Publisher’s note: Having met the energetic and confident Jess Druey, the subject of this story, I felt that some of the forward-thinking students of Seven Oaks, with future entrepreneurial dreams of their own, might enjoy hearing her success story. So, we reached out to the Virtual Enterprise team at Stockdale High School to see if one of the students might like to interview her, write her story, and perhaps use some of her insights in their own projects at school.  Here is Kai’s story. 

 

Whether you're browsing the beverage aisle at Target or Bevmo in the Shops at RiverWalk, scrolling through TikTok and Instagram, or watching Gordon Ramsay’s food competition on television, one name stands out: Whiny Baby. A wine brand marketed for GenZ … it’s perfect for a first date or a fun watch party for The Bachelorette. The face of this innovative brand is Bakersfield native Jess Druey, an ambitious and ingenious entrepreneur who transformed her “A-ha” moment into one of the most successful beverage companies around. 

 

Jess is a proud Bakersfield native, having attended Liberty High School where she began shaping her future. As ASB President, she balanced a busy student life with internships and tutoring children in various subjects. She carried her talents to Point Loma Nazarene University as a Journalism and Broadcasting major, though she soon realized that a purely academic life wasn’t enough for her. Shortly after securing a coveted internship early in college, Jess told her parents that higher education alone couldn’t satisfy her hunger—she craved something more. She recalls, “It was a calculated risk…”. Using her exceptional ability to connect with people, she landed a position at a boutique production company, assisting a leading photographer who shot sessions for some of the biggest names in rap. Her momentum didn’t stop there; her next role was with Red Bull, serving as the National Athlete Production Coordinator. 

 

Things almost came to a halt when COVID slowed her strenuous life and forced her to consider her next steps. On a date—when restaurants and stores were closing down—she was invited to a homemade dinner and was tasked to pick out wine. Wandering the aisles at Whole Foods, one thought filled her mind: “What the heck is Cabernet?” The logos were boring and nothing spoke to her as a newcomer to wine, leaving her completely lost in what should have been an easy task. In that moment, her thoughts erupted into a business idea. Instead of focusing on her date, all she could think about was how to sell wine to people like her—people wandering aisles without anything capturing their attention. She rushed home to file the business name, Whiny Baby, a name that developed spontaneously in Druey’s thoughts. After hours of scrolling to figure out how to start a wine company overnight, she realized she knew nothing about the industry or launching a company. The idea lingered on in her head and in her Notes app, but for the time being, she returned to her job at Red Bull.  

 

Following an unexpected chain of events—the passing of her beloved stepfather and the uncertainty of the pandemic — she moved back home. Yet things were different this time; she sat down with her mom and pitched her company in what felt like her first Shark Tank pitch (though probably not her last), asking for an investment of $20,000—her previous college savings—to make Whiny Baby a reality. She succeeded, and Whiny Baby was born. “I sat down, and I made my business plan,” she recalls. She immediately got to work, calling contacts from her various professional positions while crafting a strategy to build a brand from scratch. Jess relied on Google for answers, taking it one step at a time: “How do I find the wine? How do I find the license?” A wine broker who responded to her call offered to store and bottle a small batch for her. Jess then moved to phase two, transforming traditionally boring wine bottles with vibrant designs. “I worked with people who had never done wine labels before... there were a lot of imperfections. Nothing’s ever gonna be perfect—just start.” She quickly devised a strategy to launch the brand using TikTok, selling a few batches to observe responses. The plan worked—her products blew up, sold out, and people demanded for more. 

 

Determined to improve, Jess researched the wine industry’s giants, which led her to the McBride sisters—two women dominating the wine industry by breaking into large retail spaces like Target and promoting female leadership. While navigating her company’s next steps, particularly finding capital to secure the brand’s future, someone remarked, “You remind me of someone... the McBride sisters.” Jess was introduced to them, and in the following months, formulations were chosen at the winery with catchy names like “Unwind White Wine” and “Obsessed Red.” Jess even made an appearance on Gordon Ramsay’s Food Stars, winning the competition and earning a paycheck of $250,000. With strategic partners like the McBride sisters—veteran players who knew the industry’s ins and outs—Whiny Baby grew.  

 

Druey’s entrepreneurial success is a full-circle moment. She left Bakersfield in search of corporate opportunities, yet it was in Bakersfield that she committed to creating an internet sensation among Gen Z. She built a brand that now glimmers on the shelves of the very Whole Foods where she once struggled to pick a bottle.