We chat with Ashley Wineland, rising country star, about her latest single “Loving You Is Easy.” From her Arizona roots and love for the outdoors to launching her music career at just age 14, Ashley shares how her journey has shaped the authentic stories behind her songs.

She talks about writing an upbeat anthem that celebrates “love gone right,” collaborating with GRAMMY-nominated producer Marti Frederiksen, and reimagining Cyndi Lauper’s “Time After Time.” Ashley also opens up about her deep connection to veterans’ causes, the creative vision behind her “Tumbleweed” video, and what it’s like running her career completely independently — booking 60+ headline shows a year and building a devoted fanbase known as the Winelanders.

Jonathan’s Drinking: Woodinville Rye Port Finish