He is a co-founder of the Sports Leadership Institute and a former National Basketball Association (NBA) executive and ESPN analyst.
[1][2][3] Penn co-founded Major League Soccer expansion team Los Angeles FC in 2014, and served as president and co-owner before stepping down from the position in 2020.
From 2007 to 2010, he spent four seasons with the Portland Trail Blazers as vice president of Basketball Operations and assistant general manager.
During the summer of 2009, Penn was offered the general manager job with the Minnesota Timberwolves, but he turned it down, deciding to stay with the Blazers after a promotion to vice president of Basketball Operations.
He helped found for St. Jude—an NBA Cares program that raises awareness and funds to fight childhood cancer.
[14] For the 2010-11 NBA Season, Hoops for St. Jude features the endorsement of NBA stars Dwyane Wade, Dwight Howard, Pau Gasol, Kevin Love, Rudy Gay, David Lee, Steve Blake, and coach George Karl.