Born in Chicago, Weiss spent most of his youth growing up in central New Jersey where he later started playing bass with local bands while attending Princeton High School.
In 1982 he teamed up with William Tucker (guitar) and high school buddy Sim Cain (drums) to form Regressive Aid, an instrumental new wave band that released a 4-song EP in 1983 and a 6-song LP the following year.
This led to a collaboration with his friend Jeff Rusnack, partnersinWonder, and together they founded Bird'o'Pray Records, a cassette only label that featured electronic and alternative music, including the first releases by the New Hope, Pa. duo Ween.
In 1985, Regressive Aid caught the attention of Black Flag founder/guitarist Greg Ginn who then recruited Weiss and Sim to travel to Los Angeles and form Gone, an instrumental punk/jazz power trio.
It was also around this time that Weiss began to further pursue adventures in music production and engineering, enlisting Ween and local NJ act Skunk as guinea pigs.