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 Minnesot ...