Doug interviews Emmanuel Waters, CEO and co-founder of Durham, North Carolina-based Old Hillside Bourbon Company, which launched in 2020 and has since expanded distribution across the U.S. Emmanuel walks through his pivot from a career in Department of Defense contracting to entrepreneurship, describing the COVID-era moment that pushed him toward the leap and the careful planning he and his wife did around finances and benefits before he left his job.
The two dig into the tougher realities of the spirits business: thin margins, heavy regulation, and the challenge of getting a new product to stick on crowded shelves. Emmanuel recounts breaking a state sales record right out of the gate, then discusses the added hurdle of being lumped in with other Black-owned labels rather than judged purely on the product itself.
Emmanuel also details what sets Old Hillside apart: nontraditional packaging and on-bottle narratives that honor overlooked pieces of Black American history, from the Black jockeys who dominated the early Kentucky Derby to the “Trifecta” women of horse racing. He and Doug close with a broader conversation about capital access, celebrity liquor brands, and Emmanuel's advice to chase purpose over money.