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.

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.

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

Sometimes an organization doesn’t need a solution; it just needs clarity.

The bigger you get, the harder this gets because the more aggressive the people working for you are.

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.

In life, everybody faces choices between doing what's popular, easy, and wrong vs. doing what's lonely, difficult, and right. These decisions intensify when you run a company, because the consequences get magnified 1,000 fold. As in life, the excuses for CEOs making the wrong choice are always plentiful.