Drive, Determination, Discipline, Dedication
BY EVAN  WILLIAMS ewilliams@florida-weekly.com

Oswald Trippe and Company celebrates its 25th anniversary this year. It's still a company based largely around community values, says founder and CEO Gary Trippe, sitting in his office on the second floor of the Colonnades building in The Bell Tower Shops. Meeting him, one feels a little like they've pulled back the curtain, and found the wizard.

Trippe said he's slowly relinquishing control of the business, both in ownership and leadership, and that those are parallel roads which will soon intersect. He and his wife, Gay, still own about 5 percent of OTC; but each year they are selling one percent of that stock. The goal, he said, is to transfer ownership from the executives to the employees.

"From a personal standpoint, this transitioning allows my wife and I to live out our dream and vision for the agency," he said.

By the time he no longer owns any of OTC, Trippe plans to have someone else in charge: President John Pollock and Chief Operations Officer Gray Davis.

"By the end of 2008, we expect Gray to be running the day to day operations," he said. "I'll probably continue on as CEO until 2009 and chairman for a few years after that."

Average day-to-day operations have him up about 4:30 a.m., Trippe said. He likes to be at his first appointment by 7 or 7:30, otherwise he doesn't know quite what to do with himself. He spends the day managing financial affairs, and the expansion of the company's agencies (there are 13 offices in Florida and three in North Carolina).

"As a longtime insurance agent, I still have these longtime clients that I continue to be involved with personally," he said. "We have 49 other agents working on relationships with other clients. Everything we do is

"One of the highlights was then they reorganized about relationships."

Trippe said everyone who works for OTC is encouraged to participate in the community.

"That means different things for everyone," he said.

Many support United Way, some serve on boards like the American Cancer Association; others coach a little league baseball team. Trippe said the importance of community was instilled in him during his childhood in Fristoe, Mo., population 75, about 100 miles southeast of Kansas City.

"I think a lot of my drive, determination, discipline, dedication - all those sorts of things - developed in my youth," he said. "When I lived there, I was probably related to everyone in the community. When I started in school, I went to a one room schoolhouse. My mom was the teacher for first, second, and third grade."

That was not fun, Trippe said.the school district and my mom was no longer my teacher [in fourth grade]."

His father was a carpenter and the family, which included Trippe, his younger brother, and an older brother who had cerebral palsy, lived on about 160 acres.

"The focus was on my brother," Trippe said. "It was about caring and doing what was best for him."

The family moved to Kansas City to give his brother a specialized education, and Trippe, who was happy to escape the farm for the city, finished high school, then college.

It wasn't until much later, in the late 1970s, when he was president of D.R. Mead and Company, an agency in Miami, that he met Jim Pender and other members of the James B. Oswald Company, a Cleveland-based agency.

In 1981, the two combined forces and the Oswald Tripp Company was born in Fort Myers. They started with an initial "anchor client," a hospitality business, Trippe said, "our only client." Now the company provides insurance, plus a variety of other financial services, to many in the fast growing Southwest Florida area. In 1981, about 150,000 people lived in the region; now it holds over 600,000. And despite the slump in the real-estate market recently, Trippe said it's still growing, and is still the place to be.

"Even with the downturn, people are still coming here," he said. "Just not as strong as they had been in the last three to five years."

And he's still having fun.

"I love the insurance business," Trippe said. "I've been in it for 38 years. I enjoy the challenges, the relationships, and the opportunity for new relationships that come along with it." ¦