Owners of the Brazilian Court Palm Beach, the Schlesinger family pulls back the curtain on business, life and love, including how to laugh about it all along the way.
A romance story perfect for the Hallmark Channel, New York real estate entrepreneur Bobby Schlesinger met aspiring comedian and Texas native Courtney Davis while she was working in New York City as Jared Kushner’s assistant. Fast-forward to a wedding in Vail, Colo., a home in Connecticut and two gorgeous red-headed children who travel back and forth with their parents between Westport and Palm Beach. While managing it all is never easy, the Schlesingers make it all look effortlessly divine, all the while telling plenty of jokes at their own expense. They’re giving us an insider peek behind the scenes of the family who owns the historic and iconic Brazilian Court Palm Beach, which will soon be celebrating 100 years on the island—a generational property, for generations to come.
Where did you two meet, and what set off those initial sparks? Was it love at first sight?
BS: We met at Kushner Companies’ leasing office in the East Village. I was looking at buying Kushner’s portfolio of apartment buildings in lower Manhattan, and when I went in for a tour, Courtney offered to take me around. I kept asking her pretty basic questions about the real estate, to which she had no clue. As the tour ended, she gave me her number and told me to ‘ let her know if I needed anything else.’ It’s definitely the most tempted I’ve ever been in my life, but I had a serious girlfriend at the time, so I didn’t act on it until I saw Courtney at a party a few years later.
CS: When Bobby walked into the office, I instantly fell in love. First off, he was wearing the most properly tailored Tom Ford suit I’d ever seen (I worked in the men’s department at Saks for way too many years). He asked me a ton of questions and I didn’t know the answers to any of them (nothing much has changed). But we talked about life and comedy the entire time, and I would have married him on the spot. I wrote him an email that night, but unfortunately, he didn’t feel the same because he never wrote me back! I ran into him a couple years later at a party, and he asked me out. I should have said no, but between his charm and my desperation, I was screwed.
What characteristics do you admire about the other person?
BS: Heart. She’s got more of it than anyone I know. And most recently, I find myself really impressed by her ability for self-reflection and her desire to truly understand herself. Wait, do legs count?
CS: He is the most creative person I’ve ever met, and annoyingly talented at so many things—writing, composing music, designing—he does the best accents and impressions I’ve ever heard (my favorite is a character he created from the Bronx named Ira Waldbaum who complains about noise in the city and whoever the current mayor is). Most of all, he loves unconditionally and is incredibly loyal to those who know him.
What characteristics drive you a little crazy?
BS: It’s like I live in Bergdorf Goodman.
CS: My husband likes to have a full and proper meal three times a day. He also has a very refined palate. As a woman who survives mostly off of cookies and frozen burritos, I find it impossible to live up to his expectations.
Once you knew it was time to get married, who popped the question and how did it go down?
BS: We got engaged on a hike in the hills of Litchfield, Conn. We were living in the city and one of our favorite trips was to take the train out to Connecticut for the night to stay at The Mayflower Inn. On the day that we got engaged, Courtney told me while we were getting dressed that I was never going to propose to her, and that she should just give up already on expecting me to. I couldn’t exactly tell her that I had a ring in my backpack, so it was a very quiet train ride that morning.
CS: I had to make up that I was moving on and never speaking to him again if he didn’t marry me, like any good partner does. Aft er two years, he finally gave in and proposed to me on a hike (of course, it’s always when the girl is wearing no makeup!).
Where did you tie the knot and why was it special?
BS: We got married in Vail, Colo. Vail is our happy place. I grew up skiing there as a child. It was the site of our first vacation as a couple. It just has so much meaning to us. We can truly be our best selves in Colorado. There’s no pretension, no pressure—just an incredible amount of natural beauty.
CS: Vail is where he had a home and grew up skiing with his mom—his best friend and someone I never got to meet because she passed away from skin cancer before I met him. She was a very strong force in his business and especially at Brazilian Court, where she designed the entire property. To honor her, I’d love to work with brands that support skin cancer research or prevention.
From Texas to New York, to Westport and Palm Beach, your family history is a little bit of everywhere. Where do you feel most at home and why?
BS: Personally, if I had to pick a place where I feel most at home, it would have to be Colorado. I’m most comfortable there. But for our family, we have been really fortunate to call Palm Beach home in the winters and Westport home in the spring, fall and summers. We’re very lucky to have that flexibility, but we only do that because both places feel like home whenever we are there .
CS: I’m from Austin and feel most at home there. Their catch phrase is ‘Keep Austin weird,’ and I’ve always taken that phrase to heart. I absolutely love Palm Beach, though, and I think the people I’ve met here are so genuine and fun.
Where do you feel the most relaxed and why?
BS: 7AM in bed with my 4-year-old son watching Paw Patrol and him getting excited to show me a new vehicle. His little feet squirming under the covers. It’s heaven.
CS: Floating in the ocean waves on one of those days when the water is crystal clear in Palm Beach.
“For our family, we have been really fortunate to call Palm Beach home in the winters and Westport home in the spring, fall and summers. We’re very lucky to have that flexibility, but we only do that because both places feel like home whenever we are there.”
What inspires you about your family heritages? And what do you want for your own two kiddos?
BS: A lot of my identity is grounded in being Jewish. Not so much religiously but culturally, ethnically and historically. We’ll teach that to our kids for sure, but it’s up to them to choose what pieces of their heritage they identify with and what path to follow. Being decent, kind people with open minds and open hearts is all we want for our kids and for ourselves.
CS: I want my kids to feel validated every day. We really work on gentle parenting, which is harder than we thought. I’m proud that I have both a Jewish heritage (from my mom’s side) and a Mexican heritage (from my dad’s side) and that I can pick and choose different parts I want to honor in my life now. As long as we teach our kids to be confident and happy people who lead a life with integrity, I’ll be satisfied! But first, we have to get through potty training.
You manage an extensive real estate and hospitality portfolio with your family. What have you learned through working with family that has inspired your outlook on life? Fidelity. Work is tough. Business isn’t always sunshine and roses. Having partners who you trust with your life makes getting through any rough patches that much easier. Plus we all agree to pause meetings and go to the conference room during Yankee playoff games.
What’s the best piece of advice that someone has given you? Warren Miller: ‘Tell me what you need, and I’ll show you how to live without it.’
Who do you look up to and why? I am my father’s son. In attitude and in sentiment, that’s who I am. Every person tries to be his own man, but I had a great teacher, who I’m very lucky to still learn from every day.
I imagine life with Courtney is pretty entertaining. What is one of the craziest things she has ever done? She came home one night with an incontinent geriatric pitbull that was about to be put down. She saw her on Instagram and decided to step in and save it. In the morning, once I’d cooled off, we tried to take the dog for a hike in the woods. On the way there, the dog shit all over Courtney’s car, to the point where when we tried to have it professionally cleaned, the guy told us that this car would never be the same.
“In 2026, The Brazilian Court will be celebrating its 100-year anniversary, and we intend to keep the hotel in our family and continue making it the best place to stay in Palm Beach for the next 100 years.”
What does the future hold for you, both for your business and your family? There’s always a new and exciting project around the corner. I’m finishing up a big project on the Brooklyn waterfront right now, and then I’ll move on to two new complexes in Stamford, Conn., and Great Neck, N.Y. In the last year, we’ve made a big investment in Tampa, and we are creating a lifestyle brand called Innovo Living that I think will be very cool. The Brazilian Court is our crown jewel, and we are constantly thinking of new and exciting ways to make a property that we feel is already incredibly special even more so. We are celebrating our 20th year of partnership with Daniel Boulud this season, and we are very proud of the reception that the community has given The Brazilian Court Salon. In 2026, The Brazilian Court will be celebrating its 100-year anniversary, and we intend to keep the hotel in our family and continue making it the best place to stay in Palm Beach for the next 100 years. On the family front, we’re just waiting for the next season of Paw Patrol to come out.
When did you know that you wanted to be a comedian? What’s that journey been like? The way that I connected most with my mom growing up was through making her laugh (whether that’s good or bad), so I’m guessing it began when I was very young. My first stage experience was at The Improv in L.A. after I signed up for a comedy class, and it was so much fun—even though I completely bombed. There is something about telling a group of strangers your most embarrassing moments that really makes me feel alive (and that, folks, is also why I’m in therapy!).
What do you love most about life right now? I have been enjoying getting to know who I really am lately. After having kids, my sense of self and purpose have taken on a lot of turns, and I’m starting to feel more grounded in who I want to be. Now, I try to enjoy the things I can control and worry less about the things I can’t.
How would you describe your sense of fashion? My fashion is a lot like my personality—it changes every day (sorry to my husband)! I can never plan my outfits ahead of time; I always see what my mood is first—but my go-to is usually something short! Like any good suburban mom, I basically buy anything Hailey Bieber wears. I am very, very lucky that I have a husband who likes to shop as much as I do, and who has great taste. Our favorite thing to do together in Palm Beach is have an Aperol spritz at Sant Ambroeus and then do a Saint Laurent haul after.
If you were planning the perfect day in Palm Beach, what would you do? I would have croissants at Vincent’s in Lake Worth, lie in the sun and go for a swim, go shopping at Fivestory or Royal Poinciana Plaza, have a drink at the bar at Le Bilboquet, get a massage and my makeup done at The Brazilian Court, and end my night with a risotto dinner under the most romantic lighting ever at Café Boulud! Oh, and I’d try to see my kids somewhere in there.
“I have been enjoying getting to know who I really am lately. After having kids, my sense of self and purpose have taken on a lot of turns, and I’m starting to feel more grounded in who I want to be. Now, I try to enjoy the things I can control and worry less about the things I can’t.”
What’s your favorite way to give back to the community? Some of my favorite organizations are Best Friends Animal Society, Pink Aid (benefiting breast cancer patients) and Homes for Hope, but I think it’s helpful to remember that giving can be done every day by smiling at someone, helping someone pick up things they dropped at the grocery store (even though that’s usually me) or bringing a bottle of wine to a friend who had a tough day. I think that’s what life’s all about.
Photography by: PHOTOGRAPHED BY BAILEY ANN
