Founded by a group of Black veterans and entrepreneurs, Old Hillside Bourbon Company has always been about more than just creating exceptional spirits. Since its inception, the company has been committed to telling overlooked stories and challenging industry narratives, particularly those of Black pioneers who have been systematically erased from historical records.
Their new Trifecta bourbon tells a critical story often missing from history books: the remarkable achievements of Black women in horse racing. Founded by entrepreneurs committed to highlighting overlooked narratives, this bourbon does more than taste exceptional—it provides a platform for understanding the pioneering work of Eliza Carpenter, Sylvia Bishop, and Cheryl White.
These three women fundamentally transformed horse racing during periods of extreme racial and gender discrimination. Each broke significant barriers: Carpenter owning her own stable after being born into slavery, Bishop becoming the first African-American female horse trainer, and White becoming the first licensed Black female jockey at just 17 years old. Their stories represent more than historical footnotes—they’re blueprints of resilience and strategic breakthroughs.
We had the opportunity to chat with the founders of Old Hillside Bourbon Company, Brian Burton, Courtney Tucker, Emmanuel Waters, and Jesse Carpenter. These men turned extensive historical research into a meaningful product that does more than commemorate—it actively supports future generations. By dedicating proceeds to foundations supporting young Black children in horse racing, the company demonstrates how businesses can create a tangible impact beyond traditional storytelling. For entrepreneurs and professionals seeking inspiration, this conversation offers insights into transforming historical recognition into meaningful action.
Check out our full interview below.
The Trifecta is a powerful tribute to three groundbreaking Black women in horse racing. How did the idea of creating a bourbon that celebrates their legacy first emerge?
Our brand was founded in friendship to craft exceptional spirits that honor the legacy of African-American jockeys and celebrate untold stories and their profound cultural impact. The popular success of our brand and the male jockey story caused us to wonder where the women were in the sport. This led us on a two-year research journey to find these women and their amazing journeys.
Each of these women – Eliza Carpenter, Sylvia Bishop, and Cheryl White – broke significant barriers in horse racing. Which of their individual stories resonated most deeply with you during the creation of this blend?
All of their stories are captivating. Eliza Carpenter was born into slavery and sold twice before 8 years old. Sylvia Bishop was the first African-American female horse trainer in the United States. Cheryl White became the first female jockey; all these women’s stories are fascinating but all share a common word- TRIUMPH!
As a female entrepreneur myself, I’ve always been interested in the intersection of storytelling and product development. How did you approach weaving these women’s narratives into the bourbon’s identity?
Our brand identity is storytelling, what differentiates us from the bulk of spirit companies in the world is that every bottle of our bourbon tells a different story and has a very unique taste profile to match the story.
With a rich medium amber hue, The Trifecta offers an inviting aroma of caramel, honey or brown sugar, and dried fruit. The palate unfolds with layers of vanilla, butterscotch, maple syrup, dark fruits, and a hint of nutmeg, creating a bold and complex tasting experience. The finish is long, perfectly balancing sweetness and spice. Crafted from a mash bill of 70% Founders, 20% Rye, and 10% Kentucky, Trifecta Bourbon is bottled at 115 proof (57.5% ABV), ensuring depth and character in every sip.
The proceeds from The Trifecta will support foundations dedicated to these trailblazers. Can you share more about how these contributions will directly impact future generations of women in sports?
Each of these women’s foundations have been created to empower young black children to pursue careers in horse racing. We hope that our contributions from this bottle will continue that goal of inspiring the next generation of talent in the horse racing industry.
Representation matters deeply in both business and storytelling. What do you hope women – especially young women of color – will feel when they learn about these pioneers through your bourbon?
Before we became owners of this brand, we were fathers of daughters and brothers of multiple sisters. We know that black stories are often buried, and black women’s stories are six feet below that. We hope that young women of color will know that they are protected and that they have allies like Old Hillside Bourbon Company to help them shine their light across the world. Black women are the backbone of America, and this bottle and the stories being told prove just that.
For entrepreneurs reading, what business lessons can we learn from these women who transformed an entire industry despite enormous obstacles?
Often, entrepreneurs, specifically women and people of color, try to find a seat at the table. These women didn’t get a seat; they built their own! Build your table piece by piece, and don’t quit until it’s done.
What do you think they would say if Eliza Carpenter, Sylvia Bishop, and Cheryl White could taste this bourbon today?
They would enjoy the flavors of caramel, honey, and brown sugar. I think they would say this bottle is sweet but fierce, just like each of them.
What advice would you share for our audience of ambitious women about creating meaningful tributes that honor those who paved the way for us?
You will get a lot of no’s before somebody says yes. Our advice would be to make sure it’s something that you are passionate about so it never feels like work. Tributes are not just about honoring those who paved the way but also serving as an inspiration to the next generation. Please keep going and never give up.
Emily Sprinkle, also known as Emma Loggins, is a designer, marketer, blogger, and speaker. She is the Editor-In-Chief for Women's Business Daily where she pulls from her experience as the CEO and Director of Strategy for Excite Creative Studios, where she specializes in web development, UI/UX design, social media marketing, and overall strategy for her clients.
Emily has also written for CNN, Autotrader, The Guardian, and is also the Editor-In-Chief for the geek lifestyle site FanBolt.com
