This needs a citation.
The writer is probably leaning on his own extended circle of acquaintances which is likely to be, like him, young and male. This group is fairly cocky and entrepreneurs from this group could be expected, at a minimum, to be as cocky. Secondly, cocky jerks stick out more in our minds, we are less likely to remember entrepreneurs who were pleasant people.
While this doesn't run counter the title, the implication is that cocked jerkiness is a virtue for entrepreneurship. I somewhat doubt this and suspect that your average entrepreneur is less a cocky jerk than their reference group. (Unless, I guess, the RG's unusually deferent.)