In all the difficult decisions that I made through the course of running Loudcloud and Opsware, I never once felt brave. In fact, I often felt scared to death. I never lost those feelings, but after much practice, I learned to ignore them. That learning process might also be called the courage development process.

When raising money, you want to look through the lens of 'What happens when things go wrong?'

Nothing motivates a great employee more than a mission that's so important that it supersedes everyone's personal ambition.

Note to self: It’s a good idea to ask, “What am I not doing?

As a startup CEO, I slept like a baby. I woke up every 2 hours and cried.

The person they're working with, is going to be the person they'll know more. So if that person leaves, they're going to go - well, should have I left too? What did they get and how does that compare to my deal.

If you manage a team of 10 people, its quite possible to do so with very few mistakes or bad behaviors. If you manage an organization of 1,000 people it is quite impossible. At a certain size, your company will do things that are so bad that you never imagined that youd be associated with that kind of incompetence.