How To Create A Sexy Hardcover Book | #311
As you saw in last week’s email, I’ve created a fancy hardcover for The Pathless Path. I finally got my copy and am working on a couple of videos to share the story and the book itself.

I’ve gotten a lot of questions about how something like this came together, so in the spirit of sharing, I thought it might be fun to share the behind the scenes.
A quick note: This e-mail has a ton of pictures, and will likely be clipped by Gmail or others, so it might be easier to read the whole thing in your browser.
It’s April 2023.
I just turned down a two-book deal from Penguin. I shared that story last week.
Long story short, after walking away I knew I wanted to make a bet on self-publishing and do something weird, creative, inspiring, and bold.
The wheels start turning. I start reaching out to people doing creative things, like a friend at Stripe Press and others.
It’s August 2023.
I’m sitting in a Zhongshan apartment in Taipei and talking to Saeah Wood. She understands someone like me who must do things their own way, well, because she’s wired like that too. She founded Otterpine to help indie authors like me create beautiful books. I’m excited talking with he and she’s somehow the first person I am talking to in the industry who still seems inspired and creative, doesn’t make creative compromises, nor does she obsess about marketing tactics.
The fact that she handles all of Derek Sivers’ books is a plus, too. Derek’s been directly selling his books for years and doing it in his own way. He’s one of many inspirations for this project.
I also share my concerns. I tell her I’m worried about the budget. I’ve been very bootstrapped in almost everything I’ve done for at least seven years. She pushes me, telling me it will be expensive, but it will be worth it.
March 2024
I delay taking action. Afraid of actually investing money out of my own pocket. Struggling to find a work flow after becoming a dad.
But I can’t let go of the idea.
Saeah pings me. “We have availability for a new client. I’d love to work with you.”
In 2023, I made way more than I spent. I decided that I can mentally use some of this “surplus” for the project.
I put down a $1,000 deposit. The wheels are in motion.
Spring 2024 - We start brainstorming
We start slowly, brainstorming ideas. One of the biggest inspirations for the book was the Steel Brothers Walden book that my friend Steven Foster sent me.
Some people feel mimetic desire for others’ possessions. I instantly felt mimetic desire for the state of being able to create something like this:
The text on the cover also excited me, and I mocked up something for The Pathless Path. Here is my very bad, hacked-together Figma mockup I sent to Saeah.
I also started sharing other sources of inspiration
I love what fantasy authors are doing with special editions like Brandon Sanderson
Craig Mod’s books are inspiring and well-designed
Stripe Press has amazing covers and clearly cares about books
And some others that integrate text into covers
Beyond the cover, I’m also inspired by various people’s experiments over the years. Some notable projects worth mentioning include:
The Steel Brothers’s Walden Book
Kevin Kelly’s expensive and very heavy art books of photos from Asia
All of Craig Mod’s writing and art book experiments
Brandon Sanderson’s leatherbound books and kickstarter bundles
Ryan Holiday’s leatherbound version of the Daily Stoic
Gretchen Rubin’s notebooks
Baron Fig products and design asthetic
Stripe Press books and websites
We start doing the cover first. This will help us pick a direction
We start with the cover. Here are a few very early mockups:
I don’t love any. The lines and foil print are intriguing, but the only ones that make me excited are the ones with hand-drawn illustrations.
In this phase, I’m trusting my intuition. I want to feel an immediate “of course” sensation flowing through my whole body rather than “this makes sense.” I felt it when I saw the original cover of The Pathless Path.
I’m not feeling it yet, so I asked them to keep going with the illustrations.
The good thing about working with a great team is that they can take my mediocre “I don’t really like this and that” feedback and come back with something beyond what I could ask for.
The illustrator, Elizabeth Evey, comes back with this, and it blows me away.
Whoa. This is nice. The illustration with the cloth cover was exactly the vibe I was looking for. The scene depicted was one we brainstormed around the scene from the “pebble in my shoe” alive (h/t Khe Hy). Eventually, I decide that the pebble in the shoe scene isn’t right for the cover. I want to make it less about a moment of discomfort and more about wonder and taking the first step toward new possibilities. You can see some of the details we changed in the final version. In addition, here’s the back cover quote we landed on, one of the most highlighted and shared quotes from the book:
Then we focus on the inside
“We will do the font and layout test next.”
The structured process is helpful for me, because when it came to the inside, I didn’t quite know what I wanted.
I talked about clear, bold colors and simple images. Here are some of the initial versions we whipped up:
These were all a bit too intense for me, which was useful, as I then started to develop a strong and clear point of view about what I liked and didn’t like.
I started to focus on the following:
I wanted simple and bold. I didn’t want a complex mixing of multiple shades
I tend to gravitate toward blue, especially the bottom one
I didn’t want any overly complex drawings or graphics
I loved the full-page quotes
From there, we decided to do one or two blues, on cream pages, testing some of the following colors
I ended up really liking this dark blue:
I didn’t love the 2nd shade of blue, and we tried dozens of shades and ultimately decided to keep it simpler and stick with only the dark blue.
This ended up matching really well with some of the illustrations we were doing. A few iterations later, we ended up with something I loved: clean, simple, and clear:

Content + Editing
A Foreword
I reached out to Ali Abdaal last year and asked if he would consider writing a foreword for this version of the book. I was nervous asking, as I just generally am still not great at asking for support. But I’m glad I did, as he was excited to do it. I think his contribution adds a nice story to kick off the book as he found permission from it to leap from medicine to full-time entrepreneur.
Author’s Note
It’s been almost five years since I started writing this book in December 2020. A lot has changed since I published it in early 2022, too. I wrote a short reflection on becoming a father on this path, my continued enjoyment of the journey, my surprise at the success of this book, and my future aspirations. It was really fun to reflect on how this book has been such an important part of my life over the last few years.
Full-Page Illustrations & Quotes
There are at least seven full-page illustrations throughout the book, and many more small touches throughout the tie in with the images.
Here is one which I love:
And another one:
And a few of the 30+ quotes from myself and others from the original:
Some Light Editing & Design
While the book was completed years ago, I still had Otterpine’s team give it another proofreading pass. While we didn’t make any major changes, we improved the consistency of things like spacing, em dashes, spellings (toward versus towards and how we used footnotes and captions. Also, by creating the quote pages, we moved many of the quotes out from the start of chapters which improves readability.
I also used their suggestion of going to the indented spaces over blocks, mostly because I liked how it looked on our designed pages and I’ve grown more friendly toward it as I’ve read more fiction.
I also took their edits and cleaned up a bunch of stuff in the other versions and have launched these as “Version 2.0” of The Pathless Path. For now, the updated author’s note and foreword will only be in the special edition hardcover but I may update everything for the books 5th year anniversary in 2027.
An index + bookmark ribbon
The book has a ton of references. Now there’s an index at the back.
And a helpful bookmark ribbon to help you mark your favorite page.
And A Few More Things
I signed over 2,000 copies. We have about 1800ish that made it to print
This was a bit tricky to pull off as the book was being printed in Italy, the books are being shipped from the US, and I am living in Asia. Signing 500 pages a day in a coworking office in Thailand was more complicated than I expected, my signature evolved daily.
A slip cover
Adding a slip cover was expensive, adding a bit of additional cost to the book, but we brainstormed a little slot in the slip cover that matched well with the illustration.
I thought it was a fun idea, and I decided to go for it. This will likely only be a first edition thing, so if you like slipcovers, definitely grab one now.
Note Cards
We created a pack of five quote notecards with every order. These are nice, thick cards you can use to send mail or just create a very fancy to-do list. These are much higher quality than I expected too. I got a pack of these last week. Really nice.
A companion notebook
We made a simple notebook along the same lines as the book that has a couple of new quotes and some playful touches. This wasn’t as much as the slip cover, but I decided to do a bigger print run of 5,000 of these to sell on its own in the future and hopefully gift in other creative ways.
Packaging
All early bird bundles pre-ordered before December 1st will be individually gift-wrapped and handled with care. If you order, you’ll receive something like this:
Inside the wrapped package will be a shrink-wrapped book, the full notecard pack, and a notebook. In addition, you’ll get a handwritten card that we can customize for gift giving or your own entertainment.
This should make for some pretty incredible gifts. Just think about giving this to your parents who have been giving you a hard time about your life choices, or that VC in your life that keeps telling you to grind harder. Nothing changes hearts and minds like a delightful gift!
This packaging and premium shipping definitely add quite a bit to the cost as well ($7-$10 a book), but at least early in this process, I want to give everyone who takes a chance on this a premium experience.
Distribution
For now, we are focusing on selling direct, through Shopify, and via a single warehouse in North Carolina. In the future, we will explore other channels like selling through Amazon FBA and alternative distribution if demand increases, especially abroad. We’re also going to explore specialty shops, or independent bookstores that may want to carry something like this (if you are at Pier 1 hit me up!).
But for now, I’m keeping it simple and learning as we go.
The Economics Of This
TL;DR: I’m not sure if this will be profitable, but there is a long-term path to making money selling more of my books directly, packaging them with other items, and continuing to learn and improve. This feels fun and exciting for me,
For the last 8+ years, I’ve had an extreme bootstrapper mentality. Early on, I struggled to spend more than $100 on anything I’d create. Even though creating online does mean spending money and paying platform fees, I’ve had 70-80% margins for the first six years of this indie path. Investing in this project meant that those margins were closer to 50% last year, and this year, it may be much lower because I’m frontloading most of the costs.
The total investment upfront is going to be somewhere in the $75,000-$85,000 range, and it will depend on final costs, shipping, and other fees of the books and notebooks, which are still being finalized and need to be shipped to Otterpine’s warehouse in North Carolina. My goal is to attempt to approach breakeven or even profit at around 500-1000 books. This will be hard, but it will also enable me to shift more quickly to different creative pricing and bundling options in the future.
Ongoing costs will also add to ongoing costs, and this is the reason most self-publishers just stick with print-on-demand and digital books. Because Otterpine is managing warehousing, there will be fulfillment costs, shipping costs, lost package costs, unexpected customs fees, which we may not be able to predict, and packaging costs on top of printing and production. We’ve already had a minor issue with the notebooks being delayed and may have to incur an extra shipping fee, but it still should be ready by Christmas!
Because of this, I created a few tiers for people who want to support this project in a slightly bolder way, including the “Medici tier”, which includes an hour-long call with me.
One person who saw the book early last week said, “This was the best book receiving experience I’ve ever had”. Epic. That was the goal.
All of this is to say that this project was a huge bet for me, and until I launched it was quite scary. But now that people are ordering (I hit over 100 orders this weekend!) I am feeling much better.
What is this path if not for doing interesting things and actually using some of the money I make to take risks and create things in the world?
Credits
So much credit goes to Saeah Wood, who was a great co-creator throughout this process. She guided me through creative decisions, money freakouts, and helped me to dream bigger. She’s also built an incredible team. Every time she said, “We’ll come up with something awesome,” they delivered.
The whole Otterpine team (learn more about them here)
Creative Director & Production Manager: Saeah Wood
Editorial Manager: Amy Reed
Design: Ivica Jandrijevic
Illustration: Elizabeth Evey
And other shoutouts!
Original Editorial: Paula Trucks-Pape
Author Photo: Alicia Tsai
Printed in Vicenza, Italy




























This is such a great writeup, the transparency here, inviting us into the process - this is amazing Paul.
Beautiful book and post Paul!