Making sound decisions in funding youth-serving organizations can be greatly enhanced by implementing a comprehensive and inclusive learning process that embraces the perspectives of and input from a variety of stakeholders, including program staff and leadership, various community partners, and, most important, the youth. Youthprise effectively applied this collaborative approach to its grant making in 2012 when it funded Saint Paul Parks and Recreation (P&R) to continue and expand its innovations in youth work and diffuse specific strategies into other recreation centers. For a new grant-making intermediary, this was an ideal opportunity to test its priorities with an organization that had a demonstrated commitment to working with young people who were severely marginalized by other youth-serving agencies. Youthprise's relationship with P&R has yielded valuable insight that has informed its work as a grant maker and as an organization focused on systems change.