Relationships built from a business do better than the reverse.

The only thing that prepares you to run a company is running a company.

Breakthrough ideas usually come from guys who look like they're hallucinating

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.

The key to high-quality communication is trust, and its hard to trust somebody that you dont know.

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.

Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.