Stout was interested in mechanics, especially aeronautics, founding the Model Aero Club of Illinois.

In 1907 he became Chief Engineer for the Schurmeir Motor Truck Company and in 1912, he became automobile and aviation editor for the Chicago Tribune.

His "Cyclecar" had caught the attention of Alvan MacCauley who subsequently brought Stout to Packard Motors in Detroit.

He had become General Sales Manager of the Packard Motor Car Company and in 1916, when they started an aviation division, they asked Stout to become its first Chief Engineer.

[6] In the last years of World War II, Stout, in co-operation with Owen-Corning, began what was called Project Y to build a one-off car for evaluation of ideas like a frame-less fiberglass body, belt drive rear wheel drive, a suspension which kept the vehicle from leaning into turns by adjusting the suspension using compressed air, and push button electric doors.

Some firms considered producing the Forty-Six, but as Stout stated he doubted there would be much of a market for a $10,000 car, the estimated price if it had been mass-produced.

In February 1923, newspapers carried stories of the test flights of the Stout Air Sedan with Walter Lees as the pilot.

Stout developed a thick-wing monoplane, and his design of an internally braced cantilevered wing improved the efficiency of aircraft.

After his career at Packard Motors, he left for Washington to serve as the advisor to the United States Aircraft Board.

After the Great Depression in 1929 reduced sales of the Trimotor aircraft, Stout left Ford in 1930.

[10] While at Consolidated, Stout promoted three designs for postwar production, including a flying car using a Spratt wing.

[11] Stout's other innovations included the Skycar, an automobile/airplane hybrid and a Pullman Railplane and Club Car.