Gwynne's first media job was covering speedway at Belle Vue in Manchester for Piccadilly Radio in 1980. He moved onto local north-west football. Premium-rate telephone information services such as ClubCall gained popularity during the late 1980s and Gwynne worked for a cricket equivalent, "Cricket Call" covering Lancashire County Cricket Club between 1988 and 1991.
Gwynne's first job in media was covering speedway at Belle Vue in Manchester for Piccadilly Radio in 1980. He later transitioned to local north-west football, working with a premium-rate telephone information service called ClubCall during the late 1980s.  He also worked for "Cricket Call," covering Lancashire County Cricket Club between 1988 and 1991.