Kaulkin began working for the Epitaph label. His role was looking after the label's data management system.[3] In 1995, he was head of marketing.[4] He eventually worked his way up to become the president for the label, and worked there until 1998. Later he founded Anti-. Under Kaulkin's stewardship, the label began with the release ofMule Variations byTom Waits which was met with success.[5][3]
Other artists signed by Kaulkin includeMavis Staples, who came to the label as a result of a meeting between Kaulkin and her manager,[6] and Jade Jackson, whose vivid storytelling attracted Kaulkin.[7]
As a musician, Kaulkin played piano on "Haggard (Like I've Never Been Before)", which was the title track ofMerle Haggard's albumLike Never Before.[8] He had multiple roles as composer, musician and producer on theBlues Got Soul album byKing Ernest.[9]