In 2005, John won the Funniest Person in Austin contest. Since that time, he has appeared on Comedy Central's Live at Gotham, at the HBO United States Comedy Arts Festival and TBS Just for Laughs Festival in Chicago. In its September 2010 issue, Reader's Digest named John as one of three young comics to watch. Originally an attorney by profession, John spent 2010 in Kenya working as a legal fellow with International Justice Mission. While there, he performed on Churchill Live!, a late night comedy show with an audience of 10 million. He later recounted that story on the NPR program Snap Judgment. John made his American late night debut on Conan in 2012.