Kati Penn started playing the fiddle in Frankfort, Kentucky at the age of 9. Her father played several instruments (but not on a professional level) around the house when she was little. She remembers him playing mandolin, fiddle, and guitar, but the fiddle was what caught her attention. In the 1980s and '90s, bluegrass musician Pete Wernick, first President of the International Bluegrass Music Association, assembled various all-star bands of young musicians, the Young Acoustic All-Stars, which included a twelve-year-old Kati Penn. She then went on to work a stint with the New Coon Creek Girls and later joined band mate Dale Ann Bradley in her band the Dale Ann Bradley Band. She then followed that with a try at a country-oriented career before returning to Bluegrass. Her main influences were Stuart Duncan and Bobby Hicks (who performed at the 2004 Great Lakes Folk Festival) on fiddle and the singing of Alison Krauss, Suzanne Cox, Sonya Isaacs, and Lee Ann Womack.