Trevor Caldwell

CEO/ Founder

Trevor was born in St. Vincent and the Grenadines (SVG) a small island in the southern Caribbean. His family built and owned Palm Island, a 24-room resort in the Grenadines on a private 130-acre island where they settled in 1966, after sailing around the world.,_Grenadines

Palm Island is a hidden gem in the Caribbean, with gorgeous white sand beaches, turquoise water tropical breezes and more palm trees than people! It’s as if a Jimmy Buffett song has come to life!  The island itself is only a mile long and a half mile wide and at that time, only had 15 full time residents – most of whom shared Trevor’s last name!

Trevor lived on Palm Island until the age of four when family moved back to the USA. His father John W Caldwell (aka Johnny) was born in California but lived most of his life abroad, in the South Pacific, Australia, and Antigua. But Palm Island was where Johnny called home. Trevor’s mother, Christy, was born and raised in Columbus, Ohio. But her love of adventure took her to St. Vincent where, as fate would have it, she met and married Johnny.

At the age of 10, Trevor returned to Palm Island with his father; following his parents’ divorce. It was a huge culture shock and adjustment. Trevor was enrolled in an all-boys boarding school, 125 miles away from Palm Island called Mapps College on the beautiful, sun-soaked island of Barbados. Barbados is one of the most developed islands in the Caribbean and offers excellent education opportunities. Three generations of Caldwell boys had attended the prestigious Mapps College. While there Trevor learned to play rugby.

After finishing his studies at Mapps, Trevor returned the to the USA to have a go at college at age 16. It was a short-lived venture, due to his struggles with dyslexia. So, at 18, he started a career in the theme park industry. Moving up the ranks at Sea World he was given his own restaurant to run in the newly opened Key West exhibit. This fit him well as he loved the Jimmy Buffett music, serving funnel cakes and conch fritters! In a small way, it made him feel like he was back in his native land and on Palm Island.

While working at Sea World and playing rugby for Orlando RFC (ORFC), one of Trevor’s team mates asked if he would be interested in pursuing a career in insurance. Trevor jumped at the opportunity to hang up the apron. He worked at Liberty Mutual in Lake Mary, FL. For more than seven years. The ORFC often went abroad to play and he needed to moonlight to pay for trips to Canada and Costa Rica. So, he got a 2nd job, where he met his soon to be wife-Lori Jones, and they married in 2002. Son Kullen was born in 2004, followed by Daughter, Rylee, in 2005.

Like clockwork, rugby was there to give Trevor his next opportunity. The same teammate asked if he would like to join him in his new venture on the independent side of the business. So soon after Trevor was working at his agency. After four years of gaining experience on the independent side, Mapps Insurance, LLC was born. Trevor credits his beloved rugby for giving him the opportunities to get his where he is today … “In life you can count on one hand all true friends you have… most of mine are rugby guys”.

Today, Trevor and Lori live in Bonita Springs, Florida with Kullen, Rylee and their spoiled rotten Labrador, Miss Monroe. Trevor is a self-proclaimed “world’s biggest ParrotHead” and an avid New Zealand All Blacks rugby fan—often waking up 3:30 AM to watch his team play live. He has retired from playing rugby and now spends his time away from work, traveling with Rylee’s softball team and fishing with Kullen.

You can follow Trevor On twitter @thebonitaparrothead