<<We do know, for a certainty, that the company was just diluted 10% or so. That's a fact, and not a positive one. Therefore, the "unknowns" that led to this dilution could not have been positive ones either; in other words, management failed at some point.>>
This illustrates the fallacy that all bad that happens is due to management incompetence and conversely, all good that happens is due to management skill. In fact, there is a large element of randomness -- deals that were close to happening can die, markets can enter turmoil, reasonable projections are not met, etc. And while many of these risks can be mitigated, insurance (like raising capital way earlier than it is needed) is expensive. This is like blaming or crediting parents for how their children turn out -- no doubt parents play a large role, but the rest of the world, and randomness, play a role as well.