Pappy & Company

By Lisa Hornung • Photos by Matt Johnson & Andy Hyslop 

When you’re the fourth generation of a storied and extremely popular bourbon company like Old Rip Van Winkle, you could work in the family business making delicious alcoholic drinks or go your own way. Some go their own way only to end up entrepreneurs in their own right. 

Carrie Van Winkle Greener and her two sisters did just that. Greener is an identical triplet, with Louise Van Winkle Breen and Chenault Van Winkle James. Ten years ago, the three decided to launch their own business, Pappy & Company, to sell merchandise licensed by her family’s business online. The company has blossomed into an online lifestyle brand and has its own brick-and-mortar store at 843 E. Market St., in Nulu, and a fulfillment warehouse on West Main Street. 

“It was a way for us to get involved with the family business and a way for us to have a creative outlet and also provide promotional products because we saw a need for merchandise associated with such a famous brand,” Greener said. “We just evolved it quickly into a brand inspired by our heritage.” 

Greener, her sisters and brother, Preston Van Winkle, are the great-grandchildren of the original Julian “Pappy” Van Winkle. 

At first, the Van Winkle sisters created T-shirts, hats, barware, etc. But they soon began looking for other items to enhance the brand. Pappy & Company partners with like-minded, value-driven, brands to make food items such as hot sauce, bourbon maple syrup, coffee, bourbon balls, and more. 

“I feel like we found success,” Greener said. “We’re not cigar makers. We’re not experts in cigars, baking, cocktail mixers, chocolate, or maple syrup. But we partner with people who are and have those values, and together, we create a product that we find superior and unlike anything else you can find in the market.” 

The business is about more than making money, Greener said. “I think what’s really driving me as a cofounder today is not necessarily the numbers and the monetary growth,” Greener said. “It’s really all the other stuff that comes with it, like our culture and our operating systems that I found that have also been maybe even more powerful than thinking about the numbers and just thinking about the money. That’s where it’s been neat to look back on, is that that comes with thinking about all the things, about really high-quality products, partnerships that are true and real, like you really form a friendship out of it. Those are the big drivers for me and also just our internal culture with our team.”

Greener said she hasn’t experienced sexism in her workplace because she’s in a small, family-owned business. But she’s noticed a positive trend toward more women in the bourbon industry. 

“We’re in a place, especially with this whole bourbon trend, where women are being highlighted. I think it’s kind of like people are recognizing the women in the industry. And so, for us, I think 10 years ago, it wouldn’t be like it is today, but right now, there’s lots of women who have huge jobs with distilleries and are the master distillers, the master tasters, the master blenders. And it makes perfect sense because women are known to be communicators. We know we’re really good at saying what we like and don’t like, and I think we can have a high level of creativity. And so I think it’s really cool to see what women can do for the industry that hasn’t been done already.” 

The future of Pappy & Company is to evolve into more of a heritage design brand. Greener and James were both interior designers before launching their business. They want to take inspiration from their grandmother, who had great style, Greener said. “I think ideally, we would go into more categories, more female-specific categories, I think, connecting to our heritage because that’s obviously our driver, but we’d love to expand on that.” 

Greener said she is proud of how far the business has come in 10 years. “I’m just proud of continuing to do it the right way. Doing what’s right. And letting that lead us so we always feel confident in knowing that we are building a business with integrity, and that feels good. You know, I feel like, and I hope, that we’ve created a great place for people to work.”