When raising money, you want to look through the lens of 'What happens when things go wrong?'

In all the difficult decisions that I made through the course of running Loudcloud and Opsware, I never once felt brave. In fact, I often felt scared to death. I never lost those feelings, but after much practice, I learned to ignore them. That learning process might also be called the courage development process.

I believe in strength over lack of weakness.

The person they're working with, is going to be the person they'll know more. So if that person leaves, they're going to go - well, should have I left too? What did they get and how does that compare to my deal.

The key to high-quality communication is trust, and its hard to trust somebody that you dont know.

Relationships built from a business do better than the reverse.

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