I really want to break away from this idea of forty hour weeks, or 9 to 5s, or roles, or jobs, or identities. It just all feels like a straight jacket.

I've always had this view that success is not a straight line up. If you read the stories of successful people, almost every successful person has had to deal with some degree of hardship, whether that hardship is personal hardship, health-related hardship, or a business issue. And I've always had the view that how successful you are is really a function of how you deal with failure. If you deal with failure well and you persist, you have a high probability of being successful.

A really good book costs $10 or $20 and can change your life in a meaningful way

A startup isn't really a company at all; a startup is a set of founders with, hopefully, a set of proprietary insights that are a result of them living in the future.

We’re playing little movies in our heads. We’re just walking down the street, but no one’s actually there. If you started voicing the thoughts you have in your head, you’d be thought of as a madman and they’d lock you up.

Saying, 'I don't have time,' is just another way of saying it's not a priority

I think startups are so impossible that if you're not 100% committed, you just almost have no chance.

Every positive thought has a seed of a negative thought within it

Do I really care if I embarrass myself? I'm going to die anyway, this is all going to go to 0, and I won't remember anything. This is pointless.

Anger is a hot coal that you hold in your hand while waiting to throw it at somebody else

Everything that I was doing, I should have still done, but with less emotion, and especially less anger

Do what you're going to do, just with less emotion and angst

Life is a single player game. You’re born alone. You’ll die alone.

There's a line in 'Billions' where Bobby Axelrod is making a speech to all of Axe Capital, and he says 'In the great expanse of time, we're already dead' — and that's something that I believe. If you look at the great expanse of time, we're not even a dot.

You can’t just pick and choose what aspects of another’s life you want

I think education should be about learning the basics in all the fields, and learning them really well over and over, because life is mostly just about applying the basics and only doing the advanced stuff in the things you truly love, where you know the basics inside and out

Insights are usually connected from random dots getting connected. But the process of collecting dots has to be efficient for the process of connecting dots to be more efficient. And collecting dots is easier if your friends are also collecting dots to connect dots.

You don’t need to do anything. All you should do is what you want to do....No one in the world is going to beat you at being you.

Each person is uniquely qualified at something – they have some specific knowledge, capability, and desire, that no one else in the world has

It’s the mark of a charlatan to try and explain simple things in complicated ways, and the mark of a genius to explain complicated things in simple ways