Smallwood was born and raised in Huddersfield, West Yorkshire, where he grew up listening to The Beatles and The Rolling Stones on the radio and playing cricket and rugby union.

[9] After much deliberation, Smallwood eventually contacted Steve Harris, the band's bassist and founder member, and arranged two pub gigs for the group in west London, one at the Windsor Castle in Maida Vale and the other at The Swan in Hammersmith.

[12] In spite of this, Smallwood agreed to help the group, although, following his experiences with Steve Harley, he did not initially commit to becoming their full-time manager until he arranged the band's signing to EMI and publishers Zomba at the end of the year.

[17] Prior to this, in November 2006, Smallwood left Sanctuary and formed Phantom Music Management with Andy Taylor, which focuses solely on Iron Maiden.

It likens Smallwood to the Sheriff of Nottingham, due to his notorious stinginess with money, and refers to his frequent complaining about a (then recent) move to Los Angeles.