He played college football for the Utah State Aggies, and was signed by the Minnesota Vikings as an undrafted free agent in 2006.Penn attended St. Anthony of Padua, Gardena, and graduated to Saint Bernard Catholic High School in Playa del Rey, California.As a senior, Penn was a team captain, and was awarded second-team all-Western Athletic Conference honors at left tackle.He signed with the Minnesota Vikings as an undrafted free agent, but was released prior to the start of the 2006 season.He replaced Green Bay Packers tackle Chad Clifton, whose team advanced to Super Bowl XLV.[12] Penn was named to his second Pro Bowl in 2016 along with fellow Raiders offensive linemen Kelechi Osemele and Rodney Hudson.On March 15, 2021, Penn signed a one-day contract with the Las Vegas Raiders, to retire as a member of the team.