From a young age, Josh knew he wanted to act. He attended the University School in Florida for his high school years. Josh studied acting and graduated from Carnegie Melon University in 2003. He has been a member of the Groundlings and founded his own improvisational comedy troupe, The Lost Nomads. After several successful off-Broadway plays, he landed a leading role on Broadway. From there, he began to get cast in movies and landed a supporting role on the television comedy, Back to You.