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

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.'

Startup CEOs should not play the odds. When you are building a company, you must believe there is an answer and you cannot pay attention to your odds of finding it. You just have to find it. It matters not whether your chances are nine in ten or one in a thousand; your task is the same.

You know what the difference between a vision and a hallucination is? They call it a vision when other people can see it.

Yeah, I became a successful entrepreneur... Eventually

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

Over the last ten years, technological advances have dramatically lowered the financial bar for starting a new company, but the courage bar for building a great company remains as high as it has ever been.