Barbara Lipp is a graphic designer and friend of John Flansburgh. Lipp and Flansburgh met while working at MacMillan Publishers, in the art department for children's educational material. This was during the beginning of They Might Be Giants. MacMillan was where Flans found the snowman artwork used on the cover of Don't Let's Start. According to Lipp, he photo-statted the snowman illustration and made various modifications, including adding the pile of burning money. The original artist was eventually made aware of this, and was amused at the unconventional use of the snowman. Lipp herself also did some ink work for the band in its early years. She is credited with "art assistance" on both Flood, for which she illustrated the titular barnstar, and Apollo 18, for which she recreated and inked an old, atomic-looking Elektra logo. She also created a stage prop that the band used in their early shows, which was a "painted cardboard cut-out of a rabbit, a gun, a noose, and a question mark, that they rigged up onto a spinning device". Part of this prop can be seen on the photograph of the Johns from the Don't Let's Start EP.
Barbara Lipp and her friend Tom Koken were also behind the performance arts act Frieda, which had opened for They Might Be Giants, and released one single, Disco Lover / Plastic Rap, which featured Flansburgh on guitar.