Nickey was a staff writer for the Herald Times from 1999 to 2001, where he was a frequent contributer to the "Audible" feature section. He focused on local music and nightlife articles toward the end of his employment at the paper. He has also hosted numerous radio programs on WFHB.
He took over management of TD's CDs & LPs after Tom Donohue died in 2003. Later, he went on to head up sales and relations of local recording company, Secretly Canadian in early 2005. After less than a year in the job, he left to open Landlocked Music in early March of 2006.