At 17 he opened a garage behind the family home where he made spending money by working on cars and motorcycles (Hirsch & Shultz, 2001). With his profits, Wedell bought two crashed planes from Ellington Airfield for $800. Using the body of one plane and parts from the other, he managed to get the plane in working condition so that he could learn to fly.
Wedell aspired to join the Army as a pilot, but a motorcycle accident from his teen years left him blind in one eye, which made him ineligible for service. Jimmie continued to fly despite his visual impairment and became known as the "Air Hobo" in Texas (Hirsch & Shultz, 2001). In the first half of the 1920s he earned money barnstorming across the state, giving flying lessons, doing freight and charter work, and flying contraband such as guns and rum from Mexico into the United States. During this time Jimmie met his wife Mae in Port Arthur, Texas (Hirsch & Schultz, 2001).
In 1927, the brothers moved to New Orleans, Louisiana, where they continued their flying endeavors. In 1929 Wedell collaborated with wealthy Louisiana businessman and former politician Harry Williams to start a business, the Wedell-Williams Air Service in Patterson, La., ("Wedell-Williams Air Services", n.d.). The company built high-speed planes, operated a passenger service, gave flying lessons, and took aerial photographs, among other endeavors (Hirsch & Schultz, 2001). During this time Jimmie participated in a number of air races flying the machines he built with the Wedell-Williams Air Service. Wedell became a celebrated flying persona because of his piloting ability and the speed of his planes ("The First Wedell-Williams Racers", n.d.).