Winn grew up in a musical family. He started getting into the guitar in his teenage years and began taking music classes in school. He then started busking "street performing" and playing at local coffee shops.
Winn started learning songs by Buddy Holy, Elvis Presley, Sam Cooke, The Beatles and the Rolling Stones. Winn kept experimenting with writing and recording. He began playing various shows and also performed some songs live on a few college radio stations.
Then around 2009 Winn ended up in Twin Falls, Idaho and was introduced to William Jake Magee at a local coffee shop. They decided to form a group and called the band , the Precepts. They started learning more songs by the Sonics and the Beatles and performing live. Then Winn left Idaho and went back to Oregon and the Precepts disbanded. Winn and Jake stayed in touch and in 2010 formed the Indigo Art Tribe. The band eventually moved to Portland, Oregon and played live at various venues in town. In 2015 Winn and William met drummer Geoff Bond and formed a group called Radio Wolf. They played together for a little over a year but built a bit of a following. After disbanding they later formed Silverhill in 2018. Currently Winn is playing in Silverhill. silverhillband.com