Zipf was among the first to call for a shift away from traditional music marketing business models, giving away much of his music for free. Even before Kickstarter became mainstream, in 2005 Zipf funded his first tour solely off the $2 donations of his fans. In 2006, he and manager Shawn Matthews raised more than $45,000 from his fans to produce The Long Tail EP. In 2009, he released ‘’The Cowards Choir using a "pay as you can" model from his website. These music and marketing techniques caught the attention of Paste Magazine, Performing Songwriter Magazine, American Songwriter, XM Satellite Radio, and CMJ music festival. Zipf has had songs played on VH1 and MTV, and "Stumble on the Line" was featured on ABC's Private Practice. In 2008, Zipf embarked on a project and tour combining music and film in a constantly changing live performance art piece known as "Pfriends on Pfilm". Performing in all white, Zipf and his band played in front of a white canvas while thematic colors and found film were projected onto their bodies by artist Brad Wolf. In October 2009, Zipf signed to P Is For Panda and wrote and recorded with The Lost Chorus, a bandcomposed of former members of Stavesacre and Project 86. Zipf's latest album is Jealous Hands. It was produced by Jeremy Griffith and digitally released on July 5, 2011. He also offered it as a free 192kbit/s download on his website. In 2013 Zipf took the moniker The Cowards Choir and released the 4 song EP Reunion through NoiseTrade. Shortly thereafter, Zipf recruited drummer Adam Neubauer, percussionist Ben Tufts and bassist/keyboardist Ryan Walker to fill out The Cowards Choir band. In October 2014 The Cowards Choir released the 4 song EP Cool Currency'', also through NoiseTrade. After the Ben Tufts & Friends benefit show for the Craig Tufts Memorial Fund at Vienna, VA's Jammin' Java in August 2015, Ben Tufts and Adam Neubauer parted amicably from the band. Continuing to play with Ryan Walker, Zipf welcomed Alissa Moore and Dayana Yochim into the band. In 2016, the new lineup released the album "Name The Fear", in addition to a collaborative visual score by Charlotte, NC film maker Will Davis.
Charity
In 2010, Zipf toured nationwide with Damion Suomi and Lauris Vidal in support of the TWLOHA Spring 2010 UChapters Tour, "Evenings of Lyrics and Conversation".