From the goal to be a barback to now accomplished Bar Owner—Gabriel Holland on Learning Through Experience and Leading With A Humble Heart

In this episode of The Walk-In Club Podcast, we sit down with Gabriel Holland, a gentle force in Oakland’s hospitality scene and the proud owner of Theory Bar. Gabe’s journey is one of quiet persistence—learning by watching, doing, and asking questions. From his first days busing at the Claremont Hotel to becoming a barback at Pican, he never rushed the process. Instead, he kept showing up, stayed curious, and let every role teach him something new.

As a food runner at Pican, Gabe began to understand one of the most important lessons in hospitality—how to bridge the gap between front of house and back of house. Learning patience and communication in the middle of that line helped shape the way he leads today. He shares how having supportive management during those early years gave him the kind of confidence that makes delegation feel respectful, not performative.

We explore:

🍽️ Starting at the iconic Claremont Hotel and a short pivot into retail before finding his way back into restaurants🍸 Learning the craft of bartending on his own time—from shadowing to inventory to not grabbing pint glasses from the top🤝 Bridging FOH and BOH and why early support from leadership helped shape the way he leads today💥 Navigating the uncertainty of Covid and finding solid footing again🏠 Opening Theory Bar with intention—not for status, but to build something rooted in care and community

Gabe shares the kind of wisdom that comes from showing up day after day, without the need to prove anything. His story is a reminder that success doesn’t always shout—it often can move quietly, guided by heart, humility, and a deep commitment to the craft.

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