Failla was recruited out of North Allegheny Senior High School in Wexford, Pennsylvania by the University of Notre Dame, where he was a two-sport athlete, playing shortstop for the baseball team, and backing up starting quarterbacks Rick Mirer and Kevin McDougal on the football team for three years, from 1991–1993.
[1][2] When it became clear that he would not win the starting quarterback job in 1994, he entered the Major League Baseball Draft, and was selected by the California Angels in the third round.
[3] Following stints with the Boise Hawks, the Cedar Rapids Kernels and the Lake Elsinore Storm in the minor-league system, he decided to return to school in 1998, and used his final year of NCAA eligibility playing quarterback at the Indiana University of Pennsylvania, where he led the team to a 10–2 record and a playoff berth.
In 2001, he was drafted by the Chicago Enforcers of the XFL with the ninth overall selection, but lost the starting quarterback job to fellow Notre Dame alum Kevin McDougal.
He then returned to his alma mater at IUP in February 2006 as the offensive coordinator under head coach Lou Tepper, but resigned three months later to pursue business interests.