She Started a Wine Brand at 22, Knowing Nothing About Wine—Now It’s About to Go National

A Q&A with Jess Druey, founder of Whiny Baby

Jess Druey, founder of Whiny Baby

Jess Druey is shaking up the wine world with Whiny Baby—a bold, playful, and unapologetically Gen Z wine brand. Since its launch, Whiny Baby has rapidly expanded across the U.S., earning shelf space in major retailers like Sprouts, Whole Foods, and Target. Known for its approachable blends, interactive packaging, and personality-driven marketing, the brand is redefining how younger drinkers connect with wine.

We originally spoke with Jess in June for our recently launched report “The Next Era of Wine” to learn more about how she built her innovative brand. Last week, Whiny Baby was purchased by Gallo, positioning the brand for national expansion and exponential growth.

Q: Tell us about why you decided to start Whiny Baby.
A: I was 22 at the time, during the pandemic when all restaurants were closed. I had a date lined up with a guy from a dating app, and since we couldn’t go out, he said, “Why don’t you come over? I’ll cook, and you bring a bottle of wine.”

What should have been a simple ask turned into me thinking, Oh my gosh, I want to impress this guy—and I know nothing about wine!

Up to that point, my relationship with wine was pretty casual—maybe a bottle of rosé with girlfriends while watching The Bachelor. At restaurants, whether on a date or for work, the wine list felt intimidating, so I’d just say, “I’ll have what they’re having.”

I remember looking at store shelves and thinking, I don’t know what any of this means. Why do all the brands look the same? Nothing was speaking to me—and I knew I couldn’t be the only one feeling that way.

Q: Whiny Baby has grown quickly. Can you give us a sense of scale?
A: We started DTC in California, but retail is where the big growth is. Last year we sold 6,000 cases. Now we’re in over 30 states, rolling out in Sprouts and Whole Foods, and we are in Target. DTC still matters for connection—our average DTC customer is 29, and on social media, it’s 25–35—but retail is our main focus.

Q: What are some of the secrets to your success?
A: Honestly, what I didn’t know became my strength. I came into wine as a pretty naive consumer first, not an insider, so I wasn’t bound by “how it’s always been done.” That gave me freedom to reimagine the experience from start to finish. Every touchpoint—from labels to the conversation starters under the caps—was a chance to do something fresh.

Partnering with the McBride Sisters has also been huge. I’ve learned so much from their experience and infrastructure.

Q: What is it about Whiny Baby that resonates so much with your audience?
A: When I was learning about wine, I realized most people—especially younger drinkers—don’t really understand varietals. Blends are a softer introduction. Our wines are fruit-forward, crushable, chillable, and a little on the sweeter side, but still well-balanced.

They’re porch pounders—fun, accessible, and refreshing. And all of our wines can be chilled, which makes them even more approachable.

They also stand out on a shelf. Trendy or kitschy labels can get dismissed as “not serious” wines, so we made sure the quality inside the bottle matches the personality outside. Standing out is important, but delivering once you get it home is essential.

Photo Source: Whiny Baby

Q: Whiny Baby is known for its bold Gen Z personality and interactive packaging details. Can you tell us about those?
A: The conversation starters under the caps, the bottle beads (which double as phone charms), and the save-worthy back labels are all about creating a unique experience. People even call the phone number on the bottle and leave the funniest voicemails—I listen to every single one.

Our #1 customer complaint? When bottle beads aren’t on shelves. And I’m really excited that Meijer is the first store to carry the bottles with the beads on the shelf.

Photo source: Whiny Baby

Q: Gen Z is a big part of your audience but all the industry reports say Gen Z doesn’t drink wine. What advice do you have for brands looking to connect with them?
A: Gen Z has more access to information than any other generation, and they do their research. They’re drawn to the luxury and mystery of wine, but they want guidance navigating it. They’ll spend on nicer things when there’s an emotional tie-in and a good story.

Lean into the Gen Zers you know—ask them what interests them and what they care about—and weave that into your brand. Gen Z is the first generation to experience a brand across so many channels, so create a unique experience from start to finish.

Q: The wine industry can feel a little doom-and-gloom right now. Are you optimistic?
A: Very. This is a time of great opportunity—if we’re willing to rethink and rebuild. It’s not just about saving our industry, it’s about helping people reconnect socially.

A lot of the ways people used to be introduced to alcohol—big gatherings, shared occasions—aren’t happening as much. Drinking culture is learned through social experience, and wine can play a role in fostering that. Around 30–40% of Gen Z and Millennials choose wine based on personal experience, so we need to create those experiences.

Q: What’s next for Whiny Baby?
A: Continuing to evolve. As we grow, I’d like Whiny Baby to feel more gender-neutral. We’ll stay retail-focused, but someday, I’d love to open a tasting room. There’s so much more we can do to make wine fun, accessible, and part of people’s lives again.

Read more about Whiny Baby in our report, The Next Era of Wine, soon to be available for individual purchase. Paid Insight Out subscribers enjoy complimentary and early access.