https://www.shecan-collective.org/read daily 0.75 2025-10-03 https://www.shecan-collective.org/read/qajessdruey monthly 0.5 2025-10-03 https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/1759455737167-YZHQT17505N1UPUVWIFQ/SB2513-JD_0357.JPG Read - Q&A: Jess Druey | Founder, Whiny Baby Wines - 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.” https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/a20564a9-3966-4b63-a40e-80830671e761/000000780006.JPG Read - Q&A: Jess Druey | Founder, Whiny Baby Wines - 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.” https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/575b7525-57f5-4224-be5b-6b7ab43f1db6/IMG_1228.png Read - Q&A: Jess Druey | Founder, Whiny Baby Wines - 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.” https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/a7390797-d0d2-4a00-ae5e-368cdbea91ed/IMG_2461.JPG Read - Q&A: Jess Druey | Founder, Whiny Baby Wines - 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.” https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/1759428597940-4TK9J4ZDPXM6115FSU0Q/Jess+Druey+Headshot+2025+2.JPG Read - Q&A: Jess Druey | Founder, Whiny Baby Wines 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. Ready to connect with women like Jess? Join the SHE CAN Collective newsletter to be the first to hear about upcoming resources, events, and opportunities. https://www.shecan-collective.org/contact daily 0.75 2026-01-03 https://www.shecan-collective.org/home daily 1.0 2026-01-24 https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/c0fe7f7a-3d48-4fbd-b46f-f74a4f09fdb5/kaboompics_working-on-laptop-with-jewelry-flash-photography-aesthetic-39799.jpg https://www.shecan-collective.org/getinvolved daily 0.75 2026-01-13 https://images.squarespace-cdn.com/content/v1/605119cf34278f352218820c/ee007aac-79b9-4d13-b809-d80035a170a7/kaboompics_flash-photography-aesthetic-in-creative-workspace-and-modern-lifestyle-moments-39807.jpg