Napster’s launch in 1999 disrupted the copyright landscape, leading to more than a decade of innovation in laws, technologies, and business models as industries struggled to adapt. Today, AI technologies are poised to disrupt at least as much as file-sharing did. What lessons can we learn from the file-sharing experience – both positive and negative? We hear from attorneys, technologists, and policy wonks who lived through the post-Napster era as they offer their thoughts on how to navigate the decade to come.