Q&A: Jess Druey | Founder, Whiny Baby Wines
At the SHE CAN Collective, we believe that mentorship, community, and shared stories are what pave the way for the next generation of women leaders. Few embody that spirit more than Jess Druey, Founder of Whiny Baby Wines and one of our Collective Board Members.
At just 22, Jess walked into a wine aisle feeling both overwhelmed and underwhelmed. Instead of settling, she saw an opportunity to build something different, a brand that was bold, approachable. Fast forward a few years, and Whiny Baby has grown into a cultural touchpoint that’s shifting the way people experience wine.
In this candid Q&A, Jess opens up about her journey as a Gen Z founder, the lessons she’s learned the hard way, and why she believes the SHE CAN Collective is poised to be a launchpad for women everywhere.
Congratulations on the Gallo acquisition. As a Gen Z woman founder, what does this milestone represent for you? Looking back, what are you most proud of building through Whiny Baby?
JD: “Thank you so much!!!! It still doesn’t feel real. Personally, I’m most proud of how I navigated starting and scaling a business with no traditional background. I’m a college dropout who had zero formal training in wine or business. I identified a need, created a proof of concept, and quickly realized others wanted a wine that felt easy, fun, and relatable to our generation. From there, I had to figure out how to scale — which in wine is no small feat. That path led me first to the McBride Sisters and now to Gallo.
This milestone feels like proof that the next generation truly has a seat at the table. Five years ago, I was a 22-year-old wandering the wine aisle, overwhelmed and underwhelmed. Today, Whiny Baby is part of the largest wine company in the world. What I’m proudest of isn’t just the brand itself, but how we’ve shifted the conversation around wine — making it fun, approachable, and deeply connected to culture.”
You built a brand that was unapologetically bold, funny, and deeply creative. How did you stay clear on your vision while building something so outside the traditional wine playbook?
JD: “Whiny Baby’s greatest strength is that I am the consumer. This is wine made by a Gen Zer new to wine, for those who are new to wine. From the beginning, the brand was social — I documented everything on TikTok and Instagram, using in-app features to interact directly with consumers and ask them what they wanted.
I also trusted my gut — and my generation. From day one, I wasn’t trying to copy what already existed. I was building what I wished had existed when I walked into that aisle years ago. That kept me clear: I wasn’t chasing prestige, I was chasing connection.”
What drew you to the SHE CAN Collective, and what role do you hope to play in its next chapter?
JD: “The McBride Sisters took a cold call from me, and it changed the trajectory of my life. That’s the power of mentorship, and it’s the mentality I’ve carried forward — always saying yes when I can, always opening doors for others. SHE CAN represents a huge part of my journey: emerging generations paving the way through collaboration.
The SHE CAN Collective proves women don’t just belong in this industry — we can thrive, lead, and transform it. In its next chapter, I hope to serve as both a mentor and a megaphone, sharing what I’ve learned and showing that there’s no one “right” way to succeed.”
What’s one lesson you’ve learned the hard way in business that more women should hear earlier in their journey?
JD: “Humility, enthusiasm, and tenacity.
Humility: You can’t do it alone. Learn from those who’ve gone before you, own your mistakes, and remember you’re building something for others to enjoy.
Enthusiasm: You’ll hear “no” countless times. Your joy and belief in your vision are what carry you (and get others to believe too).
Tenacity: Those who succeed aren’t necessarily the smartest or most resourced. They’re the ones who refuse to quit. Success is simply not losing enthusiasm after failure.
And especially for women: show up, out-professional everyone, don’t be afraid of personality, own what you don’t know, and have fun. Asking for help isn’t weakness — it’s a power move.”
You’ve connected with a generation of consumers that often feels left out of traditional spaces. What advice would you give to other women trying to build something for people who’ve never seen themselves reflected in an industry?
JD: “That will be your greatest asset!!! Whiny Baby exists because the people in boardrooms didn’t represent me. That became my advantage.
That said, remember you don’t represent everyone. Go deeper. Listen louder than you talk. The answers aren’t in the industry playbook — they’re in the community itself. Ask questions, co-create, and don’t underestimate the power of fun. Fun is disarming, it invites people in, and it builds real believers.”
What kind of long-term impact do you hope the SHE CAN Collective has on women who are just getting started, whether they’re building a career, launching something of their own, or simply looking for what’s next?
JD: “I hope SHE CAN becomes a more formalized, easier-to-access version of what the McBride Sisters gave me when I was starting out: mentorship, networking, opportunities, inspiration, and a community of like-minded people to lean on.
Long term, I want it to be a launchpad. Not just for careers, but for confidence. A place where women come as they are, find community, and leave believing they’re capable of bigger dreams than they thought possible.”
When you think about your growth over the past few years, professionally or personally, what’s something that’s surprised you about yourself?
JD: “I’ve surprised myself with resilience. There were so many moments when things could’ve fallen apart, but instead I found ways to rebuild, rethink, and keep moving. I’ve also surprised myself with how much I’ve grown into traditional spaces I once felt unqualified for. As a college dropout with no business background, I didn’t think I could stand next to people with MBAs and decades of experience. But I’ve learned that lived experience, self-education, and hustle can be just as powerful. Presence, not pedigree, is what matters most.”
What’s something that’s fueling you right now, in work or in life? Anything that’s keeping you motivated, focused, or inspired this season?
JD: “SO MANY THINGS! A big misconception is that I’ve crossed the finish line with Whiny Baby — oh no, we’re just getting started. The brand is being redeveloped and relaunched, and I’m deep in consumer research to refine it for the next generation. That’s fueling me with so much energy and curiosity.
On a personal level, I’m diving into new inspiration — from Substack to stacks of physical magazines to my newly purchased BRICK phone (yes, really). And as always, hosting dinner parties, discovering new wines, and soaking in California vineyards keep me creatively charged.”
Jess’s story is proof that there’s no single path to success; presence, not pedigree, is what matters most. Her vision for the SHE CAN Collective is clear: a place where women come as they are, find community, and leave with the confidence to dream even bigger.
We’re proud to have Jess on our Board and even more proud to share her story with you.
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