Why he could: Conway has committed to giving away $1 billion toward programs to spur job growth - so it might makes sense that he would see the Oval Office as a way toward being able to further influence the economy.
Why he probably won't: While a billionaire, Conway's political donations are relatively sparse. In recent years, he's handed out money to Virginia Sen. Tim Kaine (D) as well as a handful of super PACs. Those donations of a few hundred or few thousand dollars are nothing compared to his recent philanthropic efforts. When he's writing checks, it seems they are most often going toward job creation - and less often toward politics.
Why he could: Labeled by some as the "Steve Jobs of investing," Dalio would have a strong economic record to run on. In fact, he predicted the global economic crisis. One of America's richest men, Dalio certainly could afford the financial investment that would be required by an independent presidential run.
Why he probably won't: Dalio doesn't seek the limelight, even in financial circles, the way many of the other names on this list do. He's known as an outdoorsman who spends his free time big game hunting in Africa. Not exactly, the kind of vacation that the partisan environment would let a U.S. president get away with.
Why he could run: A well-regarded media executive, Diller helped spur the creation of the FOX Broadcasting Co. as well as USA Broadcasting and has been outspoken critic of media monopolies. A lifelong Democrat, he has been known to open up his checkbook for like-minded candidates in the past and has been described as a bit of a kingmaker in the television industry.
Why he probably won't: While he has been an active donor in Democratic circles, Diller has not spent nearly the same amount of time or money as many of the others on the list rubbing elbows in political circles. It's unclear if he'd have the political clout to make presidential waves, even if he wanted to.