After completing secondary school in Lindsay, Ontario, he studied classics at University of Toronto, and in 1899 became an instructor in English at Ridley College in Saint Catharines, Ontario, where he began a series of Saturday morning lectures on national and world affairs.

Baldwin and university classmate Douglas McCurdy had been involved in Alexander Graham Bell's Aerial Experiment Association, along with Thomas Selfridge and Glenn Curtiss.

In 1924, Keys invested $10,000,000 in capital to fund National Air Transport with Paul Henderson, the former Assistant Postmaster General.

In 1932, Keys withdrew from the aviation business citing health reasons, but in fact the directors of North American Aviation had discovered that he had embezzled funds in order to settle personal debts incurred from his private speculation in stocks and shares.

Keys Aircraft Service Company and after World War II helped organize Peruvian International Airways in 1947.