Bill Bauman met Summer and Jeremy Gloff at the Three Friends coffee shop in Portland, OR in 2004.

Summer and Golf were songwriter friends from the East Coast who each had an act in the coffeeshop's lineup.

Bauman decided to start a label to put out her first full-length album based on this material.

Summer also released a 300-piece series of poster-size paintings to accompany the album, a collection she named The Girls.

[citation needed] In 2008, LossLess Records signed Jeremy Gloff and put out his fifteenth album, 1987.