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.

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.

Leadership is hard to train on.

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

Business ends up being very dynamic and situational.

Your employees know each other better than they know you.

Volatility and length, that's the value on an option. 10 years on a startup stock, that's a big valuable thing.