Jennings was born c. 1966, and began gaming at the age of 10, when he began playing "Dungeons & Dragons". He created his first website to post tips and tricks about the 1996 game "". Around 1998/1999, his focus shifted to "Ultima Online" (UO), an early graphical MMO first released in 1997, and one of the first to become well known in popular culture. Jennings, whose primary career was as a database programmer, became a respected critic of UO, as he posted detailed critiques of the game. Jennings's strong views on "macroing" – the practice of automating aspects of the game, effectively making it easier – made him very popular with some UO players. As noted by game researcher Edward Castronova, this was an early example of a site where a game's designers had strong opposition from certain players, who would use their websites to actively critique a game's development. Jennings' writing was characterized by a mixture of humor and vitriolic anger, and his posts were known to readers as "rants". The site became frequented by both fans and haters of UO, along with some of UO's developers and personnel, as well as developers of competitor games.