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.