A native of Hartland, Wisconsin and a 2002 graduate of UW-Stevens Point, Webb became enraptured with the Division III game during his freshman year of college as he followed the Pointers to a runner-up finish in the 1998 NCAA tournament. During his college years, his interest in Division III grew to the point he became a fervent fan of Division III as a whole. After a few years away from the Midwest, Webb returned to Wisconsin in 2005 and began tenure as U.S. College Hockey Online's NCHA/MCHA Columnist in 2006. On top of his weekly column duties, he covered the 2007, 2009 and 2010 Frozen Fours for USCHO. After resigning from USCHO in the fall of 2010 he, along with Scott Bridges, created the now-defunct d3westhockey.com with the intent of maximizing coverage and exposure for teams in the West Region. The managing editor of D3hockey.com for its first three years, Webb took a step back from a leadership role in the summer of 2014 but remains on as a contributor to the site, despite the fact we have no idea where he is living. Webb has covered eight of the last nine Men's Frozen Fours and has compiled a database of men's recruits in each of the past five years.