Jerry is the CEO of Gradual, a community platform, and is seeing the front line of how AI is effecting both online and in-person communities. We are in uncharted waters and in this conversation, we explore how AI might impact these communities, why AI could lead to more sustainable online spaces of gathering, and much more. Summary Gradual was born out of the ELC community, a community of engineer leaders. Gradual started as an internal tool for the community but eventually became its own product. The platform uses AI to provide personalized and timely experiences for community members. AI enables knowledge sharing and retrieval, making it easier for community members to find the information they need. Gradual is used by both established organizations and emerging companies to build and grow their communities. The platform empowers local moderators and volunteers, and helps companies organize and support external contributors. Gradual aims to create a unified experience for community members and is working on building a community of communities on its platform. The conversation explores the changing needs of communities over time and the impact of AI tools on community interactions. It also discusses the shift in community engagement during the pandemic and the importance of in-person connections. The conversation highlights the value of post-event engagement and the role of Gradual in facilitating ongoing community conversations. It touches on the future of community building, the potential of AI-powered virtual moderators, and the need for companies to invest in community. The conversation concludes with a discussion on the positive and negative impacts of AI in community building.