“As a company grows, communication becomes its biggest challenge.”

There is no silver bullet. There are always options and the options have consequences.

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.

The trouble with innovation is that truly innovative ideas often look like bad ideas at the time.

A lot of it is on the job training, combined with excellent mentorship.

Nothing motivates a great employee more than a mission that’s so important that it supersedes everyone’s personal ambition.

There are no shortcuts to knowledge, especially knowledge gained from personal experience. Following conventional wisdom and relying on shortcuts can be worse than knowing nothing at all.

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.

The important thing about mobile is, everybody has a computer in their pocket. The implications of so many people connected to the Internet all the time from the standpoint of education is incredible.

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

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.

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

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.

I certainly want campaign finance reform. I just wish this would do it in a way that would stand up to a constitutional challenge.

Presumption should never make us neglect that which appears easy to us, nor despair make us lose courage at the sight of difficulties.

One of the things that I learned is that you never truly know yourself until you challenge yourself.

In my career, there have been three things that were challenging: playing gay; playing a Jewish woman; and playing Anton Chekhov. The scariest part was playing Chekhov!

What is genius, anyway, if it isn’t the ability to give an adequate response to a great challenge?

It was a huge challenge to learn digital painting well enough so that computers don’t pop into mind when one sees one.

You have to meet all of the challenges, big and small. Because how you start is how you finish.

It takes no effort to be ordinary. Ordinary is not even a challenge. You can do nothing and be ordinary.