Bourbon Bromance
Old Hillside Bourbon Company Distilled With Dignity
By Brian G. Thornton / Photography courtesy of Old Hillside Bourbon Company
As a beverage, bourbon takes me back to my childhood growing up on a college campus with my parents in the mid-1960s. The memories sprang from the thought-provoking get-togethers, the meticulous cleaning of the crystal highball glasses, the serving trays, and my father breaking open the freezer ice trays just before the doorbell rang. I saw hours of spirited conversation between professors and staff when guests arrived; this became a regular learning experience. The next day, while cleaning, I was assisting my mom in gathering party garbage and glasses that lingered with the melted ice and the distinct fragrance of bourbon. The impression was that bourbon was the house’s favorite.
I was influenced by college as an adult, starting with what was reasonably priced and distinct from what my parents would purchase. Finding out that our home’s top-shelf liquors were just slightly out of reach for me opened my eyes. Having taken note of responsible drinking practices, I’m always willing to learn anything new.
Now introduce yourself to Old Hillside Bourbon Company, a fine spirit created and crafted by four astute East Coast businessmen. I wanted to learn more when I got to know one of its creators, Courtney Tucker, through a friend. I was intrigued by the brand’s history, so I got a bottle and had a bourbon tasting with some friends. It tasted considerably better because of its limited availability. We were pleased with the taste and traditional branding. Here is a fascinating tale about the founders, their distinctive brand and how they created a bourbon bromance.
Old Hillside Bourbon Company founders Courtney Tucker, Brian Burton, Jesse Carpenter and Emmanuel Waters.
Origins and Inspiration
While Sparta, Kentucky, is the current home of the brand’s distillery, Old Hillside Bourbon Company’s origins were in Durham, North Carolina, where Tucker, Jesse Carpenter and Brian Burton met during high school. Carpenter and Burton were at Old Hillside, America’s oldest historically Black high school. Tucker attended another school but occasionally met up with the other friends. Sometimes, the universe finds us in the right place at a unique moment. It may have been Carpenter’s interest in a German brewery while in the Air Force and a later move back home to Lexington, Kentucky, around 2014. Around the same time, Burton’s social media post attracted Carpenter’s attention, leading to a mutual passion for distillery tours.
Among the many exciting aspects that make Lexington unique is its lengthy history of thoroughbred horse racing, best experienced at the Keeneland Racetrack. Combine that with the best distilleries and tours in the country, and you will see the confluence of friends and a fortuitous rekindling of friendship.
“Tucker posted his first bourbon picture on his Instagram talking about how much he loved it and cigars. Two days later, Brian and I started our company,” Carpenter said. This reacquaintance began in 2019, just ahead of the pandemic. That led to a bright idea of interest in brewing bourbon. Carpenter had managerial skills and Burton had an extensive IT background, but they still needed something. Days later, that declaration of “I want to make bourbon” led Tucker to Los Angeles and to Emmanuel Waters, his cousin, who was the final piece with his expertise in scripting and negotiating contracts.
History Heritage Homage
Old Hillside Bourbon Company was formed and built on the tenets of history, heritage and homage. These elements drew from the history of the high school they met at, the heritage of Kentucky’s not-so-well-known black jockeys and racehorse owners and the homage to the vast distillery roots.
When developing the product, the founders prioritized taste above all, believing that the quality of their bourbon should speak for itself. As Tucker put it, “Though we’re black-owned, we want you to say, ‘That’s good bourbon,’ and, by the way, they’re black-owned.” This commitment to quality led to a six-month development process, during which they meticulously crafted their logo and bottle design to tell their unique story.
The logo features a bourbon barrel, symbolizing Kentucky’s deep bourbon heritage. A black Friesian racehorse and jockey on the left pay homage to the black racehorse jockeys who were instrumental in making Kentucky famous. On the right, a bull represents Durham, acknowledging the founders’ hometown and rich history, including Black Wall Street. The bottle shape was designed for easy recognition and optimal shelf placement. At the same time, the label incorporates ridges reminiscent of a Kentucky Derby ticket and copper foil lettering to catch the light. Every element of Old Hillside Bourbon Company’s branding reflects its dedication to quality, heritage and unique storytelling, ensuring its product stands out in retail and hospitality settings.
The bottle shape was chosen for easy recognition on back bars. The carefully designed label has ridges on the top that resemble a Kentucky Derby ticket, while the paper texture mirrors the texture of money. The copper foil outlining the lettering was chosen to capture light.
Targeting the Affluent Market
Las Vegas is known for its luxury and affluence. Old Hillside Bourbon Company caters to the sophisticated tastes of southern Nevada’s high-end clientele. A related product by Old Hillside is bespoke cigars. Bourbon and spirit aficionados know that the brown liquids often pair with cigars. A brief website tour assures that the quality drink is associated with its branded Mazcodellos smokes. Many cigar fanatics seek and attend cigar herfs, a casual gathering of cigar enthusiasts to smoke, trade and socialize.
“We would host private invite-only events and tastings displaying our products,” Tucker said. “Partnering with exclusive hotels and clubs to create memorable experiences is a goal. We would offer personalized services, including custom-blended spirits created by expert mixologists, and collaborate with fashion, watches, and car co-branded events and promotions.”
Challenges in Distribution
“Having done this a few times in recent years, the brand is aware of the challenges of distilling your product and expanding its distribution to states like Nevada,” Tucker said. “Complex liquor laws and regulations can be challenging. Adhering to state-specific distribution laws, complying with different tax policies, etc. The spirit market is competitive. Coming in as a new brand would require strategic marketing, ensuring a steady supply of products to meet demand, especially during peak tourist season.”
Oliver Lewis – born enslaved in 1856, Lewis won the inaugural Kentucky Derby in 1875, and placed in the top two in eight of his nine starts riding four Thoroughbreds from McGrathiana Stable. He set the record for the 1.5-mile race in 2 minutes and 37.75 seconds. Photo courtesy of Historical photography provided by the Keeneland Library Collection and Keeneland Library Hemment Collection
Luxury Branding and Marketing
Old Hillside Bourbon Company, entering a competitive market like Las Vegas requires extra care and strategic planning. Recent and upcoming sports expansions in Las Vegas, such as the Vegas Golden Knights, NFL Las Vegas Raiders, and the 2024 Formula One Races, Old Hillside Bourbon Company, will align with these events.
“We would seek sponsorship agreements with teams and events, create exclusive partnerships to become the official spirits provider, host fan engagement events, plan parties, including pre-and post-game celebrations, offer tastings including promo and giveaways and develop co-branded merchandise and bottle packing,” Tucker said.
He also mentioned targeting luxury hotels, clubs and venues and collaborating on exclusive events. “Engaging with celebrities and influencers who resonate with our target audience is also key to telling our brand’s story,” he added.
The Last Rye’d, a cleverly named spirit that pays homage to the black riders, has flavors of caramel, vanilla, mint and florals. It honors historic black jockeys Isaac Murphy, Alonzo Clayton, Oliver Lewis and James “Soup” Perkins. Black jockeys once dominated the sport of horse racing from the first Kentucky Derby in 1875 through 1903 winning 15 of the first 28 Derby races.
Vision for the Southwest Market
When asked about the long-term vision for Old Hillside Bourbon Company in the Southwest market, Tucker had this to say: “[We] would establish our brand as a top-tier quality spirit company to ensure widespread availability in the market, target high-end retail outlets, create and enhance loyalty programs that identify and reward repeat customers and build a sense of community using the three-tier system of digital and print marketing, social media and events.”
The story of Old Hillside Bourbon Company emerges as a testament to resilience, creativity and a deep-rooted passion for craft. Their journey has been nothing short of remarkable. Old Hillside Bourbon Company captures the essence of tradition and embraces the spirit of innovation. Now poised to enter the vibrant Nevada market, the founders weave a narrative that resonates with the state’s history of gaming, entertainment and fine spirits.
What began as a bourbon bromance among high school friends has blossomed into a thriving enterprise, where each bottle embodies a blend of history, heritage and the pursuit of excellence. As they embark on this new chapter, their success story inspires entrepreneurs everywhere, proving that any challenge can be overcome with determination and a bold vision.
In raising a glass to Old Hillside Bourbon Company, we celebrate their achievements and the enduring spirit driving their journey forward. Here’s to new beginnings in the Silver State and the promise of many more chapters yet to be written. Cheers to the taste of history, crafted anew!
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