These identities that we build for ourselves, this armor, these images—they're our place of comfort and safety, and we latch onto them. They're everything to us ... We believe it so strongly that we will answer questions by saying things like 'Oh, I'm a founder. I'm a tech guy. I am a VC.' And you're not; you're so much more than that.

The way a company operates—its culture, its values, the way it makes decisions—it's really a manifestation of the founders and their values.

The customer is not meant to be the one coming up with a vision for your product. They're there to share their feelings, concerns, and frustrations. It's the responsibility of the product builder to synthesize what they've heard and envision the future.

The difference between an organization of 5 people and an organization of 10 people—or one between 10 and 20—it's not twice as hard; it's far more than twice as hard. And the amount of coordination overhead that it requires when you double your head count is, again, not double; it is far more than that.

Every single human being on the planet is flawed. We're all flawed in different ways. We're all imperfect. This idealized state that our culture has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful.

Everyone goes through imposter syndrome ... When you're doing stuff you've never done before and you're changing the world, no one else has done it either ... If you don't have butterflies in your stomach each day, you're either not paying attention or you're not pushing hard enough and taking enough risk.

When I started making money, I went out and I bought a fancy car, and I bought nice clothes, and fancy stereos, and all these things, and I didn't find that it had any impact on my happiness. The only thing that had an impact on my happiness was not stressing out about rent, knowing I had enough money in the bank that I was comfortable for two or three months, I could go out and eat when I wanted and drink what I wanted.

For me, I look at money, first and foremost, as a way to protect my personal freedom, and what I mean by that is building a wall between me and things I don't want to do, people I don't want to see, [and] ways I don't want to spend my time.

I think school is often a waste of time, especially if you're in tech. My number one piece of feedback to people is get experience. If you want to be in business, start a business; don't do an MBA.

Real leadership equates to a deep connection with your purpose and your values, and any deviation from that makes for a bad leader and poor leadership.

We're never going to see hundreds of billions of dollars in rolling funds in my opinion, but what you're going to see is all of these companies that might have failed that were able to raise a $100k here or $250k there from these new emerging fund managers that have these different networks, that have these different LP bases, that are going to lead to much more interesting, different, diverse companies getting started and continuing to get to that next stage.

Drew and I, we always know [that] we're not the smartest guys in the room, but we know the work that it takes to accomplish things, and even if you're really smart, there's no shortcut through the work ... Can we make a bigger hit? Can we reach more fans? Can our show become the best show on the planet?

You could send money to this smart contract. You can send money to that wallet. And you don't own the money anymore. Now, a piece of code owns the money. And that, I think, is a very underappreciated breakthrough, because that piece of code is an entirely new entity; it's not a person; it's not a Delaware C corporation; it does not exist inside a jurisdiction; it's not in Delaware; it's not in India; it's not in China; it's not in Europe and the EU; it just lives in the cloud.

It's do, fail, learn. Do, fail, learn. There's no such thing as learn and then you're going to do. No, no, no, no, no. When you really learn in life is after you've tried to do it.

One of the sad things about our country right now, I think free speech has been crushed to a great extent. If you can say something, if you could express a political view and get fired today, which is definitely a very real possibility, only if you are financially independent... can you take the risk of speaking freely.

When I hear people say, 'Ideas don't matter,' it just drives me crazy. The idea is the most valuable thing you have when you start, and the best ones are the result of a tremendous amount of work, effort, experience, and insight. They're unique and almost magical by nature. Great ideas hold the energy that can propel a team forward through the tremendous uncertainty you face when you first get going. Often times, the idea defines the mission of some of the most important companies in the world.

I think anybody who's trying to do something that the world has never seen before... better be coachable. Because you're going to be so narrowly focused, you're going to be so heads-down, you're going to be on a mission that sometimes you're blinded, and you need somebody to come from left field to go 'Wait a second. Dude, you're not thinking about this right. You're so in the weeds. We got to pull you out. Let me give you some perspective.'

I tell myself to make progress every day. The advice I give to go those who go through similarly challenging moments... Number one, adequate sleep; proper nutrition; exercise is a huge help... Surround yourself with people who love you, and then make sure, each day, you make progress toward digging yourself out of the mess.

What's happening with crypto is that, at a 100,000-foot view, it's software eating money ... And if you believe that crypto is software eating money, then crypto is also going to eat capital markets, which is the deployment of money, or the deployment of capital. And if crypto is going to eat capital markets, it's going to eat venture capital.

That same myopia that we, at times, celebrate in entrepreneurs—they're laser-focused... You know what? A lot of times, you don't need a fucking laser focus; you need a broad perspective. And if you can't change and switch between those two at regular intervals, it's really a weakness.