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.

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.'

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.

Relationships built from a business do better than the reverse.

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

When you're making a critical decision, you have to understand how it's going to be interpreted from all points of view. Not just your point of view, not just the person you're talking to, but the people that aren't in the room. Everybody else.

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