An inspiring family is the Maccioni family [owners of restaurant Le Cirque] because it is an old-school concept—the three sons all work in the business and are passionate about it. [Their father] Sirio was a window washer in Italy, and he has done something incredible: He’s taught his sons how far hard work can get you. I think it is hard for a lot of families who are extremely wealthy and successful; the parents worked so hard, and they don’t want the kids to struggle. But then they don’t know the value of a dollar.

How did you learn the value of a dollar?

If we wanted an increase in our allowance, we had to create a business plan to convince Dad. He gave us a test once where instead of getting money once a week he gave it to us once a month. We had to learn to manage our money.

That’s not the typical over-the-top image of Warner LeRoy. There’s the story of your bat mitzvah, which featured airplanes performing acrobatics.

Yes, but my Bat Mitzvah was tough because my dad only told me I had to study for it about a year before. He had decided he wanted to throw a big party.

But there were definite rules. You didn’t get a car until your second year in college, things like that. My dad loved to shop and he loved to be over-the-top, but there were rules. And my mother definitely helped. The biggest arguments that I remember growing up were my father wanting us to get dressed up and go to a dinner party and my mom wanting us to stay home and do our homework.

Did you know you would be taking over the business once
he became ill?

He was very sick for about 15 months before he passed away, but actually he was recovering. So it was a surprise when he died. He had promoted me to director of operations of the Tea Room when I was 21, which was the most amazing moment of my life. It was a huge honor, and I thought that was a lot of responsibility.

And then you found out you were named CEO.

With the will. It read, "I love all my children equally, but there will be one boss and one boss only, and that will be Jennifer." When you’re the youngest of four, that’s surprising. But my siblings were very dedicated to my father and to the family; they just didn’t want the pressure of running the business. My sister Carolyn said, "Jenny, you don’t have to do this. If you don’t want to, we’ll figure something else out." That was a lovely thing.

Ownership of the business is shared equally among you?

Yes. I’m in charge in terms of the work, but we’re all owners. I think it’s the best thing. A family business is hard. If you have ever worked with a friend, you know that they usually aren’t your friend after that. It is a very fine line, and who wants to go home and have dinner with your family and talk about business all night?

It hasn’t been easy—you had to close the Tea Room.

We were finally making headway right before 9/11. We had merged things between Tavern and the Tea Room, and it was going really well. If 9/11 hadn’t happened, we definitely would have made it. We lost more than $1 million in business in the six months after 9/11.

The will also alerted you to some surprise debt.

There was a building loan of about $15 million from a partner, Vornado Realty, on the Tea Room. It had to be paid, and I got a little over $15 million for it. That was a huge accomplishment. I had people telling me the building was worth $6 million and to file for bankruptcy. But I kept saying, "I’m not sure that’s the right thing to do." And thank God. Moments like that are building blocks of confidence.

And now you’re expanding the Tavern brand for the first time.

We’re opening a restaurant near West Palm Beach in Wellington, Fla. We had interest from Las Vegas and Atlantic City. But the first thing to do was to have the original Tavern running tip-top. It is the highest-grossing restaurant in the country, with about $37 million in annual revenues.

So business in New York is improving?

Revenues are steady. We’ve put a lot of money into it. I put $1 million into the kitchen in 2002. All the chandeliers have been repaired; all the murals are new.

After 9/11, there was a drop in banquets and parties. Now it is about evenly distributed—$18 million in private events is incredible for one location. People think it is a huge space, but it isn’t. It is 27,000 square feet, but 13,000 is kitchen.

I wouldn’t be expanding if I weren’t confident of where we’re at with the business. We are more than ready. The new spot is the Equestrian Club by Tavern on the Green. It is a private country club, a different feel from the original Tavern. Wellington is becoming like the Hamptons. People go there from November to April. The horse show is on a 300-acre property with 5,000 horses—the top horses, the best competitors and the wealthiest people. You have the owner of Nextel, Bruce Springsteen and so on. There are tremendous amounts of charities and events. They need a place like this.

Do you have a home there?

I rent every year, but I’m going to buy at the end of the year. The investment possibility is just tremendous.

We’re partnered with Wellington Equestrian Partners. They want to turn the town into a 12-month community. They have a future project to build condos, hotels and a convention center. They bought a [restaurant] and asked if I wanted to see it. I had fantasized about this place, but it had never been run the way I thought it should be. This is my dream. I am a passionate rider and I love to go to Wellington. I’d go to parties, and people would say, "I wish you were down here to cater it," and I thought, "Why aren’t I?"

What kind of investment is it for you?

We’re 50-50 partners, putting in about $2 million each. The real thing for us is the partnership we’re establishing and the possibility of being hospitality partners in the future. The only hotel down there right now is a Hampton Inn. I’d love to be involved in a hotel project. I also fantasize about reopening Maxwell’s Plum.

Photograph by Thomas Hart Shelby.