In 1962, Ryan founded the first Finance and Insurance (F&I) department at Dick Fencl Chevrolet in suburban Chicago, which "forever changed how auto dealerships operate", and in 1964, he founded Pat Ryan & Associates, an underwriting agency.
In 1962, Ryan founded the first Finance and Insurance (F&I) department at Dick Fencl Chevrolet in suburban Chicago, selling insurance products on behalf of Continental Casualty Company, now the primary subsidiary of CNA Financial. This move "forever changed how auto dealerships operate" and in 1964, Ryan founded Pat Ryan & Associates, a brokerage and underwriting agency.