Mayer ya zo da hankali na Gregg Latterman a Aware Records ta hanyar wani acquaintance na Mayer ta, lauya, wanda ya aiko da Aware EP. Bayan hada da shi a cikin Aware Festival kide da wake-wake da kuma waƙoƙinsa a kan Aware compilations, a farkon shekara ta 2001, Aware Mayer ta internet-kawai album mai taken, Room for Squares. A wannan lokacin, Aware kammala wata yarjejeniya tare da Columbia Records cewa ya ba Columbia na farko da za a sayen Aware artists. A watan Satumba, Columbia remixed da kuma sake fito da Room for Squares. A matsayin wani ɓangare na manyan lakabi "farko", da album ta artwork aka sabunta, da kuma Mayer amfana daga wani online bi.
kakarsa, Annie Hoffman