Insuring the Future: Foundation Secure, Co-Founder Focuses On Giving Back  - CLEO Skip to main content


Oswald Trippe & Co. will celebrate its 25th anniversary this year, but longevity isn’t what cofounder and chief executive officer Gary Trippe lists as his top accomplishment.

The independent insurance agency has 10 offices throughout Florida and just opened the 11th office in North Carolina, the first outside the state.

But that’s not it, either.

Even Trippe’s many civic and charitable commitments — to the Blue Chip Community Business Awards, Hope Hospice, the Boy Scouts, the Foundation for Lee County Public Schools and many more — don’t top the list.

Trippe, 62, is most proud that the Fort Myers company he helped create — along with his wife, Gay, and the Ohio-based James B. Oswald Co. — will not miss a step on the day he walks away from the office.

‘You need to have an exit strategy,’ Trippe said. ‘I don’t have a target date. Well, I do, but not one that I want to publish.’ But the planning isn’t new.

In 1994, Gary and Gay Trippe sold 60 percent of their stock to establish an Employee Stock Ownership Plan as the first step of the plan.