Every career has to start somewhere and the career of Ross Chowles started in the studio of a small agency where he was an artist. Eight years later Chowles had moved up in the world and had found himself working as the creative director of Young&Rubicom's direct mail division. He then went on to become the creative director of Young&Rubicom Cape Town, where he met Kevin Aspoas. Together, they opened the Jupiter Drawing Room office in Cape Town.

They have spent 11 years growing the Jupiter Drawing Room (Cape Town) into a significant through-the-line creative force. When he is not teaching, painting portraits of new staff members, judging Cannes, One Show, Art Director's Club of New York or the Canadian Marketing Awards, Chowles can be found not wanting for much.