When you're making a critical decision, you have to understand how it's going to be interpreted from all points of view. Not just your point of view, not just the person you're talking to, but the people that aren't in the room. Everybody else.

As a company grows, communication becomes its biggest challenge.

Planning is valuable, tho the plan is usually useless.

Generally the reason they fail in the job is, you made some mistake in the hiring process in that you didn't match... them to the needs of your company accurately enough. That's the #1 reason this fails. And that's generally a good place to start: Here's where we are and here's what I didn't recognize about us and about you when I made the decision, and now it is what it is.

Mark [Andressen] was more popular than me at the time ... He was like Beyoncé, I was Kelly Rowlings

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.

You're better off being The Beatles than The Monkees, as a startup.