Kostas originally made his mark in Montana as a singer and songwriter throughout the 1980s.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's 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" (1994). "Blame It on Your Heart" also earned BMI's Robert J. Burton award for being the most performed single of 1994. Dwight Yoakam also recorded several songs written by Kostas, including "Nothing's Changed Here", "Turn It On, Turn It Up, Turn Me Loose", and "Send a Message to My Heart" (a duet with Loveless), all of which were released as singles from Yoakam's 1990 album If There Was a Way. Yoakam's 1993 album, This Time, included another song co-written by Kostas: the single "Ain't That Lonely Yet", which earned Yoakam a Grammy Award for Best Country Vocal Performance - Male in 1994. During the early 1990s, Kostas also wrote singles for McBride & the Ride, Travis Tritt, Holly Dunn, Martina McBride, and The Mavericks. Kostas currently resides in Belgrade, Montana with his dog Bella. He will be inducted into the Nashville Songwriters Hall of Fame in October.