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.

Leadership is hard to train on.

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.

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

The primary thing that any technology startup must do is build a product that's at least 10 times better at doing something than the current prevailing way of doing that thing. Two or three times better will not be good enough to get people to switch to the new thing fast enough or in large enough volume to matter.

What do you get when you cross a herd of sheep with a herd of lemmings? A herd of venture capitalists.

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.