Simon began his career in the music industry back in 1979, when his father, Eric Cowell got him a job at EMI records. He started off working in the mail room, but worked very hard and spent his time learning how the music industry worked. In time, he was promoted to accounts receivable assistant and eventually to a spot in the music publishing department. Having learnt what it took to make a hit record, he left EMI to form E&S Music with Ellis Rich, a former executive at EMI. Unfortunately, the company collapsed and went under a few years later, forcing Simon to return to EMI. A short time later, he was quick to set up his own label, 'Fanfare' with partner and fellow EMI executive, Iain Burton.
Proving that he had an ear for a hit, BMG offered Simon the position of A&R Consultant in 1989. His time at BMG saw him pioneer some of the biggest selling hits in the industry, including bands 'Five' and 'Westlife'. He can also be credited with the emergence of TV hits from the likes of cartoon puppets Zig & Zag, The Teletubbies and Robson & Jerome.
Not only has Simon made records, he also breaks them: over a ten year period, via his company 'S Records', he has achieved sales of over 25 million albums, over 70 top 30 records, and 17 Number 1 singles. His band 'Westlife' has achieved an impressive 10 Number 1 hits alone.
Over the past 10 years or so, Simon has been involved with many talent show competitions, both on and off screen. The first major hit was Popstars which paved the way for Pop Idol and the spin off Americal Idol which is now one of the biggest talent competitions in the world. After those he moved onto The X Factor and Britain's Got Talent as well as numerous others.