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.

Here's Kanye, the great musical genius of his generation in hip hop, but, like, society really can't even deal with him because he's always saying something that people go, 'Oh, I can't believe Kanye said that. I can't believe he did that.'

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.

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

Most large mistakes in organizational design come from putting the individual ambitions of the people at the top of the organization ahead of the communication paths for the people at the bottom of the organization.

I think theres a lot to be said about just enjoying your work. It can be very contrived when people say their work is for the good of mankind.

When I was CEO, and I'd listen to music, a lot of people listen to music and you get inspiration from it. And a lot of things in hip hop are very instructive for being in business. Particularly, hip hop is a lot about business, and so it was very useful for me in any job.