In 2014, the Nellie Mae Education Foundation began funding three projects that together comprise the Grassroots Portfolio: Civic and Family Engagement, Community Organizing, and Amplifying Student Voice and Leadership. This work was part of the Public Understanding and Demand component of NMEF's grantmaking strategy. Following a Foundation-wide equity assessment in 2017, and a review of the Foundation's strategy, NMEF commissioned Algorhythm to examine its Public Understanding and Demand evaluation and grantmaking documents, with the ultimate goal of helping NMEF better understand its role in the grassroots organizing and engagement work. This brief explores NMEF's journey in funding the Grassroots Portfolio and shares lessons learned. [This report was prepared in partnership with Algorhythm.]