Kelly Caldwell

CEO and President, Caldwell Trust Company

G. “Kelly” Caldwell Jr., Caldwell Trust Company CEO and president, began his professional career in 1988 when he returned to the Venice area after finishing college. A high-honors engineering graduate from Georgia Institute of Technology, Kelly had planned to attend law school but first wanted to learn more about his father business, Caldwell & Company. Roland had established the registered advisory firm in the 1970s to provide investment guidance for the trust industry; by the 1980s he was also publishing a respected investment newsletter and serving as trust consultant for a major Venice bank. Young Kelly joined Caldwell & Company and never looked back.

In late 1992, Roland, Kelly, and a few hand-picked colleagues decided to form a new company with a primary focus on family trusts and a commitment to remain independent. They worked through most of 1993 on their application, which would make Caldwell one of the few independent trust companies in Florida. Caldwell Trust Company received its charter on November 1, 1993, signed its first client on November 2, and has continued to grow ever since. “We still retain many of our early clients,” Kelly says.

Roland’s intimate knowledge of the trust industry and Kelly’s engineering talent—coupled with their strong entrepreneurial spirits and keen intuitions—resulted in the creation of unique proprietary software, providing a substantial competitive edge that persists to this day. Their personal emphasis on philanthropy and deep concern for individuals add to the mix, making Caldwell a juggernaut in the industry.