[3] While in Huddersfield, he took singing lessons with vocal coach Paul Wade who described him as "a great pupil".

[4] As a student at Guildhall where he studied for a Postgraduate diploma in vocal training, Stiff replaced bass singer Tom Lowe to become a member of G4 which also included final year undergraduates Jonathan Ansell, Mike Christie, and Ben Thapa, who all started singing together to raise money and gain experience.

In 2004 they later auditioned for the first series of The X Factor and despite placing second, signed a £1.5 million record deal with Sony-BMG.

They went on to produce two more albums: G4 and Friends and G4 Act Three with combined sales in excess of 1.5 million copies.

[8] In 2008, following a schedule overhaul at Classic FM, Stiff re-joined the station as a weekend presenter (he had previously hosted another show with the other members of G4),[9][10][11] after which he returned to Guildhall in 2009 for a Master of Music Opera course, graduating with a Distinction in 2011.