that he aspired to become radio DJ and asked if he could visit the station to see what it was like. He would end up running errands and doing office work at the station on weekends and over the summer. When Cipriano was 16, he was hired to work on-air at WWCO-FM, a country music station, and WWCO-AM, a top-40 station, both in Waterbury. He was soon after hired at a third radio station, WDRC-FM, a top-40 station in Hartford. He used a different on-air pseudonym at each station.

After high school, Cipriano became the youngest on-air FM