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

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.

The right answer on raises is you have to be formal. You have to be formal to save your own culture.

How do you make your company a good place to work in general? That’s a really really really large and complex set of skills.

In life, you don’t have a level of confrontation and the nonsense you run into when you’re a CEO. CEOs aren’t born.

Volatility and length, that’s the value on an option. 10 years on a startup stock, that’s a big valuable thing.

It’s pretty clear that [customers] know what their budgets are now, and what they want to spend it on.

As companies move to web-based computing they get a lot more servers, which are difficult to manage and control. All kinds of problems can arise – security, quality and worms.

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.

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

Venture capitalists are like lemmings jumping on the software bandwagon.