In this episode of the Startup CPG Podcast, host Caitlin Bricker sits down with Emmanuel Waters and Courtney Tucker, co-founders of Old Hillside Bourbon Company—a premium spirit brand that celebrates history, heritage, and homage in every pour. What started as a pandemic-era phone call between cousins and childhood friends became one of the most compelling brand stories in the spirits industry, rooted in Black history, community pride, and a commitment to craft.

Emmanuel and Courtney share how two cousins who barely knew each other connected during the height of COVID-19 to build a bourbon brand named after Hillside High School—the oldest African American high school in the United States, located in Durham, North Carolina, one of five Black Wall Streets in America. They dig into the barriers Black founders face in a $40 billion spirits industry where African Americans represent nearly 12% of consumers but less than 1% of ownership, and explain why telling the stories that history tries to erase is at the heart of everything they do.

From the black jockeys who dominated the Kentucky Derby in the 1800s, to the trailblazing female jockeys of the early 1900s, to the Harlem Hellfighters—the first African American unit to fight in World War I—Old Hillside doesn't just make bourbon. They let the stories create the bourbon. And they've broken records doing it, becoming the fastest-selling bourbon in the state of North Carolina at their very first ABC Store demo.

Fair warning: you might get emotional. Caitlin did.

Listen in as they discuss:

• How a pandemic-era DM on Instagram launched a bourbon company between cousins who barely knew each other
• The history behind the name: Hillside High School and Durham's Black Wall Street legacy
• Representing less than 1% of ownership in a $40 billion market—and building anyway
• The Black jockeys who dominated horse racing in the 1800s, featured on their Last Ride Rye bottle
• The Trifecta bottle honoring three pioneering female jockeys—and the moment two families who knew each other in the 1930s met for the very first time at an Old Hillside event
• The Harlem Hellfighters release: aged 191 days, finished in French Pinot Noir barrels, proofed at 112
• Breaking records at their first ABC Store demo and becoming the fastest-selling bourbon in North Carolina
• Bootstrapping for six years in one of the most capital-intensive industries in CPG
• Why they don't just want to be the best Black-owned bourbon—they want to be the best bourbon, period

Episode Links:

Old Hillside Bourbon Company

Website: https://www.oldhillsidebourboncompany.com

Instagram: https://www.instagram.com/oldhillsidebourbonco/

Emmanuel Waters — Co-Founder, Old Hillside Bourbon Company

LinkedIn: https://www.linkedin.com/in/emmanuel-waters-4740989a

Courtney Tucker — Co-Founder, Old Hillside Bourbon Company

LinkedIn: https://www.linkedin.com/in/courtney-tucker-79918527

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Show Links:

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• Episode music by Super Fantastics