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.

Note to self: It’s a good idea to ask, “What am I not doing?

As a startup CEO, I slept like a baby. I woke up every 2 hours and cried.

Most large mistakes in organizational design come from putting the individual ambitions of the people at the top of the organization ahead of the communication paths for the people at the bottom of the organization.

Leadership is hard to train on.

How do you make your company a good place to work in general? That's a really really really large and complex set of skills. A lot of it is on the job training, combined with excellent mentorship.

One of the great things about building a tech company is the amazing people that you can hire.