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

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: Here's where we are and here's what I didn't recognize about us and about you when I made the decision, and now it is what it is.

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

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.

Business ends up being very dynamic and situational.

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.

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