Trust Doesn’t Rust with Kelly Caldwell

August 6, 2026

Kelly and his father, Roland Caldwell, founded Caldwell Trust Co. in 1993, and Kelly became CEO in 2007. Today the company manages more than $2 billion in assets, has more than 50 employees and offices in Sarasota, Venice and Vero Beach. On this episode, Kelly tells Business Observer Managing Editor Mark Gordon about what he looks for in aspiring leaders, how he has refined his leadership style over the years and his future growth plans for the company.

3 Takeaways

(07:50) You need to be recruiting all the time
(15:15) Stay calm, don't overreact, grow
(20:10) Build the emotional bank account with your clients

Timestamps

(00:00) Introducing Kelly Caldwell, President and CEO, Caldwell Trust Co.
(03:20) What is Caldwell Trust Company?
(04:20) How did you get into this business?
(07:10) Spending a third of your time recruiting
(08:40) How have you evolved as a leader?
(11:00) Tell us about your father, the founder of Caldwell Trust Co.
(15:00) One leadership principle everyone should have
(16:15) What behaviors do you celebrate even when they are not moving the bottom line?
(19:35) How do you create accountability without creating fear?
(21:20) What is coming up in 2026?

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