Jerry served in the United States Air Force from 1981-1984, where he operated trucks and heavy equipment, including tractor‑trailers. Following his honorable discharge, he joined a commercial trucking company and drove long‑haul tractor‑trailers throughout the United States. In 1989, he founded a customs brokerage, warehouse, and trucking operation in Miami, Florida—Customs Services International, Inc. He later returned to over‑the‑road driving, logging more than one million accident‑free miles before transitioning into truck sales with Fitzgerald Peterbilt, where he sold Peterbilt trucks.