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

DM Doug:

@DougMelville

www.DougMelville.com

Doug interviews Emmanuel Waters, CEO and co-founder of Durham, North Carolina-based <a href="https://www.oldhillsidebourboncompany.com/">Old Hillside Bourbon Company.</a> 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 &ldquo;aha moment&rdquo;. 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&rsquo;s regulation and low margins. Old Hillside&rsquo;s differentiation is storytelling, using nontraditional packaging and on-bottle narratives to honor Black American history, including early Kentucky Derby Black jockeys and the <a href="https://www.womensbusinessdaily.com/business-news/sipping-through-history-how-three-black-women-rewrote-the-rules-of-horse-racing/">Trifecta women of horse racing.</a> 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:
<a href="https://www.oldhillsidebourboncompany.com/our-founders">Old Hillside Website</a>
<a href="https://www.forbes.com/sites/jeanettehurt/2026/03/12/old-hillside-bourbon-company-offers-a-history-lesson-in-each-bottle/">Forbes Article</a>
DM Doug:
<a href="https://www.instagram.com/dougmelville/">@DougMelville</a>
<a href="https://dougmelville.com/">www.DougMelville.com</a>

“DM Me with Doug Melville” is a direct, practical self-help podcast in which Doug Melville answers real questions with clear guidance to help listeners grow and take action on their careers, reputation, culture and life.

&ldquo;DM Me with Doug Melville&rdquo; is a direct, practical self-help podcast in which Doug Melville answers real questions with clear guidance to help listeners grow and take action on their careers, reputation, culture and life.

DM Me with Doug Melville

Building Old Hillside Bourbon Through Connections and Storytelling - A Sit Down with Co-Founder Emmanuel Waters

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/10e3feaa-2f06-4a34-9d63-b4950094e8e7/transcript