The two traits we really try to hire for are curiosity—people who are just relentlessly curious, want to learn new things, and put themselves in new challenges—and empathy—the ability to actually listen, change your mind, and see the world from other people's perspectives.

When I talk about moguls, I'm talking about how today's creators are going to be tomorrow's Fortune 500 founders. That's my take. In the next 5-10 years, we're going to see these creators building billion-dollar media companies and billion-dollar e-commerce & direct-to-consumer brands. They already have the distribution; they already have the community; they just need to build.

One of the things I've been thinking a lot about with the recent COVID-19 stuff is that our dashboards for society are wrong. Rather than the stock market being the expression of our country's economic health, it should be something like a histogram showing the net worth of all Americans.

It's okay to just be fucked up and miserable right now [amid COVID-19]—that's the natural human reaction. It's like that for smart people, entrepreneurs, hustlers, and all these people who'll go on to eventually do great things. It's perfectly reasonable to be self-destructively unhealthy and fucking panicked right now.

There has to be, though, some kind of national database so that if I go to a restaurant, they know that I got the vaccine. I don't want some idiot who's like an anti-vaxxer coming in the door with me.

As a creator, you don't even need that many followers. I tell creators that they need to care more about how many super fans they have versus how many followers they have. You could have 50 million followers and not be able to sell out 5,000 sweaters.

If you can make people laugh, if you can get people invested into you as a personality [and] you as a person, you will be able to build a community and sell them whatever you want to sell. There's not really a trick to it; it's just you have to actually care about people who follow you [and] people who reply to you. You need to engage with your fans.

I think that's one of the most damaging things that any of us can do, whether it's in trading, business, etc.—assume that all the upside is causal, and we created it, and all the downside is outside of our control.

Don't think too much about monetizing your audience if you're still an early creator ... You want to make sure that you're just always providing value to your audience. That's what you need to think about. Every piece of content you put out there—is it providing value to my audience?

From sundown Friday night till Sunday morning, I'm offline. So, no email, no meetings, no anything. I call it digital Sabbath ... I find that [to be] the most important reset each week for me. If I don't do that each week, I get worn out pretty quickly.

I see creators, once they hit a million followers or even 500k, they just stop replying to their fans. They stop liking their fans' comments. That is probably the dumbest mistake one can do, because if you're not replying to them, they're gonna go find other creators who will reply to them, and they're going to become super fans of those creators. They don't owe you anything.

When we're most successful at developing products, the very first & best customer for those products is 'Cloudflare' itself.

If you can find people who are curious and empathetic, you can teach them anything, and they'll learn anything. They're also more fun to hang out with.

In the US, ~90-92% of [COVID-19] deaths and 70-75% of hospitalizations are for people over age 50. In both the US and UK, ~20-25% of hospitalizations occur in people under age 50.

For the last four years, I've been quietly—and only in the last couple of months taking the covers off it—investing aggressively in both for- and nonprofit climate solutions. This just gets me excited. The ability to dramatically impact the planet and get rich again has been pretty fascinating.

You don't make money putting money in on something that the first valuation is $12 or 15 million ... Even if you look at the best venture capitalists in the business, if they let you in the back door, they made money when they put in money, real money, at $3-5 million.

Spotify has 280 million users, each of whom spend an average of ~1-1.5 hours per day on the platform.

When you come into New York and you see Hudson yards—what is completely detached from the city ... My biggest joy would be to see that entire thing become middle-income housing. What is the point of building a 1980s glittering mall in 2020?

Bottoms-up investing... isn't about not having a perspective on the future; but it is about making sure that the work that you're doing is sort of first-party, on the ground, you're not removed from what's happening, and not letting narrative drive you too much. You're staying as close as you can to the actual entrepreneurs that are building this stuff—the actual consumer behavior that's driving new adoption and the actual technologies that are coming to market.

I don't think, as humans, we have any idea what things will look like in 2040.