Meet Whiny Baby Founder: Jess Druey

Can you share more about your background and what led you to start Whiny Baby? Did you always plan to be a business owner?
I definitely didn’t grow up thinking I’d start a wine brand. My background is in video production and storytelling—I worked at Red Bull as a national athlete producer.

Like many people, my introduction to the world of wine happened during the pandemic. I wasn’t raised around wine and only really drank it on the occasional girls’ night, sipping rosé while watching The Bachelor.

In 2020, I was living in Los Angeles. Restaurants were closed, and I decided to download a dating app. For a first date, he invited me to his house, offered to cook, and asked me to bring a bottle of wine. I went to Whole Foods, stood in the wine aisle, and felt completely lost. That’s when the idea for Whiny Baby was born.

I didn’t set out to be a business owner—it came from an emotional need to create something that could help people connect, laugh, and feel something. While I never dreamed of becoming an entrepreneur, looking back, I can see the signs. At every job I’ve had, I wanted to be involved in every department. I love to work and innovate, which I think is why entrepreneurship is in my DNA.

Moving back to Bakersfield has been incredibly impactful. I’ve reconnected with my agricultural roots and felt the support of my amazing hometown.

When did you realize you had a hit product on your hands—something that could go beyond just your friend group?
It was probably when strangers started ordering it online and tagging us, sometimes with actual tears in their eyes or laughing while peeling the label off a bottle.

It shifted from “this is cute” to “this made my night” very quickly. But the real turning point was the data—selling out our first run in just days, gaining early retail interest, and receiving messages like, “I don’t even like wine, but I LOVE this.” That’s when I knew it was bigger than me.

It was great cheering for you—our hometown girl—on Food Stars! What was that experience like, and how did you use it as fuel instead of just a celebration after winning?
Thank you! Honestly, it felt like a wild dream. Competing on Food Stars with Gordon Ramsay and Lisa Vanderpump pushed me far outside my comfort zone—but it also reminded me that pressure can be a gift.

I wasn’t just representing myself; I was representing my hometown, my generation, and every young founder trying to build something real.

Winning didn’t feel like the finish line—it felt like a launchpad. It gave us more visibility, yes, but also more responsibility. The show took us from shelves in four states to more than 30!

What’s one of the biggest lessons you learned during your time on the show—personally or professionally?
Trust your gut—and trust your voice.

There were so many moments when I doubted myself, especially in a room full of more “traditional” entrepreneurs. But I learned that being the most you in the room is your power. Vulnerability, humor, relatability—those are business tools too.

I always lean into what I don’t know. Because I don’t always know how things should be done, I get to reimagine how they could be done. That’s a superpower. Never try to be something you’re not.

Did Lisa Vanderpump offer any advice after the show?
Yes, she did. Lisa told me to keep leading with my heart and instincts. She reminded me that building a brand is about storytelling and trust—and that if you stay rooted in who you are, people will follow.

She also told me never to shrink or play small to make others comfortable. That stuck with me. Lisa is the ultimate professional and always authentically herself. I’ll carry that lesson with me.

What advice would you give to someone in their 20s or 30s who’s sitting on an idea but hesitant to take the leap?
Just start. It will never be perfect.

I cringe at some of our early product versions, but if I had waited until everything was “just right,” I never would’ve launched. An object in motion stays in motion. Work hard. Network. Be good to people. You never know where one thing will lead.

Use your current position as a launchpad for your next step. I worked a full-time job while building Whiny Baby on the side for years. When the time was right, I quit and made Whiny Baby my full-time job. Every past role has contributed to my skill set and the network I rely on today.

What are you most proud of in your career so far, or with Whiny Baby as a whole?
I’m proud that we created a brand that makes people feel something.

In a world that’s so curated and corporate, we built a wine brand that invites you to cry, laugh, overshare, and just be a mess—in the best way. That emotional connection is everything to me.

I’m also proud of navigating a tough, traditional industry and paving a new way for future generations. Most of all, I’m proud I never quit, even when things got really hard.

If you could go back and tell your younger self one thing before starting Whiny Baby, what would it be?
Stop rushing. There’s a reason you are where you are in this moment. The journey is the point.

How do you stay focused and on schedule—even on off days? Any routines that help when you feel overwhelmed?
This is one of the hardest parts of entrepreneurship. It takes a lot of self-motivation.

At the end of the day, I’m the only one pushing this brand forward. So I created what I call my “bare minimum routine”: walk outside, drink water, move my body, put on music, and say one kind thing to myself.

Those simple actions usually help shift me out of overwhelm. I also set digital boundaries—turn off notifications, create pockets of silence, and schedule deep work sessions without distractions.

But honestly? Some days I still fall apart. On those days, I try to seek inspiration—go to a museum, watch a documentary, or just have a “research day.”

 What do you think is one of the biggest misconceptions about being a business owner?
That it’s glamorous.

Social media has really glamorized the founder role. But with all the fun comes serious responsibility and sacrifice. People usually only see the highlight reel—not the hard moments behind the scenes.

What’s your dream for the future of Whiny Baby? Where do you see it going?
I want Whiny Baby to welcome the next generation into the world of wine—with fun, education, and community.

I see us expanding into new formats like cans and coolers, opening a tasting room, and hosting immersive events that make wine feel like a lifestyle, not a lesson.

Long term, I want to shift wine culture entirely. Make it emotional. Make it expressive. Make it human again. I also have exciting plans that blend entertainment and wine education.

What do you hope people experience after trying Whiny Baby or attending one of your events?         I hope they put their phones down, connect with new people, and make memories.

We’re the loneliest generation. With remote work and digital overload, we’ve lost the beauty of gathering. I want Whiny Baby to help bring that back—because I truly believe it’s what life is about.

Is there anything else you’d like people to know about Whiny Baby?
I’m really proud of the ways I’m continuing to learn about the industry, winemaking, and innovation.

I’m deeply connected to my agricultural roots and passionate about honoring all the hands it takes to create a bottle of wine.

[Photos courtesy of Jess Druey]

Learn more about Jess Druey/Whiny Baby: 

In 2020 a then 22-year-old Jess Druey found herself in a situation familiar to many who are new on their wine drinking journey; staring at the wine aisle shelf feeling lost and confused. With no previous experience in the wine industry, she dove head first in self-launching her approachable and playful wine brand: Whiny Baby. The name celebrates the overly emotional reputation of her generation and nods to those who are "babies" on their wine drinking journey. After landing a partnership with The McBride Sisters, she moved home to her agricultural roots in Bakersfield, CA. Named by Essence Magazine “The Wine Getting Gen Z Into Wine” and by DTC Newsletter “The Wine Winning Over Gen Z With Innovative Packaging” : Whiny Baby offers 3 blends in their "starter pack" portfolio: a White Blend "Unwind", slightly fizzy Rosé Blend "OMG!?!" and Red Blend "Obsessed." All three are chillable, easily drinkable and offer unique details and one of a kind packaging with surprise conversation starters underneath each crown cap and peel and stick savable back labels to fill in with all the memories made while enjoying. Recently winning season 2 of Gordon Ramsay and Lisa Vanderpump's Food Stars entrepreneurial television competition, Jess is continuing her mission to revolutionize the food, beverage and hospitality industries all while documenting the journey on social media and sharing with the growing Whiny Baby community. Jess believes that the magic of Whiny Baby is thanks to the fact that because she doesn't know how things SHOULD be done, she can imagine how they COULD be done within the wine industry while being guided by industry experts and partners. Today, Whiny Baby is distributed nationwide and available on store shelves like Target, Total Wine, Bevmo/GoPuff and whinbaby.com.