Ad had been thinking about starting another band for a while. It began late in 1995 when his sister Noelle returned home to Boston for grad school after three years as a New York City librarian. She’d learned a little guitar and gave Ad a demo tape of original songs. Intrigued, he played the tape for his friend Cindy (Singaporean-born library grad student, classical pianist, and bossa nova aficionado) who presented an amazing tape of her own uniquely original pop songs. Ad played the tape for drummer Tom, and both agreed to give it a whirl with the beginners. Thus was Jumprope born.
A clean guitar-oriented pop sound emerged, but with the distinction of three lead vocalists, three songwriters, and melodic original tunes that often make use of many of Cindy’s favorite jazz chords unusual in rock music, yet sounding simple all the while. Someone described it as a confluence of Heavenly, The Go-Betweens, The Cardigans, and The Beatles. No one in the band will confirm, deny or comment on this. When asked about his songwriting influences, Ad says, "Cindy."
The band recorded a four-song demo early in 1996 and circulated the tape around Boston to get shows, and around the world to people in the indie pop community via the Internet. San Francisco’s Twee Kitten records made an immediate offer to release it, and the four-song 7" EP No Happy Songs came out in June 1996. The record charted on college radio stations in the USA, and response from all around was marvellous. The band soon received offers to do other small records, contribute to compilation projects, and even to appear on a movie soundtrack (Yellow, which premiered in San Francisco on March 8, 1997). Jumprope also performed upon invitation, at the Popfest ’97 event in New York City in January 1997, Popfest '97 1/2 in Boston in May 1997, and at a-POP-alypse Now in Toronto in September 1997.
A string of small releases continued through 1997 and continues into 2001. The band's debut full-length CD entitled Bookshelf Adventures was released in October 1998 on Reverse Curve/Section 304 Records in the USA and on the Flavour of Sound label in Japan. The group has traveled and played in over 30 cities in a dozen states. Noelle departed in October 1999 and her place was refreshed by Elbert Chang on guitar, who went on to Stanford University in August 2000, temporarily replaced by recordist/producer Ric Mosher. The second full-length CD, Suitcase and Umbrella, came out in February 2001 on Planting Seeds Records, with worldwide distribution via Parasol Records.