Michael Liebowitz says he’s ready to be an open book.
He stepped into the role of president and CEO at Douglas Elliman a little more than a year ago at a very difficult time for the brokerage. He took over after Howard Lorber’s sudden resignation, amid intense scrutiny and beneath the cloud of a weak stock price. In the months leading up to the CEO change, the company was also dealing with its connection to former top brokers Oren and Tal Alexander, who built their careers at Elliman and are in jail awaiting their sex trafficking trial.
Liebowitz’s background is in insurance, where he built a risk management empire.
Despite being an outsider officially, Liebowitz was plugged into the residential real estate industry for a long time before this gig. He met Lorber when he was in his early 20s and joined the board of Douglas Elliman in 2021. And he is partners in The Mondrian with Russell Galbut, whom he called “as connected a person as it gets” and counts other developers among his friends.
Still, in his early days as Elliman’s CEO, Liebowitz seemed like he was on the defensive, especially media-wise. Now that he’s got his bearings in residential real estate, he is ready to grow Elliman’s business (the company recently sold its property management business for $85 million), and to talk about it, he told The Real Deal in a wide-ranging interview.
Liebowitz, a Staten Island native, also discussed his long association with Lorber, whom he said he counts on for support, mentioning him more than a handful of times while acknowledging he’s taking the company on a new path.
The interview has been condensed and edited for clarity.
Born: December 7, 1968
Hometown: Staten Island
Lives: Miami Beach
Family: Two adult children
With The Closing interview, we ask for biographical information. You’re divorced, correct? Are you in a relationship?
Is this going to be in the interview?
It is in the interview.
Do we have to have it?
We always have it. Like I said, it’s a personal interview as well.
This weekend was not a good weekend for my relationship.
Stephen Larkin, Douglas Elliman’s chief communications officer, asks to “fact-check that later” and tells TRD that Liebowitz is still in a relationship.
Do you like being CEO of Douglas Elliman?
Love it.
What excites you about real estate?
It’s something everybody wants to talk about. In other CEO roles that I had before, I was in the insurance business and financial businesses, they’re only interesting to a certain group of people. Residential real estate is interesting to everyone. It’s glamorous, it’s fun, it’s just a great topic of conversation.
“You know what? I don’t give a fuck anymore. I don’t care what’s in The Real Deal. I’m going to run this business from a profitability standpoint.”
How did you get introduced to Douglas Elliman?
I met Howard Lorber when I was 21 years old, and I was on the board of the company.
Did you think that you would be in this role as CEO for the long term when you first took it on?
I’m not the type of person to go into something temporarily or short term. When I go in, I go all in. What’s a little new for me … this is the first time that I’m totally focused on one company, and it’s the only thing that I’m doing.
I had breakfast with some new agents we were recruiting, and I made a comment, “I really have to start meditating again so I can get my 15 minutes of slowing my brain down.” This industry, people are going 24/7, and I think you probably are too, right?
It’s not a nine-to-five job.
I’ve never known a nine-to-fiver. But this is another level.
Why did you stop meditating?
It was always hard for me to meditate. Meditation truly slows your brain down to allow for more space in your mind. It’s magical. I used to be a big journaler, and I need to start doing that again, too.
What was your childhood like?
I grew up in Staten Island, and my dad was a New York City taxi driver for 25 years, and then he was involved in the black car business. I was always very motivated to make money. It used to scare my mother, because she thought I was setting my expectations too high, and I’d be really disappointed.
Did becoming a parent change you?
I don’t know. I can’t imagine not having kids, and it’s amazing. I always feel like I’m kind of someone that’s always taking care of people. So it’s natural for me.
What’s your favorite thing to do with your kids?
With my older one, travel. My younger one is in the insurance business, so that’s fun for me. It’s something that I really know like the back of my hand, it’s pretty easy for me to help him and guide him.
What’s your next trip that you have planned with them?
My older son keeps asking me. Last year we did Dubai, and then I did a lot of business over there, so it was great. The year before we went to Japan. Thinking about Singapore next.
You built a career in the insurance industry before you began to dabble in real estate and advised Larry Silverstein to get additional coverage on the World Trade Center before 9/11. Can you tell us about that?
When I worked on that, I was maybe 32. It was a lot of pressure. The reason I wanted that coverage was I contemplated both buildings being destroyed, which everybody thought I was absolutely crazy for. How could both towers be destroyed? But when you’re evaluating risk, you evaluate every potential risk. The Silverstein people wanted to insure the buildings for much less, obviously, because of the premium, and I’ll never forget, they said, “Well, we have an engineering report that was done that will show $600 million worth of damage if the buildings were destroyed.” And I said, “Well, what happens if a plane hits the building?”
That’s crazy, Michael.
The morning of 9/11 I was driving to my office. I got a call from someone who told me a plane hit the building. I didn’t actually think terrorism, even though I set the program up so that they had to have terrorism insurance, which was a novel thing. They couldn’t have an exclusion for terrorism. No one did that before. That was never required in an insurance policy closing before.
We took Silverstein’s premium from like $4 million to $15 million, and back then, that was a fortune. It affected the numbers of their transaction, and they were very upset about it. But ultimately, the World Trade Center got rebuilt because of the work that we did. I testified in the trials. I was busy working post 9/11 on this claim, and it really took my business to a whole other level. But it was such a horrible event that made that happen.
Keep in mind, it was the Port Authority who was doing the lease [with Silverstein]. Their offices were in the World Trade Center. So there were people that I dealt with that didn’t make it. It was a tough time.
At your interview with Amir Korangy at TRD’s Miami Forum in 2024, you talked about all your ideas for the company. What changes have you made?
I kind of came out guns blazing. I had this vision, because I was on the board before, and I knew Howard for a long time, and he would listen. I had a lot of ideas, a lot of it was diversification of the revenue stream. But then I got into the business, and it was not possible to do all of those things at the same time.
So you are focusing on the core brokerage business.
We’re through our transition. We are so totally transitioned. We’re basically doing things on the recruiting side that Douglas Elliman never did before. It was not a recruiting company. It was a very entrepreneurial company, with Howard running the business. We weren’t really set up as a machine.
We’ve still got the highest price sales in the industry. We clearly own the luxury space with the Anywhere-Compass merger. We have no debt, we have a lot of cash in the bank. The bones of Douglas Elliman are incredible, like the bones of a house.
You were on stage, what, a couple of weeks after you became CEO?
I willingly walked into the fire, yeah.
And you answered his questions.
I’m not scripted. Nobody writes shit for me. That’s really what’s going on. And Larkin tries to, but I don’t ever read any of it.
Howard’s exit from Douglas Elliman was in part because he had [sexual] relationships with agents, according to an investigation into the company’s culture. What’s your response to that?
I wouldn’t really say that. Howard resigned. He did it on his own. We had conversations about how long he wanted to do this for. He made a lot of money from the Vector sale. He did this for a long time. He’s 77. We’re public. He wasn’t going to do this forever. I was there. The outside world sees it very differently than it really was. I have an affection for him. I know he has an affection for me. If it was a bad exit, there wouldn’t be.
What’s the last conversation you had with Howard?
I spoke to him last week.
What are you like as a boss?
I don’t see myself as a boss. I kind of see myself as a mentor to people. It gives me, you know, a lot of pleasure in being able to have superstars, and if I had something to do with getting them there…
Tell me about how the company culture has changed, if it has.
A lot of people think of culture from a drama standpoint. The big culture shift at Douglas Elliman internally is a culture of winning. That’s the difference of where this company is today than it was four and five and six months ago. [Then,] it was playing catch up. It was being worried about — nothing personal — what article is going to be in The Real Deal, about which agent we lost. Or we need to overspend to keep that agent, because we’re afraid it’s going to be in The Real Deal. You know what? I don’t give a fuck anymore. I don’t care what’s in The Real Deal. I’m going to run this business from a profitability standpoint.
What is the best advice you’ve ever gotten?
Don’t ever worry. Worrying only paralyzes you. The other thing is to be grateful. If you’re always in a place of being grateful, you’re never worried about anything.
You play padel. Is it a networking thing for you?
I try and play as much as I can. If I’m in Miami, daily. It’s not a corporate game for me, okay, it’s purely a social game. But really I just want the workout. I’m in it for the sweat, and you put your phone down for an hour and a half.
What’s your favorite Miami restaurant?
The Joyce on Española Way. You don’t know it? The Joyce is owned by a friend of mine, Andre Sakhai. It’s like a hidden place. It’s been open about a year. It’s very hard to get into it. It’s my favorite restaurant right now.
What do you order?
Oh, my God, they have so many things. They have an amazing fish sandwich, an amazing burger. They do this dessert, this ice cream dessert. Everything is good.
Favorite members’ club?
ZZ’s, or the club upstairs at Casa Tua.
What do you drive?
A Bentley.
What’s your style?
I think it’s always changing. When I lived in New York, I must have had 100 suits. And then I got out of that when I sold my companies. Now, I feel a little bit more compelled to wear a suit once in a while, but the truth of the matter is, I don’t really want to. Even though we’re a 100-year-old company, I want us to act like a new company. I think the CEO of a new company should be dressed the way I’m dressed. What am I wearing right now? A Tom Ford shirt or something.
What’s your brand of sneakers?
Kiton.
What has been your biggest success?
My children.
What industry-wide regulatory changes would you like to see?
I never thought I would ever say this but I think the industry should have a little bit more criteria. I won’t use the word regulation. It would benefit the industry if it took a little bit more to become a real estate agent than it does.
Is there anything you did not want me to ask today?
I will answer anything.
Do you have any non-negotiables?
Don’t fucking lie to me. If someone lies to me, I’m done, done. End of story.
Do you still consult with Howard about the business?
I absolutely will call him and say, “What do you think of this, and what do you think of that?” Again, I say this with affection, he’s like, my No. 1 fan. The [CEO] transition was relatively easy from an agent perspective, because agents all called him and said, “Who is this guy?” And Howard was like, “I’ve known him forever. He’s a great guy.”