From his home studio in the Boston area, Chapman began hosting the independent music-focused podcast Accident Hash in 2005 and the new media podcast Managing the Gray in 2006. During the summer of 2005, Hash was one of the first podcasts to be included in the iTunes Podcast directory and it became a featured podcast on PodShow. Accident Hash was later voted Best Podsafe Music Podcast at the 2006 Podcast Awards.
Chapman also became a popular guest and occasional guest host on many other podcasts across the world discussing topics ranging from podsafe music to new marketing. Included in his many appearances are stints guest hosting Adam Curry‘s Podshow on the Sirius Stars channel and as a panelist on The BeanCast Marketing Podcast.