This week the guys sit down with Matt McDermaid, owner and winemaker at Staysail Wines, a small-lot Sonoma County winery inspired by his background in sailing. The name “Staysail” refers to a sail used to adjust for shifting conditions—much like how Matt adapts to each unique vintage. With deep family roots in the wine world (his aunt and uncle run GlenLyon Vineyards & Winery in Glen Ellen), Matt built his own path, earning an MBA in Wine Business from Sonoma State and studying winemaking at UC Davis. After hands-on experience at Meeker Vineyard, he launched Staysail with a focus on low-intervention wines sourced from organically and regeneratively farmed vineyards. He’s thoughtful, funny, and passionate—and yes, he managed to score some fruit from Rossi Ranch this year. Keep an eye out for those bottles, and definitely grab some Staysail while you can. [Ep 387] Staysailwines.com @staysail_cellars