Simon graduated from Hopkins High School in Minnetonka, then went on to Tufts University in Medford, Massachusetts, receiving his B.A.

On Monday, May 2, 2011, Simon testified regarding and opposed a proposed constitutional amendment to ban gay marriage in Minnesota.

In 2018, Simon was reelected by a fairly large margin over Republican nominee John Howe.

Active in his local community, Simon is a member of the TwinWest Chamber of Commerce, the American Cancer Society, the local League of Women Voters, the St. Louis Park Community Education Advisory Council, and the Lenox Foundation, which raises funds for the St. Louis Park Senior Program.

He is a member of Temple Israel, serves on the board of the Minnesota Chapter of the Jewish Community Relations Council, and is an attorney.