Winn is first a husband to Miska, dad to Wyatt and Seth. Winn's spiritual journey has at times been a sputtering faith, but his heart is to live simply and authentically, honest about life and doubts and hope and pain -- and honest with how the radical claims of Jesus lay hold on our lives.

Winn has written for many periodicals, including Soul Journey, Campus Life, Leadership Journal, Radiant, Relevant, Our Daily Journal and Clear & Seven. He has also written for PreachingToday.com and for five years was the Deeper Walk editor for Relevant Magazine. His first solo book, Restless Faith: Hanging on to a God Just out of Reach is a candid exploration into Winn's struggle to come to grips with the perplexing, riveting and mysterious nature of God. His second book Let God: The Transforming Wisdom of Francois Fenelon offers Winn's introduction to the wisdom of a warm, elder spiritual guide, just the sort of spiritual guide Winn craves. Most recently, Winn authored Holy Curiosity: Encountering Jesus’ Provocative Questions. Intrigued by the fact that Jesus often asked questions rather than giving answers, Winn spent several years pondering the art of question-asking Jesus’ modeled.

Since seminary, Winn has worked as a stock broker, served in university ministry and as an adjunct theology professor. Winn currently directs The Genesis Project, a soul care community for church planters. Miska has a master's in counseling and offers her gifts as a spiritual director. The Collier tribe live in Charlottesville, Virginia where Winn continues his writing and serves as pastor at All Souls Charlottesville.

Winn and Miska hope to live simply, enjoying their boys, good conversation, laughter, beauty and fresh-brewed coffee.