Venice trust company founder dies at 89, leaves legacy of persistence

Sometime in the early 1980s, Caldwell Trust Co. President and CEO Kelly Caldwell, then in his early teens, was stunned when his dad, Roland Caldwell, came home after work with an RV camper. Dad quickly announced the new summer plan: Spend two months traveling all over North America. 

A short time later four Caldwells — Roland; Kelly; his older sister Molly; and his mom, Annette — packed up and hit the road. (Kelly’s other sister, Debbie, was in early 20s and didn’t live at home back then.) The route was a circle around North America. Starting in Venice, south Sarasota County, they went north to New York, Maine and Canada; back to the States to the Midwest for Illinois and family in Ohio; out west to Wyoming and Yellowstone National Park; south to California for San Francisco and Los Angeles; then east to Texas, a dip into Mexico and back to Florida via the Panhandle. Then 14, Kelly Caldwell even drove the RV a bit, sans drivers license, when his dad needed a break in Texas. 

“I’m 55 years old,” Kelly Caldwell says, “and I still think that was the coolest trip ever.”

That trip also captured one of Roland Caldwell’s lifelong mantras — if you can think it, then you have to have the persistence to do it. Roland Caldwell, who founded Venice-based Caldwell Trust Co. in 1993, died April 24. He was 89. 

“The No. 1 thing about my dad is he was a person who would always challenge you,” says the younger Caldwell, who goes by Kelly but is a junior, R.G. Caldwell. “He challenged you to find greatness.” 

“You have to be willing to persevere to get there,” Caldwell adds, when recalling memorable advice from his dad. “It might take two years. You’re not gonna like all of it. But that’s OK. I’m grateful to my dad for teaching me that.”

Roland Caldwell was born in Chicago, during the 1933 World’s Fair, according to his official obituary. He grew up there and later in Ohio, where he and his siblings worked the family farm, with chores ranging from collecting eggs to helping neighbors pick potatoes. He joined the U.S. Navy after high school, active from 1952-1953 and then the Naval Reserves for 8 years. He next used the GI Bill to go to Ohio State, ultimately graduating from Kent State University. 

Caldwell married Annette in 1955 — the couple met in high school, got engaged during a heavy snowstorm, honeymooned in the Pocono Mountains and remained married for 58 years, until Annette died in 2013. Caldwell entered a career in finance, working in trust departments for banks in Ohio, Indiana, and in another life challenge, he helped open a trust company in the Bahamas. 

The young family relocated to Florida, first to the east coast, then to Sarasota and settled in Venice. Caldwell opened an investment advisory firm, Caldwell & Co., and later co-founded a construction company. In 1993, when he was 60 years old, Caldwell founded Caldwell Trust Co. That company today is one of the most established trust companies in Florida, serving more than 1,500 clients with $1.5 billion in assets under care.

Yet 30 years ago, says Kelly Caldwell, getting a charter to run a trust business was a Herculean task. His father hired consulting firms and others, then decided to just do it on his own. “He just willed it,” Kelly says. “He found a way to get it done.”

Roland Caldwell retired in 2006, and Kelly took over as CEO. And while his sisters didn’t spend their careers in the firm, they also ran and owned businesses — a source of pride for Roland and Annette Caldwell. 

In retirement, meanwhile, Caldwell, whether in Venice or the family cabin in the Smoky Mountains, embraced the idea of lifelong learning. He followed the American philosopher Mortimer Adler, and was invited into Adler’s elite inner circle of attendees to the Aspen Institute’s conferences and round-table discussions on philosophical ideas. Caldwell wrote articles and books, mostly for family and friends. He chronicled his family’s history in one book and wrote another book entitled “On the Making and Drinking of Fine Scotch Whisky.” He wrote those two books, his obituary states, “after a long trip to Scotland for proper research.”

Kelly Caldwell recalls his dad, not only in personal research but with clients and in business, often asked open-ended questions. He wanted to find out what motivated his company’s clients, not just sell them investment products or trust services. Kelly says watching his dad work was learning lessons about business “I didn’t know I was learning.” 

Kelly Caldwell says Roland maintained his sharp mind even in getting sick earlier this year. He spent time with his seven grandchildren and friends and family, still dispensing advice and counsel. “He was a great father,” Kelly says, “and a phenomenal mentor.”