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Trust company executive finds opportunity during pandemic

Instead of sitting around waiting for places to open in 2020, Kelly Caldwell became a pilot.

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  • | 12:00 p.m. January 10, 2023
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Kelly Caldwell always wanted to learn how to fly. Now he gets to alongside his kids. (Courtesy photo)
Kelly Caldwell always wanted to learn how to fly. Now he gets to alongside his kids. (Courtesy photo)
  • Executive Diversions
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Executive: R. G. “Kelly” Caldwell Jr.. He's the CEO and president of Venice-based Caldwell Trust Co., which handles some $1.4 billion in assets. 

Diversion: Flying private planes. 


Positive spin

Growing up, Caldwell always thought about learning how to fly a plane. But he never got around to it. 

“It’s kind of been in the back of my mind,” he says. “Then COVID-19 hit.”

Normally, when someone says COVID-19 hit, it’s followed by something negative.

Cladwell, instead, turned it into his own positive situation. He learned how to fly. 

When his kids were much younger, Caldwell and his wife decided he should put off learning to fly until they were older. Now, the kids are 17, 16 and 14. “I was curious about it being safe as a parent,” he says of the hobby.  

“So I said, ‘you know what? I’m going to explore it,’” he says. First he started reading the necessary books. But the question of whether this was a hobby he wanted to pick up had yet to be answered. So he moved onto the next step. “Well, I guess I have to go fly.” 


Close connection

As a young child, Caldwell says he somewhat grew up in the Bahamas. 

Since moving away and living in Venice, he hasn’t been back as often as he’d like. “Getting to the Bahamas from the West Coast (of Florida) is an ordeal by boat,” he says. “It takes a while to get there.”

Thus began his passion for flying. 

Since getting his pilot’s license a year and half ago, Caldwell has been back to the Bahamas — once just to grab lunch and was back home by dinner. He's also expanded his visits to include Macon, Georgia, Fernandina Beach, Everglades City and most recently West Palm Beach, where his wife’s family lives. 

Fully committed to his hobby, Caldwell purchased a small two-seater Kitfox Aircraft and co-owns a small percentage of a Beechcraft Musketeer. 

Kelly Caldwell received his pilot's license over a year ago. His wife, Melissa, may not be far behind. (Courtesy photo)
Kelly Caldwell received his pilot's license over a year ago. His wife, Melissa, may not be far behind. (Courtesy photo)
Passing it down

Caldwell finally had his answer to the "is flying safe enough for a hobby" question when his two oldest sons showed interest in reaching the skies, too. 

“Here’s an interesting fact that I did not plan for,” he says. “My oldest two children are now flying.” 

All it took for them was one flying lesson. Caldwell promised to schedule one lesson, but any they wanted to do beyond that, they had to be responsible for. And now, his 17 year old son has a pilot’s license. 

When they visited West Palm Beach for Thanksgiving, Caldwell’s oldest son took his grandfather out flying in the plane. 

“All of a sudden I went from being a pilot to a father pilot with two boys who like to fly,” he says, adding now even his wife is interested in it. 

“It’s opened up a whole new world for us,” he says. “You think about parents having something to do with their children after they get older. This one I’ll be able to do forever.”


Anything but simple

“What did that guy on the air traffic control tower say?” 

Any hobby will come with its challenges. But not being able to keep up with the tower communications can be unsafe and frustrating for pilots as they navigate leaving and landing. 

“Those guys talk 100 mph,” Caldwell says. 

The second biggest challenge? Learning the visual cues of landing a plane. 

“Those are the two hardest things for me to master,” he says. “I’m comfortable with them and I’m still learning. Your pilot’s license is a license to continue to learn.” 

That’s why Caldwell chose to train out of the Sarasota Bradenton International Airport. It’s a tower airport and he wanted to be comfortable talking with the tower. 


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