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R.G. "Kelly" Caldwell, Jr.




R.G. "Kelly" Caldwell Jr.

CEO & President

Kelly is the CEO and President of Caldwell Trust Company. He began his professional career in 1988 when he returned to the Venice area after graduating from the Georgia Institute of Technology, where he earned a Bachelor of Electrical Engineering degree with High Honors. At that time, he started working with the family-owned registered investment advisory firm.


That company became Caldwell Trust Company, which has now been in operation since 1993. The company has offices in Venice and Sarasota and currently manages over 1.5 billion dollars in assets under management. Caldwell Trust Company serves as a trust manager and trustee for families, allocating client assets into stocks, bonds, and other investments. For larger accounts, Caldwell also serves as a 'quarterback' for client families, serving as an adviser for all family, investment, and business matters. A third focus is employee retirement plans, where Caldwell Trust provides comprehensive trust services for businesses and organizations that have retirement plans for their employees.


Kelly succeeded his father as the CEO of Caldwell Trust Company and TCA in 2007. Under his leadership, total assets under management, total annual income, and stockholders equity have increased by more than 85%. All departments have been expanded and built out especially the IT (Information Technology) function. Utilizing his technology background with Caldwell's IT staff brings real and significant productivity improvements and profitable growth to the entire company. Kelly routinely speaks about the most rewarding part of his job working with the highly skilled team at Caldwell Trust Company.


Growing up in Venice, Kelly is passionate about donating his time to the community through service to numerous organizations. He has served as a two-time past president. He is a board member of the Argus Foundation, the Florida Bankers Association's Trust Executive Committee, and the Sarasota Sheriff's Office Charitable Foundation, Inc. Kelly is a long-time supporter and board member for The Suncoast Charities for Children. Lastly, Kelly is an alumnus of the Leadership Florida Class of XXVIII.


Kelly and his wife Melissa have three boys, ages 13, 15, and 17. When not attending the boys sporting events, the family spends time together boating and fishing.

"We proudly display my father's mission statement, 'What We Believe' at the entrance of our headquarters. I remember when he wrote it. It inspires me today as if I were reading it for the first time. Briefly, it says we take care of families and we do it honestly. It's the foundation of which this company stands. It's who we are."