In 2000, Braithwaite played with a band called Mighty Joe Young Trio. In 2000 and 2002, Braithwaite performed solo acoustic shows. In 2002, Braithwaite, Aidan Moffat and Colin "Sheepy" McPherson released an eponymously titled EP called The Sick Anchors.
Braithwaite's musical technique is characterized by the heavy usage of effects pedals, used to create ambient instrumental guitar sounds. As with much music associated with the post-rock style, his playing emphasizes melody and dynamic contrast over virtuosity.