[2] Smith earned a bachelor's degree in political science from the University of Oregon, where he was a member of the Beta Theta Pi fraternity.

[2] At his father's insistence, he took a year off during college, serving as a youth counselor in Lane County and then running youth sports programs in Washington, D.C.[2] In 1993, while attending the University of Oregon, Smith was cited for a misdemeanor assault at a fraternity party but the charge was later dropped following a diversion agreement that included covering the victim's medical expenses and community service.

[3] He briefly worked for Stoel Rives, but became motivated to establish an organization dedicated to engaging young people with progressive politics.

[2] He soon left the law firm, founding the Bus Project in 2001, an organization focuses on empowering young people to participate in the democratic process.

[14] In the Legislature, Smith collaborated with representatives from rural Eastern Oregon to develop a statewide water strategy.

Smith also co-led the initiative to create online voter registration in Oregon, and carried a bill in the Legislature to allow trafficked minors to expunge their prostitution convictions upon reaching age 21 if they have had no other trouble with the law.

[15] In April 2011, Smith released the results of a video he compiled of Oregon state representatives reciting the lyrics of Rick Astley's 1980s pop hit "Never Gonna Give You Up".

[1] A series of incidents from Smith's past uncovered by The Oregonian and Willamette Week derailed his 2012 mayoral campaign.

[22] Smith conceded to reporter Nigel Jaquiss that he had thrown a punch, but argued that the blow was not aimed at the player's genitals, as alleged by witness accounts.

[7] In 1993, Eugene police cited Smith for a misdemeanor assault charge stemming from an incident with an 18-year-old woman at fraternity party.

[24] Police and the Lane County District Attorney's office dropped the charge after Smith reached a diversion agreement with the city of Eugene and the victim.

[4][6] Smith agreed to cover the woman's medical expenses, pay a $250 court fee, and complete 20 hours of community service, among other conditions.

Although Smith denied knocking the woman off of a couch later in the evening, he conceded to grabbing her and then hitting her above the eye when she confronted him.

[34] Following this article, XRAY's staff released a statement acknowledging the concerns raised and detailing their desire to move forward.