Ryan began his freelance journalism career by working at the Seattle AM Radio Station as producer and engineer in 2002. During 2003-2004 Ryan was a freelance writer for Xbox Nation Magazine after which between 2004-2005 he wrote for 1UP, Japan Times, OXM, EGM, WIRED and Metropolis.
On August 26th, 2008 Ryan left Kojima Productions in the hope of finding a job closer to his family back in the United States. He then joined Microsoft Game Studios as Creative Director of the new Halo studio.
In September, 2011 Ryan left Microsoft's 343 Industries to form his own company, Camouflaj. The aim of the company is to "create a game studio focused on creating games that have something to say"1 and is currently working on two game titles2.