Old Hillside Bourbon is a premium spirits brand co-founded by Emmanuel J. Waters, built on the history of Black Wall Street, the forgotten Black jockeys of the Kentucky Derby, and Durham’s entrepreneurial tradition. The brand entered into a $40 billion industry where African Americans represent 12% of consumers but less than 1% of ownership. In this episode, Donald Thompson sits down with Emmanuel J. Waters, CEO and co-founder of Old Hillside Bourbon, to unpack how a brand rooted in Black Wall Street, the Kentucky Derby’s forgotten Black jockeys, and Durham’s rich entrepreneurial history is winning gold medals, breaking distribution records, and building something far bigger than a bottle.
Episode Long Description
Old Hillside Bourbon was never supposed to work. Bourbon experts told the founders not to launch in North Carolina, one of the hardest control states in the country. African Americans spend nearly $3 billion in alcohol annually and own less than 1% of alcohol companies. Emmanuel had never tasted bourbon before co-founding the company.
Then they held their first bottle signing in Durham. The line wrapped around the building. People bought six, seven, eight bottles at a time. They sold 50 cases in a single day, breaking a record in the state they were told would kill their brand.
In this episode of High Octane Leadership, Donald Thompson and Emmanuel J. Waters dig into what happens when a brand is built on something more powerful than marketing: a story worth telling. From the history of Black Wall Street in Durham to the forgotten Black jockeys who built the Kentucky Derby, Old Hillside is using bourbon as a medium to recover and celebrate the American stories that have been systematically erased. And along the way, they are winning double gold medals at the largest spirits competition in the world.
In Episode 186 of High Octane with Donald Thompson, Waters and Thompson discuss what happens when a brand is built on story rather than marketing spend.
The most durable competitive advantage is a story nobody else can tell. Old Hillside Bourbon is the proof.
Key Talking Points:
- History, Heritage, and Homage: How Old Hillside Bourbon built its entire brand strategy around three pillars that no legacy competitor can replicate.
- The Economics of Black Entrepreneurship: Emmanuel breaks down what that gap costs communities and how to close it.
- The Durham Moment: How selling 300 bottles in a state they were told would kill their brand became the proof of concept that changed everything.
- The Gold Medal Standard: Why Old Hillside entered the largest spirits competition in the world, what winning a double gold medal proved, and what it means to compete not as the best Black-owned bourbon but as the best bourbon period.
- The Invisible Generals Project: How Old Hillside is honoring the first Black father and son duo in American military history with a limited edition bottle that turns history into a collectible.
Chapter Markers
00:00 – Intro: Emmanuel J. Waters and Old Hillside Bourbon
01:15 – Military Brat to Silicon Valley to Bourbon Co-Founder: Emmanuel’s Origin Story
03:30 – Why Bourbon Takes Years to Build and What That Teaches Leaders About Patience
07:00 – History, Heritage, and Homage: The Three Pillars Behind the Old Hillside Brand
10:00 – Black Wall Street, Durham, and the Responsibility of Black Entrepreneurship
12:00 – Navigating a $9 Billion Industry Where Less Than 1% of Owners Look Like You
14:30 – How to Support Black-Owned Businesses Without Asking for Free Product
17:00 – The Distribution Reality: Licenses, Control States, and Where to Find Old Hillside
20:00 – Leadership Lessons from a New CEO: Vision, Risk, and Building a Team to Win
22:00 – The Durham Bottle Signing: How Breaking a Record in the Hardest State Changed Everything
25:00 – The Gold Medal Standard: Entering the World’s Largest Spirits Competition
28:00 – The Last Ride: How the Black Jockeys Bottle Became the Bill Payer
31:00 – What Do You Have to Lose? Emmanuel’s Case for Entrepreneurship
35:00 – The Invisible Generals Project: Honoring the First Black Father and Son Military Duo
38:00 – How to Connect with Emmanuel J. Waters and Old Hillside Bourbon
About the Guest
Emmanuel J. Waters is the CEO and co-founder of Old Hillside Bourbon, a premium spirits brand rooted in the history, heritage, and homage of Black American excellence. A military brat who grew up in Japan and Europe before building a successful career in Silicon Valley’s tech industry, Emmanuel came to bourbon not as a lifelong enthusiast but as a storyteller who recognized that the spirits industry was missing the most compelling stories in American history. Under his leadership, Old Hillside has won gold and double gold medals at the San Francisco World Spirits Competition, the largest spirits competition in the world, broken distribution records in one of the country’s hardest control states, and built a brand that ships to 49 states and is carried in Whole Foods, Total Wine, and BevMo locations across California. Emmanuel is proof that the best brands are not built on marketing budgets. They are built on stories worth telling.
Resources:
- Donald Thompson LinkedIn
- Donald’s Books: https://donaldthompson.com/books-resources/
- Emmanuel J. Waters LinkedIn
- Old Hillside Bourbon: oldhillsidebourboncompany.com
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High Octane Leadership is hosted by The Diversity Movement CEO and executive coach Donald Thompson and is a production of Earfluence.
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