Evan Wolkenstein

Evan Wolkenstein he/him

Entrepreneur in Residence: Jewish Content Fellow

Bringing to light

Translating ancient wisdom into modern educational frameworks that transform how Jewish communities learn, lead, and navigate an AI-enhanced future.

The basics

Evan joins UpStart after 19 years at Jewish Community High School of the Bay, where he built programs that helped students find themselves in Jewish learning. He co-created EVERlab, an integrated design lab that won the Kohelet Prize for Excellence in Progressive Education, and redesigned the school’s capstone program through student feedback and iterative design. Beyond the classroom, Evan has worked to make Jewish learning accessible at scale—creating video content for BimBam and developing holiday curricula for college campuses nationwide. His novel Turtle Boy, which won the Sydney Taylor Book Award, grew from his experience navigating difference and belonging—themes that run through all his work. Recently, Evan has been exploring how AI can enhance Jewish education without flattening what makes it meaningful. Evan holds an M.A. in Jewish Education from Hebrew University. Based in San Francisco, he’s ready to help Jewish entrepreneurs build learning experiences that honor tradition while imagining new possibilities.

How Evan finds meaning and comes together with others

Evan finds meaning in conversations that start as small talk and end up somewhere unexpected—with other parents, with educators trying something new, with his kids when they ask questions he hasn’t thought about in years. He comes together with people who are willing to experiment, fail, and try again.