In mid-2016, two years after 12 leading funders had launched an ambitious early childhood development collaborative, the group still had not settled on any investments. Noting the lack of progress, the group's principal convener, asked the group, "Should we stop meeting?" Posing this question helped prompt the collaborative to alter course--and pick up speed. Eighteen months later, two teams within the group had pooled $26 million to pursue co-investments in two areas: strengthening the early childhood workforce of teachers and other professional care givers, and changing the standard of care in pediatric well-child visits. This is a case study of how one collaborative set a fixed goal and continuously evolved its methods to achieve it. In sharing the choices these funders made and the turning points they faced, it is the hope that this case study presents as a how to guide to help other funders chart their own course to successful collaboration.