Speight is a close friend of actor Rob Benedict. The two often appear at conventions in tandem. Together, they created the comedy web series Kings of Con (2016) based on their experiences at conventions for Supernatural, a TV show in which they both were featured actors and beloved characters.
Speight is co-writer, producer, director, and actor in Kings of Con, and plays a “heightened version of himself” as character Richard Slate. With the support of a successful Indiegogo campaign, the series launched on November 15, 2016, at Comic-Con Headquarters in the U.S., and internationally through multiple platforms such as GooglePlay. As of 2019, it is available for streaming on CW Seed. An after-show called Kings of Conversation is available through their Facebook page.