Sarcasm aside, you present an entirely simplistic view of history perfectly tailored to the point you're trying to make. The only people who are going to believe anything you're saying are the people who already agree with you, because people tend to be less than critical when it comes to their pet theories.
As a counter-point, here are some of those grey-suited company-men from the post-Teddy Roosevelt era:
There are more. So what exactly is your point? There were clearly self-made men after Roosevelt. Are you arguing that there were more self-made men before Roosevelt? I'd like to see some evidence to that. Or maybe you're arguing that the general "sentiment" was against self-made men. Again, I'd like to see evidence of that, and good luck finding it. First you'll have to define just what the national "sentiment" is, then find scientific studies of people both before and after Roosevelt that tried to discern it.
He's talking about fashion and sentiment, not the actual number of entrepreneurs.
Without answering those questions we can't rightly draw any conclusions about people's attitude towards the self-made man.
Bit of a fail here. The word meritocracy comes from a book of the same title written in 1958 by Michael Young (interesting fella, wrote the UK Labour Party's manifesto in 1945, founded the Open University).
The point about meritocracy is that it is a satirical term. (The beauty of it being that in any society the wealthy and powerful can claim they rose on merit. In the time of the Divine Right Of Kings, merit was being chosen by God.)
But don't take my word for it, read Michael Young on the subject in 2001.
Ye, this isn't really true. Lets take, for example, 18th century Naval officers from the UK:
* Captain Cook - discovered Australia, mapped the Pacific etc. Father was a farmer
* Horatio Nelson - Defeated the French, considered greatest Naval commander of all time. Father was a minister
* Arthur Philip - Commander during American Revolution, lead colonization of Australia. Father was a teacher.
It is a very common misconception that in old society it was impossible to move from the lower classes into the upper classes. The British Empire, the prototypical aristocracy, was largely shaped and developed by people who were raised in the lower classes. This is because the military, navy, their universities (eg. Isaac Newton), and many other parts of government and private societies were strict meritocracies.
The upper classes actually produced a very small number of notable people, outside of royalty (Charles Darwin, Churchill, Brunel (although his grandfather was a French farmer)
(Edit: "America became the first large-scale experiment of a society that could be called a meritocracy." - Citation needed. See above.)
Please excuse my quoting from Wikipedia: http://en.wikipedia.org/wiki/Industrial_Revolution
So using 18th century people to illustrate that hereditary factors were not dominant pre-IR is a bit strange.
The Wikipedia summary isn't wrong, it is just misleading. The inventions and innovations that lead to the industrial revolution were founded in the late 18C, but the real transformation was much later (although it did happen, comparatively, quickly)
It is a bit like saying that the 'Internet era' is from the 1950's, because that is when the integrated circuit was created
Steam engines were invented many times during and before the IR. What allowed the IR to happen was more likely coal, I think.
The fact that your criticism can be levied against any result in the world should give you a hint as to just how vapid of an idea it is.
But it is fair to say that progress and achievement depend on a certain level of social support, right? How many tech entrepeneurs come from abusive homes with no food?
You could say that, based on your logic, Hitler was not a self-made man but was the result of his social context - his rise to power was truly phenomenal and would you therefore say he had no "self-made" qualities? I tend to believe that any figure head is the apotheosis of the ebb and flow of the pool they swim in - but it does take volition and self-made qualities to become the instance for a given class of thinking.
I know Hitler and Germany as premises for an argument are far removed in many specific aspects from the discussion of self-made business men and entrepreneurs - but, one must concede, there is a curious link that runs through all men of power, wisdom, or accomplish. It is that link I'm speaking to.
I think the point here is that he's optimistic for his future because he sees a lot of opportunity opening up. I would also go so far as to say that he feels fortunate for having been born when he was.
That's hardly narcissism.
Since he's mentioned specifically, and idolized a bit, in the article, consider Andrew Carnegie. Where would he have ended up without the charitable library established by Colonel Anderson (consult any decent biography of Carnegie for the details)? Also, note that when Anderson's library encountered financial difficulties and instituted a two-dollar-a-year fee, Carnegie wrote a scathing letter of protest, demanding that the library remain free. If you must, to paraphrase a bit, demand the fruit of others' labor free of charge, than just how "self-made" are you?
(Carnegie did, at least, remain morally consistent and recognize the impact the library had on him, since he used his later wealth to establish free libraries)
And this isn't an unusual example, nor is it just a cherry-picked scene from one famous businessman's life. If you look at any highly-successful person's background, you'll find episodes like that one; success does not and cannot happen in a vacuum, and the idea that it does (and is correlated with certain qualities, such as rebellious anti-authoritarianism, which many HN readers would like to perceive in themselves) is a self-deluding myth.
But the question that's rarely asked is, who are those people that helped them create the wealth? is it random strangers? is it welfare bums? no, of course not. They were able to create great wealth by working and benefiting from other successful people, by voluntary mutual cooperation.
So you're right, people don't create wealth in a vacuum, they create it by working with other similarly ambitious like-minded people. They had the same chance to try, and fail, like everyone else has in a free country.
Which, when you think about it, isn't too far off from the old notion of the "nobleman" -- all we've done is shift nobility from something granted by God to something granted by monetary wealth.
(also, since the article contrasts the modern era with the old hereditary aristocracies, take a look sometime at how many prominent Europeans today are descended from or associated with descendants of the Habsburgs and the Bourbons, or just how incestuous US government has been over the past fifty years)
On the one hand, you are right, no success happens in a vacuum, and a lot of wealth is acquired directly through a good ol' boys network.
On the other hand, most successful entrepreneurs probably deserve credit for building a company no matter how many people help them. Aside from being well-compensated in many cases, it's a tenuous argument that the employees of a successful startup would be creating the same amount of value without the inspired leadership and focus created by the entrepreneur.
I don't think the statement: "all we've done is shift nobility from something granted by God to something granted by monetary wealth," is fair. Clearly society distinguishes between inherited and self-made wealth. The question of who deserves what is subtle, and I'm hard pressed to come down on one side or the other.
You're right everyone has the same chance to try and fail, but not everyone has the same chance to try and succeed.
Some people get the deluxe starter kit, and some people get a blank sheet of paper. You can turn both into a billion dollar business, but one's a lot easier than the other.
I don't think it has to go there. I think there can be a responsibility to give credit that is distinct from the responsibility to share the spoils.
The question here is not whether Andrew Carnegie had a right to keep his wealth, but whether we as a society have a responsibility to give some of the credit for "his" achievements to the other people who made them possible.
Everyone of us has recourse to the contextual/environmental support that you (correctly) point out. But only a few manage to use it effectively. In that context, the skillful individual has accomplished something that most other individuals apparently can not (or do not wish to do).
Carnegie stepped on a lot of heads on his way up. 
1: There was so much soot in the air, your shirt would be dirty by midday, so blue-collar workers brought spares and changed.
Also, as is widely acknowledged, union bosses were in no way responsible for any violence or wrongdoing. It's all so obvious and one-sided in retrospect, you know.
Look, on the way from a nepotist aristocracy to creating a prosperous middle class you don't get it right the first time. Shit gets fucked up, and yes lots of people do bad things along the way. It's trivially easy to look back and point out how they only got it 30% right and ignore the fact that everyone before them got it 10% right.
The truth is, both are possible. I am baffled as to how either of you thinks the question can be answered without looking at the specific history and the specific choices Carnegie made and deciding whether he was willfully destroying lives.
I think Carnegie was kind of a jerk, but if he hadn't done it, some other jerk probably would have. I try not to spend too much of my life casting moral judgements on others, so I'm still not quite how sure that shakes out.
Anyway, he loved to write about America and particularly Carnegie. So through formatting his book I learned a lot about Carnegie -- the guy came from nothing, and he was truly active. Check this out: http://bit.ly/fDMBd9
Status has always been based on power. Plenty of poor men grew up to be powerful men in the pre-industrial world. In this corner of the world (West) the routes open to the "self-made" man were the military and the clerical orders.
(It is of course true that the nobility had de facto access to the same spheres.)
It would have been nice if he at least paid homage to Ayn Rand, who he has clearly read and was influenced by (along with millions of other people.) I know it's fashionable these days to read Ayn Rand, and then discard her by the time you're 18, but she was a pretty important figure in helping turn the tide he's talking about.