On October 20, 1857, when Ryan was just 15 years old, he and his father started a fishery supply business and public house at Bailey's Cove, a section of Bonavista. This became a successful enterprise and in 1869 Ryan had acquired enough capital to purchase the business premises formerly owned by William Keen. Incorporated in 1870 as James Ryan and Company, the enterprise had expanded beyond Bonavista to other communities along the coast. Trading operations were soon established at Elliston, Catalina, Bay de Verde, Open Hall and Plate Cove.
