Kaleo performed for Hawaiian Music legends, Dennis Pavao, Genoa Keawe, George Helm, Andy Cummings and Hilo Hattie. His 1989 CD, Welcome to My Island became an instant Hawaiian hit. Kaleo has served as the Musical Director at Paradise Cove Luau (largest luau in Hawaii) for 12 years.
In Disney World, Orlando Florida, Kaleo has performed vocal, guitar and ukulele for 18 years. He sang at Mickey's Polynesian Luau and entertained guests at the Polynesian Resort.