When you're creating something, on the one hand, you have to be very optimistic because if you weren’t optimistic, you wouldn’t bother doing it, especially in the face of such hardship and uncertainty; but you also have to be very pessimistic because there are tons of problems, and you have to be tuned to spotting them so you can go fix them.

When you see a smart person holding a point of view—and especially strongly holding a point of view that's kind of different from your own—rather than try to figure out how they're wrong... try to figure out how they're right ... If they're not stupid, why would they believe this?

Outrage and offense and anger—they're sometimes useful, of course, but I think.... they're over-utilized. They're not useful as often as they are invoked.

People can improve their own decision-making by simply choosing other people... and imagining what they would say... and then averaging over the responses.

If people around you don’t think what you’re doing is a bit strange, then maybe it’s not strange enough.

If you think about what a really good website or iOS application or whatever kind of is and feels like, it's really strange. I mean, it's not easy to build a really good website or iOS app or whatever, but it's not rocket science. And given that it's not rocket science, why are there so few of them? Just think of any big major company and think of their website or app—it's probably pretty bad.

Small companies don’t realize how much of an upper hand they have ... If they can create a product that is so much better than the status quo that they start to get organic traction, once you attach a real sales and marketing engine to that, it’s going to be really freakin’ hard for a big company to effectively compete.

The question I would sort of encourage people to think more about is 'How do I get to make better decisions? ... How do I make sure the decisions I'm confronted with end up being better?' It's not 'How should I choose between option A and B?' but 'How do I make sure that both options A and B are as good as possible?'

You don’t necessarily need to be that good at decision-making if you get really good at remaking the decisions when and as necessary.

Arguably the single most important thing about our lives compared to other lives that have been lived in human history is that we have the immense good fortune to have been born in wealthy societies, and that has had so many consequences on our lives.

It’s less [about] how you make a decision and more about how you jolt yourself out of the particular furrows that you're in and realize the possibility space and the world is just so much bigger than perhaps people are thinking about.

I think you should mostly ignore the books that are published every year ... I really think people should be much more biased towards older books than they are.

If I look back at the 70+ startups in my own investment experience, the vast majority of over-performers focused almost to the exclusion of PR and marketing on product in the early days.

If your customer acquisition is predicated on paid acquisition, that makes you a sitting duck for incumbents who have larger budgets.

...the existential importance in the case of a lot of startups of being able to remain consistently optimistic enough that you can summon the energy and doggedness to continue while also being very good at envisioning problems, worst-case scenarios, and bad outcomes so you can avert them.

I find, personally, actually, that it really matters a lot when I read a book instead of the frame of mind that I'm in at the time when I stumble across it. Often, I'll start a book at some point and maybe revisit it months or, in some cases, even years later and find that it has kind of a completely renewed resonance or significance.

It’s far better to have an approximate answer to the right question, which is often vague, than an exact answer to the wrong question, which can always be made precise.

I actually find it useful to buy a lot of books that sort of seem interesting and high-quality before I'm necessarily ready to read them at that moment.

The best way to predict the future is to invent it.

More broadly, nobody is going to teach you to think for yourself. A large fraction of what people around you believe is mistaken. Internalize this and practice coming up with your own worldview. The correlation between it and those around you shouldn’t be too strong unless you think you were especially lucky in your initial conditions.