Kahn began studying the violin aged seven and is said to have learned to play eighteen musical instruments before starting to lead his own orchestra in 1923, aged only 16. At the age of ten, Kahn had bought a ukulele in a Ditson Music Shop in Manhattan together with special-priced instruction on how to play; such was his keen interest in music. The ukulele lured him away from his studies at St. Bernard's School and turned his mind toward violins, pianos, banjos and jazz orchestras. At St. Bernard's he took no more interest in athletics than he did in studies or in social activities. By the age of sixteen, he’d rejected studying at college. Instead, he formed his own booking agency and organized a paying band and installed it at the Knickerbocker Grill in New York. He could play every instrument in the outfit, all self-taught, and his favorite instruments to play were the piano and saxophone. By the time he reached nineteen, he had eleven orchestras on his books that played in resorts and hotels from Newport, Rhode Island to Florida. They’d netted him personally an average of $50,000 a year for the four years of their existence. His success enabled him to pursue his passion for composing music and aviation.