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In 2020, City Leadership announced the allocation of $60 million dollars to support the Black community. Through a community design process, the Dream Keeper Initiative (DKI) was launched. DKI is an effort to ensure San Francisco’s diverse Black communities experience joy, feelings of safety, educational and economic advancement; are holistically healthy; and are thriving. Typically, evaluation of City systems lean heavily on a context, input, process, and product (CIPP) model, focusing on improvement and accountability. During community listening sessions, participants overwhelmingly requested accountability of the funds, but also felt it important to tell the stories and understand who and how people are being served. This paper explores the financial and human cost of storytelling and the work of DKI.