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In the meantime Waterman became very friendly with the Navy flyers, who had set up a camp at the north end of North Island, and became especially friendly with Ensign V.D. Herbster, who frequently asked Waterman to accompany him on various flights, and engage in some of the experimental work that was going on at that time. As a result of one of these flights, Herbster and Waterman jointly have the questionable honor of having obliterated one third of the U.S. Navy Air Force, by dumping their  Model B Wright Hydroaeroplane into San Diego Bay.

During this era Waterman had wanted to become an exhibition flyer, because that seemed to be where the great honor and glory were, but Curtiss, well known for his guidance of young aviation talent, urged Waterman to get a college education in engineering, with the advice that the real future in aviation was in design rather than in being an exhibition pilot. With this counsel, upon completing his senior at high school Waterman enrolled in the University of California at Berkeley, Department of Mechanical Engineering. While a student there, he started building a four place tractor type flying boat, the hull of which was completed, but owing to a lack of finances the whole project had to be dropped late in 1913. His expenses at the University were largely financed by various jobs, either on night shifts or during vacations, with Early Birds Adolph Sutro and Charlie Patterson, the Hall Scott Motor Company, and others, including one short Christmas vacation job with Early Bird T.C. Macaulay, back at the Curtiss camp on North Island. 

When World War One broke, Waterman immediately went to San Diego to offer his services at North Island as a military aviator. He only got as far as the examining physicians when his broken ankles and flat feet immediately seemed to disqualify him in the eyes of the medics. The result was that he was offered the position of Head of the Department of Theory of Flight at the U.S. School of Military Aeronautics back at the University of California in Berkeley, which he finally accepted. During his tenure in this position, many later to become famous aviators were to receive their first training. Among these were later Generals Jimmie Doolittle, Harold Harris, Bob Knowland, Joe Marriot and many others, such as Major Jack McCready, Major C.C. Moseley and Captain Lowell Smith. The monotony of repetitious teaching soon made Waterman anxious to get into something more active and he went to work for the U.S. Aircraft Corporation, first as Purchasing Agent and later as Chief Engineer. This company had a contract to build 100 Jennies and had obtained the old Christofferson plant at Redwood City. At the end of the war the work was phased out and Waterman was retained as Liquidator. His last employee was Early Bird Victor (Speed) Johnston. 

Always wanting to get back to Southern California, Waterman bought up a considerable amount of the materials, parts and equipment left over from the demise of the corporation, and moved a carload of these acquisitions to Venice, California, where he leased a suitable building and set up a small aircraft enterprise known as Waterman Aircraft Manufacturing Company.
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