His record label, Old Town Records, was established in August 1953 and was active until 1966.[5] Weiss took sole control of the label in 1956. He was primarily a producer of doo wopgroups, as well as blues music.[6] Old Town had its first hit with the 1958 single "We Belong Together" by Robert & Johnny, and had further hits by Billy Bland, the Solitaires, the Capris, the Earls, and others. The Old Town catalog was sold by Weiss to Atlantic Records in 1970.[7] Subsequently, Weiss worked for Stax Records. He had a co-writer credit for the song "Foggy Notion" by the Velvet Underground, along with all the members of the band. Weiss revived Old Town as a vehicle for Arthur Prysock in 1973 and kept the label going until about 1978.
Weiss was described as "one of the most colorful characters of the New York independent record business"[5] and as "brash, miserable and explosive by turns... [He] had a bulging contacts book and was both courted and feared in an industry notoriously not for the faint-hearted." He was associated with the practice of "payola", being credited as the inventor of the "$50 handshake",[5] and once said: "Why waste time going out with someone you don't like, and sit down and feast with them when you can't stand them? Just give them the money and let them play the [fucking] record."[4]