Ezra considers it:
In college, he sold stock his father had given him to support himself. At Bain and Co., he refused to move to Bain Capital until the company agreed to bear the risk incurred by his new venture. When he went to run the Salt Lake City Olympics, he kept his name atop Bain Capital to ensure he could come back if he couldn’t find something better.
There’s little in Romney’s finances to back up the contention that the rich are insufficiently rewarded for the risks they take, and there is much in his history to support the idea and that safety nets have a role to play in empowering people — even wealthy people who don’t run the risk of economic ruin — to take on risk. But Romney’s policies seems to reflect the inverse of these lessons: They increase the rewards for taking risks that pay off handsomely while reducing the baseline level of security people need to take those risks.
Very nicely put. I'd add that conservatism as a temperament tends to be risk-averse. It worries about the unintended consequences of drastic action in public and private affairs. It's thrifty. It saves for a rainy day. That's why it's so odd to me that American conservatives have defended and want to reinstate the lack of regulation that led us to our current financial crisis. Or that they merrily load on debt in good times, only to try to slash it at the very moment it might actually help things – during a deep recession. Or that they launch wars they haven't prepared for on the basis of evidence that is subsequently revealed to be wafer-thin.
Supply side economics is a crazy abstract theory; it should have been the target of conservatives, not a darling. A strong and vigilant regulatory state is essential to capitalism's success – so why did conservatives want to dismantle it? I suspect that Romney is temperamentally conservative; but he has to adopt a radical and reckless disposition to defend the party that the GOP has become.