I just want to make two observations.
1. There is a massive social conditioning in America to get rich (in a number of places I've witnessed Americans justifying life choices by finances entirely, like you are doing here. this seems far less prevalent here (new zealand) or any other place I know)
2. The American education system is sub-par (especially further education for people with financial difficulties, maybe college degrees are also handed out to easily)
However, also, The antithesis:
1. There is massive social drive in America for great entrepreneurship (you seem to be an example of this), and to live life by your own rules
2. The American education system can cater to people who strive high and far (rather than an education which i find quite restrictive here. But this changes in further education (I've just started University)), but then a lot more is up to the individual, how they use it, and how they use everything else they've been given in life.
My major point is simply that while at first I disagree with you, i think i see why this situation is very different in the US.
However as a further note, i came across an article not so long ago which compared tertiary education (think it might've been an OECD report), which found that the US was doing far better than is commonly thought. With the average American having more funding for education, better teachers, and higher increases in salaries with a degree than most other countries.