Trust firm passes 50 employees, $2B in assets on its way to more growth

Financial services entrepreneur Kelly Caldwell once asked his dad, Roland, why they never went on any father-son hunting trips.

The answer surprised the younger Caldwell. It also framed how he thought about his dad, and later in life it framed the approach he’s taken to building what’s now one of the largest, and most established, non-deposit trust companies in Florida. That business, Venice-based Caldwell Trust Co., is growing significantly in 2025, having already hired seven people to bring the total to 50 employees. The firm, which manages nearly $2 billion in assets, also recently expanded to the east coast of Florida, with an office in Vero Beach. Another office, in Lakewood Ranch, to go with ones in Venice and downtown Sarasota, is also a possibility.

Kelly Caldwell says the growth stems, in large part, from the attention to details, careful evaluation of risk and grit he learned from his father. Roland, it turns out, never took Kelly hunting because it was too stressful. The reason? Roland grew up in the Great Depression. His father deserted the family, emptying the bank accounts. So Roland took up lots of jobs, from mowing lawns to working in the fields, to support the family, Kelly recounts in “The Way It’s Meant to Be: Wealth, Legacy and Over Three Decades of Excellence,” a memoir he wrote 2023. 

Roland would sometimes go hunting growing up — but there was a twist. "Apparently because of his family financial situation, when he went hunting, Grandma would give him one single shotgun shell or rifle cartridge, with the injunction to bring back something for dinner, " Kelly writes in the book. “He could not afford to miss, and this experience colored his later life. He became methodical and deliberate in his approach to everything he did.”

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That philosophy shows in today’s version of Caldwell Trust Co. 

Founded in 1993 by Roland Caldwell, it took 24 years to get to $1 billion in assets, Kelly Caldwell points out, but is approaching its second billion seven years later. Reasons for growth are myriad, including Florida, and Sarasota, population growth; industry consolidation; and the company’s high-touch customer service, which leads to low client churn. Asks Kelly Caldwell: “Now that we are at our second billion, that came so fast, our big challenge is, how do we handle all this growth?”

Like his dad preached, carefully. 

The expansion to Vero Beach, for example, was a few years in the making, both to find the right office and the right person to lead it. That’s David Osgood, who has worked in the field for more than 30 years, including stints at Merrill Lynch Wealth Management, Bank of America Private Bank and J.P. Morgan. 

Kelly Caldwell and Osgood toured multiple offices in Vero Beach and, in another Depression-era lesson from Roland Caldwell, who died at 89 in 2023, Kelly hyper-focused on the details. That included a large landscaping project at the new office — which it leases — so when prospective clients arrive, they know they are somewhere, not just any wealth management office. “Our new landlord there really loves us,” quips Caldwell.

That sense of place is important to the Caldwell Trust model, he adds, because the sales cycle in the industry can be excruciatingly long — five or 10 years. So the firm’s marketing and branding is built around stability and consistency, with the idea that when a life change happens and people seek trust services, they think of Caldwell Trust. “You really have to be top of mind,” Caldwell says. (A state-chartered, non-deposit trust, overseen by the Florida Office of Financial Regulation, is a fiduciary for a host of money management services for individuals and businesses, but is not a bank. There are 13 non-deposit trust firms in Florida, according to an OFR database.)

Kelly Caldwell says the kind of model he aspires to with the company is akin to an old community bank, where it was a focal point of a town. Those kinds of financial institutions have declined along with industry consolidation and digital advances. “(Many) banks have given up being the pillar for the community and have just become interested in transactions,” Caldwell says. 

One goal Kelly Caldwell has for 2025 and beyond is to spend more time recruiting talent. He recalls asking a friend several years ago, a CEO of a company that went public, how much time he spent on recruiting employees. That friend said one-third, adding if you don’t have the ‘right people you will not grow the right way.’ That resonated with Caldwell, and is why he won’t grow merely to add to the assets tally.

“There’s no point in doing this growth without a Dave in Vero Beach or a Wendy (Fishman) in Venice or a Jan (Miller) in Sarasota,” he says. “We really want to find opportunities that make sense.”