founded in


Four founders at Kentucky DerbyOne man pouring bourbon whiskey for friend laughinFour founders tasting their own bourbon whiskey
the beginning

where it all began


Before they were founders of Old Hillside Bourbon Company, Jesse Carpenter and Brian Burton were childhood friends from Durham, NC. Jesse jokes that he used to steal Brian’s lunch money, and Brian swears that he was always afraid Jesse would beat him up (thankfully, they’re still friends). Brian and Jesse eventually attended the same high school, Hillside High School, which is the oldest, historically Black high school still in existence. Meanwhile founder Courtney Tucker attended school across town, but he often went over to Hillside after school to hang out with his friends.

Years later, the friends would name their bourbon company after this historic school—not because it was the alma mater for two of them, but for what the school represented: history and heritage.

The idea

a collaborative


Fast forward 10 years, although Jesse and Brian stayed social media friends, life pulled them in different directions, making them distant friends. One weekend, Brian and Jesse unknowingly decided to go to a horse race in Kentucky. The social media post allowed for the two to rekindle their friendship, this time over their love for horse race and bourbon. Through conversation, they noticed how underrepresented African-Americans were in the sport of horse racing—somewhat ironic, considering some of the most successful jockeys in history were Black (before segregation began).

Two founders at whiskey distillery
Two founders at whiskey distillery

When COVID hit, and the world seemingly stopped, their minds began wandering to other business ventures. The two had always enjoyed bourbon, and the idea of coupling that with the history of Black jockeys, while naming the brand after their historic Black high school, made perfect sense.

And they were off to the races.

Jesse’s background running businesses and love of bourbon, coupled with Brian’s IT skills and natural curiosity, gave them the jumpstart they needed to create the bourbon. They reached out to Courtney for help with marketing strategy and communications. Meanwhile, Courtney called his cousin Emmanuel Waters to assist with contract negotiations and business development.

Brian Burton

Chief Information Officer

Cofounder Brian Burton, aka "the anchor," is a Hillside Alum who enjoys a straight bourbon any day of the week.

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Courtney Tucker

Chief Operating Officer

Cofounder Courtney Tucker, aka "the sail," is a Durham native who enjoys the art of pairing cigars with bourbon.

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Emmanuel J. Waters

Chief Executive Officer

Cofounder Emmanuel Waters, aka "the engine," is a North Carolina native who enjoys any bourbon mixed drink.

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Jesse Carpenter

Chief Product Officer

Cofounder Jesse Carpenter, aka “the architect,” is a Durham native who enjoys the art of hunting for rare whiskeys and bourbon.

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the result



The four founders readily say that Old Hillside is an “ordained” company. Why do they believe this so strongly? Well, it began when others warned them against trying to sell their bourbon in North Carolina. Because it is a controlled state, others told them that their business would fail immediately. Instead, they got into stores and sold out, breaking multiple records. The luck continued in California, when the brand was accepted into Bevmo! And Total Wine and more in three months (on average, businesses usually wait seven years to get into the chain).

A series of similar “lucky” circumstances made them realize Old Hillside was meant to be—meant to open doors, meant to create fellowship, and meant to create generational wealth.

Two founders overlooking Durham, NC

“This business is not about us. We’re just playing a part. This is higher than us," Courtney explains.

Two founders cheerings

hear the


Hear Jesse Carpenter speak on the Black and Brown podcast about the company’s founding, the history of their friendship, the creation of their product, what they have their eyes on next.


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