You gotta do it wrong before you do it right. If you know you directionally want to go into NFTs and crypto, you just kind of have to throw a bunch of spaghetti at the wall. And you gotta lose a lot of money. This might make money; it might lose money. But just starting, I think, is way more important.

Podcasting, there's 62% penetration in the United States—so, like, 62% of people are aware. But there's only $2 billion in the market—all podcasting advertising dollars and stuff. And you think about FM radio and how big that market is ... If every podcast was monetized like FM radio, it's probably that big. So, it can probably, like, 20x, 50x, 100x, I don't know.

I think, for podcasts, you don't really want to build a community as such; you want to build a cult.

Everybody wants to talk about themselves ... Find out what someone likes to talk about, and then talk to them about that, and just keep asking questions. And I realized that if I make them feel good, if they get to talk about the thing that they're interested in, they will leave that experience thinking of me as a very positive person, regardless of status.

If I lost everything, and I didn't have my Twitter subscribers, I would probably go start an agency. I think that is the easiest way to make 500 grand a year very, very simply.

You always want to be the second owner of a hotel. You want someone else to go crazy and build it out and then go bankrupt, and then you want to come in and own that. I think the same thing is true with houses. Just go buy a nice house that someone else built.

I got invited to go on $100M+ yacht ... I thought I'd love it, but I actually found it incredibly odd ... I just don't get it. Like, you spend this insane amount of money to be isolated in a floating hotel away from all the plebs.

When I first started, I was like a Jason Fried, David Heinemeier Hansson acolyte—like, 100%, every business should be bootstrapped. I now think that's crazy and stupid, and I think there are certain businesses where it's insane not to raise money.

TikTok is downloaded on, like, over a billion phones right now, and it's a Chinese company. And it has access to your camera, your camera roll, your face at all times. Plus, it has the feed, which can feed you any information you want. All right, so, this is like pretty much root access to your life and your brain.

I bought a podcast player called Castro about five years ago ... I bought the business I was excited about the space, not because I had a plan. And so, the business basically just languished ... I think I bought it for a million bucks, and it just lost $10-20k a month...

When we got into this, I thought podcasts were stupid ... What I've learned is I think it's the most powerful medium that we've ever come across.

The biggest mistake... is when I bet on the business, not the jockey ... I've realized that betting on the entrepreneur is 100% of the game, because they'll figure it out.

What Twitter lets you do is have gated tweets, so you can say anyone who pays to subscribe to me gets these extra tweets ... If someone will spend 29 bucks, which is the cost to, basically, buy me lunch, then they can DM me, then they can message me, then I'll respond.

Owning 100% or owning the majority in your business, it's like a dictatorship. And dictatorships can be very good, like Lee Kuan Yew from Singapore, or they can go terribly, like Kim Jong-Un.

If you think you want to build a house, try it. It really sucks.

Warren Buffett made, like, 97% of his wealth after the age of 55. So, it all happens very slowly. He started in his 20s or whatever, and he wasn't really well-known until the 90s.

With Obama, he had a special toilet they would bring with him, so he couldn't poo anywhere except for the special toilet. And it would incinerate his feces, because they didn't want anyone to get his DNA.

I live in fear of debt ... It's the number one way you can lose. You can already be rich and then lose everything. It's the only way, basically.