- December 18, 2025
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REVIEW SUMMARY
Industry. Insurance brokerage
Company. Oswald Trippe and Company
Key. Large insurance companies are acquiring Florida insurance brokers in anticipation of a rebound.
When Gary Trippe founded his insurance brokerage company in 1982 from his kitchen table in Fort Myers, all he thought about for the first few years was the firm's survival.
As Oswald Trippe and Company flourished in the 1990s and early 2000s, Trippe turned his attention to planning for success by hiring skilled executives, expanding into North Carolina and creating an employee stock-ownership plan. At its height in 2007, Oswald Trippe reported $28 million in commission revenues from 12 offices in Florida stretching from Sarasota to Fort Myers, Naples and Miami. It also established four offices in North Carolina in recent years to diversify revenues.