Andy Rappaport on Art, AI, and the Future of San Francisco

In this episode, Hugh Leeman speaks with Andy Rappaport, venture capitalist, musician, collector, artist, and co-founder of Minnesota Street Project. The conversation moves from the Venice Biennale to vintage guitars, from school shootings to refugee portraiture, from 9/11 memorials to the accelerating economic disruptions of AI.Rappaport discusses his collaborations with Deborah Oropallo, including works that use beauty, sound, and visual seduction to draw viewers toward painful subjects: gun violence, displacement, mass trauma, and the failures of political imagination. He also reflects on his family’s refugee history and how quickly a society’s moral assumptions can change from one generation to the next.The conversation then turns to San Francisco’s art ecosystem. Rappaport describes why he and Deborah Rappaport founded Minnesota Street Project, what gallery closures and art school losses reveal about the city’s cultural future, and why arts philanthropy must evolve beyond single-institution support.Finally, Rappaport connects his decades-old warnings about technology and inequality to today’s AI economy, arguing that society must find ways to move people “from one side of this chasm to the other” rather than leaving survival to luck.