Ross attended Columbia University, where he had studied computer science, 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 the solo project name Secret Dakota Ring. Ross described his freshman album as a 'break up album' at a Google artists performance.
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.

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