For his first job, he worked as a mailman traveling on horseback from Pittsburgh to Bethany, W. VA and back the next day. When he was 13 he became an apprentice
to learn carriage woodworking. At 18 he began working his way down the Mississippi River practicing his trade. In 1861, he came to Ravenna where he and his brother-in-law, Charles Merts took over a carriage manufacturing company. In 1891 he bought out Merts and became the head of “The Riddle Coach and Hearse Company” which produced horse-drawn and later motor-driven carriages and hearses. The business, whose name was eventually changed to “Riddle Manufacturing Company” was tremendously successful, but after metal
stamped mass-produced vehicle bodies became popular the company decided that rather than take the financial risks that modernization would entail they would, in 1925, go out of business.