Luck and Timing. There is much to be said for luck and good timing - neither of which we seemed to have. We had bad timing in bringing the best upper management in too late and lost huge contracts because of events that were outside of our control - such as new CTOs at client sites favoring other products. For a startup that had no clear definition of itself during most of its existence, good luck would have been essential to succeed but a good business with growth potential can never rely on luck as its strongest operating plan. Timing is another issue.
Good leadership is capable of bringing foresight and knowledge through experience to the table.
Failure to critically assess internal operations clearly and honestly along with undermining your own place in the market through underselling are not only key steps toward ensuring poor timing, but indicate inexperience and misunderstanding of current trends. Looking at all of this in retrospect, it's easy to realize that uncovering problem areas as they were occurring is not as simplistic as the historical review would indicate. Addressing them quickly and positively may have even been almost impossible at times. There is something adventurous in bringing new technologies and offerings to a fairly unknown market and to be a part of the growing pains of a Dot-Com just finding itself. Now, of course, though, I am in a better position to see the signs that indicate trouble ahead and when to part company.