes over this decrepit thing that's going on and they turn it into the most unbelievable business that they could, you know, turn it into. And that's the only thing you're betting on, in my opinion. There's a lot more, obviously, but that's the number one criteria for me is who's the CEO?
Scott Clary
You know, it's interesting because again, you mentioned, like the. The fact that you bought and sold this business multiple times. I've seen many times where you have this incredible. And to sort of further your point, there's always this incredible founder, CEO that builds a business and then it's sold to private equity or it's sold to a strategic buyer and then it goes to shit. And. And it's because the person isn't there anymore. And.
Michael S. Leibowitz
Well, I sold the business to private equity, okay. Before I sold it the last time, okay? So I told you about that business. I bought it, I sold it back. I sold it in 2016 to private equity. And then me and a private equity firm sold it again. Okay? The private equity funnel, I'll name them, because they're great, is Stone Point Capital. And they always understood that they couldn't run the business. They understood from the beginning who the guy is or girl is that's running that business, okay? And that's it. And when we got an offer to sell it, they said, we'll own this business with you forever. We don't care, okay? But if you want to sell it, we'll sell it, too. And again, it's the same thing. So you have private equity, you have people that, you know, companies that buy businesses and the really smart private. And I'll just give you another example. When I sold that business, I had another offer for it that was more. I chose to sell it to those guys because they've been around the block 500 times. I knew they would make me more money on the second hit, and they were going to let me run that business how it needed to be run. Right. And that's the other thing again. They were making a jockey bet. It's like, who's, you know, listen, after Douglas Elman, I got calls from, you know, other, you know, private equity funds that I did business with in the past. And every one of them called me and said, hey, is there anything for us to do with you here? They were making the jockey bet about me. Yeah, it was the same thing. Right? That's all what it's about. There's other things you have to diligence, too. But the number one thing again, I had a thing on my family office website. I don't think we have that website up anymore. But it was a quote that I had and it said, you can't do a good deal with a bad guy and you can't do a bad deal with a good guy. And like, the truth, it's the truth. And you know why you can't do a bad deal with a good guy? Because ultimately businesses goes up, down, it's dynamic, it's this and that. If you're doing it with the right person, you'll figure it out. You'll figure it out.
Scott Clary
You'll adapt as an investor, you just have to figure out that right person, the one founder, the one CEO that's really the person you're building or team. But the question or the point is, how do you take that idea and translate it into running a whole company? So how do you take the idea of finding that right person and then you just deploy that against the whole company so that you always attract the right people?
Michael S. Leibowitz
Well, there's always stages of everything, right? So it's not all come. You're not going to come up with it all day one. It's not going like, all right, we're going to put out this blueprint. I got this great CEO, I've got this great cfo, I've got this great product. And here you go. Here's the plan for the future. I've been at Douglas Elliman for nine weeks. My business plan has changed 15 times. Okay? It may be different next week, okay? And what I mean by that is, is that I keep learning new things, I keep meeting new people, I keep running across different things within the company and I adapt to it. And if I said something to somebody two weeks ago and they. And now I changed it and they call me up and say, but you said this, I don't really care, okay? I'm gonna do what's right at the moment that it's there. And if you're not a CEO that doesn't know how to adapt to current events, you're the wrong CEO. And you're running the business with your ego. Because the only person that won't change is a person that's ego is in the way, right? So for us at Douglas Elliman, our business plan may be a little bit different. It may be a little varnished, a little, or maybe a little polished, or it may be adjusted in another month or two months. Right now, we're coming up with plans. Obviously, we have plans. We, I think about plans every day. We have a team that we think about what we want to do with the business. And I think generally we have a generalized blueprint of what we want to look like. But within that blueprint, things may change. Some people may change some business plans. Maybe somebody brings us an unbelievable idea that we say, you know what? Wow, we haven't seen that before. I'm not passing on that idea. I want to, I want to, maybe I want to implement that or a piece of technology that I think is transforming to our business. And now we need to basically, you know, turn the wheel a little bit to the left. That's what we're going to do. And we're going to be dynamic. And you know, the business that I sold, that we talked about, it felt like a new business the day I sold it, because we were always innovating, we were always doing new things. And Douglas Ellerman is going to be an entrepreneurial, mean, lean, innovative, winner attitude business that's going to be dynamic. Okay. And do really interesting things. Be on the forefront of our marquee real estate business with a name that is the best in the business. And we have an amazing opportunity here. And again, we may look a little different than Everybody else in 12 months or two years. And we're excited about that.
Scott Clary
No, I think that, first of all, I think that you have the right. I think the best CEOs are entrepreneurs. I truly do believe that. I don't think that you can airdrop an MBA and be as good a CEO. I mean, this is like a. I'm sure there's some great CEOs that do have the Ivy League education, but I think that entrepreneurs, just how fast they think and how comfortable they are with radical ideas, I think that's more and more who you're gonna have to see in that C suite. Because technology changes so fast, world changes so fast. You can't just be comfortable with an idea and set it and forget it. I don't think business exists like that anymore.
Michael S. Leibowitz
Well, it's interesting. So I, I met with a, an engineering, coding, you know, technology developer a couple of weeks ago, right. And we started talking about building a piece of technology for us. Okay. I did that before and one of my insurance businesses, we built technology. They told me it would take six to nine months to build. It took two and a half years. It ended up being great technology. But the insurance business is a different business than residential real estate. And the problem with building our own right now is by the time we finish building our own and conceptualize it and beta test it, it's probably going to be obsolete. Okay. And today there are so many companies out there building technology for residential real estate. We don't need to build it. We don't need to. And it really goes along the lines of what you're saying, right? Is that you want to build and you want to do all these things, but the market is moving so fast that, you know, and listen, we have competitors that went out and built, spent a fortune of money building technology. And we see their technology, it's fine. It's not groundbreaking anymore. It may have been groundbreaking two years ago when they released it. There's nothing groundbreaking about it. You could buy it off the shelf today. So you, you know, like you said, things move so quickly. If you're not willing to adapt as a CEO in business, in real time, forget it.
Scott Clary
And when you do, when you do make those acquisitions, you have to make that, you give that acquired company the air to breathe. So you don't just stifle the innovation that made them who they are too. Because I see that happen a lot as well. You acquire a company and then all of a sudden just corporate bullshit just destroys that entrepreneurial innovation that made that company so great.
Michael S. Leibowitz
Most of the time when you see acquisitions and you know, at that company, I was with NFP while I was there, we did 400 acquisitions, okay? So you see every bit. And again, it gets back to, who are you buying? Who is that person? Because you don't want to buy a business. And the people that built it created a great leaf. Yeah, of course, like we don't, we don't want to buy a business, right? That the people. Because we're buying a people business unless we buy a product, you know, so you want to make sure that those people that you're buying are going to stay and are motivated. And like you said, most. Douglas Hellman has bought other brokerages that were profitable before we bought them and now they're not. Okay, well, what went wrong there, right? Did you buy the wrong entrepreneur? Did we put too much bureaucracy on them? You know, did we not innovate? So for us, if we're going to look at an acquisition, it's going to be an accretive from day one. It's going to add value from both businesses, right? So let's say we pay a 5 multiple for something, right? We want our effective multiple post closing to be a two or three, right? Because there are operating efficiencies. We have the platform. Maybe they don't. Or maybe we've got redundancy someplace and we're going to fold them in and eliminate the redundancy. So, like, you know, those mathematical decisions. And then again, you have the people aspect of it, too. And that's why it's also important to take your time. Don't find a deal like this is the greatest thing in a rush to close it, because the diligence period is an incredible period of time to find out about the people that you're dealing with. People show themselves, right? So go through that. It's like the interview process. Don't do one. I heard one person in my life on the spot, okay. When in my insurance business. And just so you know, she was one of the best people I ever hired. Okay. But that was lucky.
Scott Clary
I think that was very lucky.
Michael S. Leibowitz
That was lucky. My. My process after that is like a 5, 6, 7, 8, 9, or 10, you know, period of time, you know, to hire, because you learn a lot in that process.
Scott Clary
So let's talk about. Let's talk about you stepping into CEO position of Douglas Element. So you were on the board first, and what made you the jockey that the board wanted to bet on?
Michael S. Leibowitz
It was an interesting scenario because I was around the company even before I had owned an insurance business with them many years ago that we bought, that I bought, and they got a piece of the business, and then we sold it. I knew the management team pretty well for a long time. Then when we were public, I was on the board. You know, I said a lot when I was on the board. I always had kind of, you know, my ideas of what I think we should be doing or what we shouldn't be doing. Some things I listened to, some things didn't get listened to. I knew a lot of the people there. We also had the unique scenario of a CEO that was very involved and a very dynamic person in that business, you know, for a long time. And, you know, he was a guy that we knew was a board. You know, he was seven. He's 76 years old. You don't sit on the board of a public company with a. A CEO there and not be talking about secession. So we were talking about secession for a long time. We actually had one board, and then we had a bunch of people that got off the board, and then some came on. So we had some new board members, you know, as well. But it was just a very difficult position to fill for us. When Howard decided that, you know, he was, you know, finished being the CEO, it was very difficult for us to, you know, I think if we brought in a regular industry player, we. I don't think that was right. I think we needed a fresh set of eyes on it. I think everybody thought that I knew a lot of people in the business. I was at a unique slice of time in my life that I actually wasn't doing something full time. Yeah. So to speak. So I just think that the moment at that point was right. And I think, you know, when, when it got brought to me that one of the other board members said to me, you should do it, you know, I kind of shook my head a little bit. And then we kind of all, you know, talked about it and that's when it happened.
Scott Clary
Yeah. Was, was it an easy transition? Was it messy? What was it like?
Michael S. Leibowitz
Well, anytime you go into a brokerage business, that is so, you know, we've got close to 7,000 real estate agents that all, you know, a lot of them think they're the CEO of the company too. Right. They all want to have a big voice, they're all entrepreneurial, they're very aggressive, you know, in a good way.
Scott Clary
That's actually a difference from other companies. Right. Because if you walk into a CEO position of a non professional service or non brokerage business, then the employees, they don't think they're the CEO that they could do.
Michael S. Leibowitz
Yeah, you want to keep your job, you're not going to say a word. You're going to, you're going to call that new CEO and be like, oh, is there anything I could do for you? You know, how can I help? Right. This was like, am I staying? Am I going? Why should I be here? What are you going to do for me now?
Scott Clary
I never thought about that, but that's that brutal.
Michael S. Leibowitz
You have no idea. Okay, listen, we have like 800 employees, okay? And incredible people. We have some incredible people that work at Douglas Element. Really incredible. And. But the agents are like, all right, well, why should I stay here now? I mean, I don't know you, I don't know where you come from. You're not in the residential real estate brokerage, you know, So I went on a marathon of literally trying to speak to or see every single agent that we had. And they're really important people. But I will tell you, 99.9 of the conversations that I had were positive. I, I. One or two, I had one or two conversations, one or two out of thousands that were not enjoyable for me. The agents were amazing. Douglas Element has an unbelievable group of agents that are entrepreneurs, that are hungry for change, that are hungry to make money, hungry to grow. And I have met some amazing people. I can't Even like, imagine like that, you know, Now I would, like. I would have never met these people, you know. So some of the relationships that I've developed over the last couple of months with them have been amazing. And the employees of the company are truly amazing as well. And we've got, you know, normally when you come into a business, right, you think, all right, who do I have to bring in from the outside? That's your normal thing. Not here. Here we've got enough resources on the bench. They just need the ability to have autonomy, to be in an entrepreneurial. You know, prior management was older. They had a different way of thinking, you know, and all that. Listen, there's nothing wrong with older, right? There's, you know, you need experience. And, you know, I'm not 30 either, okay?
Scott Clary
So I'm not 28.
Michael S. Leibowitz
Yeah, exactly. I'm not so young myself. But. So we've got some great senior people. Matter of fact, I elevated one of them, you know, that we elevated a guy that's. I think he's in his 60s.
Scott Clary
I think.
Michael S. Leibowitz
I don't even know. But, you know, so I think that we've got some great senior people. We've got some great, you know, youthful people. We've got a real mix, and we like a real mix. We want everybody from all over the place, but really amazing. But it was. It's really a challenge when you go in to become the CEO of a company and you've got independent agents that can leave tomorrow.
Scott Clary
I mean.
Michael S. Leibowitz
I mean, there's nothing that holds them back.
Scott Clary
So what. What would make somebody want to stay? Because I don't come from a real estate world at all. I have no idea. I don't even understand how some people choose the brokerage that they, you know, they hang their license at. To me, it just seems like a crap shoot because I'm not in this space. So what makes somebody actually want to stay versus go?
Michael S. Leibowitz
Well, listen, I think. I think the other thing is, you know, a lot of agents, I think, look to the company. At the end of the day, it's about the agent, right? It's about who they are. They're building their own business. We have what they call teams as well, which is teams of agents actually create their own that create their own brand. It's like a brokerage within a brokerage. But I think people believe number one in their brand. They think they've got a great brand that gives them the ability to sell more, gives them the notoriety of that brand, I think the resources. But I think ultimately it's the people. I think people want to work in an environment where they trust the management team, they like them, they think they're going to take the company to a good place. And I think that's the one of the main reasons that people come or go at a brokerage. And I think there's a lot the company can do, I think there's a lot I can do to give them the environment that makes them the most successful, that they can be and want to be with us. And I think we are a really unique option for agents. We're not our, I think our competitors are much different. I think if you want, I think people, if they understood what Douglas Ellman is all about and our history and the people that we have, especially about some of the things we're going to be doing in the future, where the option, in my opinion, and I'm not saying that because I'm the CEO, I believe it. If I didn't believe it, I wouldn't be outing another reason why, you know.
Scott Clary
No, I get it when, when you walk into so real estate. All I know is that it's, it's old, it's an old industry. It's been around for forever. I'm sure there's a lot of legacy best practices that may not even serve people as well as they used to. And like you're alluding to sort of innovation and change and you're going to do things differently. You're going to be the name in the space. So what are some of the, you know, the quote unquote sacred cows that you have to, you have to kill right away that you think, don't serve agents, don't serve the actual buyers or sellers. Like, what is outdated? What is legacy? What doesn't, shouldn't exist anymore?
Michael S. Leibowitz
Yeah, I think that's a great question in the sense, because the residential real estate brokerage in general is becoming somewhat outdated. Right. And it's a changing business, right? You have the commission structures are changing, the competitive landscape of the business is changing. But then at the same time, the traditional business will stay. Right. You can't go see a home with a robot. Right? The robot's not going to negotiate the deal for you or tell you, you know, about your neighbors or about the school systems. And I mean, listen, you could pull that, a lot of that data on your own today and all that. You could do your own research and all that, but there's a lot of things we all can do as people, but we still hire people to do it. Of course, Right.
Scott Clary
And it is a emotional decision too.
Michael S. Leibowitz
Yeah. And we're busy. We don't have time to do everything and you know, all of that. So I think that, you know, ultimately, you know, this business is changing. When you talk about sacred cows, we don't have any sacred cows. We are a non discriminating business that is there to make it better. So there is no one. I'm not. This is another, was another advantage I think of me becoming the CEO is that I don't have any legacy relationships that I need to protect. I don't have any legacy projects that, you know, I, you know, bet the ranch on that. I need to make sure work or else I look stupid. Right. I, I have none of that. I only want what's best for the company. What's going to make us a better business, what's going to make us a more profitable business. That's all I care about. And my ego is checked at the door. I don't need to be on tv. I don't need to, you know, you know, do any of it. I, I just want to basically make sure that we build a company that's going to, you know, last for the next hundred years. Like we lasted for the last hundred it. So there's nothing, there's no sacred cows here.
Scott Clary
So then look outside. There's going to be brokerages that aren't going to survive. Why do you think some brokerages won't survive? You don't have to name names obviously, but in terms of practices, why do you think they won't survive?
Michael S. Leibowitz
Well, I think some won't survive because the financial condition, because of some of the conditions that some of the decisions that they've made have not been that smart and they put themselves under the gun. Right. The most important thing is making sure you have your capital reserves because you're going to have ups and downs in cycles. And if you can survive those cycles within those negative cycles are the times you should be the most opportunistic. But if your financials are not in order, you can't do that. Okay. So that's one of the reasons some of them won't survive. I think some of them are chasing business models for the wrong reasons. And they're not focused on profitability, they're focused on revenue, revenue, revenue. Well, that's great. But at some point it has to be earnings, earnings, earnings. Right. So I think that, you know, and there's a lot of people in this business, in the residential, there's a lot of them. Yeah. But you know, when you get to the bigger ones like us, there's not a lot of them. And I think I would not be running those businesses the way some of the people I'm not going to obviously mean, you know, are running them. And I'm, I'm trying to run this one much different than it's been run in the past, and I want to run it different in the future. And I think there's a lot of things that we can do to bring this business into the future that I don't think are that hard. We just, you know, we just have to have our plans, you know, the right way and do and execute A.
Scott Clary
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Michael S. Leibowitz
Standard from what I I'm. I was always a guy that never really paid much attention to his competitors.
Scott Clary
But I don't know anything about real estate. So I'm trying to figure out. I'm trying to figure out the most the Most, you know, illuminating questions to ask about, I think.
Michael S. Leibowitz
No, I think. I think you're asking the right question. I think what's interesting about it is that I think that a lot of the residential real estate brokers are following the playbook. Let's just hire as many agents as we can, and that's what our competitors are actually doing. We don't want to do that. Number one. We don't want to create a crowded train, okay? We don't want to be where, you know, you're holding onto the, you know, onto the pole, you know, and you got a person's nose, you know, half an inch away from you. We don't want to be the crowded train. We want to be the luxury brand with quality agents, and we want the right agents, and we're going to be selective on the agents that we hire, and we're not going to hire every agent for. Because we think that we can make a ton of money on them. Yeah, we want to make money. Of course. We're in the business of making.
Scott Clary
You're not in the business of churning and burning?
Michael S. Leibowitz
We're not in the business.
Scott Clary
Correct.
Michael S. Leibowitz
We're not in the business of churning and burning. We're not in the business of, you know, we want a honorable play nice in the sandbox. We want agents that can be collaborative with one another where everybody wins. They don't have to worry about being stabbed in the back. And I only say that because, listen, it's not me. Michael Leibowitz didn't invent this stuff, okay? The residential real estate business, like every business, not just residential real estate, have, you know, people that aren't so honest and all that. And listen, you're a big company. You're always going to have that issue. But I think what we want to do is really target the right agents and the right places that are going to do business in a way that you want them on your team and not just hire anybody for the sake of it, which is what our competitors are doing.
Scott Clary
And when you get. I mean, that's a bad experience for the agent. That's a bad experience for the. The buyer and the seller. When you just have a massive amount of people because what's your brand?
Michael S. Leibowitz
You're also. We're going to ruin your brand if you have some bad person out there, you know, carrying around your business card. I don't want that. And if we'll make. If we have to be a little smaller for that for now, like, one of our mottos internally is shrink to grow.
Scott Clary
I Like that? Yeah. No, I mean quality, quality wins. I mean if you think about from my world, it's, it's product led marketing and product led growth. And what's the center of that is having a good product. If you don't have a good product, yeah, you can market and you can, you know, push it out to the masses. But if people, it's not, it's just going to let people discover a shitty product. Quick with her.
Michael S. Leibowitz
Right.
Scott Clary
You have to have that good product. And in real estate, agents are the product. Without sounding like crass, but they're the, they're the thing that makes the business grow. So if you just accept anybody and everybody, then you have a bad customer experience, correct? Yeah. What, I mean there's been a lot in real estate. I would actually lean on you to sort of educate me as to some of the things that have happened with like commission structures and things like that. And there was obviously the, the, there was a massive amount of legal and lawsuits around commission structures. And that was earlier this year for people that are listening, that are in tune with that, which would probably be agents. What, what are some like insights or words of wisdom around whatever was the outcome of that, like how should that affect how an agent does their job or how they interact with buyers and sellers.
Michael S. Leibowitz
Yeah, I mean it hasn't had as big of an impact on the industry as one would think. I mean, there's some paperwork obviously, which is. Nobody wants more paperwork. Right. So it's created, you know, some more paperwork. I think it also is creating a little bit more, you know, the buyers and the sellers kind of know where they are a little bit more in terms of who's paying the commission, you know, and who's getting the commission and how is that being broken up? I think that's probably going to create a good thing for the industry ultimately where you'll have people that are much more professional. I think it makes it a more professional transaction, but you got to roll with it. I mean that's, that's the environment we're in. You have to adapt to it and we'll adapt to it. And we're all adapting to it. It hasn't thrown the business into. We have a lot of other issues that we think are much more important than we need to deal with. Believe it or not, wasn't it, it was like the.
Scott Clary
Not. It was like the nar. Yeah, yeah, yeah.
Michael S. Leibowitz
It was a lawsuit. NAR and lawyers, they got, they made a lot of money. You know, we all, we always do.
Scott Clary
Make a lot of money.
Michael S. Leibowitz
Yeah, we all paid a lot of settlements. You know, you've got some, you know, again, additional paperwork you have to do in terms of disclosure, and we do that, but there's a lot more things in the residential real estate business going on than just that.
Scott Clary
Okay. Yeah, gotcha. What is keeping your agents up at night then?
Michael S. Leibowitz
Listen, I think, you know, when you're. I was always a guy that, you know, I always owned the business, right. So I always worked on commission. I always got a piece of the, of the revenue. I never got a salary. So I think for agents, you know, they don't know where the next dollar is coming from. Right.
Scott Clary
But that's always been the case. It's not.
Michael S. Leibowitz
It doesn't. It does, but it never gets easier. I'm gonna. I'll give you an example. Okay. Obviously, you know, I've obviously made a lot of money. Okay. But I spend much less as a person than I really could. Okay. My kids actually push me to spend more money. They don't think I enjoy myself enough. But I think what it comes from is that I never knew where my next meal was coming from, so to speak, Even though I made money early. Right. I was really young, but I still have the mentality that I need to have X amount. Because, you know, this is, you know, this is actually the first time I ever got a salary, by the way, really, like a technical salary. So I, I. And so I really relate to the agents, really, you know, how they think. And they don't know where their next commission's coming from. It's their business. You know, they don't, you know, they're not on a salary. They buy their own health insurance. They have all of that. And I think what keeps them up at night is the traditional things of how am I going to get the next listing, is this deal going to close? You know, I think those are the typical things in 23, 24 were very difficult years, you know, in residential real estate. I think 25 is going to be a much better year. So. And I think we're going as a company for, for my agents at Douglas Elliman. We really want to be supportive, helpful, entrepreneurial with them, you know, do everything we can to get their commissions up through everything that we can do for them. And, you know, we really want to be a partner and be really helpful to them because we're really all in it together. And, you know, a lot of, you know, companies will say, oh, the agent splits or whatever. We don't make money on whatever B.S. okay, we make what we make on these, on the agents. They make. They get what they get from us. This is the nature of the deal. We all need to accept it and be. One plus one is five, right? This is the reality we're in. Okay? Whatever the commission structures are today, other companies and managements may not like it. It's what it is. So let's figure out a way to coexist in an environment. Thrive, right? And, and grow our numbers. The greatest way to get along and be happy together is make all the numbers go up. You'll get a bigger, more dollars on your bigger percentage. We'll get the dollars on whatever percentage we get and we'll all win. And that's how you got to think about it.
Scott Clary
Do you have advice for agents? Because again, like that, paycheck to paycheck, it's very stressful. Do you have advice for agents just in terms of how they operate so they don't have to deal with that as much?
Michael S. Leibowitz
Don't overspend, okay? If you're looking at a $3 million house and you can afford three, don't spend five, okay? I tell it to my kids all the time too. Yeah, okay.
Scott Clary
It's good.
Michael S. Leibowitz
Life within your means because it makes you. Again, I was never like an overspender, so I always had capital and that's what made me a much stronger player. Right? But listen, there are other people give you this, the opposite analogy, right? Someone like me would say, oh, spend and go crazy. Why? If you tell them to do that, they'll keep working even harder and harder and harder and they'll make more commissions and more commissions. Okay? There's truth to that. But I would rather be a little bit more caring and tell someone, you know, that like, try and live within a reasonable, you know, have fun, enjoy yourself. You only live once. I'm all for that, don't get me wrong. But also, when you're running your own business, it's very important to know that you got a rainy day fund for yourself. It's slow, you know, 100%.
Scott Clary
And listen, you also, you know, if you tell somebody just like spend everything they've ever made, you know, buy the, buy the five million dollar home, go on the vacations, whatever. There's a point where they can burn out. They're no good anymore.
Michael S. Leibowitz
And it's mentally draining, of course.
Scott Clary
Yeah, of course. Mentally drained. What keeps you up at night? Not the age. What keeps you up?
Michael S. Leibowitz
Nothing.
Scott Clary
I love it.
Michael S. Leibowitz
Nothing. I have to tell you. Nothing. I don't, I don't wake up in the middle of the night worried about what's going on at Douglas Element. I actually go to sleep. I've really kind of always been that way. It's funny, my son said this to me yesterday about something and I remember, I forget what it was. Oh, I wasn't feeling that like, you know, from all this flying and all. I had a cold that like wasn't going away or whatever. As almost every. Yeah, everybody's been, you know, you shake enough hands, you know how to catch something, right? I literally not joking. When I go to sleep, I can't wait to wake up in the morning. I cannot wait. My favorite part of the day is putting CNBC on at 5:36am I have coffee. The minute I get up, like literally I walk straight to the coffee machine and I cannot. I am so excited to wake up. There is nothing that keeps me up at night because you can deal with everything. I'm going to be less effective if I'm worried about it and if I'm nervous about it. And you know what, if you have your health and everything else is going well there and your family's pretty healthy, everything else you could deal with. Okay, so maybe we have some financial thing we need to deal with. We deal with it. Maybe we have some crazy agent that's screaming at another one. Okay, you deal with it. I mean, nothing really keeps me up. I'm going to be honest.
Scott Clary
I love, I mean that's, that's the way you have to operate from. Because then your, your decision making framework is just healthier. I think that when you operate from places stress and anxiety, I think that decisions you make are just horrible.
Michael S. Leibowitz
Yeah. And I'm always thinking about offense. I'm always thinking about, all right, what can we do to grow? It's like, what can we, what are we doing tomorrow that makes it bigger? Are we going to hire this agent? Are we going to get that? Are we to get this new development deal? Today I had a two hour meeting with a bunch of great developers. I have three. I can't talk about what they are, who they are, but three unbelievable projects that I love. I'm not saying it because we're going to get the projects. I think they're amazing. So like that's what makes me excited. You know, we have our holiday party tonight. I'm excited. I can't wait to go. Same thing.
Scott Clary
If you thought about a piece of, of your life, you were just a pure entrepreneur. Now you step into like, you know, C suite role. What would Be some things that you carry over from entrepreneurship. What are some things that definitely don't translate?
Michael S. Leibowitz
I carry it all over all of it. I'm not joking. I. I literally apply every single thing that I learned as an entrepreneur and in my other businesses to what we're doing at Douglas Element. The only difference at Douglas Element is we got. I have so many people and resources that can help me as an entrepreneur. It was like I was doing. I felt like I was doing it all myself.
Scott Clary
So this is easy then compared.
Michael S. Leibowitz
It's much easier. I have much more resources. The only thing is, I'm also an operator at heart. So I also say to myself, do we need all these people? I mean, I don't. I mean, we have so many people and so many resources. Like, do we really need all this? So that's the evaluation process also that I'm going through now and saying to myself, you know, do we need X number of people in accounting? Do we need X number of people in this piece of the business or that piece of the business? So I think it all translate over. But again, it's interesting. Your question before was so interesting when you asked me about is it easier to come into a brand that's already established or one that you started? And this is so much easier, so much easier than starting the business. That was hard. This is not. This isn't so hard.
Scott Clary
It's just because you have. You have so many resources. Obviously, you don't want to have bloat in the company either. How do you make that. This is a lesson for somebody that has built a company and they have. They have a whole bunch of resources, but they want to make sure they're still efficient. So how do you make sure that you are operationally efficient? What's your. How do you think through that problem?
Michael S. Leibowitz
Well, you have to, number one, look at what the problems are, right? So if people are complaining about, you know, this check didn't get paid, or this, you know, you know, you know, AR is complaining about, we didn't, you know, someone's complaining we didn't collect this dollar or we didn't pay this we. Well, then your radar's got to go up that maybe I have an issue in the accounting department, maybe my systems aren't up to snuff, or do we have the right people there? Who are they reporting to? And I get. Every day, right. I talk to agents every day. I promise you, by the way, that's.
Scott Clary
That is. I mean, if you are CEO, you have to be talking to everybody.
Michael S. Leibowitz
I'M talking to the agents. I get the complaints about what's wrong. I get. I had one yesterday. I was on the phone with someone that said, I don't know, something happened with her check and it went to the wrong address. And first thing I said there was, why are you still using checks? You know, can we wire to you? I mean, but again, that's what it gets down to. Right? We had an agent that still is waiting to get a check in the mail. What does that tell me? That tells me that our systems maybe should be upgraded. Maybe we're using an antiquated system because it should be something where she could see the thing pop up on her phone. Right. So that's. There's a multiple failures there. Yeah, right. You got, okay, go up to our head of accounting, go down to our IT people. Why is that not connected? Look at the environment we're in. That should be a click, boom, boom, done. We shouldn't be talking about that right now. You know, there's a lot of that. There's in our marketing department. Right. Some people in marketing feel that decisions aren't made at a local level, that everything gets made out of hq. Right. Well, there's some accountability to why that should happen. But then there's also the thing is that most things are local, so maybe we should have a hybrid kind of approval process in this, you know, so there's a lot of things. And so for me, I'm a very good listener. Okay. I listen to it all, I hear it all. And when I talk to people every day and people mention things that are going on, a light goes on in my head to say, all right, I got to call this one, I got to call that one, and this and that. And that's why it's really been interesting, is that we've made so much progress. Because in my everyday travels, I've literally been to almost the whole company in the last eight weeks. I think I visited. I think I've got two cities to go. And I've learned all of this on the road. I've hear every single thing that they say. And then I go and I try and go to the various departments to try and fix them.
Scott Clary
How much of. How much of your success you think has been. Has been tied into you being so hands on?
Michael S. Leibowitz
It's all of it. You ever see the movie Bronx Tale?
Scott Clary
Yeah.
Michael S. Leibowitz
Okay. When he says, you know, I could live in any neighborhood I want to. You know why I live here? Because I could spot trouble in an instant. Trouble is like a Cancer, you got to get it early or it kills you. Okay? You are not involved in the business and you are not hands on in the business. How are you going to see the accounting example I gave you probably would continue for five more years if I didn't speak to that agent. And then tell me something. We had some other technical kind of thing going on that somebody told me about in California that I dealt with. If I'm not hands on and I'm not out there, who's going to do it? And listen, the company's been around for 100 years. So the problems that we have now have probably been going on for the last five or 10 or 20 years that nobody has fixed. Now we're fixing them.
Scott Clary
Hands on. It's always hands on, 100%.
Michael S. Leibowitz
Forget it. Go do something else. Go buy a company that makes tractors or something. You know, don't be in a business like this.
Scott Clary
Even that, I think if you're not hands on is a point where you're going to be disrupted by somebody who is, no doubt.
Michael S. Leibowitz
Okay. Active management. Yeah, very active.
Scott Clary
What would be some of the tough questions that I wouldn't know from shareholders that they're asking you that you want to put on the record?
Michael S. Leibowitz
Well, I don't know if I. If I was a shareholder, you know, obviously we're public, so I'll be, you know, I got to be a little bit careful. But me being a shareholder, what are the questions that I would be asking? I'll give you that. I'll give it to you better, right? Because I. So the same thing as you say that I'd want to know who my management team was. I would want to know who the CEO is. Obviously, like we're talking about. I would want to understand the competitive landscape. I want to understand our financials. And I speak, just so you know, I speak to a lot of our shareholders. Okay. I spoke to one of our shareholders last week. I was on the road. I was in Texas and on the road. You know, he emailed me a couple times and, you know, he was away, then I was away, whatever. But I got on the phone with him and the first thing he said to me was, wow, you're the first time I was able to get someone on the phone like this. And I said to him, which is 100% accurate. I go, I will speak to any shareholder. They can own one share or a million shares anytime they want. Because if they tell me one thing, okay, that can help our company. Okay. Or increase our value, I want to hear about It. And I said to him, I never understood how Disney would ignore Nelson Peltz. You know, Nelson Peltz was all over Disney. They didn't want to give him a board seat. They didn't want this. The guy's a productive guy. The guy's a multi billionaire. He's made an absolute fortune. Why would you not give him. He owns a lot of stock. It's not like he's a guy that owns no stock. Why wouldn't you put him on the board? What are you afraid of? Okay, So I never could understand at me, but this is before being in the role that I'm in, why a CEO wouldn't want to talk to shareholders. Betting on you. Yeah, Stock. Because they're betting on you. Okay? So we. I listen, I spoke to another, a much bigger shareholder a month or two ago. I said, I'll tell you anything you want to know, obviously. And obviously it's got to be within the SEC and the rules and all that kind of stuff. I'll tell you anything you want to know. And I said to him, which is true. I go, listen, if we don't do well, I promise you one thing, it's not going to be out of a lack of effort, okay? I literally, at that time, I was literally sticking three hours a night. I'm not joking, okay? I said, I'm putting 247 into this. I'm doing the best that I can do. I'm working my butt off like you've never seen. That's the only thing I can guarantee you, okay? And I think we've got a good plan. Okay? I think we've got a tough industry that we're in that's going through a lot of changes. Interest rates are high, right? There's a lot of headwinds that have nothing to do with us, that are macro, you know, difficult to deal with. But the one thing I could assure every single shareholder is I am working my butt off like you've never seen, okay? And I bought a million shares of stock, like, three, four weeks ago, okay? My own money.
Scott Clary
You're invested in this.
Michael S. Leibowitz
Okay? With my own money. And I can tell you another thing is as long as I'm the CEO, I'm a buyer of a stock, not a seller of a stock, because I bet on myself. As simple as that. And I think that, you know, we're working really hard. But you know what? When you say this, I don't look at. I have, like, three constituencies, right? I've got shareholders, I've got agents, and I've got employees. And I'm really a believer in this, though. I believe if you treat your agents the right way, if you treat your employees the right way, who are your team members, right, Your stock will take care of itself. Okay, I'm not a believer in, oh, my God. I got to focus on the stock to stock the stock. Of course I care about the stock. My, my own compensation is tied to the stock. I own stock that I bought in the market. Okay, I was, I care about that, but I care about where I get to at the end. And I really believe the result of a higher stock price will be the. I'm sorry, the work with the agents, the work with the employees, the work with getting the company's financials where it will be ultimately gets the stock where we need it to be. And it's a, it's a multi pronged thing and all of that matters. It's not like you just say, all right, I'm focused every day. I'm making sure my stock price goes up. If you do everything that you need to do, the result is your stock will go up.
Scott Clary
Is that a, is that like a novel way of thinking?
Michael S. Leibowitz
Well, listen, I, I sold to private equity before and one of not Stone Point, but a different private equity kind of business that I sold to. All they cared about was they would literally on the day 15 of the month, they'd be like, what's the numbers going to be like in 15 days? What, 12 days left in a month? What are the numbers? They would literally call us every day and say, what are the numbers going to be? And I used to say to them all the time, guys, we can get to the same place without running the business this way, because it would rattle the hell out of our employees. They felt so under pressure. They felt like they couldn't work. They felt like they were getting denied the resources that they needed to grow the business. And I just thought the tone and how they did it, I thought that if we just let me deal with this, that's what I would say to them. Okay, I promise you the numbers will be where you want them to be. We don't have to be like a Darth Vader ish way of thinking. Right. Ultimately, at the end day, because what makes stocks go up are earnings and good businesses. And the only way you can do that is by having agents that are really happy to be there, employees that are working hard every day. So it's a cumulative thing. It's not a one, oh, my shareholder, my shareholder, my shareholder it's almost like.
Scott Clary
When you focus on stocks, you're focusing on the lagging indicator, not the leading indicator of success.
Michael S. Leibowitz
Yeah, yeah. Well, some of them, they, the, they're, they're way higher than they should be. And then reality comes in. All of a sudden the stock goes to nothing.
Scott Clary
Well, because you don't add those, you don't define mentals correct.
Michael S. Leibowitz
Where you do a bunch of press releases that are BS and you know, a bunch of people buy the stock and it goes up. But at the end of the day, you pay the piper. You got to build a good business. And if you build a good business, you should have a good stock price.
Scott Clary
What, what do you want to tell people about the future of Douglas Elliman? What you're going to do, things to look forward to.
Michael S. Leibowitz
Listen, I think there's a lot to look forward to for us because I think that, you know, we're very focused on our technology, we're very focused on our brand, we're very focused on our marketing. We think there's an international opportunity for Douglas Elliman. I think that the residential real estate brokerage is going through a lot of changes and I think the size of our company and where we are positioned in the market is going to give us a lot of opportunity. And that opportunity is going to be organic. But I think we could have some M and A opportunity. I think there's going to be, we're going to get the ability to swing at our pitch. We're going to do it the right way and we're going to wait for the right pitch to come in. But I think that we can ultimately be really opportunistic, whether it be in more residential real estate brokerage, buying more of that, whether it be more diversified, you know, type businesses that are out there. We're looking at some really interesting things now. You know, on the insurance side, on the technology side, on, you know, traditional type businesses like mortgage and title, the things that everybody, you know, does. Obviously nothing specific. You know, we're a public company, obviously, so, you know, but we're always looking and everybody should know, you know, that we're always looking.
Scott Clary
I love it.
Michael S. Leibowitz
Okay.
Scott Clary
What would be some last words of wisdom for the entrepreneurs in the audience? We've gone through a lot and gone through a lot of your career, but something else you just want to leave them with.
Michael S. Leibowitz
Yeah. What I would say is, is that, you know, I kind of get back to that, you know, hard work thing. You also have to be smart, right. I mean, you can't Just be a hard worker and that's it. You have to pick something or go into an industry. The first thing is do something that you really enjoy and you love doing because you will work harder at it. You'll enjoy working harder at it. Be really straightforward and honest. Get as many constituencies and people around you. I had a lot of mentors. Some don't even know that they were mentored to me as I was coming up and look at successful people and try and replicate their habits. So like I had known, I was lucky that I had met a lot of successful people as I was growing in my 20s and 30s and I would, I would try and replicate their habits. So it's not really even so specific of can I replicate the business that they're in, all that. You always have that. But look at the things they do, like calling someone back immediately, responding to emails and texts right away. Right. Those were habits that I saw of really successful people. I mean, billionaires that didn't have to do that and they still do it. Me, I'm one of the most responsive people you will ever see in your life. I'm still that way. I have not changed. And it just, it breeds good things. But watch what successful people do and try and emulate them.
Scott Clary
I love it. What would be one habit outside of just being responsive and being on it and sort of all the, sort of the, the traditional entrepreneurial tropes and whatnot that I think people understand. What else would be like a unique habit that you've adopted that's worked really well for you?
Michael S. Leibowitz
Well, you always have to be thinking outside the box. You've got to be like, I'm always thinking like, I'm going to leave here, get in my car, I'm probably going to look at all of my texts and I'm going to be thinking about the meetings that I had today and what I could do with them, what I have tomorrow, like constantly.
Scott Clary
But you give yourself space to be creative, to think.
Michael S. Leibowitz
So in the shower, that's where I have my space.
Scott Clary
I was going to say no, because if you, if you hammer yourself all the time with non stop work, you can't really think outside the box because you're always.
Michael S. Leibowitz
Yeah, that's, that's 100 true. You do have to find. You know, I'll tell you what I did do for a long time I haven't done in a while. I used to journal.
Scott Clary
Yeah. Yeah.
Michael S. Leibowitz
I used to journal about a lot of different things. I mean, that's. We could have a podcast on how I. How I came to journaling and how I kind of used to study the mind. I used to read a lot about the human, human behavior, the mind, why people do what they do, how people think, you know, why people think a certain way. How to judge how somebody thinks, looking at somebody's actions and see the actions that they took is because of the way they think. I've spent a lot of time over the last 20 years studying how the mind works. And it has done it has given me enormous tools to be able to truly function in an environment and see what people do, the good parts of it, the bad parts of it. Maybe not judge something that you may have judged before. Right. But the other, that's the other thing I would actually say to that. You know, I'm glad this came up because that's what I really should say is study the human brain and its emotions. And really YouTube has an. As I have people on YouTube, you could literally. I'm not a big book reader. I'm a big. Watch a clip for 15 minutes or 20 minutes, maybe read 10 pages of something, whatever it may be, find my information online. But try and understand human behavior and human thinking because it will help you enormously as a leader and let you see through people. My ex wife says to me, I'm a human lie detector.
Scott Clary
I like that.
Michael S. Leibowitz
And it's, it's, you got it, but you got to do the work. You have to do the work. And I will tell you, I have done the work for 20 years. And when you asked me before is what doesn't keep me up at night? I used to be kept up at night 25 years ago, 20 years ago. I used to worry about a lot of stuff. I used to have anxiety of, oh my God, what? This doesn't work, that doesn't work. I don't have that anymore. I really kind of did a lot of learning about the mind, the inner child, why you became who you are, you know, what's the. What emotional things that you have left over from childhood. There's a lot of things that go on there that you really need to understand.
Scott Clary
What I mean, that is an entire podcast. So we don't go down that rabbit hole. Maybe one time you can do another one. But what would be words of wisdom for people that do have a lot of. Again, entrepreneurs have a lot of anxiety. Entrepreneurs have a lot of built up emotion. Is there some quick ideas, meditation? Is that it? Meditation?
Michael S. Leibowitz
It's very hard to do. It's very hard to. When you're an entrepreneur. You have so much going on to stop your mind. Even if you do 5 minutes, 10 minutes, whatever it may do, go find a chair that's really quiet. Close your eyes, Come up with a mantra. I did tm where they actually give you a mantra. Okay. Come up with a mantra that clears your mind. Do some meditation. Obviously, exercise is a very big thing. I play paddle padel, you know, like five days a week. There's a lot of things you can do, but you gotta slow that mind down. You gotta slow it down. It's really, really important because that five or ten minutes that slows your mind will give you three more hours of power in your mind, you know?
Scott Clary
And I also believe that if you're already. If you're always running with anxiety, then it's like elevated cortisol. It's a clock on your life. It can just be.
Michael S. Leibowitz
Stress will kill you.
Scott Clary
Okay. You've gone through a lot. I want to give people a chance to connect with you, reach out with you. Where should they go? You use any social LinkedIn? What do you want to.
Michael S. Leibowitz
I mean, I guess. I mean, I guess I'm on Instagram. I mean, I don't know how people can, like, reach out or whatever. I mean, obviously I'm always. Or where.
Scott Clary
Where do you want to send people? Doesn't have to be you.
Michael S. Leibowitz
If you.
Scott Clary
If people want to learn more about Douglas Element, if they want to get in touch with. I mean, they have the website.
Michael S. Leibowitz
They have the website. We have. I think we have, like a name. Do we have, like an email? I don't know. I don't know if we want to give that out. Right. That would be crazy, the amount of email.
Scott Clary
We don't have to give any email out, but if you want to, any links you have, just put them in the show notes, if there's events coming up or anything, whatever, it doesn't matter.
Michael S. Leibowitz
We'll do that.
Scott Clary
Last thing I like to ask, obviously, you've had a lot of. A lot of different lessons you've spoke about on the show. Out of all the things you've learned, if you could only pass on one thing to your kids, only one lesson, the most important one, what would it be?
Michael S. Leibowitz
Don't worry. Worrying is the worst thing you can do. It's use. It's useless. It doesn't help you. And nobody on their deathbed said I didn't worry enough. I wish I would have worried more. Right. Worry is the worst thing you can do. And I was a worrier too. I used to be a worrier. And I undid it.
Podcast Summary: Success Story with Scott D. Clary – Episode Featuring Michael S. Liebowitz
Title: Michael S. Liebowitz - Serial Entrepreneur | How Taking Calculated Chances Built a Business Empire
Host: Scott D. Clary
Release Date: April 11, 2025
In this insightful episode of the Success Story Podcast, hosted by entrepreneur and business executive Scott D. Clary, listeners are introduced to Michael S. Liebowitz—a seasoned entrepreneur with over 25 years of experience in insurance, finance, and real estate. As the President and CEO of Douglas Elliman Inc. and founder of Harbor Group Consulting, Michael shares his journey of building, leading, and scaling high-impact ventures. This episode delves deep into Michael's strategic decisions, resilience in the face of crises, and his unwavering commitment to success.
Michael begins by recounting his early days, growing up in Staten Island with modest beginnings. At 21, he exhibited remarkable fearlessness, venturing into the insurance business despite limited resources.
Michael S. Liebowitz [00:00]: "I was fearless at 21. I grew up in Staten Island. Very modest beginnings. So I grew up always wanting to kind of get out of that. Doing that at 21 was tough, but I was never afraid of it."
Starting MSL Associates from a shared desk, Michael quickly established himself by building strong relationships and delivering exceptional service. Unlike many entrepreneurs who navigate multiple failures, Michael’s initial ventures thrived, setting the stage for his future successes.
Michael's ability to identify and seize opportunities is evident in his strategic decision to merge his businesses into National Financial Partners, backed by Apollo Investment Fund. This move exemplifies his knack for scaling operations and navigating complex financial landscapes.
Michael S. Liebowitz [05:49]: "When I came into Douglas Elliman, the number one reason that I took this role was that the Douglas Elliman brand was a built brand, already internationally known as the best brand in residential real estate."
A pivotal moment in Michael's career was his role in insulating the World Trade Center before and after the 9/11 attacks. His foresight ensured comprehensive coverage, significantly impacting both his business and the rebuilding efforts post-tragedy.
Michael S. Liebowitz [17:02]: "We handle the insurance on the World Trade Center really for 9/11. And that business after 911 went through the roof."
His testimony during the World Trade Center trials not only bolstered his reputation but also established him as a leading insurance advisor to major financial institutions globally.
Central to Michael’s success is his emphasis on work ethic and building a committed, high-performing team. He believes that surrounding oneself with the right people is crucial for sustained growth.
Michael S. Liebowitz [13:04]: "The one common denominator between the people that are incredibly successful and aren't is work ethic."
Michael champions a culture of dedication and mutual support, fostering an environment where agents and employees feel valued and motivated to excel. His hands-on approach ensures that every team member aligns with the company’s vision and goals.
As CEO of Douglas Elliman, Michael underscores the importance of operational efficiency and adaptability. He discusses the challenges of inheriting a legacy brand and his proactive measures to modernize processes and integrate technology without losing the company’s core values.
Michael S. Liebowitz [46:13]: "I keep learning new things, I keep meeting new people, I keep running across different things within the company and I adapt to it."
His ability to pivot and embrace change has been instrumental in maintaining the company’s competitive edge in the dynamic real estate market.
Michael offers valuable advice tailored to both entrepreneurs and real estate agents. For entrepreneurs, he emphasizes the importance of honesty, building strong teams, and continuous learning.
Michael S. Liebowitz [35:09]: "You have to be a motivator. You have to make people want to be on your team because you can't do it alone."
For real estate agents, Michael advises financial discipline and maintaining a rainy-day fund to navigate the uncertainties of commission-based earnings.
Michael S. Liebowitz [75:11]: "Don't overspend... Life within your means because it makes you stronger."
Looking ahead, Michael is optimistic about the future of Douglas Elliman, focusing on technological advancements, brand strengthening, and strategic acquisitions. He is committed to fostering an entrepreneurial spirit within the company, ensuring its longevity and adaptability in an ever-evolving industry.
Michael S. Liebowitz [89:39]: "I think there's a lot to look forward to for us because I think that, you know, we're very focused on our technology, we're very focused on our brand, we're very focused on our marketing."
In his closing remarks, Michael imparts a powerful piece of wisdom, encouraging entrepreneurs to let go of unnecessary worries and focus on constructive actions.
Michael S. Liebowitz [97:43]: "Don't worry. Worrying is the worst thing you can do."
Fearlessness at a Young Age:
"I was fearless at 21. I grew up in Staten Island. Very modest beginnings. So I grew up always wanting to kind of get out of that. Doing that at 21 was tough, but I was never afraid of it." [00:00]
Work Ethic as a Success Factor:
"The one common denominator between the people that are incredibly successful and aren't is work ethic." [13:04]
Leadership and Team Motivation:
"You have to be a motivator. You have to make people want to be on your team because you can't do it alone." [35:09]
Operational Adaptability:
"I keep learning new things, I keep meeting new people, I keep running across different things within the company and I adapt to it." [46:13]
Financial Discipline for Agents:
"Don't overspend... Life within your means because it makes you stronger." [75:11]
Embracing Change for Future Success:
"I think there's a lot to look forward to for us because I think that, you know, we're very focused on our technology, we're very focused on our brand, we're very focused on our marketing." [89:39]
Final Wisdom:
"Don't worry. Worrying is the worst thing you can do." [97:43]
Michael S. Liebowitz’s episode on the Success Story Podcast offers a deep dive into the mind of a serial entrepreneur who has successfully navigated the complexities of building and scaling businesses. His emphasis on work ethic, strategic adaptability, and fostering a motivated team provides invaluable lessons for both budding entrepreneurs and seasoned business professionals. Michael’s journey underscores the importance of resilience, continuous learning, and maintaining a clear vision, making this episode a must-listen for anyone aspiring to achieve lasting success in the business world.