This chapter chronicles the entrepreneurial journey of a woman who aims to honor the legacy of Nearest Green, an overlooked black distiller, by launching the billion-dollar bourbon brand Uncle Nearest. It delves into the historical complexities of the whiskey industry, the challenges of representation, and the innovative strategies employed to build a brand with deep narrative roots. Through personal exploration and strategic marketing, she navigates the hurdles of this often-homogeneous market, highlighting the importance of resilience and storytelling in achieving success.