Fear Is A No-No
At the VCs Who Code panel at Google I/O yesterday, Dick Costolo asked the assembled VCs the biggest no-nos in a startup. Everyone gave excellent answers but my personal favorite came from Brad Feld who said "fear is the biggest no-no."
If I look back over 20+ years of entrepreneurs I've backed, the ones who were anxious and afraid of failure most certainly had worse outcomes than the ones who were agressive and confident. You simply can't be tentative in a startup. You have to go for it at every chance you get.
And if the leader of the organization is anxious, his or her fear pervades the organization. Everything comes from the top in a company. So it is best to have to have a leader who exudes confidence.
You can certainly have too much confidence. Arrogance and cockiness can be as harmful to a startup as anxiety and fear. A person who is quietly confident makes the best leader.
So if you are starting a company or building one, face your fears and move past them. It's critically important to your company.