Hallman was born in Olympia, Washington, and began wrestling when he was eight years old. He was on the wrestling team at Yelm High School and won the 135-pound state championship in his senior year. Hallman had planned to continue his career at a community college, but broke his leg during the pre-season training, and had to be sidelined for the entire season. A former high school classmate was sending in video tapes to Battlecade and invited Hallman to fight him because Hallman was a well-known wrestler. Hallman won the fight by a guillotine choke, and his opponent's praise of Hallman's potential encouraged Hallman to pursue a career in MMA. Hallman had an exhibition match three weeks later against a Japanese fighter who was training with Matt Hume, which Hallman also won.
Two of Hallman's biggest achievements are his wins (both by submission in a combined 38 seconds) over UFC Hall of Famer and former welterweight champion Matt Hughes. Their first fight was in 1998 at Extreme Challenge 21, the second in December 2000 at UFC 29: Defense of the Belts.
After his second victory over Matt Hughes, Hallman moved down in weight and fought Hughes' teammate Jens Pulver for the lightweight UFC championship in September 2001. Both Hallman and Pulver wrestled at the high school level in Washington. Hallman claimed to know Pulver since high school and expressed dislike toward the fighter. Although Pulver denied knowing Hallman personally, he knew of Hallman through their state champion wrestling careers (at different weight classes).

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