If you have never done the job, how do you know what to want?

Groupon looked like a very high valuation, but any investment in a great company at any stage is almost always a good investment.

There are no shortcuts to knowledge, especially knowledge gained from personal experience. Following conventional wisdom and relying on shortcuts can be worse than knowing nothing at all.

You know what the difference between a vision and a hallucination is? They call it a vision when other people can see it.

In life, you don't have a level of confrontation and the nonsense you run into when you're a CEO. CEOs aren't born.

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.