Gaining support from the small but committed Hamilton music community, he released his breakthrough album Means and Ends independently in 2002.

He has toured extensively with artists including Buck 65, BOY, Joel Plaskett, Emm Gryner and Matt Mays and El Torpedo.

Signed to Warner Music Canada, he released the EP title The Story of Your Life in 2004 and the full-length album Sweet Nothing on September 27, 2005.

Sweet Nothing's debut single and music video, "Soft One," became a major hit in Canada, reaching number one among most-added tracks and the top 20 tracks overall at hot adult contemporary radio in Canada, and receiving regular play on music video channels including MuchMusic, MuchMoreMusic and MusiMax.

In the same year, Jill and Matthew Barber collaborated on a cover of The Hardship Post's "Your Sunshine", which appeared on the charity compilation album Have Not Been the Same – Vol.