Penn, of course, is too savvy not to keep in mind that the cameras are watching, so of course, the best spin is put forward. He says he believes that Clinton is the most electable candidate in the general election and is leading the race. In fact, according to the latest polls, Clinton is running neck and neck with the Republican front-runners.
Penn's philosophy when it comes to this election is that Americans should not focus on what he calls the "elites obsession with the personality of the candidate" but on the issues that affect the average voter. That was the basis of Hillary Clinton's successful Senate campaign in New York and is central to her presidential race.
But not all of Penn's client's have taken his advice.
While working for Al Gore in 2000, Penn said they had a fundamental disagreement. "He thought there was Clinton fatigue. I thought there was Clinton nostalgia but not fatigue. I think that was his view at the time, and that was my view."
"I think when you look at it, when you look back, I think that had he embraced the policies of President Clinton and embraced the President Clinton who'd been with him for so many years, I think it might have made the 1 percent difference," Penn said.
The 1 percent difference is at the heart of Penn's new book, "Microtrends," in which he identifies 75 micro groups inside the United States. "The old view of America was we had a melting pot. It was all about so many different cultures coming together into one, and I think now it is a more niching of America," he said. "People are making many more choices in these lifestyles, and they're being put together not just by class, and not just by race, but by these choices that really sit at the core of the microtrends."
Penn said that if you have a movement that approaches 1 percent, you have something that is small, yet potentially very powerful. He said that "Today 1 percent is a best-selling book, the best-selling car there is -- it is a dynamic movement." Not all the trends are political or even serious: cougars, unisexuals, second-home buyers, do-it-yourself doctors, Protestant Hispanics and old new dads are among his microtrends.
Penn is an old new dad himself. In addition to three older children from a previous marriage, Penn has a 5-year-old daughter with wife Nancy Jacobson, who fundraises for Hillary Clinton. He credits Jacobson with helping him shed his old nickname from his White House days, when he was affectionately called Schlumpy. He still retains some of his rumpled professor style and readily admits to wearing two different shoes for a meeting in the oval office.
"I've never been one to, you know, to put good dress above letting the substance out, and so for me sometimes, I just get so wrapped up with what I'm doing and in this case, I can't remember why I wound up with too different shoes, and another time, I took the president's coat on the way out, only to discover out later it was his."
Surely the president gave his pollster a pass.
Penn rejects the idea that Sen. Clinton's gradual shift to an antiwar position -- a movement that's in line with public opinion -- reveals a close reliance on polls. He said that his serving as the senator's pollster and chief strategist doesn't mean that there is necessarily a hard connection between the two roles.