The Wine CEO Podcast

The Wine CEO Episode #205: From Loss to Legacy: the risk that changed everything. Interview with Debra Mathy, Dutcher Crossing

May 6, 2026·21 min
Episode Description from the Publisher

What would you do if life forced you to stop waiting? In this episode of The Wine CEO Podcast, I sit down with Debra Mathy, Proprietor of Dutcher Crossing Winery, to talk about the deeply personal moment that led her to leave the corporate world and pursue her dream of owning a winery in Sonoma County.  After her father's stage 4 melanoma diagnosis, Deb made a bold decision—to stop putting life on hold. Just months after purchasing the winery, her father passed away, leaving her with a powerful symbol that still defines the brand today. In this episode, we talk about: What it really takes to build a successful winery from the ground up The challenges and opportunities of being a female winery owner How personal loss can shape your leadership and legacy The story behind Dutcher Crossing's iconic penny farthing logo Deb's newest venture and what's next in her winemaking journey Whether you're a wine lover, aspiring entrepreneur, or someone navigating a major life pivot, this conversation will inspire you to take action on the life you truly want. 🍷 Don't forget to like, subscribe, and share with a fellow wine lover! Subscribe to my newsletter for a FREE GUIDE to Food and Wine Pairing: thewineceo.com Today's guest: https://dutchercrossingwinery.com/   #WinePodcast #WineCEO #SonomaWine #WomenInWine #FemaleEntrepreneur #WineryOwner #WineEducation #WineLovers #EntrepreneurJourney #LuxuryLifestyle #WineBusiness #CaliforniaWine #SommelierLife #WineStories #WomenInBusiness

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