 Caldwell worked as a cover presenter on Dublin's FM104 from October 2010 and until May 2012 he also worked briefly Sunday afternoons and a regular fill-in on Wicklow's radio station East Coast FM February to December 2011.On 3 December 2012, Caldwell also assumed the position on "DSN Hits", an internet radio station broadcasting from Alliance, Ohio in the United States.He then moved to the midday (US Eastern Time) position, before leaving the station on 7 May 2013.