The weaknesses in the system are collectively what create the proverbial 1 and 99. Mitt Romney was in a privileged position to game them.
In reading Romney's biography on Wikipedia, I don't believe that is fair. His father was Governor of Michigan, but not particularly wealthy. According to Wikipedia, Mitt Romney had a steady set of chores and worked summer jobs, including being a security guard at a Chrysler plant. Mitt Romney started out after college as an entry level consultant in 1975 at the Boston Group and worked his way up.
"In 1977, he was hired away by Bain & Company, a management consulting firm in Boston that had been formed a few years earlier by Bill Bain and other former BCG employees. Bain would later say of the thirty-year-old Romney, "He had the appearance of confidence of a guy who was maybe ten years older." With Bain & Company, Romney learned the "Bain way", which consisted of immersing the firm in each client's business, and not simply to issue recommendations, but to stay with the company until they were changed for the better. With a record of helping clients such as the Monsanto Company, Outboard Marine Corporation, Burlington Industries, and Corning Incorporated, Romney became a vice president of the firm in 1978 and within a few years one of its best consultants and one sought after by clients over more senior partners. Romney became a believer in Bain's methods; he later said, "The idea that consultancies should not measure themselves by the thickness of their reports, or even the elegance of their writing, but rather by whether or not the report was effectively implemented was an inflection point in the history of consulting."
"Then in 1984, Romney left Bain & Company to co-found the spin-off private equity investment firm, Bain Capital. Since the inception of Bain Capital, it has invested in or acquired hundreds of companies including such notable companies as AMC Entertainment, Aspen Education Group, Brookstone, Burger King, Burlington Coat Factory, Clear Channel Communications, Domino's Pizza, DoubleClick, Dunkin' Donuts, D&M Holdings, Guitar Center, Hospital Corporation of America (HCA), Sealy, The Sports Authority, Staples, Toys "R" Us, Warner Music Group and The Weather Channel."http://en.wikipedia.org/wiki/Mitt_Romney
Bain Capital is where Romney made his money, and had nothing to do with what he was born into. Private Equity (Venture Capital) firms have been behind 99% of every start up company in the last 40 years including Microsoft, Intel, Apple, Google, Facebook, etc, etc. For every company that survives, 10 go under. Bain specifically focused on buying existing companies in trouble, turning them around (this is where his management consulting background came in handy) and then taking them public or selling them. That is what made Bain different from many Venture Capital firms, in that Bain bought troubled companies and took an active role in fixing them, rather than just making passive investments.
A lot of people complain that Romney has only paid 15% income taxes in recent years. All his investments are in a blind trust and probably all of his income is from dividends and long term capital gains which are both taxed at 15%. I have not heard any Democrats suggest that the tax rate for these be raised (most divends and captial gains are paid to pension funds and personal retirement accounts), but some people are put off by the fact that Romney's total wealth (not yearly income) is about $200 million dollars. He is no longer employed by Bain, and does not draw a salary from anywhere that I was able to discern, so that is why his only income is from investments.
Personally, I think Romney is one of the most competent persons on the planet, but I don't necessarily know if that will guarantee success as US president, since the problems of the US are mostly political. What I mean is that even if Romney knew what to do to fix the economy, the president does not have the power to make the changes necessary without the backing of the Congress and the American people. But I guess that at least knowing what should be done, is better than not even knowing, even if it would hard to get everyone to agree.