Connie Collingsworth “Tired of Selling a Message”

Artist and creative entrepreneur Connie Collingsworth joins Mark Brickey for a raw and inspiring conversation about reinvention, resilience, and the hat that changed everything. From weathering historic floods in Kentucky to building a new business with an old friend, Connie shares how her brand Happy Jack evolved from a personal tribute into a growing custom hat company powered by collaboration, color theory, and unshakable attention to detail.

You’ll hear about making space in a crowded market, finding product-market fit without losing your soul, and why the best ideas sometimes need a partner to come to life. Plus, Mark and Connie swap war stories about their favorite hats, building community through merch, and the beauty of designing for people who truly care.

This one’s for anyone who’s ever had to start over—or who’s sitting on a great idea but doesn’t know what to do next.