At age 11 Endicott began playing guitar and at 12 switched to bass guitar. By age 13 he was an established bass player in the Washington, D.C. area, playing in numerous punk and harDCore bands, most notably Stain, with Geoff Turner of Gray Matter and Colin Sears of Dag Nasty. He has stated that his biggest influence as a bass player is Joe Lally of Fugazi, and he initially sought to emulate Lally's melodic style of playing.
While attending Vassar College in Poughkeepsie, New York, Endicott was classmates with future Bravery keyboardist John Conway. The two began a musical partnership, playing together in various projects in the Poughkeepsie area. After graduating with B.A. in Psychology, Endicott and Conway moved to New York City, where their musical partnership continued. In 2003 he switched from bass guitar to vocals and began writing, recording and producing the music that would become the first Bravery album. Guitarist Michael Zakarin joined after answering an advert in a local paper, and brought with him bassist Mike Hindert, a classmate of his from Georgetown University in Washington, DC. Drummer Anthony Burulcich was living in Boston where he had studied percussion at Berklee College of Music. After the death of his sister, Burulcich moved back to his childhood home in Long Island New York to be with his family. On the day Burulcich was moving, while driving with his belongings in a U-Haul truck, Endicott called him. The Bravery went on to release their debut album in March 2005.
Endicott is a multi-instrumentalist playing guitar, bass, vocals, keyboards and programs electronic drums and synthesizers. Endicott has also co-directed and written a number of the Bravery's music videos, making his music video directing debut with the video for the Bravery's "Believe" in 2008. He is also credited as producer on the Bravery's debut album, as well as the "Moon" portion of their The Sun and the Moon Complete, described as an "alternate take" on their second release The Sun and the Moon. Endicott co-produced the Bravery's third studio album Stir The Blood.

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