The title is the most important marketing decision the author can make for the book, because virtually all books that sell more than 10 ,000 copies are driven by word of mouth.
The title has to do a lot of things.
When a person says it, it has to evoke curiosity, FOMO, some sort of emotional reaction, whether it's intrigue or even repulsion, in some cases, it should be almost a tip of the tongue thing that gets triggered regularly in conversation.
An example we used was A Meeting Suck by Cameron Harold.
Even if you didn't necessarily like the book, people would complain about meetings.
Meetings were a constant in companies, and so this book would just kind of organically come up as like, you ought to read this and it would just naturally be recommended.
Welcome to The Knowledge Project.
I'm your host, Shane Parrish.
In a world where knowledge is power, this podcast is your toolkit for mastering the best of what other people have already figured out.
Today's episode will transform how you write and communicate.
My guest is Charlie Hoen, the secret weapon behind bestsellers like The 4 -Hour Workweek and dozens of other books that have collectively sold millions of copies.
While Charlie isn't particularly well known to many people, he's the book whisperer to the people in the industry.
Whether you're crafting crucial emails, high -stakes presentations or reports, or that book you've been meaning to write, Charlie breaks down exactly what makes writing connect and convert.
We explore everything from book -driven titles that grab attention to structures that keep readers engaged, to marketing strategies that make ideas spread.
We also dive into the real trade -offs between self -publishing and traditional publishing, what actually makes book covers work or fail, and how AI is changing the game for writers.
This conversation is packed with immediately useful insights on how to make your ideas stick, something Charlie has helped authors do repeatedly at the very highest levels.
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How would you summarize what you do?
I help authors go from idea to successful book.
It takes a variety of shapes.
Sometimes I'm helping them with the actual production of the book, sometimes just editing, other times focusing mostly on the launch.
I'm an author myself.
I've done 20 years in video productions, but mostly it's...
I'm just helping authors with their books.
You're three times, if I understand this correctly, New York Times bestselling editor.
What have you learned about writing that you wish more people knew?
The best books are written for one or two real people on the other end, and a lot of authors write as though they're speaking to a huge general audience or to their perceived fan base, the entire fan base.
It's the fastest way, in my opinion, to kill a book, because it's not interesting.
They start speaking in terms of, we need to do this.
We should be like this.
And it's like, who are you talking to?
There's one person on the other end of that book.
Speak to them. Or speak about yourself.
I learned this. And if you want to apply it, you can do this.
So the most powerful, interesting books tend to be written for one real person in mind.
In the paradoxes, they tend to reach a lot more people that way.
And that person can be the author.
Are you making something that you want to consume repeatedly?
And if you are, it's probably pretty good.
It'll find an audience eventually.
Do you think most authors, especially in nonfiction, are working through the subject that they're talking about and that's the writing?
Mark Manson. He cares, right?
The subtle art of not giving a fuck is him trying not to care as much.
James Clear was really working on his habits when he was writing about habits.
So you're writing the book you almost want to consume?
Yes and no. So you have to become the embodiment of the book first.
So you can't really write it as though you're that person that you haven't become yet or the person that you're becoming.
You kind of have to write it from a place of, I've already become this.
I've already grown into this and I'm the embodiment of this.
Naval Ravikant had a great quote where he said, in order to write a great book, you must first become the book.
I work on prescriptive nonfiction exclusively.
I don't help with memoirs.
I don't help with fiction.
Just business books, self -help, personal development, that type of stuff.
If you think of the author, their expertise is a ladder, right?
And so they've climbed so many rungs to where they are.
If they're trying to write for people on their rung or above, it will not be a good book.
They need to write for the people below them and address those people.
Because they can pull those people effectively up to their rung.
They can't push somebody who's on their rung up further, you know what I mean?
Because they're not there themselves.
Is that the transformation for the readers?
I start at X and now I get pulled a little higher.
Yeah. And I might not reach the level of the author, but I'm moving forward or towards them.
Yeah. Or I have a blueprint to get me there.
How do you write for a particular person?
What does that look like?
Well, there's a variety of ways.
One, you can be talking to them in real life, right?
So a lot of authors who've written good books are like, yeah, I've been coaching clients or consulting with these companies for years.
I have this stuff down cold.
I know the questions they ask.
I know their common emotional challenges, the technical obstacles they face.
Those, that is a great way to write a book is like, you know that person very intimately or that avatar.
And other ways are you can do it kind of online now.
You still need that.
Real feedback though, from actually helping a person transform.
Just to clarify on that, like you could, in theory, be writing for an online audience, right?
In helping them with a particular topic and seeing, oh, they left a comment here about this.
They had a question about this.
Okay. But when you go to, to write the book, you're not actually witnessing what they're going through.
It's similar to for like software development.
You think you have a good app that you've developed and you're like, this is awesome.
Cool. Go put it in front of somebody and watch them use it and watch how quickly they get stuck or they're confused or they're bored.
It's the same with books.
And so I think it's important to get that real, you know, personal feedback that you can see here's where this person is struggling.
Here's where they're succeeding.
How does an author do that?
They were writing the whole book, right?
So like you can't write the book, publish it, then get feedback and sort of like, okay, now what do I do with this?
Well, you can, but I'll circle back to that.
Uh, the, my, the, the method I encourage is teach it in real time first.
And ideally you're somebody who's already transformed numerous people, at least three with the transformation that you're trying to codify into a book.
So, um, generally speaking, you ought to have coached, consulted, helped at least three people achieve the transformation you're, you're trying to make into a book.
You can in theory, publish a book and then it's, see where people are getting stuck, see their reviews, and then adjust the book afterward.
I don't recommend it.
It's not as it's not a strategy that most authors will stick to, but like how L rod who's based here in Austin, he did that with the miracle morning.
And so in the first year, he promoted that book, sold like 13 ,000 copies or something like that, uh, which is quite good for its first year.
With every negative review that he got, he went back into the manuscript and made revisions so that that feedback couldn't be given again.
So that review couldn't be given again.
And he's just kept doing that until the negative reviews stopped.
And to date it sold millions of copies.
I think he said in year six, it sold its millionth copy, but he, he stuck with that book and he was like, I really believe in this.
I'm going to keep modifying this as though it is software.
I'm going to release V1, V2, V3, V4, et cetera.
Most authors don't do that.
One of the reasons that I am reluctant to advocate for the traditional publishing processes, like your book is set in stone there.
You might, if you're lucky, get a 10 year update, you know, the 10 year anniversary, but you're, you're not going to touch that book again.
What's your take on the pros and cons of sort of self publishing versus publishing?
What are the considerations that you look at?
When does it make sense?
When doesn't it make sense?
How do you think about that?
I agree with my buddy, Nat Eliasson's, um, take on traditional publishing.
And it's a very simple lens to look through, uh, overly simplistic, I guess.
But if you can get a publisher to give you a $100 ,000 advance or more, you should probably do it.
I mean, if you have millions of followers, $100 ,000 is not enough, but like you get the general concept.
You want them to have enough skin in the game to take you seriously.
You want to get as substantive of an advance as you can to actually, you know, put some money into doing the book as well as you can and launching it as well as you can.
For 95 plus percent of authors I talk to, I tell them it doesn't really make sense for you to do that.
There's a number of reasons.
Most authors care about financial ROI.
We can start there.
Granted, the worst way to make money with a book is by selling lots of copies.
Um, uh, with a, but with a traditional publisher, they're going to be taking.
You know, I think it's upwards of 90 % of your royalties.
It may not be quite that high, but I remember talking to James Clear, and we were talking about how much he would have made.
How do you go on the self -publishing route with atomic habits?
And I did the math and it was like, oh, it's about three X more per copy.
But would he have sold as many copies?
Exactly. Would he have sold as many?
It's a great question.
We'll never know. The distribution is much higher with a traditional publisher, right?
You're getting into retail stores.
That's not an easy game as a self -published author.
But my argument is over 90%.
I believe it's it's at minimum of 80 % of books, book purchases are through Amazon online.
So if you're applying the 80 20 to book sales, self -publishing typically typically makes sense.
You should invest in making the best possible product.
Other things to consider with traditional publishing.
What a pro is like they'll assemble your team, your production team, so they'll help with editing.
They'll they'll prevent you from getting into legal issues in their editing process.
They will help you design the cover.
The con is I've seen their processes.
It's not that you've seen the cover of my books.
Like you know how terrible it can be.
I won't say a bad word about your book.
But yeah, I mean, what is your what was your experience actually?
I don't know. The whole thing for me started in 2018 when the New York Times wrote this article about me calling me out as a spy who helped people on Wall Street.
And within 72 hours after that became public, I was the number one story on the new yorktimes .com for two days.
I had all of these inbound contracts basically from publishers.
No book title, no book, a lot of money.
And I was like, Oh God, I don't even know what to do.
I don't have an agent at this point.
And so I remember Nikki from portfolio had come to one of my events in 2015 or 2016.
And so I just reached out to her and she's one of the people sort of like bidding on this too.
And I was like, Hey, can we chat like as friends, right?
Like not as you as an editor trying to buy a book, but I don't know what I'm doing.
I don't know like who to talk to.
I need an agent. Like do I even want to do this?
I don't have a book idea.
And so I finally ended up interviewing a couple agents, got an agent and then the money was I mean, it made sense in my case to do it, but I didn't take the money and use it.
I just sort of like put it in the bank.
So this was a weird thing too.
Like as an entrepreneur, I don't want to boss.
And for four years, I basically felt like I had a boss, right?
I would get this email, you know, at the start, it's like this trickle once every two or three months.
And it's like, where are you out on the book?
And I'm like, I don't know.
I haven't even started the book.
I don't even have the idea yet.
You know, like I have some ideas and then all of a sudden towards the end, it was like weekly, you know, it's like, where are you?
Finally, I was like, do you want your money back?
Like I'll just give you your check back and we can just call it a day.
Because I don't want the pressure.
It's going to be done when it's done.
I know I agreed to a timeline.
COVID happened. Timeline changed.
And the process from there was actually pretty good.
Like Nikki's an amazing editor.
She added a lot of value to the book.
There's pros and cons to it.
You know, I sort of ended up with a cover that I don't personally like.
I don't think it did the book justice sort of like the titling could have been better.
And I don't know what I don't know the first time.
And so I'm relying on the recommendations of sort of the publisher and they do know.
I mean, they have a lot of data.
I don't know how accurately they use that data, but my experience was pretty good.
And I know people have different experiences with publishers, but we also got worldwide distribution.
We're in like 28 languages now.
And I don't know if that would have happened if I saw public.
I might have made more money, but the goal wasn't sort of make money.
The goal was distribution.
How do we pull people back into our ecosystem?
So when I think of like Farnham Street as an ecosystem, remember that Disney map from like the sixties, it's like theme park characters.
It's like, well, I want this to reach people that I haven't reached yet.
And then a certain percentage of those people will come back to the website.
A certain percentage of those people listen to the podcast.
And how do I pull people into our ecosystem?
So I lifted the book as like, I don't want to make any money on the book.
I really just want to grow the business and get better at what we're doing.
Because if we get a bigger audience, the optionality for the future is huge.
And the optionality is we get better guests on the podcast.
We get more advertising revenue, which doesn't come out of any individual pocket, sort of comes out of corporations in a win -win way.
They're reaching an audience that's hard to reach.
We have one of the smartest audiences on the internet.
And so like, this is how I thought about it, which is like, how do I just maximize my optionality?
And I don't know if that's right or wrong, because we never talked before I published that.
I wish we had, I would have changed the cover.
So when the paperback comes out, we're definitely going to do that.
So like what you said is a common thing, is just wanting to raise visibility and create opportunities or bring more opportunities in.
So it tends to be like raise visibility, bring in opportunities, grow the business, leave a legacy, tends to be with non -fiction.
I'm curious with your cover in the title, what was the process with, how did you end up there where you're publishing a cover in a title that you're not crazy about?
Well, the subtitle came first, actually.
So I had the turning ordinary moments into extraordinary results and I loved it.
And then the title was like 10 people basically brainstorming a title from my agent, the editors, to people who work at the publisher.
And we're just back and forth until you know, we're like weeks away from printing.
This is where it gets really tricky, right?
So it's like in everything in my body and I'm writing a book about decision making, I'm like, this feels push and I'm like trying to pull back, right?
I'm like slow down.
Like it doesn't matter if we hit this deadline, it doesn't really matter.
But they're like, no, we've got the book.
Like you're booked into the printing queue.
You're like, this is happening.
And effectively, it's like, we will take over one way or another and the book is no longer yours.
And you sort of get this message and it's like, well, I want to slow it down.
I want to test it. I want to sort of like figure it out.
And I want to come up with different options.
Didn't have time to do that at that point in time.
So the process sort of like you get to a certain point in that, no, had that been three months earlier, I totally could have stopped it before it was sort of like booked into printing.
Before we had the buyers buying it, before the bookstores have bought it, before the sales agents go out, you can sort of slow it down.
But once that process gets rolling, you're sort of at the whim of them and you do the best you can given the situation, right?
Now having written a book, if I write another one, that would be all take a different approach to that whole thing.
So you lost creative control, which is like a common thing.
Well, sort of. Yeah, I mean, effectively, that's what happened.
I mean, that sounds a little, you know, on a continuum, it sounds probably very far right.
Right. Where it's like slightly more pulled in than the screen.
You were a participant, obviously, and you were the main.
But once they accept your manuscript title or not, like they can pretty much do what they want with it.
Contractually. And that's like two entrepreneurial people.
I find that that is very difficult oftentimes.
And like obviously you and I are friends with people who thrive in that and like have done extraordinarily well.
Ryan Holliday. You mentioned Tim Ferriss, James Clear.
Like these guys have and continue to do well.
I'm not taking anything away from that, but I have seen the other side as well, where entrepreneurs are dumbfounded by decisions made by their publishers or like creative control being taken in a way that they're like, this actively hurts us.
Because both sides have pros and cons and both sides can be done wrong.
I do want to say like, most people screw up self -publishing.
They don't do it well.
And so traditional publishers are right to stick up their nose at self -publishing, but it's like to your point, if it's your first go around as an author and you don't know what you're doing, the likelihood that you'll step on a landmine that hurts your book during the self -publishing process is even higher
than if you're working with a traditional publisher.
Well, I've done self -publishing too.
So we took the great mental models.
I created a publisher effectively from start to finish where we created content.
We got creative. We laid it out.
We found printers. We printed.
We found distributors.
We stored. We monitored story and we fixed the updates.
We're constantly doing Kindle revisions.
It's a lot of work.
Yes. It was like a full -time person, if not more, just from a maintenance point of view for four books, let alone sort of like doing any other books.
Yeah. Yeah. It's a lot.
It's also expensive upfront.
Oh, totally. I was paying eight dollars.
Like I said, people don't understand the economics of self -publishing from a hardcover perspective.
Sort of like audio and Kindle are great because the margins are good, but from a hardcover perspective, we were paying $8 US, $7 US approximately for printing.
We were charging $30 for the great mental models on Amazon, which means we get 15.
Then the distributor takes approximately $3 per book.
Then there's shipping costs per books.
There's storage costs per book.
By the time the hardcover sort of worked out, I think we made like 50 cents to maybe a dollar a copy from a hardcover point of view.
It wasn't worth doing, but we weren't doing it for money.
We were doing it for just one of these books to exist, still do.
It didn't make sense from an economic ROI point of view to do what we were doing in any way, shape, or form.
Yeah. I would argue that the perception of Shane after doing those books was elevated.
Well, I don't know.
Originally, we didn't even have my name on them.
It was like, that's right.
It was all about the ideas.
We basically created this niche encyclopedia of big ideas.
That's what it is today, still.
It's morphed into something.
Hopefully, think it's better distribution.
We created this niche idea and it came from talking with Charlie Munger.
I was like, oh, I'm going to all do this.
Why doesn't this exist?
Did you actually talk to him?
Just a very quick side note, and then I don't mean to cut you off.
One of my good friend's moms was the CEO of Johns Manville, and so she would hang out with Warren Buffett and stuff.
I was like, it's begging her, please tell Charlie Munger when he was live to publish a book on mental model.
That would have been amazing.
Yeah. The closest he came was, I guess, the psychology of human misjudgment, which if we had a fifth book in the series, I wanted to tackle psychology, but we couldn't do it as well.
He actually gave us permission to distribute the accurate version of his talk online.
That was awesome. As a bonus, if I was publishing a fifth book, that would be it.
But I can't tackle psychology as well as he did by any shape or form.
I wish he would have done what we did in his words with his ideas.
I mean, we did the best we could.
It took seven years to create four books.
Oh my gosh, dude. Yeah.
There was you, and I think Michael Simmons did a course on mental models, and it was like, I'm grateful you guys did that.
If Munger, all he did was poor Charlie's almanac.
I feel bad even saying that because he's so ridiculously great.
Yeah, I so wish that he had done that while he was live.
Me too, 100%. And so my name wasn't even on it.
I don't even know if it was in the original version.
It was all co -author.
We had multiple people.
We had no bylines. We're not into that stuff.
It was more like The Economist, right?
It was like, let the ideas stand on their own.
And we did that for three versions, and we had three different people working on those versions.
And now, my name is on the cover, but there's massive contributions from everybody else.
Sometimes I'm the least of the contributions, but from a sales and distribution point, it makes sense to have my name go first, because we can't fit all three names on the cover the way that we design them, and the covers actually look really good for us.
Yeah, they're great.
So where do people go wrong in self -publishing, you said?
Where to begin? I think there's a lot of places they go wrong, from the reader's perspective, I would say they typically don't have a good cover.
And so they immediately kind of shoot themselves in the foot.
Traditional publishers will typically put out solid covers.
When you're self -publishing, and you've invested a bunch of time and money, and you haven't made any money on the work, and it comes time to putting a face on the thing.
A lot of self -published authors are like, I'll go to Upwork, or I'll hit up my designer friend who puts together PowerPoints, and I'll pay them $500.
And it always results in something unremarkable.
You have to pay an artist, a book cover designer specialist, to create the boldest thing that you possibly can.
So go deeper on that, like what does a book cover artist know that most people don't?
What makes a great cover for a book?
And does cover matter?
Yeah. So this would probably be a conversation you'd want to have with like, who did Adam Grant's covers, James Clear's covers, he's brilliant, or Zoe Norvell.
She created a great site called I Need a Book Cover.
And it's just a directory of the top cover designers in the world who consistently work with the big five publishers.
So they're specialists in cover design, not in general design, they just do covers.
What does that mean?
What are the nuances to cover design?
I reached out to Pete, actually, because I was like, Oh, for the paperback, but we're years away from that.
But for the paperback, I was like, I want to work with you.
I think it was Chip Kidd, the guy who did the Jurassic Park cover, effectively said something like, it's a haiku all in on one page or something, but it's basically the embodiment of the entire book within an image that you instantly understand what the book is trying to communicate in a way that compels
you to pick it up and read the dang thing.
Which, like when I say it sounds like kind of mechanical, because I'm not a designer, I'm not, I don't pretend to be one.
But I've talked to enough designers to realize like, this is a real legit specialty.
And it's similar to YouTube, where the right thumbnail versus a average mediocre thumbnail that's clearly been created in Canva by the producer of the video, the right thumbnail outperform 1000x.
And it's, and I'm not saying like a cover will make or break a book.
That's not true. Like the book has to stand alone as as a good product, regardless of cover.
So I don't want to sound too cross met.
You like pick it up.
Yes. And it's, it's got to evoke the right feelings and from from the target reader, like your target read and it should be aligned with the story of the book and everything.
So like, there's, there's a cover by an I think he was in the FBI or CIA, but he was he was basically basically a guy who would build rapport with people in other countries and flip them like make them into informants.
So it was a very social or very specialized social skill to be able to do that very difficult.
And so he wrote a book I think it's called It's Not All About You or It's Not All About Me.
And this cover looks like it was created in Microsoft Word.
And it's it's the classic like, white 3D clay, you know, image with like, very basic arrows pointing out from it.
It's an awful cover.
But it's actually aligned, because he wrote the book for people in the military, right?
And people who aren't trying to appeal to a mass audience.
No, but the book was so good that it ended up reaching a lot of people.
But like, it was for the target reader.
And they were like, Okay, this is exactly what all military presentations look like this level of design, a worthwhile expense that instantly communicates, are you legit or not?
Are you is this a good book, it covers a direct representation of all of the inside?
Yes. Okay. Absolutely.
I wonder if we could go through like, what makes some of the popular books like great covers.
And this is again, a conversation more with a designer, but I think there tend to be they tend to be iconic.
And in that it is bold and differentiated.
A lot of cover designers find themselves being given creative direction of like, I just want it to look like that person's cover, right?
I just want it to feel like that.
And that's useful on some levels of like, hey, kind of stay within these guardrails.
And it's also helpful to give a designer like, Hey, these are covers that I hate, right?
There's there's kind of genres of of cover design, like, you'll see kind of Malcolm Gladwell type, rational optimist type where it's, it's all white.
And there's like one little image.
And then the rest is like kind of an elegant serif font, right?
That's that communicates this is an intellectual book.
So you can give them kind of guidelines to stay with and to communicate this is that type of book.
But if you're if you're wanting it to be too derivative of everyone else, it just kind of blends into the sea.
So I think great covers often are iconic and bold in that they're, they're claiming the, the most courageous representation visually that the author could possibly put forward.
So like then title, subtitle, subtitle promise sort of what titles, what titles, like what goes into a good title and subtitle title is the most important marketing decision the author can make for the book, because it's virtually all books that sell more than 10 ,000 copies are driven by word of mouth.
The title has to do a lot of things.
It is the when a person says it, it has to evoke curiosity, FOMO, some sort of emotional reaction, whether it's intrigue, or even like repulsion, in some cases, it has to be fun and easy to say.
So like, I always struggle with that FBI book that I mentioned, I always forget the title, I cannot remember it, but it doesn't really matter because there's a story that I'm telling with it.
But with a title, it's, it's kind of like it should be almost a tip of the tongue thing that comes up that gets triggered regularly in conversation.
This dovetails a little bit with what you what you've written about or like the problem you're attempting to solve, right?
So an example we used was like Meeting Suck by Cameron Harold would always come up, even if you didn't necessarily like the book, people would complain about meetings.
Meetings were a constant in companies.
And so this book would just kind of organically come up as like, Oh, have you read, you got to read this and it would just naturally be recommended.
Authors also kind of need to take into consideration like, what are the tip of the tongue conversations are going to be happening?
And how does this sound when it's being recommended?
So a title can't be embarrassing to say either, like play it away.
A book that I wrote is like, play it away.
I originally was going to get my working title was like, how I cured my anxiety, which was like, saying that is a mouthful.
It sounds like an attack.
If it's recommended to you, you ought to read how I cured my anxiety.
It's like, whoa, you're making it's almost like you're making a statement about the other person right and yourself when you say that.
Yeah. If you say read meeting suck, it's like, I'm not saying meetings suck.
But his book might be arguing that testing titles in person and saying, like, have you read this?
And watching the person's reaction, like do their eyes glaze over?
Are they curious? Are they leaning forward?
Like these are important things that you kind of have to measure before title is the thing that you should take a lot of time, invest resources in figuring out and gathering some data.
Is this going to be the best option?
How do you test it?
My process I'll tell you after after I tell this quick story about Tim Ferris.
So Tim and I worked together for years.
And one of the stories he told about the four hour work week, which I would still argue is in the top five titles of all time in the nonfiction space.
He did tons of testing.
He tested like, I don't know, 30 to 50 different title ideas.
A lot of them he'll admit were bad, you know, stuff like the chameleon millionaire, you know, drug dealing for fun and profit and like and he tested them at the time on Google ads.
And so he would just see which had the highest click through.
And the four hour work week, I think had a to 2x over the second place highest.
So he had some data to stand on other ways you can test is like, is there a phrase that you're constantly using with clients?
If for your book, do you find yourself constantly leaning on this one phrase and that's like the unlock phrase for them?
That's the one that they're like, I always I always return to this.
Okay, that's memorable.
Good. The process I use, I have like a list of criteria that I lay out, which is like FOMO, fun to say, memorable, it's like seven criteria and I rate them all on a scale of one to 10.
I plug it in, I kind of made my own GPT book title score.
So now I just punch in, here's all the title ideas and I'll spit out, here's its score.
And here are the top ones.
It's not perfect, right?
It's not a guarantee, but it gives me some sense of like, okay, these ones are strong, these ones are weak.
Anything that is under a score of 50, it tends to be like, that's probably not going to perform well.
And then after I do that, I put them through pickfu .com p -i -c -k -f -u .com.
And that allows you to do real quick testing with audiences and polling and to see their feedback on why they like a title or why they dislike a title.
So an example was, I was working on a book that I was trying to figure out, should I call this paid to play or fuck work?
I pulled on pickfu and F work performed pretty well.
But when I dove into the data, all of them had the wrong expectations for the book that can kind of be solved with a subtitle, but not really.
Right. It's showing that, oh, all these people want like a funny book about venting about how much they hate work.
I'm not writing that book.
That's not what this is at all.
If that's their expectations going into this, that's going to equal negative reviews.
Because you're not meeting the expectation.
Precisely. Yeah. You want to get that data.
You want to test your assumptions.
With standup comedians, they'll sit and write a joke, right?
And then they'll be like, that's pretty good.
And then they'll go perform it in front of 10 audiences.
And they're like, oh, my assumptions were wrong.
This is off just enough.
And I think the title needs to be treated with that same kind of respect.
It can't just be, oh, I like that.
No, you need to test it.
How important is the structure of a book once you, so you've got a title, you've got a cover, now it's structure.
This is like the thing I geek out on a lot, because I think this is the thing that if you over index on structure, you'll be in a really good spot.
I can send a self -published author confidently off to do their thing if they over index on structure.
So what I mean by that is you should be spending a ton of your time, you don't have to decide on a title till the very end, really.
You can be playing around with it forever.
But you should not write a word until you have solidified your table of contents.
And your table of contents is the thing.
It is the structure, the makeup, the foundation of your book.
And so the exercise that I like to do with the table of contents, how do I take my one reader, my perfect target reader from zero to hero?
What are the exact steps?
And it tends to be like the big milestones, there'll be two to four of those typically.
So if you look in table of contents of best selling books, they're typically divided into two to four parts, often three.
So I just as a general rule, and like just do three parts, right?
So three big milestones that help them go from zero to hero within each of those parts, you have these sub steps, right?
These little things that they have to do during that major milestone to ensure that they get there.
Or you have questions that they're going to ask during those phases.
So you take your table of contents, and then you spend a bunch of time talking to real target readers, showing them your table of contents before you write a word.
And you say which of these is a hell yes, which of these is a and which of these is like not relevant.
And that's the data you gather on early.
And so like bloggers do this by writing articles and they see, Oh, that one kind of you know, that's a clock that headline and then that content is really strong.
Cool. That's potentially a chapter.
The table of contents is this is the menu of the book.
Do you want to eat here or not?
If they say hell yes to everything, you have a really strong book on your hands.
And it makes the writing so much easier after that because you're confident that you can help the person you're trying to reach and it doesn't feel like guesswork.
That's so interesting.
I mean, this is one of the big mistakes I made writing clear thinking is like I just sat down and wrote it like a blog article the first time and then the second time and the third time.
And even now I was like the actual structure that I would do today is different than the structure in the book.
But I felt like it had been published for two or three weeks.
And then I was like, Oh, I missed it.
Like I know exactly what it should have been at this point.
How did you know what was like the aha moment where you're like, ah, that's how it should have been?
Well, I like the idea of showing readers.
I think, you know, I didn't have a structure.
I wrote the book, I deleted it, I had a loose structure.
I wasn't confident with it, wrote the book, deleted it, and then I sat down and I was like, I'm going to do that thing.
Ryan told me to do like in a structure of the book.
And I sort of came up with something that made sense to me, but I never verified it with a public, like even my editor with anybody else.
And so I came up with it.
But I have all this knowledge about the subject in my head, which is different than where the reader meeting the reader where they're at and taking them from, you know, you said the word zero to hero, but like that's different than positioning it for where they're at.
I would not change the content of the book, but I would change how I structured the content of the book.
And I think it would have made it an easier read for people because I do think structure does some of the lifting for you if you let it, either a headwind or a tailwind.
And in my case, it's probably neutral, but it could have been a tailwind.
And I don't think I nailed it.
But what's the difference between like, if you're looking at a structure and I give you like four or five different ones, like what's the difference between a good and great structure?
Hmm. That's a good question.
Well, I'll say to that point.
I had an author come to me recently and he was told like, Hey, the publishing house that I'm working with, they gave me this as like the template to write my book.
He said, I feel like I don't know if it's good book or not.
I'm too close to it.
What's your take on this?
And I looked at it and within a few pages, I was like, dude, I'm sorry.
Your publisher screwed you because there's no structure here.
The table of contents was literally like, it looked like an afterthought.
Like I think here's what you fill in after you're all done.
It's the exact opposite.
It'd be like, uh, we're building a house.
So I want you to start picking out light fixtures and like your furniture.
It's like, what are you doing?
Like, no, your publisher made a very bad move that wasted you a bunch of time.
And now we have to figure out how to structure this.
And like that takes almost as much time as just like rewriting the thing.
The writing is super easy actually when you nail the structure.
Cause then you just do a substructure.
Like what does the chapter look like?
Right. And then you can sit down and it's really easy at that point.
Do you sort of write it out?
Oh, not easy, but you know what I mean?
Right. It's easier.
And so it's, I'd imagine it's pretty similar in like songwriting, right?
If you don't know the concept of a bridge and a chorus and like all the, like these beats you have, and you're just told write a song, you're probably going to write a terrible song.
But if you have the structure that you can lean into, it will at least be more representative of what humans process.
Similar with stories, right?
You talked to a storytelling expert recently.
Story structure is always the same pretty much.
It's once upon a time and every day until one day and because of that and because of that and because of that until finally and ever since that day, right?
Or it's the three act structure, you know, climax resolution, all that stuff.
I think the best structures quite simply are what the reader wants, what the reader wants and needs.
And so you can't get that if you're guessing, you said it yourself, you have the curse of knowledge, of expertise.
And so you're so close to your topic.
What is remarkable to you is confusing to who you're trying to reach.
And what's boring and trite to you is fascinating to who you're trying to reach.
And so if you're not having this be an interactive communal process of producing a book, you're shortchanging yourself.
And so this is another common assumption that people have.
We all have the idea of Hemingway and JK Rowling in our heads of like, this is how to make a book, where they're holed up alone, they're being a torture genius grinding through and like, yes, that is how you can make a book.
If you're a really good writer, you can do that.
But I think people should lean more toward Brene Brown's production style, where she actually will come up with like her talking points and rent an Airbnb, bring her girlfriends and a bunch of wine and be like, can I just like present this to you for a day or two?
And then they talk about it, they give her feedback, and she's like, Oh, okay, that works.
Similar to stand up comedians, right?
And so I think the, yeah, the great structures are co created, rather than isolated by the author, created in isolation.
Man, I wish we hadn't met before I published that book.
What about chapters?
I mean, these nonfiction books, they seem almost formulaic.
Yeah, they are. Here's a story.
Here's the point I'm trying to make.
And here's like a summary, you know, that's sort of the, why does that work?
And is there more effective structure?
Yes, you should lean into a formulaic structure for chapters when you're writing it.
And I want to differentiate between writing and editing.
Writing is getting the clay on the table, editing is shaping it into the sculpture, right?
And so when you're writing, yes, lean into this structure, you have a hook, something that grabs the reader, usually a story or a bold statement that feels novel or even dangerous, right?
Then you have your thesis, which is in this chapter, I'm going to yada, yada, yada.
Then you have the body, which is just making up all the points that you're trying to get across.
And this can go on for a long time.
This is the meat of the chapter.
And then it's key takeaways and segue into the next chapter.
If you follow those five beats, like you have a solid chapter, since you have no thesis, body, structure, link takeaways, segue.
And you can you can open the chapter with a hook, or I'm sorry, with a quote that can come before the hook.
If you want, you can pepper quotes throughout doesn't matter.
But when you're writing, yes, follow that formula.
There are other slight modifications.
But generally speaking, prescriptive nonfiction books tend to fall within that structure very consistently.
It's in editing where you can make the chapter really sing.
And so like we were talking about video before this, right?
Similar in video, it's shooting in, okay, I want this act first, I'll shoot in this next act, this next act.
Just because you have the structure of the story that you're telling in the acts does not mean people want to watch that video, right?
You now need to edit it to retain their attention and keep them going through it.
And then in a book's case, you're doing the exact same thing with your editing, you're you're editing it in such a way that they are not only staying engaged, they're they're taking action and implementing when you want them to implement they are highlighting stuff like it feels important.
They're they're maybe even taking pictures of stuff.
It's like you have these key points that you know, similar to software.
When the reader gets here, I know they will do this.
Talk to me about editing.
So we have at this point, we got a cover, we got a structure, we got a chapter.
And then we have a book.
So we have a series of chapters.
So we have a rough draft and rough manuscript.
Should we allocate our editing time like 80 % of your editing time, you have 100 blocks of editing, right?
Like no matter what, it's a finite amount of editing time.
Should you allocate 80 % of that to the first like 50 pages and then, you know, 20 % to everything thereafter.
So I think it's like the average person, I think Amazon released this once.
It's like they read 15 % of a book, 16 % of a book, and they get all the stats from Kindle.
They know exactly where people drop off.
Just like YouTube gives you like, here's the drop off points.
Spotify does the same thing.
Amazon doesn't give that to authors, but there's drop off points.
And so should you allocate your editing time equally across the book or up front?
Up front? 100 % you are correct.
It's the YouTube hook.
It's the retention graph.
It's the exact same with books.
And so with a book, if you assume that maybe 60 % of readers are going to read the introduction, 100 % of people who open the book are going to read the first page of this book.
Can I get them to read past this first page and sear the message in the best possible story that's the embodiment of what I'm trying to communicate with this book?
Can I sear that into their brain so that they can recall it five years later?
James Clear with Atomic Habits, which is a great example because sold 15 plus million copies over the last few years.
Been number one on Amazon overall for five years.
He starts his intro with a general recommendation I like to make, which is put them in the most intense moment of your life basically.
Put them in a situation where they're like, oh my gosh, you grabbed them by the throat.
And it's like this was a personal thing that I went through.
That's the introduction.
That's an opening hook.
In his case, I think he got hit in the face with a baseball bat.
And he had to do like, fly for life or something like that, I can't remember.
So you're like, whoa.
Okay. But that's just the introduction.
The whole purpose of the introduction is just to sell you on reading the book.
That is it's the sales page convincing you this will be worth my time, which is you've got smart readers.
The thing that they're going to value the most is, is this worth my time?
Yeah, right. And then the first story in chapter one should be the encapsulation of the message that you're trying to get across.
It should be the most memorable.
It should be the thing that you're like, Oh, yeah, of course.
And so like, if you look at great Ted talks, Simon Sinek, if you just watched the first two minutes of his start with why he does a dead simple draws three circles that anybody a five year old could remember and then draw and show their friends like instantly gets the point across.
Similarly, that's that's what you can aspire to with prescriptive nonfiction.
What I think James did so well in Atomic habits is he front loads the book with the best stuff and a lot of authors make the mistake both self published and traditional.
They'll bury the best stuff in the back of the book.
And it's like, what percentage of your readers are even getting to that?
You know, they'll, they'll start with theory of like, here's how we got here.
Yeah. You know, here's the history of this topic.
Can you believe the guess what, like I'm trying to change my life and I'm busy and I have it right.
Make it practical. Let's go, dude.
Yeah. Like, hit me with your best stuff right here.
If you want to spend some time pointing out the stakes of how important this is cool.
Like, let's talk about that.
And I'll pay attention.
But like, I'm on this journey.
I signed up. Let's go.
Don't make me work for it.
I love that. We've talked about a lot of numbers.
I think so far we've had like 10 ,000, 100 ,000 million books.
We've used these milestones.
How do we think about those in terms of percentiles?
So like, what would be a 90th percentile and 99th?
And I'm imagining a million is like 0 .001 percent.
0 .003. Of all books ever published, right?
Like so, so what would be the 90th is that like 10 ,000 copies?
I'd say 90th is a thousand copies, probably.
90th percentile if you've sold a thousand copies of your book.
Yeah. Most books do not sell.
There's a great article called No One Buys Books.
And it breaks down what the Department of Justice forced all the big publishers to like reveal their sales numbers on books.
And it was like, oh wow, this is shocking.
These publishers are taking the funds from books, book royalties that they published 50 years ago to fund all these little projects, right?
And the vast majority of them don't sell a damn copy.
Part of that is authors neglect marketing and sales and they just kind of like they don't do it in the right sequence or whatever.
Other parts of it is people didn't even want those books.
Like the market doesn't demand them and the book wasn't good enough to take off on its own.
And so it's a mix of variables.
But yeah, like the average book sells less than a thousand copies over the course of its lifetime.
And so my focus with clients I work with is like, let's get you to that threshold as efficiently as possible.
Anybody can do it if you're doing the right sequence of things.
Most authors don't do it.
So it would be a thousand for 90 percent.
Okay, so what's 100 ,000?
100 ,000, that I would probably put at 98, I'm just making this up.
I don't know the exact, but 98, 99 percent for sure.
All books ever published?
For sure. There's 500 ,000 books plus published every year.
That's crazy. 20 of them sell a million copies and most of those are fiction.
Nonfiction tends to not move huge volumes.
Have we lost track of sort of like what numbers mean?
I think of this politically when we toss around billions, but in the context of books, I'm thinking people are like 10 ,000 books.
That doesn't sound like many.
I got 12 ,000 Twitter followers.
But it doesn't translate.
10 ,000 is a lot of books.
It's a lot of books, yeah.
Especially if you've written one that actually impacts those people, that they actually read, that they actually implement and use to get real tangible visual change in their life.
I mean, that's what ultimately propels these books to do well.
That can be scary too.
I've gotten two emails now from people who've read the book and they're like, I broke up with my fiance after reading this book.
Oh, God. You ultimately did them a painful favor.
Right, B? But I've been reading this going, oh, boys, what have I done?
I would absolve yourself of that guilt because they made that decision already.
We talk about inertia and how you take over a relationship.
You end up just sort of progressing, but you're not consciously progressing, right?
They were like, yeah, I realized this was just happening.
It was like, oh, God.
These emails, about usefulness, they don't always put a smile on your face.
True, but our brains, unfortunately, are hardwired to pay attention to the negative.
See a power cleanser.
What is an email that you were like stoked to get from a reader?
Well, I have this weird thing and just being a little bit vulnerable here, I don't hear compliments.
And like my mind - Like you reject them or they just have to be or what?
My mind turns off. I'm working on this because I do want to, I think at some point, if you want to dive into the roots of it, it's like somebody used it against me or took it away, right?
Like used it as power, which removed my freedom.
If somebody says something nice about you and you believe it, then you want them to keep thinking that.
And so if they're manipulating you, it becomes like a source of power of them over you.
Well, this is how I don't know.
Like I'm working through this because what happens with me is like the minute I think I'm predictive, right?
Like the minute I think somebody is saying something nice about me, my brain turns off.
Like it literally just passes through.
But on the other hand, you have a program that says this is not helpful to me.
Nothing. You know, like, and I might love the person.
I might respect them a ton, but like, oh, this is good news.
Like I don't need to hear the good news, but on the other hand - This isn't a self -worth issue.
It's literally like this is not useful to me, no thanks.
But I have a predatory almost like instinct when somebody's saying something negative.
It's like, what are they saying?
Is that true? Is it not true?
Like, how can I use this piece of feedback to, is there a hole in my boat?
Is there, you know, do I need to fix this leak?
And so it's like always skewed towards the negative.
I've talked to people about this, like even James is like, I remember the negative reviews.
Of course, everybody did positive reviews.
Yeah. So it is a common thing.
I don't want to ask like, you're completely normal in the front that you pay more attention to the negative than the positive.
Are you that way in like reports and stuff?
You're only negative, only negative.
It's almost only yeah.
I would encourage you to consider, it sounds like a super boring book.
Have you read The Inner Game of Tennis?
Yeah. A long time ago.
Right. Right. Yeah.
Probably. Maybe it's been at the wrong time.
Yeah. I mean, you've seen with kids, right?
Like you're a dad. So do kids flourish under negativity criticism or under reinforced positivity?
It's obviously a balance, parrot and stick.
But like, if it's all stick, it stops the work.
But it doesn't impact anybody.
I don't want to go too easy and read something.
It doesn't impact my happiness and my satisfaction.
Like if I see a five -star review on Amazon, I'll read it.
But like has no, it doesn't stick.
It's a part of you like, yeah.
Yeah. I know. No, not at all.
It was just sort of like, this isn't necessarily useful and please don't go leave like negative reviews down.
Do you want me to read them and like assimilate the works for any compliment in life, right?
It could be like, you've hosted a good party.
As soon as somebody's like, oh, I had so much fun, like my brain and I'm still paying attention.
I'm in the moment, but I'm like, oh, this isn't.
As long as it's not like a self -worth issue.
Like one of my best friends, like he, for a long time, he would reject compliments because he was like, you're wrong.
You know, like that's not.
And so now he has that at like repeat the compliment, sit with it.
And, uh, but yeah, that's not your case.
Talk to me about lists.
Uh, like a lot of authors have the goal of making the lists, right?
So the most common ones being the wall street journalists, which went away, which was a pure bestseller list for people who don't know that was statistically the books that sold the most regardless of publisher, no editorial control, the New York times list, which is the only major list now these days that people
think people think in their minds that they hold the market qualities.
Right. And that's an editorialized list.
And so a lot of people set their goal as like, I want to be a New York times best -selling author.
I've helped authors hit the list in various capacities.
Um, some a little bit, some like very intensively.
I've had authors come up to me and say, my goal with this book is to hit the New York number one New York times, sell a million copies and get on Oprah's couch.
You are going to be disappointed.
Yeah. The joke I make is it'd be easier for you to do six months of therapy instead, because a lot of, I want to hit the list is at its core.
I want to be validated as super legit.
I want to be picked.
You know, it's, it's, it's similar to the traditional publishing and in some ways for some authors, not all authors, right?
But some want to just be picked by the tastemakers and say you're good.
There is a validation.
Yeah, absolutely. There's validation.
But I would argue that like, it's, it's so let's get into the logistics before we get into like the psychology, I guess of it.
So I hate hitting the New York times best seller list in, in how much effort in logistical headache that comes with it.
You have to sell. Um, if you, if you're going like in an average time of year, anywhere between probably 10 to 20 ,000 copies, a safe place to bet is 15 ,000 copies.
So you have to sell 15 ,000 copies right out of the gate.
How many copies did I say the average author sells over the course of their lifetime?
Less than a thousand.
Most week sales, 15 ,000 people try to manipulate it, but you can't.
It's very difficult to do.
You can, but it's very difficult.
And it's, it's just, uh, it's a pain.
Like there are service providers out there who will funnel your bulk orders.
Let's say, let's say you do pull it off, right.
You sold 15 ,000 copies, uh, you know, that's times like 30 bucks, right?
So you have sold $450 ,000 worth of books.
That's a lot. Now you have to hand that money to a service provider who will then funnel it through certain retailers who will make it look like they aren't bulk orders and that they're geographically distributed across the United States.
They need to couple those 15 ,000 copies with as many individual addresses as they possibly can and then send those books to those people.
That alone is just ridiculous, right?
Because you have to, you have to communicate like these are legitimate sales.
There are other service providers and I'm reluctant.
I'll say Rory Vaden.
He's, he's great. Like he knows what he's doing.
I'm reluctant to mention other service providers because this space of, we'll help you launch your book and hit the New York Times is filled with people who will charge you hundreds of thousands of dollars and not guarantee a thing.
Like the New York Times is pretty dang sophisticated.
Well, they must be on to this, right?
Because the worst thing that could happen to them is like, people gaming the list.
Exactly. So they need to have reputable choices and they like, they were sued by the author of The Exorcist years ago and there was a big lawsuit.
He said, you're withholding because I'm outselling it.
I think I can't remember his name, but he was selling tons of copies and they won the lawsuit because they're like, it's an editorial product.
It is not a pure sales list.
We get to decide and so political things can come into consideration with the New York Times and them curating.
Are you a minority?
Are you a doctor? Like these are actual factors that influence whether you're on the list.
Allegedly. I don't want to say like.
I guess no natural.
Nobody knows, right?
It's like, nobody knows how the Google algorithm works.
Like at the end of the day, there's humans on the other end being like, should this be on the list or not?
I think it was Dave Ramsey who sold 60 ,000 copies at his lunch and didn't hit the list.
Well, think of this psychology of money.
It never made the New York Times best -selling list.
Yeah, that's happened to a lot.
Sold five million copies of...
Ryan Holiday didn't hit number one on New York Times until his ninth book.
Yeah, I mean, but that he was trying to manipulate this.
He was very, not on his book, but he had talked about all the ways he had manipulated media.
Oh, for his first book.
Why are they going to validate him at that point?
You know what I mean?
Like if I'm the New York Times, I'm like, I'm not.
This is what I've heard.
They have screwed over enough politicians and billionaires with their books at this point that they had to come up with a set of criteria that guaranteed you hitting the list.
Not necessarily number one.
Interesting. But they can put you at number eight, number ten.
What's the criteria, do you know?
The criteria in this, again, is put a big asterisk of Charlie probably doesn't have this right at all, but it's a certain number of copies sold through certain retail people or retail that geographically maps.
It is a percentage of those being e -books, not audiobooks, e -books that have been read a certain percentage.
Interesting. And so you can't just buy a bunch of e -books and they all register as zero percent.
Which would actually be a sign of your manipulating it, right?
Correct. Yeah. Okay.
Again, New York Times, they got a budget to set up some sophisticated trackers and they've had this list for many decades.
So a mix of traditional PR legacy PR.
So you're on radio, newspaper, TV shows that are hitting a certain number of regions in the United States.
You're hitting all these markets.
Okay. That tracks to the number of sales that you have.
Digital. Interesting.
A certain number of, and this is, this is pure guesswork, but a certain number of blog articles that have come out, a certain number of podcasts that have come out, a certain number of Facebook engagements, Twitter engagements, and I mean comments and re -shares, not just likes.
And so it has to basically map.
They have to be able to see on a holistic level is all this tracking with the minimum number of sales that we require.
Ollie, Abdull, I don't know how many copies he sold, but it was under $15 ,000 at his launch.
It was a lot, but it was under like the general recommended.
This is the other thing you have to take into account is which month are you releasing the book?
If you pick December, like my client, Cody Sanchez, who is very confident she can hit it.
But I was like, dude, this is the worst month you could pick because you have to sell double.
It's a book buying policy sales.
Yeah. Whereas August is like for nonfiction.
Atomic habits will sell 50 ,000 copies that month.
And like, it's been out for five years.
Good luck hitting number one in December.
Yeah. Selling 20 ,000 copies versus 50 ,000.
It's exponentially harder.
It doesn't guarantee you anything either.
Right? Like 20 ,000.
You can do as much as you possibly can.
But yeah, I mean, you're right.
Things go wrong too.
Not everybody's publisher's keen on you working with these service providers who do these services.
It's so much. And I think it's just kind of not worth it.
And so that's one of the reasons, frankly, I like the self -published route, is you don't have to play that game at all.
It is a political, logistical nightmare.
And I will say to people who hit the list, like, congrats, it's hard to do.
And you're probably going to make whatever investment you made into hitting that list back, but it won't be because of the list.
It will not be because of the New York.
It will be correlative.
In other words, all the marketing that you had to do to get it on there marketed you in your business and you will reap the benefits of that.
There's a great video by Anna David about the, called the truth about hitting the New York Times bestseller list.
She's hit it and she's like, it was the brokest I ever was.
I think she wrote a memoir, I think.
And she was basically like, look, it didn't change my life.
I eat out on the title and whenever I can, and I'll say it for the rest of my life.
It's a legit credential.
So I made it through luck, right?
Like just totally didn't follow the publisher's advice on how to go about it.
Had a big list, sort of just marketed it to the list, but didn't do bulk orders.
Just said, Hey, you buy one copy, we'll give you the pre -order bonuses, not by 10 or a hundred or a thousand.
It was just sort of low key.
And I was like, I make it and make it, and if I don't, I can hold my head high.
What was your number?
How many did you sell?
I'm not going to reveal that.
Oh, can you give a range?
Yeah. But so I made it and the only change that I saw really, and you're right, you do all the work beforehand.
I did all the work when I was like, what's the key message of this book?
How do I market that to my audience?
How do I get people to read it?
How do I write a good book?
And the only thing that really changed was the distribution in the physical stores.
They moved it from the shelf of new to a New York Times section for a week or two.
And then it goes back to the whatever, I think we made it twice, maybe three times.
I think it was twice.
I felt good about it.
That was something where I was like, Oh, I have this thing that I can't, I didn't know you could buy it.
I can't buy. Somebody's given me this thing and for the rest of my life, I'll forever be sort of like a New York Times bestselling author, which is kind of cool, but it doesn't, you know, my signature block in my email doesn't say like, you know, Times bestselling author.
It's just shame. There's a clip of Jim Carrey where he goes up and he's introducing an award and he's like, I'm two time Emmy winning Jim Carrey.
And he's like, when I dream at night, I think about being three time and me winning because then I'd be enough.
Yeah. And so I think it's a cool credential.
Like you can add it to your thing or to your list, but - I will say the traditional publishers.
Yeah. Cody's with portfolio, right?
So like, if they definitely wish you to try, not to, I would say they don't cross the line in terms of like, manipulating it, but they're definitely trying for you to hit that list.
I don't know if internally they have some sort of incentive or bonus or something if their authors hit it, but they definitely, like, they give me a whole bunch of ideas.
And I was like, I don't like that.
I don't think that's like high integrity.
I know, you know, it might be right, but it's not something I want to do.
I don't feel comfortable with it.
So like I rejected a lot of the things that they were sort of trying to get me to do.
And they weren't crossing a line into like illegal.
It was just things that made me uncomfortable.
Yeah. Like, yeah, I was like, well, if I was the New York Times, I'd just put myself in their shoes.
And I knew I was doing this.
That's probably detrimental to their thought process on an editorialized list where it's like they're trying to come up, you know?
I'm like, what are the reasons that they would exclude you, but what are the reasons they would want to include you too?
And I didn't put a ton of thought into it, but I'm lucky because I have a big audience that I've built up over a number of years.
So it's a lot easier for me to do that.
Right. And your brand has a prestigious reputation, right?
Like, Farnham Street is known as kind of catering to a very smart audience.
The New York Times, that's like a good association with them, right?
And so I'm not saying that's why they put you on the list necessarily, but certainly it's something they took into consideration.
I'm like, oh, they're shooting.
I actually love to see like any book, little in mind, but like watch the algorithm in process, right?
People involved, like, what are the considerations that'd be fascinating to watch?
I don't know if it'd be revealed.
It would be. But like at the, the whole, my whole feeling on these lists is like, you're not writing it for the list, you know?
Like you don't make a movie to win a trophy.
You don't play a sport to win a trophy.
Like you do it because it matters to the people that you're trying to serve.
Am I helpful to the reader?
Right. And I don't think hitting the list equals you will get stronger visibility and reach more people for any significant period of design.
The list is a byproduct.
It should be a byproduct.
You can do stuff at launch and you should.
And like, I don't advocate not doing your best at your launch, but it's kind of like how Bo Burnham's like, if you can live your life without being famous, you should.
I think if you can write and publish a book without chasing a New York Times bestseller list or any list you should.
Yeah. You shouldn't be chasing anything, right?
Right. Just your hatters.
How do I serve? The best book possible for exactly.
As a writer, how do you see the impact of AI?
The cost of writing dropped 10 ,000 % with the advent of AI, which like, historically, it's been over $100 for, you know, writers to write.
And then it just dropped precipitously.
A few years ago, when chat GPT came out, I would stay up after I put my kids to bed and I would just see what it could do.
And it became very clear very quickly that, hey, this isn't a great writer.
It can be kind of an okay editor.
Where I had an unlock was realizing, oh, it's really good at cleaning up transcripts.
And if you give it a clean input, a clean structured input, it can do some crazy stuff.
So now take this and make it into a chapter.
So now the, not to plug my stuff or anything, but I developed a process called first draft in a week where we over index on structure, we get all the clay on the table as efficiently as possible by using AI on the back end.
Like there's no interfacing with it, but like you feed it the right transcript and it will just spit out a book following all these prompts I've laid out using Zapier and chat GPT and Claude and Airtable and all this stuff.
But it's like magic.
It's magic. And there's been these book in a weekend programs forever and they produce garbage.
The way people are thinking about AI right now, I found in publishing, there's two camps.
There's one that's like sticks up their nose at it.
They're like, it's a parlor trick, it's garbage.
And to those people I say, you don't know what you're doing with it.
You haven't experimented enough to make that claim.
If you're making that claim, I guarantee you, you have not put in the hours and run the experiments.
To the others who are AI enthusiasts, they're like, let's strip away the creative process entirely and generate books in 15 minutes.
And it's also a disaster because they're going off minimal inputs and they're like, fill out a form and you can create a book.
Isn't that great? It's like, no, it's embarrassingly bad because AI sucks as a writer.
It's not a good writer.
I don't know if I agree with that and I'll tell you why.
So I put two paragraphs in clear thinking that are completely AI generated.
My editor couldn't tell and to date, no reader has correctly guessed the paragraphs that are completely generated by a.
Keyword paragraphs.
Yeah. You didn't write a chat.
No, I did it just as like a fun.
Right. Because I thought it would be like a nice Easter egg.
Of course. That's my point.
Yes, it works for a paragraph or two or three even.
But once it hits a certain point, it stops being good.
And you can run it through zerogpt .com and it will show you this percent was written by AI.
Oh, interesting. It can tell in the data on this is readers will, as soon as they detect its AI, their retention drops in half.
If the exact same paragraph is presented to a reader, I say it's AI generated, the retention drops.
None if you say it, if they detect it.
Oh, if they detect it.
Yeah. You have read blog posts and articles, I'm sure, where you're like, this is AI.
Yeah, a lot of them know.
Right. Yeah, exactly.
And so if it doesn't feel human, if it doesn't feel conversational, right and accessible, people won't read it.
And so that's what I mean by it's a bad writer.
It can do a little bit.
It can't do the whole thing.
Where do you see this going though?
Because I mean, this is the worst it's ever going to get at writing.
Yeah, I don't know.
I honestly, I don't know if it'll be able to thread the needle for hundreds of pages.
I don't. I'm not sure.
But for now, what I do know is you can produce a book that is conversational and accessible written entirely by a human being, but leveraging AI in the right way to produce it 90 % faster at 90%.
So how do we leverage AI for writing?
I mean, with my kids, I'm like, you need to do the work yourself and you could submit what you wrote to AI and be like, where's it week?
Where's it? Like, what am I missing?
Yeah. And I keep the full history because I'm like, if I ever have to go to the school and sort of like anti AI, and I'm like, this is ridiculous.
So you're growing up and this is like telling me not to use Google.
Don't use calculators.
And so I'm like, you can, but I need the full chat history.
Right. So that if I ever have to go to the school, it's like, here's what you submitted.
Here's what happened.
But like, how do we leverage AI from a writing point of view today?
The ways that I have found that I really like are for idea generation, structures, suggestions.
I'll often tell chat GPT or Claude, which Claude, by the way, I found is the strongest editor, but it's not perfect.
I'll say, interview me on this one question at a time for up to five rounds.
Until you can come up with the strongest whatever I'm going for.
Because people I think are either not very good at or just don't want to go through the whole process of laying out.
Here's the precise context.
AI is way better at like, let's pinpoint precisely what I need to do a decent job.
So if you want to draft something, I would do that as the precursor moves.
It will yield better results pretty consistently.
My favorite use is what I baked my process around is cleaning up transcripts.
Because conversational is eight times faster than sitting and typing.
And it is very rarely do people get talker's block.
They get writer's block all the time.
Because the reason people say, but I'm such a better writer than I am a speaker.
It's like, yeah, because you get to edit while you write.
And you're so much slower too.
And you're also hitting imposter syndrome, perfectionism.
You're hitting these emotional landmines that are effectively emergency breaks on your process.
So I say, do it conversationally, but structure it, and then use AI to clean up those transcripts and retain it in your words.
You can crush with putting out content.
That's crazy. One thing people don't understand about AI that I teach the kids is you can actually get AI to generate a prompt for you that you feed into AI.
I found this better because I'm like, summarize the podcast.
And I'm like, well, I'm writing, summarize a podcast, forward prompt.
And I was like, well, one day I was like, okay, well, you need to write me a prompt on what matters that I can feed into AI somewhere.
And it writes back five or six sentences.
And it's like a way better job.
Oh yeah, summarizing the podcast and what I was doing.
What have you learned about prompt A?
Yeah, that's precisely what I do too.
I say, give me the ideal prompt that will achieve this outcome.
AI is better at communicating with itself than you are.
So just prompt it to do.
I think the key is people just don't tend to experiment with this stuff.
I think we're probably in a small segment of society that actually, a lot of people have used chat GPT, they know about it, et cetera, but kind of in the same way that a lot of people know about Bitcoin.
People aren't actively using it all the time.
You might be around people who are, but the vast majority of people aren't.
And so I don't know.
We're in such an exciting, unique time where it's like, all you have to do is play around with this stuff on a regular basis.
Like that's all you have to do.
Just see if you can break it or impress yourself or whatever.
And exciting things come from that.
Let's switch gears to marketing.
What strategies are most effective when it comes to marketing?
Most authors lose up marketing because they miss their shot during the production process to sow the seeds with their readers.
Here's the typical journey of a self published author releasing a book in the eyes of their friends.
Their friends share with your friends and their friends are like, where the hell is this coming from?
I haven't heard from you, or their business contacts.
And so no one takes any action because all of a sudden it's just being thrust upon them that you're in charge of my success person that I haven't really connected with at all.
And it has no idea that I'm making this book or why they should even care.
There's zero emotional investment into the book.
And so I say most authors lose because they could have been co -creators with their readers.
They could have done really simple, easy things that would make the reader feel like, oh, this is just as much mine as it is the author's.
Send a survey to your list and say, I'm writing a book on this topic.
What are the two questions that you have on this that if I answered them, it would make it worthwhile?
Or what are the two biggest pain points you have in relation to this?
The two things that you're stuck on that if I helped you with this, it would be amazing.
That's an easy one to start with.
Just announcing it and hinting at it, movie studios do this.
They spend hundreds of millions of dollars on movies.
It's never like, hey, the movie's out right now.
You should go see The Dark Knight.
It's like, no, they teased little behind the scenes photos.
They had little whispers the whole time.
And then you finally got the trailer and the trailer was a big event, but the movie's still not coming out for months.
There's this whole buildup of building anticipation and teasing and whispering that authors neglect.
And so you could also send out, hey, here are some title concepts.
I'm thinking about, can you vote on these?
Right? Get them involved in that.
You don't have to do pick food.
That's another alternative you can do.
Hey, I just got my, I'm thinking about doing a cover.
This is where I'm at.
Just sharing updates and being like, this is where I am in the process of this.
Even sharing, today was horrible.
This went wrong. They're not on the journey with you at all unless you are sharing those types of things.
And it's normal to want to resist those during the creation process, but it's a lost opportunity, right?
Because you could be letting them in on showing how hard you're working on this or showing that you value what they care about.
You could be using helpthisbook .com, which is a service for beta readers where you can upload chapters or your whole manuscript and see data on what they found confusing, what they found valuable, insightful, boring.
You can see with very clear data where they're dropping off in those chapters.
You can show them multiple cover concepts and have them vote.
Do you think, I love the idea of going out and being like, hey, I'm writing on this topic.
What are the two things that I need to include?
Or what are the biggest problems you face here?
Do you think you can do that at a chapter level?
Or do you do that at a high school?
Oh, I have a chapter on focus.
What are the... Yeah.
Yeah. My point being, the more involved you can get your community into them feeling like, man, this is really a thing, the easier promotion is.
Because when you pre -launch, they're buying copies of your book, they're actually talking about it.
They're like, I've been so excited about this for months.
It's a natural thing.
It doesn't feel weird.
It doesn't feel forced.
They're in it with you.
So we have pre -launch, we have launch, and then we have post.
So what do I do during launch, and what do I do post -launch?
Do you make the book evergreen or constantly bring it up without being obnoxious?
Yeah. So I'll define pre -launch to...
You're building up hype.
You're like, the movie hasn't come out.
You've got the trailer.
You've got people invested, and then launch.
The movie's out this week.
The movie is out right now today.
What changes from a marketing perspective?
I'll answer that. I just want to make one point about the pre -launch and the launch.
These are the two windows where sales will spike.
So the announcement of the book, basically, that it's up for sale, and then the announcement that it's officially live.
Those have the two highest conversion rates for sales.
So authors need to optimize for those by offering...
There's a saying that people will buy what you're selling when you start selling what people are buying.
If you can package buying multiple books with services or products that you know people are already buying from you, it makes it easier for you to sell a bunch of books during those windows.
So basically, it's easier to sell a lot of books at once than one book at a time.
And to couple it with something that you know people value and purchase.
So like coaching calls.
You can just package those with buying three to 10 books or whatever.
During the pre -launch, it's having that infrastructure set up so that they can buy more than one copy, basically, and then sending emails, just leading up to it, and then closing it out.
It is boring product launch.
It's like the excess notes, blocking and tackling.
Yeah, it's just setting up those emails and seeing them through.
And it's similar with the launch, but my philosophy on launches is if you're self -published, if you do not care about lists, your launch should be your victory lap.
It should be the least stressful week.
The pre -launch is where you determine like, hey, I'm going to set a goal that's modest, but it's a bit of a stretch.
I'm going to hit it, and I'm going to go into launch week knowing I sold a thousand or two thousand copies or 500 copies, whatever.
And when you get to launch week, it should be a celebration.
Right, you're not stressed.
You just achieved a huge milestone.
I know so many people who watch like launch week, like every minute, like they're so stressed.
Yeah, it's horrible.
An intellectual baby has come out of your body, and you're like yelling at it to like grow up, you know, like be a fully formed adult.
And it's like, dude, like celebrate, like this should be a blissful week that you're celebrating with friends, with family, with peers.
You just hit a bucket list item that most people never accomplish, celebrate.
And so that's my emphasis during launch week.
You can do an event, and if you want it to be a big thing, if you don't, it doesn't matter.
But I firmly believe the launch week should be as enjoyable and low stress as you want.
And so what about post launch?
So like book came out, it's like a week later now, how do I, as an author published with publishing hours or self publish, how do I remind people that already know about the book, that the book still exists, that I bought maybe, or how do I let new people know about it without being, like I think we've
all been on those email lists where we get like 30 emails, a bit of book.
And it's like, I got the hint, you know, like create products you want to consume.
So like if you got 10 emails about my book and like they were dedicated emails with no other value add, like I wouldn't want that as a viewer.
And so like, how do we do this subtly?
Like who does this really well?
Like what can we learn from them?
The launch week, the only metric I care about is reviews, is hit a certain number of reviews based on the number of copies.
So 1 % of copies you have out in the world, try a name for that number of reviews.
It's a good metric, because then you lay the foundation for the book converting indefinitely, or converting well.
So what do you do to set up kind of an evergreen system?
You set it, which is set up an email sequence, but have actual value from the book be delivering it.
So it should be like standalone stuff from the book.
So for Play It Away, I set up a 10 -day series helping people who are struggling with anxiety.
And I've restructured parts of the book so that the quickest wins were first.
So it was like, I know somebody who's anxious, all they want to start is give me a pill.
So I'll recommend the couple supplements that actually make a difference when you're in that state.
And then we're going to go on to a little bit bigger stuff.
And it's going to be a 10 -day journey, taking them from zero to hero.
And in each email, I mentioned this is excerpted from the book.
And so like that, because it's like, I'm offering value.
It's a subtle, it's not overbearing.
It's not sort of like, buy this book right now.
It's an automation sequence, so that I added it to a blog post that was doing really well for years.
And so I think 30 ,000 people or something went through that series.
This is excerpted from the book.
I think it was like every third email, I would be like, if this was helpful, this is from Play It Away.
If you wouldn't mind leaving a review, that'd be great.
I have a three times higher conversion rate from sales to reviews than a typical book because of that.
Interesting. It's sold plenty of books too.
So I think it's just you set up that system that's effectively like a car wash that cleanses the person who signed up and introduces them to the best parts of the book and encourages them to grab a copy if they want.
But then you move on, it's in your ecosystem now.
So you should be focused on, let's keep creating and let's keep doing stuff.
And you can be the person who keeps pounding the drum, the same drum for years and years.
But most creatives have other things they want to say.
So let opportunities kind of come to keep putting yourself out there, but move on.
That is my philosophy.
What I kind of like about books and podcasts, at least if they're done in a certain way, is that you fight up front.
You do all the work.
You launch, you have your systems and processes in place.
You can earn money while you sleep at that point.
Like this conversation, hopefully people are listening to it in 10 years.
All the work's done, all the editing's done, all the costs are already incorporated.
And then hopefully it just keeps adding value to people.
But you do that by not talking about topical things, but being classical.
What else do you think goes into creating an everlasting book?
Obviously, content matters.
Structure matters, title matters.
But what makes a book shareable?
I wrote an article that basically breaks down the 12 tests that consistently determine whether a book will sell a million copies or not.
It's not comprehensive, but it gives a good idea.
The big ones are, does this transform the reader in a visible way that other people want to talk about and ask about?
This is why a lot of diets will take off is because it literally changes the body of the person in such a remarkable way.
Let me tell you about this diet.
I'm doing carnivore, I'm doing keto, I'm doing blood.
And it's like, which diets, right?
It doesn't matter. They all transform the person.
Like even David Goggins book can't hurt me, which is a great book just on its own, but he used exercises in there and inspired people to do what he does.
And so they would physically transform.
I saw this consistently with a lot of books is like, do they provide a quick transformation that the reader wants to talk about and the people around them can't help but notice and talk about?
Right. The other things are, has this kind of hit a zeitgeist of where it's kind of a contrarian message during a time of peak people grappling with this?
It's kind of unexpected or it goes against what most other books are saying.
So let me give an example.
So I thought Mark Manson's book, The Subtle Art, came out at a time of peak social media awareness that this is creating a lot of mental health issues.
It's too much. It felt like too much.
It felt like it was finally under the microscope of like, how bad is this problem?
Really? And Mark came in with a proven mass market product, Buddhism, and he millennialized it.
He made it through here's what's happening in the zeitgeist right now.
I don't know how intentional he was around like, this is the zeitgeist.
I think he hit at a perfect time for that book.
It was similar to like, one of my buddies and long, long time clients, Tucker Maxx.
He came out with I Hope They Serve Beer in Hell at a time of kind of like, peak college partying awareness, I guess.
No one had done that type of book before.
It was like contrarian for its time.
And so it was novel and unique in a way.
I must wonder if you could, maybe this is a great idea for people listening who are looking for book ideas.
Go back to the 1920s, 1930s, what are the best selling books?
How do I take that concept and reposition it for today's world where we have the core concept that still exists, which is timeless?
You filter for Buddhism or something like, this is enduring, it'll be talked about every 100 years, 30, 40, 50 years.
Go back, and then you take that concept, and then you write about it now.
But you're really just positioning the exact same thing for today's world.
It's possible. The challenge with it is the zeitgeist changes faster than ever now.
And it can be kind of a dangerous game to play the topical thing.
But I hear you. If you can root it in timelessness, this was one of the tests I say, is it timely and timeless?
Right. Mark's book wouldn't have worked if it wasn't rooted in a timeless concept.
People who write about Trump, when he was in office in hotel hall, sales go up, fall crashing down and never return ever again.
You got to balance it.
So what else goes into making a book shareable?
You had a list of things.
Again, is the author, the embodiment of the message?
I think there's a lot of books out there where the author, and this is part of the problem with the creation process if they isolate themselves.
The author's trying to project that they're somebody that they're not.
They're hyper aware that this is going to be read by people, and so they want to put on this false bravado and act like they've achieved more than they have.
And it's like, no one wants that.
It's boring. Humans have really good BS detectors.
We can tell when you're effectively lying to yourself.
Not even consciously.
I mean, no, when somebody's walking towards us and they're suspicious, and we're not consciously paying attention to it, we just feel it.
But the same way, we feel like it comes across, but not in a way that is necessarily quantifiable.
But you feel it when you read it.
Same as, oh, I feel this is AI generated.
Even if I don't go to this, I can't prove it, but I feel it.
And the minute I feel it, I discount it.
Yeah. And one of the guys who's really interesting to watch in YouTube videos is Jordan Peterson, because he'll say something and you'll watch him check in with how he feels about what he just said.
And he's like, that didn't feel authentic.
You can see him being like, that wasn't authentic.
And he'll pivot and say it in a way that he's like, that's truthful to me.
It may not be the truth, but it's truthful to him.
A lot of the stuff he says, it feels solid and substantive.
What are the, maybe a different direction on this is, what are the tips and tricks that you see authors doing today that you're like, oh, that's really clever.
The last time I was like, oh, that's a clever way to go about that.
Interesting. Was seeing Oprah and Tim Ferriss produce books that were interview -based.
You know, Tools of Titans.
And I forget, Oprah, I think has done a couple like this and maybe that format was common before, but I just didn't notice it.
I don't really know.
I remember thinking that was a very clever way to produce a book that was fun, sustainable, and not a huge heavy lift.
I think it's a really hard to pull off for the average person.
You've to have an audience listening to your interviews for you.
Exactly. I've seen other people try and do that and it doesn't really work.
It's kind of a very small segment that can do that.
I've been most impressed, Ryan Holiday and I, we started our careers at the same time and we were kind of on similar tracks.
He's always wanted to be an author.
I've always wanted to be just like an entrepreneur who does creative things.
I've just been super impressed just watching him through the years.
It's been awesome to see his like just steady beat of the drum coming out with books a year.
And what people don't necessarily know or remember about him is he started writing marketing books.
And I think to this point, he's written like three, maybe four marketing books and they just don't perform as well.
What he did though, was he created a category for himself with stoicism with kind of a dead or obscure topic and he revitalized it.
We were just talking about that, like going back, taking a subject and putting it in position for today's world.
Yeah, absolutely. Somebody might be able to do that for Epicureanism, who knows.
But I thought it was a really cool to watch him test, test, notice that that's a thing and then basically create this blue ocean category for himself.
That would be like the ultimate tip and trick.
And that's actually on my list is does this create or revitalize a category?
Interesting. And so if you can do that, it's like winner take all scenario.
Tim Ferriss did this with lifestyle design.
And so tons of other books came out after him on lifestyle design and businesses, but he'd already won because he'd like name that thing.
It was a new thing.
Lulu Lemon did it with athleisure.
Mark did it with the subtle art too, because remember all those books came out after with like fucking the title.
Right. He created a category that swears on the cover.
He was the first that I noticed that did that.
Creating a category is difficult.
And there's a good book by these guys called The Category Pirates called the 22, I think it's called The 22 Laws of Positioning, where it might be the 22 Laws of Category Design.
That book, I think was really smart of them to write because category design is super important, positioning super important.
It's not intuitive.
It's not easy. It's similar to like coming up with a book title where you're like, I know this is the most important thing I could do.
It's not something you can just snap and figure out.
You've got to really sit with it.
You just don't sit down.
And I mean, I don't anyway.
Right. It comes with a lot of experimentation.
And I think that's the ultimate tip and trick.
Experiment in public.
See what hits. And once you've found an oil well, just drill.
Keep going. Yeah. Well, this has been a fascinating conversation.
We always end with the same question, which is, what is success to you?
It would have been a different answer several years ago.
But success to me now is just a house full of love with my kids, for sure.
My kids and my wife, and that is my daily marker of success.
What changed? You had kids or something?
I had kids. For a long time, I was just career focused.
I felt like I was good at what I did.
And then I had these narratives around having kids pulling me off of that track.
And it's just realigned my values.
Thanks for listening and learning with us for a complete list of episodes, show notes, transcripts, and more.
Go to F S dot blog slash podcast, or just Google the knowledge project.
Recently, I've started to record my reflections and thoughts about the interview after the interview.
I sit down, highlight the key moments that stood out for me.
And I also talk about other connections to episodes and sort of what's got me pondering that I maybe haven't quite figured out.
This is available to supporting members of the knowledge project.
You can go to F S dot blog slash membership, check out the show notes for a link and you can sign up today.
And my reflections will just be available in your private podcast feed.
You'll also skip all the ads at the front of the episode.
The front of street blog is also where you can learn more about my new book, clear thinking, turning ordinary moments into extraordinary results.
It's a transformative guide that hands you the tools to master your fate, sharpen your decision making and set yourself up for unparalleled success.
Learn more at F S dot blog slash clear until next time.
