A lot of ink is spilled and awards are bestowed each year celebrating the success of the social sector—and there is much to celebrate. But the truth is, if innovation is essential to the ultimate achievements of the sector, we should spend less time on success, and more time on failure. We lament the inability of the social sector to scale, but we do not support organizations to innovate on a continuous basis. We know that acceptance of failure is an essential part of innovation, which in turn is required for successful outcomes. Yet, we do not bridge the gap. Progress on this issue will require candid communication between social entrepreneurs and the philanthropic community. Unfortunately, such candour is rare. This article presents the perspectives of two sector leaders: Rohini Nilekani, philanthropist, social entrepreneur, and writer; and Kyle Zimmer, award-winning social entrepreneur and Schwab Foundation Fellow. Hopefully, it will spark further conversations within the sector.