An accomplished multi-instrumentalist, Milan often jokes that he first moved to Nashville in 1999 because he “heard they were running out of guitar players,” but with light speed picking and his trusty tenor voice, he has built a reputation as an adept artist, songwriter and collaborator. Traveling the world, Milan has made appearances at venues ranging from Colorado’s Red Rocks Amphitheater to Buck Owens’ Crystal Palace in Bakersfield, California, and from the Grand Ole Opry to Symphony Hall with the Boston Pops Orchestra.

As a songwriter, Milan’s songs have been recorded by some of the biggest names in bluegrass, ranging from the traditional sounds of the Lonesome River Band to the progressive leanings of Steep Canyon Rangers. The fruits of this labor have yielded twenty-eight number one songs in the genre, over three dozen others that have graced the top twenty, two nominations for Song of the Year and receiving the award for Songwriter of the Year from the International Bluegrass Music Association in 2020.

In addition to the standout solo recordings Timepiece and Coon Dog Cemetery, Walking Home to Wexford with Tim O'Brien, and the chart-topping collaborations Adeline, Who Are You Redbird and The Last Moonshiner with Buddy Melton, popular songs from his pen include Pretty Little Girl from Galax by Russell Moore and IIIrd Tyme Out, Terry Baucom’s Every Road I TravelHere Come the Teardrops and What’ll I Do, along with Ain’t Going Down to the River, Creeping Round My Cabin, My Remedy and Broke Down in Arkansas by Missy Armstrong. His compositions also cover a long list of fan favorites from the Balsam Range catalog, including Caney Fork River, Papertown, Chasing Someone Else's Dreams, Grit and Grace, Eldorado Blue, and Something 'Bout That Suitcase.