Bess Freedman is the CEO of Brown Harris Stevens, the 146-year-old brokerage known for its luxury niche. Freedman was named co-president of the firm alongside Hall Willkie in December 2017 and was appointed the company’s first CEO less than a year later. That promotion put her at the helm of one of the oldest and most prestigious firms in the city and charged her with overseeing about 1,000 agents — who collectively closed about $4 billion in 2017 — at a financially precarious time for residential brokerages. A native of upstate New York, Freedman graduated from Ithaca College and from the University of the District of Columbia law school. She then worked at the Legal Aid Society before joining the Corcoran Group, where she spent 10 years until jumping to BHS in 2013. At BHS, which is owned by Terra Holdings, she’s earned a reputation for bringing fresh blood and ideas to a traditional and stodgy operation by spearheading a flashy rebranding and pushing for new technology. She’s also emerged as an outspoken critic of StreetEasy and pushed the brokerage community to syndicate listings itself through the Real Estate Board of New York — a position that has pitted her against other brokerage heads at times.
Name: Bess Freedman
DOB: May 31, 1969
Lives in: Upper East Side
Hometown: Troy, N.Y.
Family: Divorced, two kids (daughter, 16; son, 13)
What was it like growing up in Troy? Troy was a dump. I shouldn’t say that. It’s industrial. It was known for its glove factories, and it had a small-town mentality. My dad had a scrapyard that was my grandfather’s. When I was 12, we moved to Albany, which was more sophisticated.
Have you been back to Troy since? I go to the cemetery to visit my dad. He died in a car accident when I was just starting law school.
What impact did his death have on you? I lost my biggest cheerleader. I was in shock and devastated for a long time. He was very generous, and so I’ve tried to live my life the way he would have wanted me to.
Shifting gears, how long did you practice law? After law school I worked as an assistant state’s attorney in Montgomery County, Maryland, where I met my ex-husband. We moved to Spain [where he’s from] and lived there for a year. Then we moved to Miami for a year. We moved back to New York City on Sept. 11, 2001. We met the movers at the apartment at 7 a.m.; I remember it like it was yesterday. The mover was like, “A plane just hit the World Trade Center.” It was completely surreal.
What kind of cases did you handle at the Legal Aid Society? I worked as a juvenile rights attorney, so I was helping kids who got into trouble and representing babies who were born addicted to crack, and trying to figure out parental rights. It was very hard stuff to deal with. It’s not a coincidence that everybody who came in that door was poor.
Are there any cases that have stuck with you? There was a young man who was 14 or 15 and got arrested for stealing. He was going from foster care to foster care. I remember thinking this kid had so much potential. His circumstances just put a ceiling on it. He was black, he was in a gang, he didn’t have money. How the hell was this kid ever going to do it?
How did you go from that world into brokerage? I was on maternity leave from Legal Aid. I was at my mom’s knitting store — the Wool Gathering [which she owned] — on the Upper East Side. I met this woman who said, “You should get into real estate.” I met with Corcoran and I was like, “Ooh, I can make my own hours and do all this stuff?” It seemed so freeing.
Did you ever look back after switching careers? I never felt the sense of regret. Even the mistakes I’ve made have taught me. Like when I finished law school, I couldn’t get the job I wanted in a law firm. But I went to Legal Aid. If I had taken a different turn, where would I be? Maybe at a law firm sitting behind a desk, bored shitless.
How do you square your Legal Aid experience with brokerage, which involves selling properties to the 1 percent? People say all the time that I’m such a contradiction. Like you’re supposed to be either this or that. I understand sophistication and high-end, billionaires and private planes. But I also like to help people and will hit somebody on the subway if they don’t give their seat to an old person.
Where did you get your moral compass? I had great parents. They were crazy and funny and just spilled love onto everybody. They were warriors of doing the right thing. When I was 10, my mom took me to see Bella Abzug. I remember she stood up and was like, “Women belong in the House … of Representatives.” She lit a fire in my body that I was going to be this social advocate.
What kind of parent are you? My kids would say annoying. I learned all of Drake’s album “Scorpion” and sing all the songs. My son is like, “Mom, please. You’re embarrassing us.” But I think I’m fun.
What’s it like to have a 16-year-old daughter? It keeps me very current. Do you know what tea is? Tea is gossip. When you tell somebody, you’re spilling tea. She’ll say, “Mom, what tea is brewing at BHS?”
What’s your relationship like with your ex-husband? He’s one of my closest friends. It was just kind of like, love faded. There was just no more romance. I go to Spain every summer and stay with his family at the beach. It recharges my batteries. When we’re at the beach, there’s this thing called a chiringuito, or beach kiosk — they have fresh fish and grill it with salt. You eat it with an icy cold beer. It’s the best ever.
Do you think you’ll get married again? Of course, I would consider it. It’s just, what do I need it for? I’m probably going to get criticized for this, but I feel monogamy is very overrated in the sense that I don’t think you have to have that stamp in order to be fulfilled. And I’m kind of picky. I’m very protective of my personal space.
You were named CEO of BHS in November. Was there any tension with Hall, who ran BHS for so long? I don’t think he ever wanted the position — at least that’s what he said, and I believe it. He kind of took a minute, was shocked for a second, but then called me like literally five minutes later and was like, “This is the best thing that’s ever happened to this company, and I’m going to help you every step of the way.”
You’ve advocated for innovation at BHS. How has the old guard taken it? [Some] are frustrated with the fact that we changed a lot of things. We changed technology. We changed the marketing, and we’re going to keep changing. We have to. You can’t be static.
You’re active on social media. Is there a topic you won’t touch? There was a time when I’d put up negative posts. I think that was a mistake. One of my best friends was like, “I love you, you’re incredible, but I think you can use your voice in a more positive way.” And I said, “You’re right.”
What was the fallout from the recent fight you got into with billionaire John Catsimatidis? You called him a “disgusting troll” after he called an alleged sexual assault by Supreme Court Justice Brett Kavanaugh a “romp.” After the story hit, I got emails and calls from people saying thank you. I think they appreciated that I stood up to somebody who is powerful — who has a lot of coin and influence and is friends with the president of the United States. If there was negative fallout, I didn’t hear about it.
How do you feel about your reputation as the industry’s progressive voice? It’s just who I am, and I’m honest about it. A lot of leaders out there are very neutral. I don’t know how to just be transactional.
Do you ever feel like the deck is stacked against you — or other women who have to work harder to succeed? Not me in particular. I’m fortunate because I’m in New York City. It’s very progressive, and I have a lot of support. But I do think, in our environment, women still play not to lose and men play to win. I kind of do play to win, which has helped to get me where I am.
Do you have any vices? Scotch, single malt. French fries. I love cigars. My best friend sends me cigars. I love the smell partly because my dad used to smoke them. I like to have one, but it’s a little nostalgic for me.
What are your hobbies? I do kickboxing. I love music. I play mahjong as much as I possibly can with a group of women I love. One’s a writer, one’s a lawyer. They were all moms at the Rudolf Steiner School. We went to Turks and Caicos recently and had energy healers, a private chef and played mahjong on the beach.
Do you guys play for money? No, never. We just play for fun and for bragging rights. We love to brag, you know?
Where do you live? I’m on 85th and Second Avenue in a cond-op. My mom’s in the building. I like Second Avenue because I feel like I’m in the middle of the vibe. I have a little deli under my building that I call, and they deliver my coffee and newspapers while I’m in my pajamas.
What keeps you up at night? Oh God, that’s a good question. What concerns me deeply is how divisive our environment feels. I see a rise in anti-Semitism, racism and all that stuff. I worry about the fact that people are so angry.
You’re Jewish – was your family religious growing up? My dad was. We kept kosher. My dad was so proud of being a Jew, and we always carried that in our back pockets. I’m more spiritual — though I’m on the verge of being atheist sometimes. But culturally, they’re my people. The food, the humor, that’s my vibe.
What’s your biggest pet peeve? I hate waste. I hate people who are late, too. And I hate rude. I hate bullies and I hate indifference.
—Edited and condensed for clarity.