In today’s start-up landscape, competition is fierce—and so is the pressure to tout your upside. That’s why in places like Silicon Valley everyone adopts a pose of world-winning invulnerability. Everyone is “crushing it.” Success is the lingua franca of the realm.

In the nonprofit world, the hype may resonate at a subtler pitch. But the need to project a façade of success may be even stronger. Philanthropists aren’t looking to invest in people or organizations with a track record...

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