The Silver Oak Apprenticeship Program: The Perfect Transition

by SaCha Stewart-Coleman

Music is a powerful form of expression, and as someone with two ears and a beating heart, it has always been important to me. Just like wine, music can connect people. So, when the marketing team suggested creating a Silver Oak Spotify Playlist to tell the story of our 2020 Silver Oak Napa Valley Cabernet Sauvignon release, I was thrilled. Curating wine events in New York always requires a great playlist, but in California, car culture demands the same. I quickly realized the importance of good tunes while exploring my new home, full of winding roads. Whether it’s long drives to San Francisco, early morning commutes to the winery, or your first time driving down a quiet back road, a stellar playlist is key. What better way to reflect on my apprenticeship than through the art of curation? My first deep breath after moving to California was accompanied by the song “Late Bloomer” by Mereba, paired with a glass of 2020 Silver Oak Alexander Valley Cabernet Sauvignon.  

Follow your curiosity. 

Late Bloomer by Mereba

Switching careers to wine was not planned. I was a 21-year-old aspiring playwright and actor, simply looking for a job. A family friend offered me the opportunity to work at his wine shop. Luckily, the wines were well curated with intentional selections like Twomey. My curiosity grew, and soon I found myself diving into the world of wine. From not knowing what a Côtes du Rhône was to understanding the nuances of Barbaresco, Barolo, and Barbera, my knowledge expanded rapidly. By age 22, I felt like everyone around me was miles ahead, but the Veraison Project Apprenticeship with Silver Oak seemed like the perfect opportunity to catch up. Living in New York, I knew I wanted to pursue wine beyond hospitality, but it felt like an impossible dream—until I was accepted into the program. When I finally unpacked my rental car at a picturesque house in Calistoga, with a vineyard in the backyard, I took a deep exhale with a glass in hand and knew it was time to evolve in this industry.  

Nothing comes easy in life.

Work by Charlotte Day Wilson 

Adjusting to life in California was a job itself. Coming from the fast-paced, public transportation-dependent, “what’s that smell?” vibe of New York to a rural, slower pace where the cows and the people take their time was a major shift. This apprenticeship didn’t just immerse me in the wine industry but also in agricultural California living. I even created a new Amazon wish list for my car with items like a chargeable tire inflator. As a proud New Yorker, I am confident in my adaptability, so I dove headfirst into everything unfamiliar. I set my ego aside, kept asking questions, and learned the value of patience—from unclogging a pump to driving through fog for the first time. In the vineyard and cellar, keeping your head on a swivel is key. Having worked on a previous harvest, I knew the winemaking process isn’t always linear. It’s unpredictable, much like life. But watching the experienced team at Twomey navigate each hurdle with grace and care was inspiring. They truly looked out for one another, and that collective dedication motivated me to apply the same diligence to my own life.  

This work ethic was evident across every department I worked with. Customer Care showed me the importance of making each customer feel special. Marketing demonstrated that no project—big or small—should ever be overlooked because it all contributes to the bigger picture. Every task, every position, carries immense value, reflecting Silver Oak’s long-standing reputation. It would’ve been impossible to sustain their legacy without a team that pours their heart into the work. 

Never forgetting to capture these moments.

DtMF by Bad Bunny   

I’ve been lucky to create lifelong memories at Silver Oak—whether it was sabering my first bottle, operating a scissor lift, or experiencing the infectious joy of Release Day. This apprenticeship has shaped me not only as a future wine professional but also as a young person navigating life. I’ve learned that I can move across the country, far from friends and family, and still find a sense of community and belonging. Now, halfway through my apprenticeship, my list of valuable lessons and memories continues to grow.  

In an industry where many people don’t share my background or look like me, feeling truly included has transformed my perspective on what’s possible in wine with the right community. I aspire to be part of the next generation of wine professionals who prioritize creating safe, inclusive spaces for individuals of all backgrounds.