Pick up a bottle of pinot grigio or a signature red blend from The Random Whine, and you’ll notice something different about the label. The fuchsia and turquoise lettering flashes from the bottle like neon. The pale script against the black of the label suggests the hum of voices in the background. That’s the goal of The Random Whine founder Kaye Jackson: to create not just wine, but a spark of conversation, a space between sips to release stress and follow wherever a discussion—and the wine—leads.

“I appreciate Cherokee County supporting the brand and supporting me.” — Kaye Jackson

“Some people say it’s not a typical wine label, but it’s not supposed to be,” says Kaye. “It’s supposed to bring conversation.”

Chat comes easy with Kaye, a Woodstock resident with an infectious laugh and a refreshing, introspective candor. She says she’s not a “bite-my-tongue kind of person.” No stranger to challenges, in 2014 she was diagnosed with stage 2B breast cancer and spent years undergoing treatment while raising two boys as a single working mother. The Random Whine [TRW] formed in that crucible.

“My friends brought me candy and cards, and I thought, ‘This is too much. I’m watching these flowers die and everyone’s talking me to death with this diagnosis,’” Kaye says. She suggested they bring her wine instead.

“It probably tasted a lot better to them than to me.” Kaye laughs. “Everything tasted like I was sucking on a mouthful of pennies. But I said, ‘I’m going to take a sip, and we’re just going to start talking.’ It opened them up and lightened the conversation and gave me a sense of normalcy. We were talking about husbands, boyfriends, and our kids. I noticed we were having random conversations and not sitting there talking about my diagnosis or me being sick. It left that space.”

In 2020, after years of treatment and reconstructive surgery, Jackson was breast-cancer-free and retired from her corporate IT role. Her love for wine and conversation and her desire to give back coalesced into development of the first two TRW varietals.

Kaye and her staff spent their first year working to develop flavors with Scotto Cellars in Lodi, California, and hosting tastings in Georgia through stores, restaurants, and eventually, Eagle Rock Distributing Company.

Breaking into the wine business, however, was another challenge. As an African American woman, Kaye faced resistance. Only 10 percent of wine labels are Black-owned businesses, and she faced pressure not only as a Black woman but also for her play on the word wine and the less-than-typical label on her bottles. Kaye, who loves the word persnickety, brought a fresh concept to a traditional business.

“I wanted something different, something fun and attainable,” Kaye explains. “I believe in my product, and I push my distributors, my stores, and my staff. We deserve a space on the shelf. There’s room for all of us. I’m not doing this just for me.”

Indeed she’s not doing it just for herself. The Random Whine also partners with Loving Arms Cancer Outreach, a Georgia nonprofit providing education, financial assistance, and emotional support to empower patients and their families throughout the cancer journey. As a single mother for many years of her treatment, Kaye understands the need for the support Loving Arms provides beyond medical treatment. She was once so sick after a chemotherapy treatment that her Uber driver helped her up fourteen floors to her condo and offered to pick her up after subsequent treatments. His kindness resonated with Kaye, and she connects those experiences with Loving Arms.

“The Loving Arms Cancer Outreach people sat with me,” says Kaye. She said if she hadn’t been working at a job that provided good insurance, it would have been a struggle. “They covered all the things I felt I needed during that time. They touched on everything: copays, prescriptions, light bills, groceries, rides back and forth.”

Through TRW sales and special events, including a fall gala, the company donated more than $20,000 to Loving Arms in 2022. The 2023 goal is set for $100,000.

Members of The Random Whine team present a check to Loving Arms Cancer Outreach of Woodstock. Learn more about Loving Arms Cancer Outreach or make a direct donation at LovingArms.Support/Donate.

Janet Graham, director of Loving Arms, describes Kaye as the best possible cheerleader for their organization. “Kaye has not only committed to donating a percentage of her profits to Loving Arms, she also is actively involved with our organization, board, volunteers, and support group clients,” Janet says. “The light Kaye shines on others is indescribable. She truly makes you know she cares about you through her actions and words.”

Kaye adds, “I believe when you get that [cancer] diagnosis, it’s about keeping that positive attitude as opposed to thinking about all the negative things that could happen. When we do fundraiser events with Loving Arms, it allows their clients to have that random conversation, to whine about cancer for a little while, but then we’re going to talk about something else. We get to have fun.”

The Random Whine is now sold in more than fifty stores and restaurants in Georgia and has expanded to seven varietals. Kaye’s plan to expand The Random Whine includes development of new wines, including a luxury reserve called Kaye, and to find permanent partnerships with similar nonprofit organizations as the brand moves into other states. She also mentors budding wine entrepreneurs and produces content on social media, including a short #LetsWhineAboutIt Wednesday segment designed to spark conversation she describes as therapeutic. Kaye’s partnership with Loving Arms continues, including planning future fundraising events and the 2023 gala.

“When I go into the store I get excited when I see [The Random Whine] on the shelf because I think about who it’s going to benefit at the end,” says Kaye. “I believe everybody has something we want to gripe and complain about. We can whine for a few minutes and keep going. Let’s turn a woe into a win.”

The Random Whine is available online and at over forty retail locations including Lucky’s Beverage World in Woodstock.



Pair It Up

Pairing Suggestions from The Random Whine

Pinot Grigio

The Random Whine Pinot Grigio is delicate and neutral. The higher acidity and light body make it an excellent companion for seafood or lemony dishes. Avoid anything that’s too heavy. Mild goat cheese, brie, and gouda are delightful with our Pinot Grigio.


Pinot Noir

Recipes with earthy ingredients taste delicious with The Random Whine Pinot Noir. Think mushrooms, lentils, and truffle pasta.  It is also delicious alongside salmon. The light-bodied and savory depth is also delicious with bruschetta pizza.


Red Blend

The Random Whine Red Blend goes perfectly with lamb or steak and is also a tasty complement to pasta dishes and even Mexican food.

Sweet Red

The Random Whine Sweet Red is versatile and complements a wide range of food. It can be paired with steak, vegetables, rich seafood dishes, and roasted chicken, as well as chocolate torte or cheesecake.



The Random Whine Moscato is already delightful by itself. Paired with dessert, it accentuates fruit flavors and plays nicely with figs as well as apples. A honeyed fig crostata with our Moscato is a chef’s kiss.



Served cold, The Random Whine Brut makes anything a celebration. A dry wine perfect with scrambled eggs, caviar, risotto, lobster, and even popcorn, potato chips, and nuts, it steps anything up a notch.


Brut Rosé

The Random Whine Brut Rosé offers the acidity of white wine while having the fruit characteristics of red. Our Brut Rosé pairs beautifully with rich dishes as well as fresh and complex salad, charcuterie, or grilled fish. Grilled cheese may sound simple, but a grilled gruyere and sweet onion on buttery-crisp whole grain bread is divine with our Brut Rosé.




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