There wasn't much of a music scene in Marietta, but this did little to discourage Bolden. He started playing and recording songs soon after he moved there, gaining a cultish online fan base with his humorous indie pop tunes and earning a local following with his eccentric live shows. He released a couple albums in 2003, Goodbye Emo Kid and Mixing It Up, Vol. 1. One of the songs on the second release, "I'm So Awkward," spread like wildfire on the Internet shortly after it was released. He continued to write songs and released an EP with Pat Hanlin in the following year called Jon Holden/Pat Hanlin Split EP. The EP was followed by a full-length album in 2005, entitled I Need Money Before I Graduate.

Bolden was pretty well known online and had a strong enough fan base to keep him touring; unfortunately, the music industry just didn't take notice. So in an attempt to distance himself from his previous, more humorous work, Bolden recorded and self-released a second full-length album called Choose Your Own Adventure in 2006, which featured new songs in addition to "The People I Know" and "Trying to Define It," both of which appeared on previous releases. He moved to Austin, TX, that same year and continued to work on his music, returning to Marietta on occasion to perform at the American Legion Hall on 8th and Wooster Street. ~ Margaret Reges