As a radio performer, Sims had a late-night program called "Piano Moods" over the Chicago NBC affiliate station, WMAQ. He founded the Lee Sims School of Music, and one of his pupils was Ilomay Bailey, who had been a vocalist with the Paul Ash and Ben Pollack orchestras. Prior to singing with these orchestras, Ilomay had had formal vocal training. The two were married and formed a team. Sims introduced Ilomay Bailey on his "Piano Moods" radio program and created an instant sensation.