Kostas performed in Montana as a singer and songwriter throughout the 1980s. Eventually, he was discovered by record producer Tony Brown, who was searching for new material for country singer Patty Loveless. Kostas' first cut as a songwriter, "Timber, I'm Falling in Love", was recorded by Loveless; released as a single in 1989, it went to number one on the "Billboard" country charts, becoming Loveless's first number one hit. She would also release three more of his songs as singles: "The Lonely Side of Love" (1989), "On Down the Line" (1990), and "Blame It On Your Heart" (1993). "Blame It on Your Heart" also earned BMI's Robert J. Burton award for being the most performed single of 1994.