In the late 1970s and early 1980s he studied law at Monash University, Clayton campus. Faine began his professional career practising as a solicitor in various Melbourne law firms, also combining work with his love for cars as a motoring reporter for a lawyers' magazine. In 1989 he began working in radio, producing and hosting "The Law Report" on ABC Radio National. Since that time he has worked on various ABC radio and television programs. From 1997 he has hosted ABC's local radio morning program from 8.30 am to 12.00 pm in Melbourne, including the Conversation Hour which is heard across Victoria from 11.00 am.
Faine is known for his ability to vigorously debate and foster conversation on politics, law, arts or sports. His political views are known to be left-leaning. Enjoying high ratings peaking in September 2002, he was found to be Victoria's top talk-show host (AC Nielsen survey). In 2003 he received the ABC Local Radio 'Broadcaster of the Year' award. Jon has also worked on scripts for a number of TV and feature films. In 2005 he undertook study in Mechanical Engineering Technology at NMIT to be able to machine parts for his hobby of working on old cars in his spare time.