“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.’”

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.

In a company, hundreds of decisions get made, but objectives and goals are thin.

A manager can’t act like a role model. They need to BE a role model.

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.

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

It’s hard in daily life. It’s even harder in management because it’s the stress of the moment.

In Silicon Valley, when you’re a private company, the entrepreneur can do no wrong.

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

One of the great things about building a tech company is the amazing people that you can hire.

Mark [Andressen] was more popular than me at the time … He was like Beyoncé, I was Kelly Rowlings

As a company grows, communication becomes its biggest challenge.

In my experience as CEO, I found that the most important decisions tested my courage far more than my intelligence.

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.

You don’t need every investor to believe that you can succeed. You only need one.

A CEO needs great intelligence and great courage. And I always found my courage was tested more.