His dad taught guitar lessons and his mom who studied music at college, played organ at the local church.

In 2005 Aaron Pomerantz (dobro/mandolin) and Rory Brown (bass) joined Shearer and took John Weinland from a solo project to a trio.

[6] Released on July 4, 2006, Demersville[7] was recorded at Portland's Type Foundry and was produced by John Weinland and Adam Selzer.

In addition to Aaron Pomerantz (dobro, mandolin, harmony vocals) and Rory Brown (bass); Ian Lyles played drums and banjo on the Demersville album and later became the primary drummer for Weinland.

For the Demersville sessions Shearer also recruited Alia Farah to play piano on Piles of Clothes, The Letters, In Which Case, From a Town You Left.

Rachel Blumberg of The Decemberists, Norfolk & Western, M. Ward and Bright Eyes sang harmony vocals on The Letters, In Which Case.

Two other musicians who contributed to the Demersville album are Jesse Richter and Katie O'Brian of Dolorean and The Corin Tucker Band.

[8] On July 14, 2006, John Weinland played a sold-out show at Mississippi Studios which included Paul Christensen on keyboards.

[12] With the addition of Ian Lyles (drums) and Paul Christensen (keyboards), Shearer wanted to distance himself from the solo origin of John Weinland and foster a band-like ambiance.

Shearer wanted to create an environment that could produce the energy and beautiful moments that happen when a band performs a song for the first time.

[25][26] Shearer worked at a mental health facility helping at risk kids when he wrote the songs for Demersville and La Lamentor.