“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.”

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

Planning is valuable, tho the plan is usually useless.

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

Your employees know each other better than they know you.

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.

Breakthrough ideas usually come from guys who look like they’re hallucinating

Wartime CEO is too busy fighting the enemy to read management books written by consultants who have never managed a fruit stand.

When you’re making a critical decision, you have to understand how it’s going to be interpreted from all points of view. Not just your point of view, not just the person you’re talking to, but the people that aren’t in the room. Everybody else.

These decisions intensify when you run a company, because the consequences get magnified 1,000 fold. As in life, the excuses for CEOs making the wrong choice are always plentiful.

Business ends up being very dynamic and situational.

I don’t believe in statistics. I believe in calculus.

Early in my career as an engineer, I’d learned that all decisions were objective until the first line of code was written. After that, all decisions were emotional.

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

Hire sales people who are really smart problem solvers, but lack courage, hunger and competitiveness, and your company will go out of business.

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

There are no silver bullets.

Making mistakes is a lot better than not doing anything.

We’re only human, we’re supposed to make mistakes.

Journalists who make mistakes get sued for libel; historians who make mistakes get to publish a revised edition.

You can walk away from your mistakes You can turn your back on what you do Just a little smile is all it takes And you can have your cake and eat it too.

Why is marijuana against the law? It grows naturally on our planet, serves a thousand different functions, all of them positive. To make marijuana against the law is like saying that God made a mistake.

I think it’s really important to be able to be honest with yourself and to know philosophically speaking what you’ve done wrong and when you’ve made a mistake, and acknowledge that, because you only learn from it.

The only time a mistake becomes a failure is when we look for someone to blame.

Impact lies in the vicinity of mistakes.