Alumni Parent Profile:
Duncan Winecoff

Duncan’s parents found Ojai in 1990 and enrolled him in first grade at Oak Grove School. His family was a part of a larger Tibetan Buddhist community, and they felt Oak Grove to be a place where those values could be easily expressed. According to Duncan, “Oak Grove felt like home.” Joined by his three siblings, Duncan stayed at Oak Grove through eighth grade.

At 18, Duncan moved to New York City, where he began exploring what he wanted to do with his life. As he describes it, he was working odd jobs and delving into life as an independent entrepreneur. It was while his younger brother Stuart was studying film at NYU that he discovered his passion. Duncan wrote a short film, and his brother acted as cinematographer. From there he continued to follow this passion, eventually carving out a commercial directing career.

 “I always knew I would like my kids to go here.”

In 2019, while living in Berlin, Duncan and his wife Sheila made the decision to move back to Ojai. He felt the urge to find his roots and to uncover a place where he and his family could live a more balanced life in a peaceful and down-to-earth place. Describing Ojai he says, “I’m lucky to have known it, so I knew where to go.” Explaining the role of Oak Grove in his family’s decision he states, “Oak Grove was a big part of the pull to go back,” and “I always knew I would like my kids to go here.” Duncan says that what he has learned as a parent is that the school’s environment and philosophy are very important, but it is also vital to have a community where that philosophy is supported outside of the classroom. He believes he has found that.

This alumni profile was featured in the 2021-22 Annual Report

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Recent Blog Posts:

50th Anniversary, May 16-17,2026

50th Anniversary Weekend

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Join Us May 16-17, 2026! Our 50th anniversary events will be open to anyone who has been part of the Oak Grove School community over the past 50 years – everyone is welcome.

First Day of School 2025

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From joyful skips to heartfelt hugs, and high-fives flying everywhere, it was wonderful to see the community together again. This year is extra special as we celebrate Oak Grove’s 50th anniversary — a milestone that makes today’s beginning even brighter.
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VC Star Article: Supporting Children to Build the Struggle Muscle

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Solving problems is how children build competence – both in the classroom and in life. The aim of a healthy life is not to eliminate hardship but to develop the skills and inner resources to meet it.