Restaurant family shares their secret: Failure is not an option

Company: In 1989, Tony Caragiulo sold his bakery in Brooklyn, New York, to set out for a new dream: a mom-and-pop New York style pizzeria in Florida. He packed up his wife, Anna, and five sons — Paul, Rob, Mark, Anthony and John — for a two-week trip throughout the state. 

“Basically, my dad wanted to retire to Florida and have a business that he could generate some income,” says Mark Caragiulo. “It was two-fold in the sense that it was giving us an opportunity and giving him a retirement income.”

The family almost ended up in Tallahassee after making an offer on a space. But at the last minute, the owner backed out. So the family kept driving south, all the way to Sarasota. 

“We literally drove down Palm Avenue and saw a for lease sign,” Anthony Caragiulo says, prompting his father to stop the car. “The rest is history.” 

The first two weeks the restaurant — Caragiulos, on Palm in downtown Sarasota — was open Anthony remembers recording everything. “I was the videographer,” he says. “My older brother John was behind the pizza oven with my dad. My dad would be teaching him how to make pizzas.” 

Some 33 years later, with a failure-isn't-an-option approach, the family is still thriving in the tough restaurant business. “We were very naive to consider that things would work out,” Rob says. “We didn’t realize it could fail. So we just trudged ahead and good things happened.” 

The family has opened 10 or 11 restaurants. A few have closed. In addition to Caragiulos, an Italian-American restaurant, the family runs Owen’s Fish Camp, a Southern seafood restaurant, which is also in Sarasota, in Burns Court.  

The brothers, along with their sister Michele Sullivan, are also in the middle of opening up another fish camp restaurant in Lakewood Ranch and in the beginning stages of bringing a Florida ranch concept to Palmer Ranch, in south Sarasota County. Sullivan recently moved to town after retiring from being a school teacher in New York. 

Challenges: Working with a family as big as the Caragiulos can present some issues from time to time. But it can also come in handy. 

“When you have family working around you (with) 10 jobs to fill and eight of those jobs are (filled by a) brother, sister, mother or father, it’s a little easier,” Rob says. “But when you expand to 30 employees and you have to manage staff, it gets very difficult.” 

"We were very naive to consider that things would work out." – Rob Caragiulo

Of course hiring now is even more challenging in the sense of being short-staffed. The brothers explain that with the population boom in the area, they’re seeing up to 4,500 guests in just a week at Owen’s Fish Camp. To make matters worse, Mark says the lack of staff has forced them to turn away close to 2,500 guests. 

“It’s been crazy the last eight or nine months in terms of functioning because we’re so short-staffed and have a lot of people coming in,” Rob says. “It’s a huge challenge to overcome that at this time.

“We’re in a precarious position now where we’re looking to operate a new facility,” he says, adding they’re hoping to hire 50-75 new employees. “That’s going to be a daunting task.”

Succession plan: The five brothers all helped Tony get this dream off the ground. Since then, John has moved on to North Carolina for a career in real estate. And Tony died in 2015. But most of the dynamic has stayed the same. And Anna, their mom, still makes biscotti for the Caragiulo restaurant.

But the brothers are hopeful the restaurants will continue in one shape or form when they are gone — and that could include their kids, who, right now, are in college or school. Some of the children have expressed interest in carrying on the legacy.  “We’ve got another generation coming up now,” Mark says. “Maybe we can extend our legacy in the same way that my dad extended that to us.”

The succession to the third generation holds true for other aspects of the business. “We’ve got a next generation of staff,” Rob says. “We see not only the kids coming, but now the kids’ kids. It’s scary and great.” 

What the company will look like in five years: For a family who came into the business believing success was the only option, answering a question about the future can be tough. 

“I hope we’re running a nice, healthy business,” Mark says. “Maybe there’s more locations. I don’t know that we’re skyrocketing to grow more." 

Adding a third fish camp wouldn’t be the most interesting opportunity for the owners to pursue, Mark says, adding that the second location, in Lakewood Ranch, is going to be a different expression of the original in Burns Court. That’s what led to the new Florida ranch style concept that incorporates outdoor cooking in Palmer Ranch, on the Legacy Trail. “That could be a fun little thing to engineer and figure out,” he says. 

Looking ahead also glosses over, a bit, how hard the here and now can be. 

“This business chews you up, and tears you out,” Rob says. “I just feel like it's a daunting task to be successful. It feels like you’re juggling while ice skating on one foot. It feels like at any time something could collapse. We experienced that in the last couple of years and to make it through that and still be operating and employing people in the community is a great feeling.”