The Wisdom Wall

“Every time you raise more money, your success chances go down, not up. That's, that's the big aha, is that every time you, you move the goalpost, You're the chances of you actually having a meaningful outcome go from, you know, 20% to 10% to five percent to one percent to half of one percent to. And when you start to…”

“of all the businesses that we've built in the past three years, we've learned that the group coaching model is the fastest to scale, probably most profitable, like probably doing another group coaching program would be low hanging fruit. Cause you can get a group coaching program to, to five, ten million. Like if you…”

“in actuality, what the reader cares about is you in the context of the niche that solves a problem for them. And the moment you step out of that niche, Completely. And you start thinking it's just about you and how special you are and how famous you are and how big your audience is. The great dissension begins.”

“So if you add AI into the equation, it's not that AI removes people's jobs. AI becomes the stress test of, do you know how to use this to double, triple, quadruple your output? If yes, you will make even more money than you were making before because you are more valuable.”

“the thing that most writers and most people who want to write don't realize is that many of the decisions get made before you start writing. So if you start, if you come up with an idea, and your first thought is I should open a Google Doc and I should start writing, you've already failed. You already did it wrong. And…”

“every time you sit down to write, your brain is cycling through previous quote unquote templates that you have seen work. Either something you've read and were inspired by, or something that you've done already and you received a positive response from.”

“You could reverse engineer 99% of all nonfiction writing back into these 10 ways.”

“if you're creating something new, you publish it wide, but if you're creating something really niche, ah, you should look at the existing categories in Kindle Unlimited, and then basically, like, try and stay in that category, and then you're just playing the, the better best game.”

“I think it's not writers that do that. I think it's entrepreneurial people who do that. And then they are just like, and I'm just going to write to fulfill on the demand. But I think the people who are actually talented at writing almost never think about this”

“Because I think the real value is you build a niche library, and then you train AI on how to write that specific subject.”

“Every time you raise money, your chances of success don't go up. They go down. You just kicked the goalpost way further, right?”

“most founders, if you were cash flowing two million dollars a year, you would re your desire to go build a billion dollar business would not go up. It would go down.”

“You know, cause you know, when someone offers you two million dollars or someone offers you a hundred million dollars, like they're not just giving you that, that there's a lot of strings that come with that. And all of a sudden you have a boss and all of a sudden you have expectations, right? And, and, and the life…”

“Something I recognize is it's really not about the money. It's actually more about the status. It's more about the, like you feeling chosen. You know, like you feel special that it was offered to you.”

“if you're generating all that attention and you're not monetizing it, something else is going on. Because it's not that you can't. Like, the opportunity is there. It's just either you have a skill deficiency, like you haven't really learned or taken the time to understand how to monetize business models, you know,…”

“it's not, you build attention and then you build a business because if you build a ton of attention, posting memes, and then you try and go launch a business, like it's it, people aren't brain dead. It's not like just because they followed you, they're just going to miraculously buy the thing that you sell. You know,…”

“I think, you know, he, cause I'm assuming he, he got a, uh, like a publishing deal. Totally different. It's like venture backed versus bootstrap. Totally different set of expectations, right? He, his book needs to sell a million copies or it's a failure, right? Like VC, you're either a billion dollar company or you're…”

“So when someone sits there and goes, I'm upset that I'm not winning. What they do is they point and they criticize everybody and go, you're cringe. Imagine taking that seriously. Look at you. And it's like, all you're doing is just admitting that you don't know how to play the game.”

“people expect AI to automate and do things that they don't understand how to do themselves. And so it is worth recognizing that, you know, AI is not a silver bullet. On some level, you do have to have a baseline understanding of how the thing is supposed to work so that you can prompt AI in order to do it, right?”

“The, the majority of people don't have a talent problem. They have a, a thing called, I don't want to practice and execute the basics, and I would rather, no offense, drink a bunch of coffee, close my eyes, and hope that something smart comes out when I hit the keyboard, right? And that's, that's not a very reliable…”

“instead of me passing this along to my junior columnist, I'm going to feed this to ChatGPT, which means we just got to elevate ourselves up to editor in chief, where our primary value is taste.”

“And this is something that took me a really long time to understand, is that 90% of the value of a piece is the headline and the quality of the three main points.”

“I think that you should always try yourself first and then weigh it against what ChatGPT comes up with and then improve the quality together. That is why I don't defer the writing to AI. I write with AI”

“I've always found that the best main points and subheads are actually more like sentences.”

“The mistake that I see is one, one is the person sees that opportunity and then goes, okay, I'm just going to go write one book for that keyword or that subcategory, and then I'm going to do it again in a different subcategory And then do it again. And then do it again. And you don't ever have density in one. You're…”

“if you look at the best-selling nonfiction authors, James Clear, Mark Manson, whatever, they are a 10th of the best-selling fiction writers. The, the IP value is astronomically different, you know.”

“A paid newsletter, the way to think about it is it's a book that never ends. So it has to be a topic That you want to repeat infinitely, the reader wants to consume infinitely, and every issue has to feel like a tangible object.”

“The missed opportunity is realizing that the recurring revenue is the beginning, not the end. So what you, what happens is you have all these creators that go, I started a paid newsletter, and then they reach success. You have paid newsletters on Substack doing hundreds of thousands or even millions of dollars a year.…”

“There's a lot of context stuff, like people taking lifetime revenue and calling that the revenue of their business. So they'll be like, I've done, you know, five million bucks over the past five years. And then you'll see them go on podcasts being like how I built a five million dollar business. That's not a five…”

“You go into the tea aisle, and it's just white label green tea, but one of them says calm, and one of them says energy, and one of them says focus. You're gonna buy the one that says the word of the thing that you Associate with. So you could easily do that for any category or any niche.”

“when you're the leader in a category, the best thing that you can do is grow the category. The more that the category grows, the more that you benefit”

“if you want to make money as a writer, it's significantly easier to start with the end in mind, start with a problem, and then use writing as a vehicle to solve it.”

“It's like the background in gaming clearly primes your brain for certain skills, for certain ways of thinking, for a certain threshold of pain, for strategy, for learning rules, then bending rules. You know, it's like video games prime all of that.”

“there is a drastic difference between doing something and being really good at explaining how to do it. And so a lot of times when I would go straight for a founder, they'd be accomplished. But then when I asked them, can you explain how you solve these problems? They can't articulate it. Right? So they got good at…”

“And I think we always want to listen to people more than we want to listen to entities.”

“The whole thing is not for you. It's not, it's not for Dickie to be famous. It's not for me to be famous. It's not for Greg to be famous. It's for each one of us to become known for a niche that we own. It's, it's to be known for a category of thing.”

“And once you start unlocking rewards in a niche, you realize that the switching cost goes up. Right. So the more that you dominate a niche at this point, if Ryan holiday went to his publisher and went, I'm doing a hard pivot pivoting out of stoicism, that's like a code red publisher calls in 12 people being like, we've…”

“Where, where do you create the most demand? It's all the people who haven't started yet beginning, right? So take any niche, any category, anything. Web three, get more specific. Start web three. Community, get more specific. Start a community. And if all you did, as Dickie and I are learning, if all you did was drill…”

“ShipThirty and TypeShare is a really, they complement each other well, and I think the key is if you're gonna build things, if you're gonna build multiple things, they have to work together, right? Because if they don't work together, then there's no compounding. It's just You're signing yourself up for more work…”