In a concrete example of this belief, Rubenstein currently serves on a number of boards—31 at the time of his interview with Bridgespan. Yet, he also believes in being strategic with one's precious personal resources, especially time, and to that end he is currently in the process of narrowing his focus so he can concentrate on a few organizations and causes, recognizing that by doing so he can increase his impact. Being strategic is especially important since Rubenstein is engaged in his very busy career alongside his active philanthropy.

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Instead of building up an entirely new skillset for philanthropy, Rubenstein says, "I’ve tried to...take my private sector skill and translate it into the philanthropic sector," he says. A key talent he uses? Asking people for money. It’s no surprise that many people have difficulty asking others for money, so Rubenstein happily steps in and applies the unique skills that brought him success in his business—fundraising and persuading others—to his philanthropy.  "[O]ne of the skills that I’ve tried to bring to the philanthropic area is...to try to help the organizations by helping them raise money in addition to just giving my own money."

Philanthropy—on top of his for-profit career—creates a virtually nonstop schedule, but Rubenstein is grateful for what giving has brought to his life. "I could have spent my entire life just building my company and making more and more money, and then on my deathbed say, 'Here’s all the money. Somebody give it away,'" says Rubenstein. "I wouldn’t have been involved with any of the giving away; I think that would have been a less rich and less enriching life."