Schmidt released his first album, Broken Summer, under the moniker And Then I Turned Seven in August 2003 before leaving his hometown of Duluth, Minnesota, to attend college at Moorhead State University.

[citation needed] While at school, Schmidt started playing shows in the Moorhead, Minnesota, and Fargo, North Dakota, area to promote his music.

In the fall of 2004 Schmidt put Broken Summer up for stream on PureVolume, a fast-growing music website, and quickly became one of the site's top unsigned artists.

After two solo tours on the East Coast and in the South, he recruited local musicians Pat Tarnowski, Kieren Smith, Trevor McKenzie, and Indianapolis, Indiana-based drummer Chris Lee to join the band.

McKenzie was replaced by local musician Sam Dean while the band continued to tour the US before putting their music on the popular social networking site Myspace in early 2006.

After signing with music distributor Tunecore, One Last Breath was released on August 9, 2007, along with "Sing It Loud"'s self-titled EP, which Schmidt played drums on.

In late 2009 Schmidt met Brandyn Anderson, a local Minneapolis-based musician, and the two began playing Jamestown Story shows as a duo.

Schmidt made frequent writing trips back to Minneapolis to work with Anderson before they began recording the album in March 2012.

Throughout 2013, Schmidt wrote and recorded with numerous Nashville songwriters and released an EP of those songs titled Jamestown Story & Friends on September 9, 2013.