In 2020, a 22-year-old with a first date that night stood in a grocery store wine aisle and realized she had no idea where to start. She didn’t grow up in a wine family, didn’t know what a varietal was, and bought her bottle on the label. The cashier told her she did the same thing. That was the whole insight. Jess Druey walked out of the store, called her mom to say she was starting a wine brand, and built Whiny Baby.
Today that brand is part of Gallo. In the first episode of the Wine Business Innovation Series, Jess Druey, founder and head of Whiny Wines, sits down with Stephanie Gallo, Gallo’s Chief Marketing Officer. They cover how a brand launched just as the market turned went from zero distribution to roughly 10,000 cases, why Druey let her own customers overrule her, and what a century-old winery can learn from a 29-year-old about reaching Gen Z.
Six takeaways worth stealing
1. Wine doesn’t have an old-people problem. It has a discovery problem. At 22, Druey’s rallying cry was that “the wine industry has an old people problem.” Seven years in, she has revised it. The industry is full of stories, she argues, and Gallo’s own family history “could be a television show.” They just aren’t packaged for the person standing lost in the aisle. ▶ Watch at 10:07
“I would say the wine industry has a discovery problem.”
Jess Druey, founder of Whiny Wines
2. Design for the moment the bottle opens. Every packaging detail answers something that already happens when people drink wine together. Built-in conversation starters fill the silence on a first date. A peel-off “savable” back label gives people room to write down the memory, and one guest at a baby shower framed hers and hung it in the nursery. ▶ Watch at 19:39
3. Pay your customers for their opinions, not their posts. Druey’s TikTok following of about 90,000 is entirely organic; she has never paid for followers. At Gallo she turned that audience into a formal tastemaker program: 14 consumers from around the country, paid the same fee whether they had 800,000 followers or 2,000. “They weren’t paid to post, they were paid for their opinion.” In a day-long workshop they tasted two blends of each SKU, reviewed 14 branding options and debated closures. ▶ Watch at 24:18
4. Even the founder’s non-negotiable went to a vote. Druey told Gallo her crown caps were not up for discussion. Gallo didn’t overrule her; its team asked whether a crown cap was really best for her consumer, so she asked her community on Instagram. The answer came from young women living alone and cooking for one: a crown-capped bottle can’t be resealed and laid flat in a small fridge. Whiny is moving to screw caps. “We mutually agree that the consumer is correct.” ▶ Watch at 45:40
5. Trade equity for mentorship. Druey’s first launch was done alone. She Googled the best-selling wines in the U.S. (Chardonnay and Cab), shipped direct-to-consumer in California out of her mom’s living room, and sold out. She has never raised money. In 2023 she pitched the McBride Sisters on a partnership they weren’t looking for: they would run winemaking and distribution, she would keep building the brand, and they would take equity. Asked why Gallo came in, Stephanie Gallo’s answer was blunt: most founders never call. ▶ Watch at 30:59
6. Give Gen Z something to say about the bottle. Her advice to a 100-year-old brand is that “Gen Z loves lore.” Cabernet Sauvignon being the offspring of Cabernet Franc and Sauvignon Blanc is exactly the kind of fact her audience wants to repeat at dinner. As for price, the $60 Cab may not look like it’s for her generation today, “but guess what? I’m quickly approaching a time when I do want to buy something nice.” ▶ Watch at 37:43
Jump to a chapter
- 0:00 Welcome from Wine Industry Network and Sonoma State University
- 6:53 A 22-year-old in the wine aisle
- 10:07 From “old people problem” to “discovery problem”
- 11:59 Learning wine at Gallo’s blending table
- 18:08 The intentional details: conversation starters and the savable label
- 20:56 Why Whiny Baby is becoming Whiny
- 24:18 Building a community, not chasing virality
- 28:48 The tastemaker program
- 30:59 Going solo, then partnering with the McBride Sisters
- 35:38 How Gallo came into the picture
- 37:43 Advice for a 100-year-old brand
- 40:03 Which channels reach younger drinkers
- 41:43 Wine in 2036
- 43:47 One thing to start tomorrow
- 45:40 Crown cap vs. screw cap: letting the consumer decide
- 50:07 Lessons from the episode
Add your voice, and ask your question
This is an interactive series. Answer the episode’s audience polls and post your questions for Jess Druey and Stephanie Gallo on Slido through Tuesday, October 13. They will answer the top-voted questions before the next episode.
Up next: Tuesday, October 27, 11:00 AM PT
Episode 2, The Foursight of Good Wine Business, goes from a brand scaling with Gallo to a small producer that nobody was betting on. Joe Webb, proprietor and winemaker at Foursight Wines, explains how a little-known winery kept growing while the market shrank around it.
About the Wine Business Innovation Series
The Wine Business Innovation Series is a collaboration between Wine Industry Network and Sonoma State University’s Wine Business Institute, featuring interviews with the brands and leaders who are winning in a challenging market. See every session.
