For a black kid, seeing black people in leadership roles does matter. It's a reality that for many poor black kids in America, the only obvious path out of poverty is sports or drugs, neither of which are very good options...especially for nerdy black kids living in poverty. That's not to say entrepreneurship is an obvious path out of poverty for anyone (white or black), but being technically savvy is extremely good for your value in the employment market, no matter what you choose to do.
Anyway, I believe you are underestimating the amount of self-imposed race-based limiting factors. I think we're all probably also underestimating the external society-imposed limiting factors on people of color in America, as well (because most of the people on HN are white, grew up in a middle class household, and male).
In addition, it's not at all unreasonable to think that way. Why waste your time on something that you will ultimately likely not be allowed to do? That's good decisionmaking, not "self-imposed race-based limiting factors."
Having a clear line of progression into a career, validated by people you feel connected to, is important. I would say that having a familial connection is strongest, followed by a social connection, and lastly followed by cultural/ethnic connection.
For many of these kids, the first two types of connection are already very weak for high paying careers. Well, at least for those careers that have reasonable prospects of success (ruling out music performance and sports). It can be transformative to these kids to have some example to follow. Believe it or not, not everyone in America is born believing in the reality of the American Dream. It just seems that way to many, because they have been surrounded by people for whom the American system is working from their earliest memories. Many others grow up awash in evidence the game is strongly rigged against them. If that's what the preponderance of evidence tells you, then why try?
I would go further and say that not all the limits black people face in this country are self-imposed. Even if you're doing all the right things, there is a burden to constantly prove you're not one of those black people on the evening news. Not to mention, black people disproportionately lack the privileges of wealth and social connections compared to other ethnicities. This leads to a vicious cycle of self-fulfilling prophecy on the perceived capabilities of black people, as perceived from both within and outside of many black communities. I would argue that institutions should feel some responsibility to recognize these inequalities and even act against them in ways that align with their philosophies.
I have no idea about yc; but you might find this answer on quora useful: http://www.quora.com/Who-are-some-notable-African-American-f...