I found this post by Guy Kawasaki about serial entrepeneurs (spurred by the thoughts of Glenn Kelman) surprisingly 'emperor has no clothes' for a VC.
It's also a fascinating topic when viewed through the lens of "Attribution Theory". A lot of Guy's & Glenn's comments seem to have unknowingly stumbled into Psychology's well-studied world of "Attribution Theory." In a nutshell, people attribute success or failure to luck or ability depending on their expectations for success or failure. For example, I know that passing the Bar Exam (for lawyers) is hard, so if I fail it that was expected and hence bad luck, not a measure of my innate ability. On the other hand, if I fail an exam for a driver's license (that is simple and hence expected to be easily passed)... well then i might have to attribute my failure to lack of ability.
For a dry, scholarly look at the topic you can read this.
This topic gets very interesting when you start to bring in gender differences. Most studies find that gender differences in expectations and attributions arise primarily from stereotypes about the task itself. Given that women generally have low expectations for success when completing "male" tasks (like business & entrepreneurship), they tend to attribute their success to luck and to attribute their failure to lack of ability. However, men, who generally expect success, often attribute their failure to luck and their success to ability. [paraphrased from above source]
As a woman, I have to say I have fallen into this trap myself and looked enviably at my male counterparts who, after failing right along side me, could chalk it up to just 'bad luck.' And speaking of failing - we always hear how you learn more from failure than from success... where are the VCs looking to find the 'smartest' entrepreneurs based on this metric?