Ross attended Mass Academy,[1] then Columbia University, where he studied computer science,[2] and became the bassist for the band Unsacred Hearts and guitarist for DraculaZombieUSA.

Ross was also the bassist for a brief stint in early 2000s indie band Cold Memory, and was also the headliner for The A-Ross Experience.

Other early bands include Phter, D-Funky and the Beechmont Chilles, and Conjugal Visit.

In 2004, he released an album, Do Not Leave The Baggage All the Way, under his solo project Secret Dakota Ring.

In early 2005, he became a member of OK Go after auditioning to replace the band's former guitarist and keyboardist Andy Duncan, who left after production on their second album, Oh No, was finished.