Doug interviews Emmanuel Waters, CEO and co-founder of Durham, North Carolina-based Old Hillside Bourbon Company. Launched in 2020 and expanding across the U.S., Emmanuel shares his pivot from a Department of Defense and contracting career to entrepreneurship after a COVID-era “aha moment”. He talks about breaking a state sales record at launch, but not before planning his career exit with his wife by reviewing finances, relying on benefits, and reviewing the spirits industry’s regulation and low margins. Old Hillside’s differentiation is storytelling, using nontraditional packaging and on-bottle narratives to honor Black American history, including early Kentucky Derby Black jockeys and the Trifecta women of horse racing. Emmanuel and Doug discuss product persistence in the spirit market, capital access challenges, celebrity liquor brands, being lumped with other Black-owned labels, and advice on chasing purpose over money.

More of Emmanuel:

Old Hillside Website

Forbes Article

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