Whiny Baby →Whiny. Jess Druey built a gateway wine at 22
Now she's rebuilding it. And she's dropping the baby.
If you’ve spent any time in wine circles the past few years, you’ve seen Whiny Baby. Jess Druey self-launched it at 22, DTC, California only. By 2023 she’d brought on partners and taken it nationwide into major retailers. Last September, Gallo acquired it.
Ladies and gentleman, that’s a 3-year launch to exit trajectory which we found f-a-s-c-i-n-a-t-i-n-g.
But Jess isn’t chilling, basking in the sweet glow of the acquisition dream on a beach. She’s working. She is now rebuilding Whiny Baby as “Whiny,” in public, inside a much bigger machine, with a brand that’s had one identity for six years and is new getting a new one.
I sat down with Jess to talk about what that rebuild actually looks like.
The rebrand is a graduation, not a pivot
Whiny Baby is becoming Whiny. Four blends launch this spring, up from three, with a new orange blend joining the lineup. The wines are drier than before but still fruity, juicy, and approachable. The philosophy underneath hasn’t moved: begin your wine journey with a blend.
“I found myself feeling like I’d outgrown it,” Jess said of the old brand. “I still love those wines. I still love the packaging and the branding. But I wanted something that could grow with our consumer.”
The target isn’t college kids trying to get drunk cheap and fast. It’s what she calls early career adulthood, people who just got their first job and their first apartment and are figuring out what a weeknight glass of wine actually means. Price point is still being finalized, but her stated bar is specific: approachable enough for a weekly grocery run, elevated enough that you’d feel good gifting it to a friend.
Even the design process reflects the same instinct, expand without abandoning the origin. Jess described a three-way build: Gallo’s in-house creative team, an outside agency that had never touched wine before, and the original designer she DM’d on Instagram seven years ago with no budget to offer. That designer is still on the brand.
She’s using transparency as a defense against dilution
Many founders fear their brand getting swallowed by an acquisition. Jess’s answer wasn’t to shield the brand from Gallo. It was to over-share the process with her own audience.
“This Gen Z consumer has access to more information than any consumer before,” she said. “I’ve been really passionate about being super transparent, super honest. Some consumers care, some don’t, but really showing them that although I’m with this large organization now, it’s actually opened me up to way better quality wine, the most incredible winemakers in the industry, the resources.”
Basically, she’s owning the narrative. Document it and narrate it yourself, in real time, before someone else fills in the gaps. Smart.
Clever idea alert! She’s paying her “taste makers” the same, no matter how many followers they have
This is one worth stealing: Jess built a 14-person panel to weigh in on blends and packaging before launch. Not influencers, in her words, “taste makers,” defined by whether their recommendation actually moves people, not by follower count.
“I don’t care if you have 200 followers or 200 thousand,” she said. “It’s someone who, when they give a recommendation, their community listens.” She sourced them by asking her own audience who they trusted, then vetted the list to make sure it represented different regions, incomes, and backgrounds. One member was an intern who worked the bottling line on her very first production run and is now a lawyer.
Everyone got paid the exact same amount, whether they had 800,000 followers or 200. “We’re not asking them to post. We’re paying you for your opinion.” She said the people with the biggest followings, the ones used to huge influencer budgets, were the ones least bothered by the flat rate. It was the structure itself, everyone doing the same job, that made it feel honest.
She says Gen-Z drinks after all.
“I appreciate you calling it a narrative,” she said, “because that’s what I believe it is.”
According to Jess, this was never really about wellness. It’s about a generation that lost casual mentorship culture, the kind you pick up watching your boss order wine at a work dinner and quietly taking notes. She started drinking wine at 22, during the pandemic, working remotely with none of that in-person modeling available to her. She thinks a lot of what gets labeled generational abstinence is actually a mentorship gap.
She also thinks the tide is already turning. She pointed to the backlash against the Diary of a CEO episode where the host Steven Bartlett said three glasses of wine ruined his entire week, and to the rise of what she calls optimization fatigue, a generation that turned rest and productivity into a second job and is now exhausted by it.
Her evidence isn’t just anecdotal. She cited Barnes & Noble quadrupling its store count in five years as a signal that reading, cooking, and staying in are back in a real way, and argued that all of it is upstream of wine, not competing with it.
She says none of this reads as panic. It reads as a legacy portfolio with decades of stories nobody has told well yet, sitting next to Whiny that still has to prove itself. She’s also fighting a smaller, more structural battle: getting her four blends merchandised together on shelf instead of scattered across a store’s varietal categories, a layout decision retailers control and most consumers are not thinking about.
It’s a rare spot to be in. Jess is working with her brand that’s six years old and already on version two, inside a company with brands older than her parents, proving to both the internet and the wine aisle that growing up doesn’t have to mean losing the plot. She doesn’t treat the scrappy origin and the corporate resources as a tension to manage. She treats them as the same asset, and she’s using one to build the other.
THE NEW RULES
Jess believes in radical transparency. Not as a crisis response, as a default. Tell people what’s happening to the brand before they have to ask.
And underneath that: stop solving problems for a consumer you’re guessing at. Put her in the room, pay her fairly for her opinion, and build from there.
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