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.

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.

In talking to people who are older, I've realized that, ultimately, the main [things] that matter are being part of a community and having activities you can engage in, having great friends, and having a wonderful family and grandchildren.

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.

I have a system that I call 'anti-goals.' Every year, my business partner and I sit down and say 'What does our worst possible day look like, and how do we design our day to avoid that?'

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...

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.

We [Tiny Capital] don't want to be in a situation where we're buying a company where billions of dollars are going to flow into competing with it tomorrow. We just think that's too difficult. So, that's why we like to choose industries that are sleepy where nobody really cares about them ... Maybe there's not a multi billion-dollar opportunity, but there's a ten or a hundred million-dollar opportunity.

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.

I would say my superpower is pace and delegation. So, I'm like an icebreaker—I know how to make teams move quickly and blow down barriers and get things done very, very quickly using delegation.

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

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.

When it comes to social networks, usually the largest network always wins.

Like a lot of founders, I'm very urgent and I love doing things quickly. I love ideas. I love strategy. What I don't really like is implementation and follow through and managing people ... I'm very good at laser focusing for a short period of time on one company, deal, idea, strategy, whatever it is. But I don't enjoy spending the next 60 days implementing a plan and building that plan.

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.