Names appear from left to right: Courtney Tucker: Chief Operating Officer, Jesse Carpenter: Chief Product Officer, Brian Burton: Chief Information Officer, Emmanuel J. Waters: Chief Executive Officer

Founded in Friendship

     Before they were founders of Old Hillside Bourbon Company, Jesse Carpenter and Brian Burton were childhood friends from Durham, NC. They attended the same high school, Hillside High School, the oldest historically Black high school still in existence. Founder Courtney Tucker, who attended Pilgrim Church Center Pre-K with Brian and Rogers-Herr Middle School with both Brian and Jesse, often hung out at Hillside after school.
     ​Jesse and Brian, despite their divergent paths, maintained their connection through social media. Jesse’s journey led him to the Air Force, where he explored the world, lived near a German brewery, and developed a background in manufacturing. After his service, he relocated to Lexington in 2014. That same year, a serendipitous Instagram post of a downtown Lexington building, identical to one Brian had posted a week earlier, rekindled their friendship. This prompted Brian, who was planning a return visit to Lexington, to invite Jesse to join him on a distillery tour at Old Taylor Distillery. The tour marked the beginning of their shared passion for distillery visits. During one of Brian’s visits to Lexington, he and Jesse were drawn to a horse race. The thrill of the event turned horse racing into a regular pastime for them and their friends. Their calendar soon filled with visits to the Keeneland Spring and Fall meets and the occasional Kentucky Derby in May, with each trip including a planned distillery tour. Amidst the thrill of the races, they couldn’t help but notice a stark demographic contrast among the hundreds of attendees: “We were the only black people out there,” said Jesse.
       The post prompted Jesse to coerce Brian to reach out to Courtney, who lives in Los Angeles, to tell him about their new venture. Courtney joined the team on the spot.​This observation sparked Jesse’s curiosity, leading him to Google, thinking, “There’s got to be some black people here [in the sport’s history].” His search unveiled a forgotten era: “African Americans dominated the sport in the 1800s near the end of slavery. If you know Kentucky history, you know that Kentucky was the last state to find out that their slaves were free.” Among these riders was Oliver Lewis, the first winning jockey of the Kentucky Derby. This revelation opened the floodgates to research further, unearthing records few have seen and shedding light on a forgotten chapter of horse racing history.

​    ​In 2019, COVID hit, and in 2020, the races were canceled. “We had a huge Keeneland planned for April with seven to eight of our boys coming up. I had got monogrammed glasses, and then the whole thing got canceled,” said Jesse. Then, in June of that year, Jesse had an idea. “On June 1st, I woke up after dreaming about starting a bourbon company and naming it after the high school we went to. On the label, I wanted to capture where we went to school and name the brand Old Hillside Bourbon Company. This was non-negotiable because our friendship formed at Hillside. So, the first person I called at 6:00 in the morning was Brian. This dude was like, ‘Well, good luck.’ But I was like, ‘I need you to do this with me.’ About 2 hours later, we had a tax ID, a company name, and we were filing for trademarks.” “Two days after Brian and I started our company, on Instagram, Courtney posted his first-ever bourbon picture, talking about how much he loved it and cigars,” said Jesse. While they had not spoken for over 20 years, Brian and Jesse admired Courtney’s news media career in Raleigh and Los Angeles from afar. “Since second grade, Courtney has excelled,” Brian said. The post prompted Jesse to coerce Brian to reach out to Courtney, who lives in Los Angeles, to tell him about their new venture. Courtney joined the team on the spot.
​     To round out the team, already armed with Jesse’s background in Lean/Six Sigma, Brian’s background in Information Technology (IT), and Courtney’s background in broadcast media, they called Courtney’s cousin Emmanuel Waters, who has a background in corporate contract development. ​“During that summer with George Floyd and a lot of black entrepreneurship, Courtney called me and said, ‘Hey man, we got this opportunity to start something big.’ I had literally said the day before that I wanted to create generational wealth, but I didn’t know how. Not even a day later, my cousin calls me about a bourbon company,” said Emmanuel. “We want to build generational wealth to pass down to our children. Much of American history starts with African Americans, but nobody knows about it. We also wanted to inspire the next generation to start something. Corporate America isn’t for everybody,” he added.
     ​Despite the COVID-19 pandemic, the team remained undeterred. Balancing day jobs, they met on Zoom every Sunday and Wednesday for 18 months, spending four and a half hours each time strategizing and planning without a product at hand. While the pandemic caused delays, it also allowed them to develop camaraderie. “We literally talked for hours and created kind of this bromance,” said Emmanuel.
      ​The brand received help along the way, as they had no experience in the beverage alcohol industry. Jesse recalls reaching out for assistance. “I reached out to a lot of people who shunned us. Then I started following St Cloud Bourbon. Ray Walker opened his Rolodex and connected us with our current distillery. We were just going to have them bottle for us, and Royce Neely said, ‘Hey man, I distill too. Let’s create a custom mash bill.’ So we went to Neely Family Distillery to meet Royce, whose family has been distilling for generations.”

Formulation of Flavor

When developing the product, taste was paramount. Jesse explained, “Though we’re black-owned, we want you to say, ‘That’s good bourbon, and, by the way, they’re black-owned.’ People will only rock with you based on how good your product is, and we want to make sure you come back.” For this reason, extra money was spent on development.
Flavor profile development started with lots of bourbon tasting, recording preferences and production techniques on a spreadsheet, and narrowing down the list. “We all bought a lot of bourbon and tasted it. Then, we found out the mash bill percentages of the brands we tried and narrowed it down to about four brands that we liked. We also added notes such as: ‘This would be perfect if you had a little more of this.’ We noticed that everything we liked was on the sweeter side and between 71 and 75% corn, and it was a toss-up between the secondary grains, so we built our flavor profile based on that data,” Jesse added.

​However, high-quality whiskey demands years to mature. To establish the Old Hillside brand and minimize upfront costs, Royce proposed a model many new whiskey distilleries use — sourcing products with a similar flavor profile. In selecting the whiskey from Neeley Family Distillery, Royce presented Jesse with several samples. Jesse recalls, “We had a variety of samples laid out, and one of them just stood out to me immediately. I knew it was the one, but I kept it a secret from the rest of the team. I just told them, ‘When we get to Atlanta, I’ve got a surprise for you.’”
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Eighteen months later, Old Hillside had their product ready for sale in Kentucky and North Carolina.

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The Brand Name and Tagline
Old Hillside is in homage to Hillside High School, the alma mater of Burton and Carpenter, who graduated in 1993. The company tagline of history, heritage, and homage refers to the team’s relationship with Hillside High School and the school’s history of being the country’s second oldest majority African American high school.

Old Hillside Bourbon Company Logo
Created by Brian with input from the rest of the team, the logo encapsulates Old Hillside’s motto of “History, Heritage, Homage.” “We knew what we wanted, but also what we didn’t want. Brian and I got into our first-ever argument designing these labels. It was a three-week project that took six months. But our company prioritizes quality over quantity, so we kept going back, calculating the story we wanted to capture and figuring out how to put it in the logo,” said Courtney.
Courtney further explained the elements of Old Hillside’s logo:

• Center: A bourbon barrel represents Kentucky’s history, as the state supplies 98% of the world’s bourbon.
• Left: A black Friesian racehorse and jockey symbolize heritage. “Old Hillside Bourbon Company will focus on the black race-horse jockeys that history forgets made Kentucky famous. Due to racism and Jim Crow, much of our history was erased, so we wanted to focus on that.”
• Right: A bull represents Bull City Durham (North Carolina), the founders’ hometown. “When people think of Black Wall Street, they automatically think of Tulsa, Oklahoma, but there were several black wall streets in America. Durham, North Carolina, was one of the first with black banks, movie theaters, and insurance buildings, so we wanted to pay homage to that.”

Bottle and Label Design
The bottle shape was chosen for easy recognition on back bars at on-premise accounts and easy stocking on top or middle shelves while avoiding placement on bottom shelves where it might go unnoticed.
The label was also carefully designed. While the specific label varies by SKU, there are some common themes.

• The ridges on the top of the label resemble a Kentucky Derby ticket, while the paper texture mirrors the texture of money from cashing in a winning ticket.
•  The copper foil outlining the lettering was chosen to stand out against the lights.

Hillside Highschool

Inspiration: Black Jockeys

The success of Black American jockeys in the late 19th and early 20th centuries led to the growth of horse racing in America. These jockeys, often slaves or born to slaves, developed their riding skills as they learned horse care and blacksmithing from a young age [1]. Despite the segregation, resource disparity, and implicit bias, these jockeys exhibited resilience and excellence, winning 15 of the first 28 Derbies between 1875 and 1903 [1][2]. Backing these jockeys were black trainers, breeders, grooms, and horse owners[1] [3].

​However, Plessy v. Ferguson resulted in the Jim Crow laws of the post-Reconstruction South, and led to the expulsion of Black jockeys from the sport and erasure of their records from the history books by the early 1900s [4]. Even in the 1960s, black breeders and owners were not allowed in the stands at Churchill Downs [3].

Recently, historical research has been inspired by a desire to unearth forgotten stories and rectify racial injustices. This has led to the following books and films that help tell this story of resilience and black excellence.

Sylvia Bishop
Born in 1920, she became the first African-American woman thoroughbred horse trainer in the United States. Between 1987 and 2000, her horses won 44 races, paving the way for other black women in the sport.

Cheryl White
At age 17, White became America’s first licensed Black female jockey, tallying 750 winning rides. She won the Appaloosa Horse Club’s Jersey of the Year award four times and was inducted into its Hall of Fame in 2011.

Eliza Carpenter
Born enslaved in Virginia, she gained freedom after the Civil War. She learned horse racing and became a jockey and stable owner. Eliza was a pioneer in a time when women were unheard of in the horse racing industry.

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Alonzo “Lonnie” Clayton
Born in Mississippi on January 4, 1876, he began working part-time at a hotel at age nine while still attending school. He started riding horses at age 11 and won his first Kentucky Derby at age 15 in 1892. From 1894-1895, he won 144 races, making him a multi-millionaire by age 20.

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.

James “Soup” Perkins
Born in 1880 to freed parents, “Soup” started racing at age 11 and won his first Kentucky Derby in 1895 at age 15, riding Halma. This made him the second-youngest Derby winner.

Isaac Burns Murphy
Born into slavery on January 6, 1861, Murphy is considered the G.O.A.T. of horse racing. His unmatched record boasts a winning percentage of 44% and includes three victories at the Kentucky Derby. In recognition of his achievements, Murphy was the first jockey to be inducted into the National Museum of Racing and Hall of Fame in 1955.

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Sources and Suggested Reading

[1] Mooney, K. C. (2014). Racehorsee men: how slavery and freedom were made at the racetrack. Harvard University Press.
[2] Kentucky Derby Museum. (n.d.). Black Heritage in Racing Collection. from https://www.derbymuseum.org/blackheritage.html.

[3] Teo, T. (2023, May 4). The Kentucky Derby’s forgotten Black past. BBC Travel.
From: bbc.com/travel/article/20230503-the-kentucky-derbys-forgotten-black-past.

[4] Leeds, M., & Rockoff, H. (2020). Jim Crow in the saddle: The expulsion of African American jockeys from American racing (No. w28167). National Bureau of Economic Research. doi.org/10.3386/w28167

Bickle, T. (Director). (2023, November 20). The Legacy of the Black Horsemen. Kentucky Educational Television. From ket.org/program/the-legacy-of-black-horsemen-w8dk0z/the-legacy-of-black-horsemen-v28q4x/

Rust, S. (2020). Black Horsemen Matter: A Look Back at History.
pastthewire.com/black-horsemen-matter-a-look-back-at-history/

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Bourbon Ingredients

Grains

• Corn: Historically, heirloom corn was used in whiskey and moonshine distilling instead of the commodity No. 2 Dent Corn. While more expensive, “This variety tends to put the bourbon more on the sweeter-tasting side,” Jesse explained.  This corn is only found in the Old Hillside Bourbon. 
• Barley: An intensely kilned barley
• Intense kilning adds aromas like caramel from caramelization reactions and toffee from Maillard reactions that are similar in flavor to how brown ales differ in flavor from golden ales. While more expensive than standard pale malt because it yields lower quantities of whiskey, Jesse explained, “We prefer the intense kilning process for our barley because the higher heat produces a darker malt with more intense flavor and aroma.”
• Rye: Winter Rye.

​Yeast
A proprietary yeast strain that is native to the distillery has been cultivated.

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Production Process

In the American Whiskey business, many distillers of sourced products keep much of their process proprietary outside of a few parameters. In the procurement process of sourced products, purchasers are generally provided the mash bill but must rely on taste to select the specific product.

​Mash

• Bourbon Fermentation: Sweet Mash
• Last Rye’d and Founder’s Select: Proprietary

Distillation
“The whiskeys are crafted using traditional pot distillation techniques, as the immediate plan is to remain a craft whiskey brand and use the same distilling methods across all products,” said Jesse.

Maturation Process
Barrels
New white oak barrels with either a number 3 or 4 char. “Most of our barrels are charred for 55 secs (Char 4),” said Jesse.

Barrel Procurement
     While the final selection of what is bottled is similar to a retail single-barrel program, the initial procurement process allows for more flavor influence by the Old Hillside ​team. The process starts with purchasing multiple barrels from the same distillation run that use the same char. Individual picks are not feasible at this point because of the volume of barrels being selected. The specific age, however, depends on how soon the whiskey will likely be bottled. Jesse provided the following example: “If we know we’re not bottling for another year, we’ll purchase younger whiskey and let it sit for a year.”

Maturation Duration
​     Upon procurement, the barrels are primarily aged in open-air rickhouses in Sparta, Kentucky for up to seven years. Jesse sheds light on the process, stating, “Kentucky has four distinct seasons, so we wanted at least four summers and four winters because that’s when you get the most movement in the barrels and when we felt comfortable enough to release them.” As the company has grown, so has the maturation period of the barrels.
​     Jesse further elaborates, “Initially, we bought enough barrels so we could choose to wait past four years if we wanted to, like our Rye. We had enough in the pipeline to bottle those at seven years and allow some of the younger stuff to reach around six to seven as well. That’s why we say 4-7 years is what we’re targeting.” This strategic planning has allowed them to maintain a consistent supply while ensuring optimal aging.

​Single-barrel selection
     At Old Hillside, the barrel “does what it does,” said Jesse. During maturation, the team samples the whiskey at least every six months. During this sampling process, each founder looks for approximately five barrels that will be named and used in that bottling run. Those that are not get rechecked in six months. “We basically buy barrels and sample every six months and then decide which we’re going to bottle from there,” Jesse explained. During this selection process, the team follows the African proverb of allowing the ancestors to speak through them.
     ​While some general consistency exists in using identically produced and aged distillate, consistency is difficult in single-barrel programs. Old Hillside, however, celebrates the distinct character of every barrel, which arises from variations in the wood. These barrels are assigned unique names that hold special meaning for the team, and these names are displayed on the labels for easy recognition. Tucker illustrates, “We name them after friends and family. The barrel Marshall, which won the gold medal, was named after a friend’s first child. So when ​he found out it won gold, he went nuts. Burden 2s are among the most popular. Brian’s barrel had one of the highest yields with about 280 bottles.”.
Jesse added, “Using unique barrel names forces people to go out and hunt for them per se because we don’t say where we are going to send particular bottles.”

Proofing

​Proofing Water
Limestone-filtered water. “Limestone filters out iron, sulfur, and other impurities often found in surrounding states’ water sources. Because of that, we bottle and proof all of our products in Kentucky because of the limestone-filtered water,” said Jesse.

Proofing Approach
“Some of our guys could not do the triple digits, and right around that mid-nineties is where all our favorites landed,” said Jesse. The final proof of each bottle is intended to preserve viscosity and complexity while enabling the fatty acids to remain in solution.

Future Plans
Contract Distilled Product
Further maturation and sampling of the contract-distilled product are ongoing. “Once we are all satisfied with the profile, we will start incorporating it into our product line,”said Jesse.

A Durham Distillery
“If we opened a distillery, we would want to do it in our home state, our hometown, and bring the Kentucky Distillery experience to North Carolina. However, we know the terroir and what Kentucky brings to the table. And its going to take a lot of resources as far as water sourcing and all that. So eventually, it’s the game plan, but there’s no timeline.” said Jesse..

Old Hillside Line Up

Kentucky Straight Bourbon Whiskey
White Label was the first SKU in the product line and, in Brian’s words, “tells everybody who we are, where we’re from, and what we’re about.” Featured on the label is Hillside High School, one of five still operating historically black high schools. This is done in homage to the company’s namesake and the alma mater of some of the brand’s founders.

Product Technicals

• Source: Neely Family Distillery
• Mash bill: 71% Corn, Rye, Malted Barley
• Maturation: 5-7 years
• Proof: 97

Tasting Notes

• Color: Reddish-brown
• Aroma: Woodsy, smokiness char
• Taste: Caramel, vanilla, citrus, fig
• Finish: Kentucky Hug

Awards

• Gold Medal at the 2024 San Francisco Spirits Competition
• Gold Medal at the 2023 San Francisco

Spirits Competition

• Best In Show at the 2023 TAG Global

Spirits Awards

• Gold at the 2023 Sip Awards

​Suggested Retail Price: $55.99

Founder’s Select Straight Bourbon Whiskey
Jesse describes their bottle as a tribute, stating, “This bottle is more than just a creation; it’s a tribute to the journey we’ve embarked upon, the traditions we uphold, the passion that fuels our craft, and the pursuit of excellence that defines our journey.” When developing this product, the team wanted a Tennessee-style Whiskey that met specific production parameters rather than flavor profiles to round out the portfolio. Jesse explained, “We didn’t want the Jack Daniels profile, and we wanted the barrel entry proof to be 62.5% ABV and to put our charcoal filtering process on it, so there were only a few mashbills that did it.”

​Founder’s Select production involves the Lincoln County Charcoal filtration before barrel maturation, Old Hillside’s light charcoal filtration process, and finally, proofing and bottling without chill-filtering.
Product Technicals

• Source: Undisclosed Tennessee

Distillery

• Mash Bill: Undisclosed
• Maturation: 5 years
• Proof: 90

Tasting Notes

• Color: Medium Amber
• Aroma: Sweet fruit spice, nutty flavor
• Taste: Vanilla notes and apricot
• Finish: Long applewood linger

Awards

• Gold at the 2024 San Francisco Spirits

Competition

• Double Gold at the 2024 TAG Awards

Suggested Retail Price: $39.99

The Last Rye’d Straight Rye Whiskey
“This bottle tells the unsung story of our culture that we wanted to share with everyone,” added Brian. The whiskey’s name comes from Frank X. Walker’s stage play about Jockey Isaac Murphy, who is featured prominently on the label. ‘He has a stage play named The Last Ride, so we took a play on that and made it “The Last Rye’d,”’ explained Brian.
“We initially weren’t going to release a rye. However, we got commissioned by the Kentucky Derby to bring awareness to African American jockeys,” said Jesse. While the initial bottling was 1000 bottles of a pre-Prohibition style Rye of 104 proof, people loved it so much Old Hillside decided to make it a permanent SKU.”

Product Technical

• Source: MGP
• Mash Bill: 95% Rye, 5% Corn
• Age: 5 Year
• Proof: 104

Tasting Notes

• Color: Dark amber
• Aroma: Bold rye spice and floral notes
• Taste: Caramel, vanilla, mint
• Finish: Slight notes of nutmeg, cinnamon, and mint

Awards

• Double Gold Medal At The 2023 TAG 
• Double Gold Medal At The 2023 San Francisco Spirits Competition
• ouble Gold 2023 Sip Awards

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Suggested Retail Price: $69.99

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