In 1953, Leo traveled to Salem, Oregon, where he competed with other amateur musicians in various forms of entertainment.  Those who passed an initial screening were invited to compete on the program.  Winners were determined by viewers who voted via letters and phone calls, and winning contestants returned to compete against a crop of new talent on the next program.  Contestants who won three times earned cash prizes or parts in a traveling stage show associated with the program.  In the early 50s, five such shows toured the country.  Leo was offered a "job" touring with the stage show, but turned it down because the starting pay was too low.  While most contestants fell into obscurity, others became major stars like Gladys Knight, Pat Boone, Teresa Brewer, and Frank Sinata.  Back home in Stanfield, Oregon, Leo often entertained patrons at the Jesse James Club, but eventually had to discontinue this due to the demands of raising five young children in rural Eastern Oregon.

Leo could play a variety of county & western, middle of the road, and classical melodies without sheet music. In 1940s he, along with brother Lyle, performed live country music regularly at KRJF, a Miles City, Montana mutual radio station.  During the war years the station featured local live acts entertaining area residents with their 250 watt omnidirectional signal.  Leo and his brother were known as the "The Twilight Boys".   Lyle remembers being able to "break glass" with their harmonizing.

Leo also enjoyed repairing musical instruments. (He purchased a player piano in the early 60s and completely refurbished it by gutting the insides and replacing plastic tubing. The piano provided many years of enjoyment for the Koffler family.