Roger Hertog believes philanthropists should ask the same key questions at the outset of philanthropic ventures that they would of business ventures. For example, what vacuum in the market are you filling with your investments? Why do you think you're particularly good at this? “Small mistakes at the beginning have enormous significance,” he says.

Roger Hertog candidly tells grantees, “We’re going to be a real investor in you, but we just want you to know, here are the kinds of things we’re looking for. And if we can’t do it, we’re going to slowly extract ourselves.”

Learn more about building healthy grantor-grantee relationships at The Bridgespan Group.