The Book Whisperer: How to Write a New York Times Bestseller | Charlie Hoehn
What this covers
Discover how bestselling editor Charlie Hoehn helps authors create million-copy books. Learn the exact structure that hooks readers instantly, why your first 50 pages matter most, and the counterintuitive marketing strategies that create rabid fans. From cover design secrets to positioning tactics that make readers talk about your work - these insider tips will transform your writing process.
Charlie has worked with James Clear, Ryan Holiday and Tim Ferriss.
00:00 Introduction 01:04 Helping Authors Succeed 01:38 Writing for a Specific Audience 05:14 The Importance of Real Feedback 08:18 Traditional vs. Self-Publishing 18:50 The Economics of Self-Publishing 22:42 The Art of Book Cover Design 28:29 Crafting a Compelling Title 34:42 The Importance of Book Structure 45:22 Editing: The Final Touch 49:35 Book Sales Percentiles 50:32 The Harsh Reality of Book Sales 52:20 The Emotional Impact of Writing 53:12 Dealing with Compliments and Criticism 56:24 The Quest for Bestseller Lists 58:04 The Complexities of Hitting the New York Times List 01:10:25 Leveraging AI in Writing 01:18:21 Effective Marketing Strategies for Authors 01:26:14 Creating Evergreen Content 01:33:30 The Importance of Authenticity in Writing 01:38:54 Final Thoughts
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The quality and commercial success of non-fiction books depends primarily on structure, audience alignment, and iterative validation with real readers before and during writing, not on polished solo authorship or hitting industry lists.
- Best books are written for one specific person, not a general audience, and this paradoxically reaches more readers
- Authors must validate table of contents and structure with target readers before writing, not after
- Hitting the New York Times list requires massive logistical overhead and doesn't correlate with long-term book success or reader impact
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A book creates lasting sales if it produces visible transformation in readers that others want to ask about and replicate, making the transformation sharable and word-of-mouth generative.
“does this transform the reader m 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 lost way oh let me tell you about this diet I right I'm doing carnivore I'm doing keto I'm doing and it's like which diet's right it doesn't doesn't matter they all transform the person like even David goin's book can't hurt me so 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 a quick transformation that the reader wants to talk about and the people around them can't help but notice and talk about”
Books that hit a zeitgeist with a contrarian message at the moment peak awareness of a problem perform better than books arriving early or late to the conversation.
“the other things are uh 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 um so let me give an example so uh I thought Mark Manson's uh book The subtle art came out at a time of peak social media awareness that this is creating a lot of mental health issues”
Books that create or revitalize a category (e.g., Tim Ferris inventing 'lifestyle design', Ryan Holiday revitalizing 'stoicism') capture disproportionate market share in that category.
“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 win or take all scenario Tim Ferris did this with lifestyle design right and so like tons of other books came out after him on lifestyle design and businesses but he'd already won because he 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 [ __ ] the title right he created a category that swears on the cover yes he was the first that I noticed that did that”
Authors who are the embodiment of their book's message perform better than authors projecting a false persona or trying to appear more accomplished than they are.
“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 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 uh it's boring we humans have really good BS detectors we can tell when you're effectively lying to yourself we sense it right not even consciously like we know when somebody's walking towards us and there's sort like suspicious yeah 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 right but you feel it when you read it”
What is remarkable, interesting, or boring to an expert author is often the opposite of what actual readers find remarkable, interesting, or boring, because the author's expertise makes familiar what is novel to readers.
“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”
Title is the most important marketing decision an author can make for a book because virtually all books that sell more than 10,000 copies are driven by word of mouth, and the title must evoke curiosity, FOMO, and emotional reactions.
“title is the most important marketing decision the author can make for the book because uh 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 um when a person says it it has to evoke curiosity fomo some sort of emotional reaction”
The speaker was targeted in a 2018 New York Times article calling him a spy who helped people on Wall Street, which became the number one story on NYT.com for 2 days and generated numerous unsolicited publisher contract offers within 72 hours.
“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 a spy who helped people on Wall Street and within 70 2 hours after that became public we were the I was the number one story on the New York times.com for 2 days”
Tim Ferris tested approximately 30-50 different title ideas for The 4-Hour Work Week using Google ads to measure clickthrough rates, including options like 'The Chameleon Millionaire' and 'Drug Dealing for Fun and Profit', and The 4-Hour Work Week had approximately 2x higher clickthrough rate than the second-place option.
“Tim and I worked together for years and one of the stories he told about the 4-Hour Work week which I would still argue is in the top five titles of all time in the non-fiction space um he did tons of testing he 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 uh drug dealing for Fun and Profit like and he tested them at the time on Google ads...the 4-Hour Work week I think had a two 2x over the second place highest”
Once a book is committed to the printing queue with pre-orders placed and bookstores have bought inventory, the publisher effectively takes over and the author loses control over decisions like title and design, even if the author has concerns.
“it's like in everything in my body and I'm writing a book about decision- making and you know I'm like this feels push and I'm like trying to pull back right...but they're like no we've got the book like you're booked into the printing queue you're like this is happening...effectively it's like we will take over one way or another”
Chip Kidd, who designed the Jurassic Park cover, described great cover design as a 'high coup all in on one page'—embodying the entire book within an image that instantly communicates what the book is trying to communicate in a way that compels people to pick it up.
“it was ship kid the guy who did the Jurassic Park cover uh effectively said something like it's it's a hi coup all in on one page or something but it's it's basically the embodiment of the entire book within an image that you instantly understand what the book is trying to communicate”
There are recognizable genre conventions in book cover design (e.g., Malcolm Gladwell / rational optimist style with white background and elegant serif fonts) that communicate the intellectual nature of the book, and designers should work within these while still being bold.
“there's there's kind of genres of of cover design like you'll see um kind of Malcolm Gladwell type rational Optimist type where it's it's all white and there's like one little image in the the rest is like kind of an elegant serif font right that's that communicates this is an intellectual book”
Hal Elrod, based in Austin, published The Miracle Morning and sold approximately 13,000 copies in the first year, then iteratively revised the manuscript with every negative review he received, treating it like software with versions (V1, V2, V3, etc.), eventually reaching millions of copies sold with his millionth copy sold in year six.
“like Hal Elrod 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...with every negative review that he got he went back into the manuscript and made revisions...he just kept doing that until the negative review stopped...to date it sold millions of copies...in year six it sold its millionth copy”
The cost of writing dropped 10,000% with the advent of AI (after ChatGPT's release), with writers historically costing over $100, but modern AI tools have fundamentally changed writing economics.
“the cost of writing dropped 10,000% with the Advent of ai ai sucks as a writer I don't know if I agree with that and I'll tell you why the 12 tests that consistently determine whether a book will sell a million copies the big ones are”
Over 90% of book purchases are through Amazon or online retailers, so applying the 80/20 principle to book sales, self-publishing typically makes financial sense because physical retail distribution is no longer the dominant sales channel.
“there's a number of reasons...over 90% I believe it's it's a minimum of 80% of books book purchases are through Amazon on online so if you're applying the 8020 to Book Sales self-publishing typically typically makes sense”
Brené Brown uses a collaborative production style where she presents talking points to girlfriends and wine at an Airbnb, gets feedback on what works and what doesn't, and then uses that input to refine the book.
“I think people should lean more toward brne 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 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”
AI-generated content becomes detectable at scale: when writing extends beyond 2-3 paragraphs, AI patterns emerge, and tools like ZeroGP can identify AI content, though the identification isn't 100% accurate.
“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 zerog gp.com and it will show you this percent was written by AI”
The best books are written for one or two real people on the other end, not for a huge general audience or perceived fan base, because writing for a general audience is the fastest way to kill a book by making it uninteresting.
“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 uh because it's not interesting”
Most authors do not treat their published books like software and continuously update them; instead, traditional publishing locks books in stone, and authors might only get a 10-year anniversary update if they're lucky.
“most authors don't do that one of the reasons that I 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”
Traditional publishers assemble a production team including editors, legal review, cover designers, and help prevent legal issues during the editing process, which is a significant advantage for authors who might not navigate these areas effectively alone.
“what a pro is like they'll assemble your team your production team so they'll help with editing uh they'll they'll prevent you from getting into legal issues in their editing process they will uh help you design the cover”
Simon Sinek's TED Talk 'Start with Why' uses a simple three-circle diagram that a five-year-old can draw and understand, immediately getting the point across—this is a model for prescriptive non-fiction where ideas are made simple and memorable.
“if you look at Great TED Talks uh Simon synic if you just watch 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”
Authors must pay a book cover design specialist to create the boldest thing possible, not hire a generic designer, as book cover design is a specialized skill distinct from general design.
“you have to pay an artist a book covered designer specialist to create the boldest thing that you possibly can”
For the speaker's book, he eventually realized his cover design was a worthy expense that directly communicated quality and legitimacy to the target reader, illustrating that good design is an investment, not a cost.
“a worthwhile expense that instantly communicates are you legit or not uh are is this a good book that covers a direct representation of quality inside okay yeah absolutely”
James Clear's Atomic Habits begins with an intense personal story (getting hit in the face with a baseball bat) that puts readers in a dramatic moment, which grabs attention and establishes why the topic matters, as a general recommendation would not be as engaging.
“he starts his intro with uh a general recommendation I like to which is like put them in the most intense moment of your life basically put them in in a situation where they're like oh my gosh like you grabbed them by the throat...I think he got hit in the face with a baseball bat and he was he had to do like fly for fly for life or something like that”
Most authors never sell 1,000 copies lifetime, so requiring 15,000 copies in one week for the bestseller list is astronomically difficult for the average author.
“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”
The New York Times was sued by the author of The Exorcist over list inclusion and won the case by arguing the list is an editorial product, not a pure sales ranking, giving them discretion over which books appear.
“they were sued by the author of The Exorcist years ago and they were it was a big lawsuit he said you're you're withholding uh because I'm I'm outselling...they won the lawsuit because they're like it's an editorial product it is not a pure sales list we get to decide”
A military audience would accept a poorly designed cover that resembles military presentations because it signals legitimacy within their context, even if it would fail with a mass audience—demonstrating that cover design must align with target audience expectations, not universal aesthetic standards.
“this cover looks like it was created in Microsoft Word and it's it's the classic like white 3D clay you know image uh 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 in the military right and people who weren'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”
One tip for aspiring authors is to go back to bestselling books from the 1920s-1930s, identify the timeless core concept they address, and reposition that concept for today's world while maintaining the enduring truth underneath, creating a 'timely and timeless' approach.
“go back to like the 1920s 1930s like what are the best selling books how do I take that concept and sort of like reposition it for today's world where we have the core concept that still exists which is timeless like you filter for sort of like Buddhism or something that like this is enduring it'll be talked about every I don't know 100 years 30 40 50 years like 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”
The author's expertise can be visualized as a ladder, and they can only effectively pull people from the rungs below them up to their level—they cannot push someone already at their level to go higher because the author hasn't been there themselves.
“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 Rong 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 Rong they can't push somebody who's on their wrong up further”
Amazon data shows that the average person reads approximately 15-16% of a book, and Amazon can track dropoff points similar to YouTube, though this data is not shared with authors.
“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”
Hitting the New York Times bestseller list requires selling approximately 10,000-20,000 copies in a short timeframe, with 15,000 being a safe target, and the list is editorial rather than purely sales-based.
“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”
There are service providers who will funnel bulk book orders through multiple channels, geographic distribution, and individual addresses to make sales appear as individual purchases rather than bulk orders for the purpose of hitting bestseller lists.
“you can 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 a 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”
Dave Ramsey sold 60,000 copies at his book launch and didn't hit the New York Times bestseller list, and Ryan Holiday similarly sold millions of copies before hitting number one, suggesting the list isn't purely sales-driven.
“I think it was Dave Ramsey Who Sold 60,000 copies at his launch and didn't hit the list well think of the psychology of money it never made to New York Times by selling that's happened to aot Sold 5 million copies of Ryan holiday didn't hit number one on New York Times until his nth book”
Most books sell less than 1,000 copies over their lifetime, and there's an article called 'No One Buys Books' that breaks down Department of Justice data revealing that publishers fund new projects using royalties from books published 50 years ago because most books never sell meaningful quantities.
“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...most authors neglect marketing and sales...the average book sells less than a thousand copies over the course of its lifetime”
Authors writing online can develop audience knowledge through comments and questions, but this is insufficient without directly witnessing what readers go through during actual transformation, which requires real personal feedback.
“you could in theory be writing for an online audience right and 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”
Authors should not constantly promote their book post-launch but instead move on to creating new work, letting the book operate as evergreen content generating sales while they focus on new projects.
“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 in years but like most creatives have other things they want to say uh so let opportunities kind of come to you keep putting yourself out there uh but move on you know like that that is My Philosophy”
Creating categories is difficult and not intuitive, which is why there's a need for frameworks; positioning and category design are the most important decisions authors make but receive the least attention and experimentation.
“creating a category is difficult and there's a good book uh by these guys called the category Pirates called the 22 I think it's called the 22 laws of positioning or it might be the 22 laws of category design that book I think was really smart of them to write because um category design is super important positioning is super important it's not intuitive it's not easy”
The ultimate book tip and trick is experimenting publicly to identify what resonates, then drilling deeper into what works—similar to finding an oil well and drilling rather than constantly searching for new wells.
“the ultimate tip and trick experiment in public see what hits and once you found an oil well just drill keep going”
The speaker's primary goal with the book was not to make money but to achieve visibility and grow his business by pulling people into his ecosystem (like a Disney map), with the understanding that a small percentage would return to the website and further percentage would consume other content.
“the goal wasn't to sort of make money the goal was distribution how do we pull people back into our ecosystem...I want this to reach people that I haven't reached yet and then a a certain percentage of those people will come back to the website and a certain percentage of those people will listen to the podcast”
Despite the poor financial returns per book, the speaker's self-publishing of The Great Mental Models was worthwhile for non-financial reasons: the books didn't need his name, they created a niche encyclopedia of ideas, and the perception and quality elevation were valuable.
“and it wasn't worth doing but like we weren't doing it for money we for just we wanted these books to exist...you know I was a high production value but I would argue that like the perception of Shane after doing those books was elevated”
Success is measured by a house full of love with one's family, not career achievement—a value shift that occurred after becoming a parent.
“success to me now is just a house full of love with my kids for sure my kids and my wife and uh that is my daily marker of success what changed you had kids or I had kids I had kids for a long time I was just career focused I 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 um yeah it's just realigned my values”
The difference between good and great structure is that great structure aligns with what the reader wants and needs, not what the author thinks is important, requiring an interactive community process rather than isolated author judgment.
“it's a good question well I'll I'll say to that point...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 have the curse of knowledge of expertise and so you're so close to topic what is remarkable to you is confusing to who you're trying to reach”
The opening story of chapter one should encapsulate the book's core message and be the most memorable part, as this is where readers make a lasting impression that they'll recall years later.
“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”
The expert's perspective is that making a movie to win a trophy or playing a sport to win a trophy is missing the point—you do creative work and sports because they matter to people you're trying to serve, not to achieve external validation.
“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 survey”
Writing is the process of getting the clay on the table (generating raw material), while editing is the process of shaping that clay into the sculpture (refining and polishing), and these are distinct processes with different skills and mindsets.
“writing is getting the clay on the table editing is shaping it into the sculpture right”
The goal of a book's introduction is to sell the reader on reading the book—to convince them it's worth their time—and should not try to deliver content, as the introduction is purely a sales page.
“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”
AI cannot thread the narrative needle for hundreds of pages and remains poor at sustained, conversational writing that doesn't feel generated.
“I honestly I don't know if it'll be able to thread the needle for hundreds of pages I don't I I'm not sure but for now what I do know is you can produce a book that is conversational accessible written entirely by a human being but leveraging AI in the right way to produce it 90% faster at 90% less”
Most non-fiction authors write while also working through the subject matter they're discussing, meaning they are becoming the embodiment of the book as they write it, rather than writing from a place of having already achieved mastery.
“most authors are especially in non-fiction are sort of like working through the subject that they're talking about and that's the writing Mark Manson like he cares right so the subtle art of not giving a [ __ ] is sort of like him trying not to care as much James CLE was really working on his habits when he was writing about habits”
Table of contents functions as the 'menu' of the book—if readers say 'hell yes' to everything on the menu, the author has validated that the book will help their target reader and writing becomes much easier with that confidence.
“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 it doesn't feel like guess work”
The speaker has difficulty accepting compliments and good feedback; his mind dismisses them as not useful, while he simultaneously is attentive to negative feedback with a predatory instinct to analyze it for truth and areas of improvement.
“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 pass through you or what my mind turns off...on the other hand you have a program that says this is not helpful to me I'm going to nothing...but I have a predatory almost like instinct when somebody's saying something negative it's like what are they saying is that true”
The speaker initially found the traditional publishing process frustrating because as an entrepreneur who doesn't want a boss, the publisher's escalating pressure and deadlines made him feel controlled, even though he had already received and deposited the advance.
“as an entrepreneur I don't want a 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 at on the book...towards the end it was like weekly”
When recommending a book, if the title itself makes a statement or creates awkwardness (e.g., 'How I Cured My Anxiety'), it implicates the recommender in a way that discourages word-of-mouth recommendations compared to neutral titles like 'Meetings Suck' that describe a general problem.
“you 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 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 uh it's almost like you're making a statement about the other person and yourself when you say that”
When polling titles, if all respondents have wrong expectations for the book (e.g., expecting a funny venting book when you're writing prescriptive advice), this reveals a problem that can't be fully solved by subtitle alone and indicates the title creates false expectations.
“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”
Many people believe in the Hemingway and J.K. Rowling model of the tortured genius writer grinding away in isolation, but this is a limiting belief—most books benefit from collaborative writing processes rather than isolated authorship.
“the the idea of Hemingway and JK rolling being a tortured genius grinding through if you're a really good writer you can do that but I think people should lean more toward writing is getting the clay on the table editing is shaping it into the sculpture”
Conversational speech is 8x faster than typed writing, and people rarely experience writer's block from talking but frequently experience it from writing, because talking involves less self-editing and emotional interference.
“conversational is8 times faster than sitting and typing and it is um it very rarely do people get talkers block they get writers block all the time because the reason people say but I'm 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 impostor syndrome perfectionism”
Authors should make readers co-creators by involving them during the book production process through surveys asking about their pain points or questions, sharing cover concepts for voting, providing title voting, and discussing book decisions.
“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”
The typical self-published author sends a single email announcement when the book launches to friends and business contacts, but recipients have no context or emotional investment in the book, making the request jarring and unlikely to generate action.
“here's the typical journey of a of a self-published author releasing a book in the eyes of their friends their friends receive an email one day hey I wrote a book it's out today please buy it please review it please share with your friends and their friends are like where the hell is this coming from haven't heard from you uh or or their business contacts and so no one takes any action because all of a sudden it's just being thrust upon them”
The NYT list also considers traditional PR (radio, newspaper, TV shows hitting certain regional markets), digital engagement (blog articles, podcasts, Facebook comments/shares/retweets, not just likes), and correlates these to actual sales to detect fraud.
“a mix of traditional PR Legacy PR so like you're on radio newspaper TV shows that are hitting a certain number of regions in the United States...digital...blog articles that have come out a certain number of podcasts that have come out a certain number of Facebook engagements Twitter engagements like and I mean comments and reshares not just like likes right and so it has to basically map...is all this tracking with the minimum number of sales”
The speaker created a custom GPT scoring tool based on seven criteria to evaluate title ideas (scoring them 1-10), plugging in all title options to get relative rankings, where titles scoring under 50 tend to perform poorly.
“I have like a list of criteria uh that I lay out which is like fomo fun to say memorable it's it's like seven criteria and I rate them all on a scale of 1 to 10 I plug it in I I kind of made my own GPT book title score so now I just punch in here's all the title ideas and it'll spit out here's its score...anything that is under a score of 50 it tends to be like that's probably not going to perform well”
The speaker created a process called 'First Draft in a Week' that uses AI (via Zapier, ChatGPT, Claude, Airtable) to convert structured transcripts into book chapters efficiently, demonstrating AI's value as infrastructure rather than as a writer.
“I 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 ends like there's no interfacing with it but like you feed it the right transcript right and it will just spit out a book following all these prompts I've laid out using zapier and shot PT and clad and air table and all this stuff but it's like magic”
The speaker references a book about an FBI or CIA officer who specialized in building rapport and turning foreign informants, and the book had a deliberately poor Microsoft Word-style cover with 3D clay image and arrows, which was actually well-aligned with the target military audience's expectations for professional presentation.
“there's there's a cover um by uh an I 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 informance...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...it's an awful cover but it's actually aligned because he wrote the book for in the military”
The recommended method for authors is to teach the material in real time with real people first, and ideally the author should have successfully coached or consulted at least three people through the specific transformation they plan to codify into a book.
“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 specify into a book”
The collaborative writing process mirrors standup comedy, where comedians write in isolation but test material with audiences repeatedly before finalizing, treating writing as iterative development rather than isolated creation.
“similar to standup comedians right and so I think the yeah the great structures are co-created rather than isolated by the author”
The speaker maximized optionality through the book by growing audience, which enables better future podcast guests and creates win-win advertising revenue from corporations reaching a smart, hard-to-reach audience without coming from individual pockets.
“if we get more a bigger audience the optionality for the future is huge and the ality 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”
Self-publishing hardcover books is economically inefficient; the speaker was paying approximately $7-8 per book in printing costs, selling at $30, earning $15 before retailer commissions of $3 and shipping/storage costs, resulting in approximately $0.50 to $1 profit per hardcover copy.
“I was paying $8 a like people don't understand the economics of self-publishing from a hard cover perspective sort of like audio and Kindle are great because the margins are good but from a hard cover perspective we were paying $8 us $7 us approximately for printing we were charging $30...we get 15 then the distributor takes a approximately $3 per book then there's shipping costs per books there's storage costs per book by the time like the hard cover sort of worked out I think we made like 50 cents to maybe a dollar a copy”
The Great Mental Models project originated from talking with Charlie Munger, and initially didn't have the speaker's name on the books—they were positioned as an encyclopedia of ideas modeled after The Economist's approach of letting ideas stand on their own.
“we created this Niche idea and it came from talking with Charlie Monger...I didn't even know if it was in the original version like it was all co-author we had multiple people we had no by lines we we're not into like that stuff it's more like The Economist right is like let the ideas stand on their own”
The right book cover (or YouTube thumbnail) can outperform a mediocre one by 1,000x, though the book itself must be a good product independent of the cover, as covers drive selection but don't determine content quality.
“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 will outperform 1,000x”
Title testing in person—observing people's reactions when you say 'Have you read [title]?' and watching for glaze-over, curiosity, or leaning forward—is an important data point before finalizing a title.
“testing titles in person and saying like have you read this and watching the person's reaction like do their eyes glaz over are they curious are they leaning forward like these are important things”
One way to identify a strong title is to notice if you're constantly using a particular phrase with clients—if you always return to this one phrase as the unlock for them, it's memorable and good candidate for a title.
“is there a phrase that you're constantly using with clients if 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 ah I always I always return to this okay that's memorable good”
The publishing industry can be more confident in titles because they have many decades of data about what works and what doesn't, unlike new authors who are making these decisions based on intuition.
“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 yeah this is off just enough”
Book structure is more important than most other elements; if authors over-index on structure, they can confidently self-publish, because structure is the foundation that makes writing, editing, and reader experience manageable.
“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 you'll be in a really good spot like I I can send a self-published author confidently off to do their thing if they over index on structure”
Within each major section of a book, authors should identify subsections representing either smaller steps needed to achieve the major milestone, or key questions the reader will ask during that phase.
“within each of those parts you have these substeps 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”
The speaker would not change the content of Clear Thinking but would change the structure, believing that good structure makes the book easier to read and does some of the lifting to engage readers.
“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 um an easier read for people um because I do think structure does some of the lifting for you if you let it it's either a headwind or a tailwind”
When writing, authors should lean into formulaic chapter structures (hook, thesis, body with supporting points, key takeaways, segue), but when editing, this formula can be modified to make the chapter sing through refinement and polish.
“when you're writing yes lean into this structure you have a hook some something that grabs the reader usually a story or a bold statement...then you have your thesis...then you have the body which is just making up all the points...and then it's key takeaways and segue into the next chapter...when you're writing yeah follow that formula...it's in editing where you can make the chapter really sing”
Authors should allocate approximately 80% of editing time to the first 50 pages of the book, with only 20% for the rest, because most readers only get through the early pages and dropoff is critical.
“should you allocate your editing time equally across the book or upfront upfront 100% you are correct it's the YouTube hook it's it's the retention graph it's the exact same with books”
Authors often make the mistake of starting books with theory or history ('Here's how we got here'), but busy readers trying to change their lives want practical value first ('Let's go dude') and will only pay attention to historical context if they understand the stakes.
“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 history of the well guess what like I'm trying to change my life and I'm busy and I 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”
People may lose track of scale differences (e.g., confusing 10,000 books with 12,000 Twitter followers) but 10,000 copies is actually a very large number of books—if each one truly impacts a reader who implements and achieves tangible results, that's a substantial achievement.
“have we lost track of sort of like what numbers mean like I think of this politically when we toss around billions but in the context of books I'm thinking like people are like 10,000 books that doesn't sound like many I got 12,000 Twitter followers you know like how but it doesn't translate like 10,000 is a lot of books it's a lot of books yeah especially um if you've written one that actually impacts those people that they actually read that they actually Implement”
Receiving reader emails about tangible life changes (such as someone breaking up with their fiancé after reading) can be emotionally difficult and guilt-producing, but ultimately the author did them a favor by helping them recognize an unhealthy situation through inertia.
“I've gotten uh two emails now from people who've read the book and they're like I broke up with my fiance after reading this book and I'm like wow oh god well you you ultimately did them a painful favor right”
Movie studios spend hundreds of millions on films and never announce 'movie out now'—instead they tease behind-the-scenes photos, provide whispers and hinting, build anticipation, and release trailers months before release.
“movie studios do this you know they spend hundreds of millions of dollars on movies how it's never like hey the movie's out right now you should go see the dark night it's like no they teased like 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”
Pre-launch and launch windows are the two highest-conversion-rate periods for book sales, when authors should optimize marketing and offers.
“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”
If an author doesn't care about bestseller lists, launch week should be a victory lap and celebration, not stressful, and the author should have already hit sales targets during pre-launch.
“my philosophy on launches is um if you're self-published if you do not care about lists your launch should be your Victory lap right it should be the least stressful week...you went into launch week knowing I sold a th000 or 2,000 copies or 500 copies whatever”
The single most important metric during launch week is hitting a target number of reviews based on 1% of copies sold, which establishes foundation for indefinite book conversion.
“the launch week the only metric I care about is reviews is hit hit a certain number of reviews based on the number of copies so 1% of copies you have out in the world try and aim for that number of reviews um it's a good metric because then you lay the foundation for the book converting indefinitely”
Authors should set up an email sequence delivering book value as standalone content, restructured from the book with quick wins first, that mentions the book is from which it was excerpted and encourages reviews.
“you 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...I set up a 10day series helping people who are struggling with anxiety...I restructured parts of the book so that the quickest wins were first”
Authors should ask themselves if they are making something that they want to consume repeatedly, as this is probably a good indicator and will find an audience eventually.
“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”
The speaker has done self-publishing work, creating The Great Mental Models, producing the entire book from content creation through cover design, printing, distribution, and ongoing maintenance, which required approximately one full-time person just for maintenance across four books.
“well I've done self-publishing too right so we took the great mental models I created a polisher 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 storing we fixed the updates we're constantly doing Kindle revisions it's a lot of work yes it was like a full-time person”
Most authors lose at marketing because they miss the opportunity during the production process to sow seeds with readers, rather than surprising them with a book announcement.
“most authors lose at marketing because they they miss their shot during the production process to like sow the seeds uh with their readers”
When readers detect AI content, their retention drops by 50%, but if they're not told it's AI, they don't necessarily detect it, suggesting AI quality is proximity-dependent rather than intrinsically poor.
“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 not if you say it if they detect it”
The New York Times list is curated with political and demographic considerations in mind, including factors like author identity (minority status, professional credentials), making the list non-objective and influenced by editorial taste.
“political things can come into consideration with the new yorktimes in them curating are you a minority are you a doctor like these are actual factors that influence whether you're on the list allegedly”
The opportunity of the current moment is that experimentation with AI tools is low-hanging fruit—most people just need to play with it regularly, break it, try to impress themselves, and exciting things will emerge.
“I 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 like break it or impress yourself or whatever and um exciting things come from that”
A simple lens for deciding whether to pursue traditional publishing is: if a publisher offers you a $100,000 advance or more, it probably makes sense to do it; for 95+ percent of authors, traditional publishing does not make financial sense.
“if you can get a publisher to give you a $100,000 advance or more you should probably do it...for 95 plus% of authors I talk to I tell them it doesn't really make sense for you to do that”
Book sales percentile milestones: selling 1,000 copies puts a book in approximately the 90th percentile; 100,000 copies is approximately 98-99th percentile; 1 million copies is approximately 99.9%+ percentile.
“how do we think about those in terms of percentiles so like what would be a 90th percentile a 99th and I'm imagining a million is like 0.001% 03 of all books ever published right like so so what would be the 90th I'd say 90th is a th000 copies probably so you're the 90th percentile if you've sold a thousand copies of your book”
Ali Abdal hit the bestseller list with fewer than 15,000 copies sold because he had strong digital following and engagement, but the timing (season) and months matter significantly—December requires double the sales than August for same list position.
“Ali abdal I I don't know how many copies he sold but it was it was under 15,000 at his lunch...which month are you are you releasing the book if you pick December...you have to sell double Booky sales whereas August is like for non-fiction Atomic habits will sell 50,000 copies that month”
AI is a poor writer on its own but can be effective for specific tasks: cleaning up transcripts, providing editing feedback, idea generation, structure suggestions, and working with clean structured inputs.
“ai sucks as a writer I don't know if I agree with that and I'll tell you why...I developed a process called first draft in a week where we over index on structure...the not to plug my stuff or anything but I 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 ends”
The speaker embedded two paragraphs of completely AI-generated content in Clear Thinking, and his editor couldn't detect them; to date, no reader has correctly identified the AI-generated paragraphs in the book.
“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 chapter no I did it just as like a fun because I thought it would be like a nice Easter egg”
Authors can leverage AI for idea generation by asking it to interview them one question at a time for five rounds to develop the strongest possible ideas or structures.
“I'll often tell chat GPT or Claude...I'll say um 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 or just don't want to go through the whole process of of laying out here's the precise context”
James Clear would have made approximately 3x more money per copy if Atomic Habits had been self-published instead of traditionally published, though the distribution advantage of traditional publishing is a trade-off.
“we were talking about how much you would have made had he gone the self-publishing route with Atomic habits and I did the math and it was like H it's about 3x more per copy but would you have sold as many coply exactly would he have sold as many”
Title is the thing authors should take a lot of time, invest resources in figuring out, and gather data on before making a decision, rather than treating it as a minor decision made late in the process.
“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”
Bloggers can validate content ideas by writing articles and seeing which headlines and content take off, providing early signals about which chapters might work well in a book.
“bloggers do this by writing articles and they see oh that one kind of you know that took off that headline and then that content is really strong cool that's potentially a chapter”
The speaker's book achieved worldwide distribution through the traditional publisher and was translated into 28 languages, which he questions whether he could have achieved through self-publishing.
“we also got worldwide distribution we're in like 28 languages now and I don't know if that would have happened if i s public”
Cameron Harold's book 'Meetings Suck' works well for word-of-mouth because meetings are a constant pain point in organizations, so the title naturally gets brought up in conversation as a solution to a recurring problem.
“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”
The speaker made a mistake with his book Clear Thinking by not validating structure with readers first—he wrote multiple drafts, deleting and restarting, before finally creating a structure that made sense to him, but never verified it with anyone else.
“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 going to structure the book and I sort of came up with something that made sense to me but I never verified it with a public”
The expert's goal with clients is to help them reach the 1,000-copy threshold as efficiently as possible, since most authors never hit this milestone and it represents a major achievement.
“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”
This feedback asymmetry (strong responsiveness to negative, filtering of positive) is a common pattern even among successful people like James Clear, who remembers negative reviews as a matter of course.
“I've talked to people about this like even James is like I remember the negative Ries of course everybody positive yeah so it is a common thing”
Authors can theoretically publish a book first and then see where people get stuck through reviews, making revisions afterward to address feedback, though this is not the recommended strategy that most authors will actually follow through on.
“you can in theory publish a book and then 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”
Most people know about AI tools like ChatGPT but don't actively use them regularly, similar to how most people know about Bitcoin but don't use it actively.
“I think we're probably in a small segment of society that actually is like a lot of people have used chat GPT they know about it Etc but kind of in the same way that a lot of people know about Bitcoin people aren't actively using it all the time”
After the initial conflict, the speaker's relationship with his publisher (Nikki at Portfolio) became productive, with the editor adding significant value to the book, though the process also resulted in a cover and title the speaker didn't personally prefer.
“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 I don't personally like”
Claude is the strongest editor among AI tools, though not perfect, compared to ChatGPT and other alternatives.
“I'll often tell chat GPT or Claude which Claude by the way I found is the strongest editor but it's not perfect”
The transformation for the reader is moving from point X to a higher point, where they may not reach the author's level but are moving forward and have a blueprint to get there.
“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”
Traditional publishers can produce poor covers and other editorial decisions that don't serve the book well, as the publisher's judgment doesn't always align with what the author or market actually needs.
“the con is I've seen their processes it's not that we've seen the cover of my books like you know how terrible Hing be”
The speaker did not meet with the publishing expert before publishing, and wishes he had, as this conversation would have changed his approach to the cover design.
“I wish we had I would have changed the cover so when the paperback comes out we're definitely going to do that”
By now having written a book and learned from the experience, if the speaker were to write another book, he would take a completely different approach to the entire process.
“now having written a book if I write another one it'll be all take a different approach to that whole thing”
The speaker had to convince a friend's mother (CEO of John's Man Bill) to ask Charlie Munger to publish a book on mental models, which he believes would have been amazing, but it never happened.
“my uh one of my good friends moms was the CEO of uh John's man Bill and so she would hang out with Warren Buffett and stuff and I was like begging her please tell Charlie muger when he was live to publish a book on mental model that would have been amazing yeah”
Charlie Munger gave permission to distribute the accurate version of his talk on the psychology of human misjudgment online, which was offered as a bonus with Great Mental Models, and the speaker wanted to create a fifth book on psychology but felt he couldn't do it as well as Munger.
“he actually gave us permission to distribute like the accurate version of his talk right online and if awesome as a bonus if you sort of get if I was publishing a fifth book in the series like I wanted to tackle psychology but we could do it as well so...I can't tackle psychology as well as he did no by any shape or form”
Tim Ferris has experience hitting bestseller lists, and Tim's perspective on list success suggests it can be achieved but is more about the work required beforehand than about the list itself.
“I'm curious with your cover in the title what was the process with how how did you end up there where you're publishing a cover and a title that you're not crazy about well the subtitle came first”