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

To succeed at selling a losing product, you must develop seriously superior sales techniques. In addition, you have to be massively competitive and incredibly hungry to survive in that environment.

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.

Every time you make the hard, correct decision you become a bit more courageous, and every time you make the easy, wrong decision you become a bit more cowardly. If you are CEO, these choices will lead to a courageous or cowardly company.

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

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

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