Reynolds made his first game sale with Quest 1 to SoftSide magazine, its August 1981 cover feature. He was a gamer in high school, and a SysOp on Randolph School's PDP-11 mainframe computer. A 1990 graduate of the University of the South, Reynolds briefly pursued graduate studies in Philosophy at the University of California, Berkeley. This influence is evident in the emphasis on philosophy encountered in one of his more famous computer games, Sid Meier's Alpha Centauri.