John Meacham, Franklin and Winston: An Intimate Portrait of an Epic Friendship (Random House, 2004).

“The future is unknowable, but the past should give us hope.”

—Winston Churchill 

I write these words on the eve of the first debate between the two major party candidates for the American presidency in 2016. This year’s contest has me, like many of you, shaking my head with despair. Yes, I will vote for one of these candidates, but not with any enthusiasm. In that respect, I think I share something with most other Americans, regardless of whom they support. We’re choosing who we perceive to be the lesser evil, or even choosing one candidate simply because that candidate is not the other candidate.

Although this election has plumbed new depths when it comes to the popularity—or lack thereof—of the major party nominees, I have to remind myself that at times in the past the best of our leaders have been neither popular nor even merely likable. Jon Meacham, in his Franklin and Winston: An Intimate Portrait of an Epic Friendship, reminds us that neither Franklin Roosevelt nor Winston Churchill was a pillar of virtue, but “together they managed to bring order out of chaos,” which is a skill that is also useful if you are to be a successful entrepreneur.

Each had his own strengths. Harry Truman, Roosevelt’s successor, once wrote that Roosevelt was “the coldest man I ever met. He didn’t give a damn personally for me or you or anyone else in the world as far as I could see. But he was a great President.” Meacham agrees, and observes that “Roosevelt was the better politician, Churchill the warmer human being.” Their successful partnership defending democracy in the face of totalitarianism “suggests that the unlikeliest of people—those who are underestimated or discounted by the conventional wisdom of their own era—can emerge as formidable leaders.”

As any entrepreneur surely knows, context and perception are everything. We should keep this in mind both was we think about ways to advance our entrepreneurial interests, and as we make our choices in November.