Kevin Caldwell, CFP®️, headshot.

Kevin A. Caldwell, CFP®

Professional Kevin

Financial planning doesn’t need to be a painful experience when you have a partner you trust.

With over a decade in the financial services industry, Kevin provides knowledgeable guidance in comprehensive financial planning services to assist our clients. He focuses on behavioral investment consulting, aiming to help clients make sound investment decisions while embracing emotions, but not succumbing to them at the detriment of their long-term financial well-being. Warm and genuine, Kevin enjoys distilling complex information into actionable advice to help the families and individuals we serve thoughtfully pursue their goals. 

Before forming Golden Road Advisors, a registered investment advisor practice, Kevin was a financial advisor with Raymond James. Prior to that, he was a financial advisor with Morgan Keegan and a financial services specialist at AmSouth Bank. He earned a bachelor’s degree in finance from the University of Florida.

Kevin is an active member of his community and has been a member of the advisory board for The First Tee of Tampa Bay since 2011 and a committee member of the Tampa Bay History Center since 2013. He is also a board member of the Gasparilla Music Foundation, a charity he has been heavily involved in since 2012, and was previously the lead concierge for Safety Harbor SongFest. As a member of the Coppermugs, he is a community ambassador for the Valspar Championship at Innisbrook. Kevin is a member of the Propeller Club Port of Tampa and the Florida Gators Golf Boosters. He is also an alumnus of the Tampa Connection class of 2014 – members of which must be in or near middle management and destined for leadership in their community and company.

Originally from Clermont, Florida, and a sixth generation Floridian, Kevin lives in South Tampa with his wife, Stephanie, and their kids, Cole and Charlotte.

Personal Kevin

Whenever I’m walking somewhere, I’m always listening to music on headphones. Live music is even better – I just love the feeling of being consumed by loud, live music.


A. You can often find me golfing, cooking, collecting vinyl or chasing my kids around. I’m an indulgent consumer of music and love seeing bands perform live. As a Florida alum, I’m also a big fan of Gator athletics.


A. Gasparilla Music Festival. It’s a wonderful confluence of amazing live music, great food from local restaurants and awesome people. I have a blast working with this organization to make the festival successful year after year, and am so grateful for the community of business and social contacts I have made over the years by getting involved.


A. My family.


A. My wife, Stephanie. She is the hardest-working person I have ever met, but is also laid-back and fun. 

Certified Financial Planner Board of Standards Inc. owns the certification marks CFP®Certified Financial Planner,   CFP Logo Flame Design   and   CFP Logo Plaque Design  in the U.S., which it awards to individuals who successfully complete CFP Board’s initial and ongoing certification requirements. 

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