Dayssi Olarte de Kanavos — then Dayssi Olarte — was studying at New York University’s Schack Institute of Real Estate and selling gym memberships at an Upper West Side synagogue when she met Paul Kanavos at a dinner party in 1991.
Paul was working for his family real estate development firm, Florida-based F.L.A.G., which stood for Florida Acquisition Group. Their conversation turned to environmental impact statements, which Dayssi had just covered in her final project.
“I thought I was the utmost expert in this topic at the moment,” Dayssi recalled. “Basically, everything that he was saying, I was tearing him apart to pieces and he just sat there like, ‘who’s this person telling me my business?’”
Yet within two years they were married and starting their own company, Flag Luxury, which now owns 10 properties in Miami, Orlando, Las Vegas and New York. The company has developed $6 billion in projects and has another $2 billion in the pipeline, including a plan to combine and expand the Ritz-Carlton South Beach and adjacent Sagamore Hotel. Flag has entertainment and retail projects but focuses on luxury hotels and residences, despite Paul’s initial foot-dragging.
“When we started our family business, he said to me at first, ‘I will never be in the hotel business. My dad had so many hotels. He built so many properties and we got burned on so many of them,’” Dayssi recalled. And I said, “Well, if you’re not doing that, we cannot be partners because that is the only thing I will do.”
Of course, they went into hotels.
Dayssi leads the development and construction side of the business and specializes in guest experience. Paul heads up finance and acquisitions. Their two oldest children, Peter and Sophia, recently joined.
Dayssi sat down with The Real Deal at her newest hotel and first ground-up project, the Ritz-Carlton NoMad, to talk about her career path, Flag’s current projects and what it’s like working with your husband for almost three decades.
This conversation has been condensed and edited for clarity.
Born: December 1963
Hometown: Bogota, Colombia
Lives: Upper East Side, Manhattan
Family: Husband, Paul, three children (Peter, Sophia and Nicholas)
You grew up in Colombia and New York. Tell me about your childhood.
I was born in Colombia and was about 1 ½ when I came here. My mother moved us to Greenpoint before it was cool. It was this amazing place to be, a very Polish community. A lot of people didn’t even speak English. When I went to middle school, my parents divorced, and we lived in Colombia. Living there between the ages of nine and 15 was transformative for me. Before that, I was just like any other New York kid where you really think New York is the center of the universe and nothing else exists outside of it. I returned here for high school. We moved to Forest Hills because the school system was good. My mother didn’t realize that it was a heavily Jewish neighborhood, and so coming from Colombia where 99 percent of the population is Roman Catholic, that was a whole new education for me to learn more about the Jewish culture and community.
Did you feel like a fish out of water?
Honestly, I feel like everywhere we lived, we were a fish out of water. When we first got here we were this Colombian family living in a Polish neighborhood. When we moved back to Colombia, we were “la gringa.”
You went to the Cornell School of Hotel Administration. Was your plan always to develop hotels?
The hospitality business when I was living in Colombia became really hot and trendy, so the top schools were adopting [it] as a major. My sister really wanted to be in the hotel business and she went to Florida International University. I followed in her footsteps but decided to go to Cornell instead. [When] I was a sophomore, I realized that I never wanted to operate a hotel and didn’t want to be a manager. It was devastating to me because I loved the business. I loved the design, the architecture and, you know, it just seemed like it was a perfect fit. But then when I really understood what operations meant, I realized that — especially as a person with ADHD — that’s a really hard business.
But we had a great dean’s lecture series. There was a real estate developer there and he showed us pictures of empty land and then these beautiful hotels that he was building. He showed us the experiences that he wanted to create and how he brought his imagination to life with the help of different hotel companies and architects and the whole thing. I thought, well, that’s something I can do.
“There are so many buildings in Miami Beach that are ultra luxury, but they have like a million square feet, and that just doesn’t feel so luxurious, to live with so many people in one building.”
But then you pivoted after school and became a leasing broker. Why the switch?
The thing is that it was very hard in 1985 to try to find a job with a real estate developer and I didn’t have any family in the business. I thought commercial leasing brokerage and being an analyst would give me an insight of who owns these buildings, who manages them and what is happening in the hotel world.
When did you meet your husband?
I felt that I still needed to learn more, so I applied to the master’s in real estate development and finance at NYU, and I was actually in the very first cohort. (That’s how old I am.) I had one class left to finish. A friend of mine was looking for investors for a restaurant. So I put together a group of people that I thought would be interesting for him and one of the people I invited brought Paul along. Paul was developing with his family in Florida and we ended up talking about the environmental impact statements.
When did you get married and decide to go into business together?
He asked me to marry him on the third date, and we had agreed to get married within a couple of months. I was looking to partner with two friends of mine in the graduate program to start developing real estate here in New York. And my husband said, “You know, I have to travel so much to Switzerland [where the Kanavos family had partners] and to Florida. I’m going one way, you’re going another way. I don’t know if our lives are gonna ever connect for us to plan our whole future together.” Then he said: “You know, my family business is dwindling down, my brothers don’t want to be in it anymore. We might as well partner together.”
How did you go from that conversation to Flag Luxury?
I started out as his analyst, helping put together offering memorandums and investment proposals and things like that to finish up some of the projects with his family, and then we were going to focus on our new business together.
What was a turning point for the company?
We secured the exclusive in Miami Dade for the Ritz-Carlton in the ’90s and then were able to build the Ritz-Carlton Coconut Grove and residences, the Ritz-Carlton in Jupiter and the Ritz-Carlton in South Beach. And now we’re working with our partners and another family that coincidentally I went to Forest Hills High School with who own the Sagamore Hotel right next to us at the Ritz in South Beach. So we’re annexing that and making that part of the Ritz-Carlton South Beach. Out of the 100 rooms, we’re creating 55 suites and we’re adding 30 ultra-luxury residences on the beach.
What excites you about the South Beach project?
There are so many buildings in Miami Beach that are ultra luxury, but they have like a million square feet, and that just doesn’t feel so luxurious, to live with so many people in one building. Living in New York on the Upper East Side, we have these co-ops that are not huge buildings, where we know everybody in our building, and it’s a really nice private way to live where your kids are running up and down the hallways and your elevator bank opens up into your apartment. So this is sort of that — but on the beach.
How has your role at the company evolved?
It’s changed a lot because we also started a family and I wanted to spend a lot of time with the children. And so I took on the kinds of roles, once I became a mom, that were more limited. Not roles where I would be available at all times and drop everything and work 24/7, the kind of effort that you really need to be a developer. I worked mostly on organizing the guest experience from the beginning and critiquing design but not really managing it. I managed our marketing efforts and things like that.
Once my kids started going to school full time, I started managing small renovations and then I started managing bigger renovations and then I went on to manage $100 million renovations and then the hotel where you’re sitting right now. This is my first new build.
So this is your newest baby. Tell me about the project.
We just opened up two years ago. I had the honor of my life to work with Rafael Viñoly on this project. I wanted to have a building that can stand the test of time and be of a great quality and of a great design. We have this very small footprint here. We were fighting for every square foot here. Everything had to be so efficient. And our goal here was to create the next-generation Ritz-Carlton, because customers at the Ritz-Carlton are getting younger and younger, and people are more willing to spend money on their experiences rather than on things. We brought in Chef José Andrés, we had five different interior designers here, three different lighting companies. It was complex and complicated, but I’m really proud that we delivered on that promise. And our average age here is 32.
What’s it like working with your husband?
We spent so much time talking about real estate in the beginning of our relationship, that’s all we talk about and that’s all we like to do. We enjoy looking at all the new hotels and all the new buildings and land. Over the years, we’ve each really focused on the things that we love and so it makes it easier to work together.
And now some of your kids are involved in the family business?
My two oldest kids decided to go to the hotel school at Cornell as well, which we did not push them into. But the truth is they grew up going to construction sites with us looking at land, looking at things that we were building and then seeing them actually being built, so they did develop an interest and an expertise. But we told them if you really do want to come into the family business, you need to get your own experience outside of the family business. You both need to work elsewhere, which they did. Sophia works in acquisitions and development. Peter works in construction and development.
And what does your third child do?
My third child did not want to have anything to do with what he calls the family school. He went to the business school at Georgetown and now works for Goldman Sachs in their equity derivatives department.
“We told [our kids], if you really do want to come into the family business, you need to get your own experience outside of the family business. You both need to work elsewhere, which they did.”
You climbed Mount Kilimanjaro. What was that like?
I thought it was going to be a lot harder than it was. You find people of all walks of life, all different levels of fitness doing this at all ages. That last climb, you start at 11 o’clock at night and then you climb until 7 in the morning to see the sunrise. There was one part of the climb in the middle of the night where my heart was just beating out of my chest, and I thought I could have a heart attack. I said to the guide, “I think maybe I need to slow down.” He looked at me like, “Hallelujah. We’ve all been suffering because you’re the oldest one in the group and we didn’t want to be the ones to slow down.”
You’ve had a lot of famous chefs cook for you. What’s the best meal you’ve ever had?
One of my favorites was David Bouley, who passed away recently. I was always trying to get into his restaurant and could never get a reservation. This is before Paul and I were married, but we were dating and I had to organize a birthday party for him. His birthday is in March, and there was a huge nor’easter. We called Bouley, and they said, if you can make it here, we will serve you. And then we got there and ate in our socks. We ate everything because he wouldn’t stop feeding us — he was so happy that people were in his restaurant.
What is the best advice you’ve ever gotten?
To learn to say no a lot more.
What’s the number one piece of advice you give to your kids?
I think to be authentic and to be true to yourself. And to not be afraid of hard work, of course.
What’s your favorite book?
Some of my favorite books are Colombian. But I also love Malcolm Gladwell books, like “Outliers” and “Blink,” and I love sci-fi too. I just started reading “Elon Musk.” I’ve always been a big fan. I purchased the Roadster, so I was an early believer in what he was doing.
Do you have a Cybertruck?
No, that’s definitely not my genre, but my little roadster is super cute and I drive it in Southampton all the time. It’s not a gas guzzler, and it’s so small that I’m the only one in the family that fits in it.