I agree that it's a bold title, and agree that the the collected essays probably aren't going to measure up to the historical standard. But I think this is central to Yang's thesis that the standards of behavior are different for Asians in America than they are for others.
For me, I think the title choice works because it calls attention to the fact that Asian American culture is not particularly open to the strategy of aiming really high and being likely to fail, and instead favors targeting a more modest level of success that can be attained with greater likelihood. Braggadocio and overconfidence are not considered typical traits.
Yang's title is high-risk high-reward high-likelihood-of-failure, and I do find my self surprised (in what is likely a racially biased manner) that an Asian American male would choose such a brazen title. That I have this thought (as a non-Asian Amerian) makes me suspect that Yang is on to something.