Leland first encountered Woodrush at an outdoor festival in Spring, 2003 in one of those six-degrees-of-separation sort of situations, except there were really only three degrees of separation. After developing a great friendship with Woodrush founders Jim and Kelly, Leland began to occasionally sit in with the duo, and eventually began to co-produce tracks with them.

By the end of 2008, Leland had sat in with the band at well over half of the shows they'd played during the previous year, and they invited him to officially join the band.

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