Since leaving the Army in 2003 (and again in 2006), Anderson has been an operations leader in the wine business in northern California. He is currently responsible for a network of eleven wineries producing wines ranging from $10 to $250 per bottle.
Anderson and his wife, Cally, graduated from the United States Military Academy in 1998. Anderson served in the Armor branch, and Cally served in the Medical Service Corps branch. They both served at Fort Stewart, Georgia and deployed to Bosnia-Herzegovina in 2000-2001. Anderson also deployed to Kuwait / Iraq in 2002-2003 as part of Operation Intrinsic Action and later, Operation Iraqi Freedom as part of the 2nd Brigade, 3d Infantry Division.
Anderson and Cally live in Healdsburg, California with their two children.