"Smart Money: Recommendations for an Educational Technology and Digital Engagement Investment Strategy"—compiled by Lewis J. Bernstein and Associates, is the result of a co-investment. It includes a provocative set of recommendations for the Jim Joseph Foundation and William Davidson Foundations to consider and an illuminating landscape analysis of the educational technology field. The report was initially commissionedfor the foundations’ internal purposes, without explicit plans to share it widely. However, after reviewing it, it was understood that the learnings here are highly relevant to others in the field: funders, practitioners, community leaders, and anyone interested in how tools of educational technology and digital engagement could advance cultural and religious learning and engagement. Because of the report’s substance, there is a desire and a responsibility to share it. There is also the belief that it offers an important look into the process foundations undertake to explore a new space in which to consider developing an investment strategy.