Ryan Holiday

Ghost Town Living: buying a $2M abandoned mine town and documenting the rebuild for YouTube

Brent, a partner of Ryan Holiday, bought a 500-acre abandoned mine town in California for roughly $2 million and documented converting it into a hotel on YouTube under 'Ghost Town Living.' Every video gets around a million views, proving that radical life commitment generates massive organic content reach.

“Where is that? California. And then the pandemic hit and Brent, who was kind of the main guy leading the charge, he was like, screw it, I'm gonna go live in that town. And now he has a YouTube channel with millions of followers. And if you go to YouTube and type in ghost town living, every single one of his videos gets a million views. It's crazy.”

Bestseller lists toss out sales from author-owned bookstores

Ryan Holiday explains that BookScan (Nielsen) and the Wall Street Journal flat-out exclude sales from bookstores owned by the author, and a 'dagger' next to a title on a bestseller list flags suspicious bulk purchasing.

“If you ever look at the, at the bestseller list and you see like a little— they call it a dagger, it's like a little cross next to certain books— that means that there was a lot of bulk purchases, um, or like suspicious activity.”

Nobody buys a book because they saw it on a bestseller list

Despite authors and publishers obsessing over the New York Times, Wall Street Journal and USA Today lists, Ryan Holiday argues being on a list doesn't actually move copies because almost no reader buys based on a list they couldn't even find.

“But as someone who buys a lot of books and talks to a lot of people who buy a lot of books, I have never once heard of someone buying a book because they saw it on a list. Most people don't even know where they would find such a list.”

Why authors should avoid paperback: the 15% vs 12.5% royalty math

Ryan Holiday explains that authors earn 15% royalty on a hardcover's MSRP (~$27) versus 12.5% on a paperback that sells for $10-15 less, so going to paperback can mean selling a third more copies just to make the same money. This is why Tim Ferriss's and Jim Collins's books stay in hardcover for decades.

“So my agent very early who was in publishing, he was like, he was like, I will never let your books go into paperback. He's like, you have to sell about as third, you have to sell a third more books to make the same amount of money that you've sold in hardcover. And this is why Tim Ferriss's books are not widely available in paperback. Good to Great by Jim Collins, which has sold tens of, you know, probably 10 million copies, still in hardcover even though it's a 20-year-old book.”

Steal thisKeep a strong-selling nonfiction title in hardcover only to protect the higher royalty rate.

Why authors should avoid paperback: the 15% vs 12.5% royalty math

Ryan Holiday explains that authors earn 15% royalty on a hardcover's MSRP (~$27) versus 12.5% on a paperback that sells for $10-15 less, so going to paperback can mean selling a third more copies just to make the same money. This is why Tim Ferriss's and Jim Collins's books stay in hardcover for decades.

“So my agent very early who was in publishing, he was like, he was like, I will never let your books go into paperback. He's like, you have to sell about as third, you have to sell a third more books to make the same amount of money that you've sold in hardcover. And this is why Tim Ferriss's books are not widely available in paperback. Good to Great by Jim Collins, which has sold tens of, you know, probably 10 million copies, still in hardcover even though it's a 20-year-old book.”

Steal thisKeep a strong-selling nonfiction title in hardcover only to protect the higher royalty rate.

Rich people want to write books; authors want to get rich

Ryan Holiday observes the grass-is-greener irony: every author he knew wanted to start a company and invest like Tim Ferriss, while the very rich people he met all wanted to write books. The lesson: doing meaningful work you love is what people do with money once they have it.

“And then I would meet really, really rich people and they wanted to write books. And it was a reminder to me that like, uh, doing stuff that's cool that you like, that, uh, means something to you is what people do with their money when they have it.”

Quantity is how you earn the right to charge for quality

Ryan Holiday rejects the quality-vs-quantity tradeoff: like a stand-up comic who needs stage time, you get good by doing a lot, and especially online where you give work away free, volume is how you reach a level worth paying a premium for. He has shipped a free daily email for six years.

“And so especially online where you're giving the thing away for free, like you should be focused on quantity because quantity is how you get to a place where what you do is worth paying for at a premium level, like with a book or something. So I like, I've done a free email every day for 6 years, right? Um, that, that's built a business.”

Steal thisShip free volume daily until your reps earn you a premium-priced product.

Holiday's content buffer: write batches, stay weeks ahead

Ryan Holiday runs a tracked pipeline for his Daily Stoic and Daily Dad emails: scheduled out two weeks ahead, with 10 written and ready to record, 16 recorded but unscheduled, plus a stocked Daily Dad queue. He can knock out a week of content from one-sentence ideas in 30 minutes.

“I am, I'm scheduled out on Daily Stoic through, and Daily Dad through October 14th. And then I have 10 written that are ready to record. 16 that are recorded but not unscheduled, and then 9 on Daily Dad that are ready to record, and 8 that are recorded but not scheduled.”

Steal thisTrack your content pipeline in a doc with explicit stages (written, recorded, scheduled) and stay weeks buffered.

'Quality over quantity' is usually procrastination in disguise

Ryan Holiday is skeptical of people who claim a book took five years for quality reasons: when he looks at the output, he rarely sees five years of work, and suspects it would have been better or faster if they'd actually shown up like a job every day.

“When I look at what those people make, I very rarely see the quality, right? Like they're like, oh, you know, this book, it took me 5 years and I'm like, where? Show me 5 years of work in this thing, right? I'm not arguing with you that it, it transpired over 5 years, but I don't think you showed up and worked on this, as you said, like a job every day for 5 years.”

Write once, translate into every medium

Ryan Holiday's content engine is built on a single source: the writing (especially the books) generates the vast majority of material, and a team repurposes it into YouTube videos, podcasts, and emails the way a translator turns it into Spanish editions.

“So for me, the writing, particularly of the books, is what generates the vast majority of the content. And then I have people who help me just, just in the way that I don't do the Spanish edition of my books. I have people who help translate what I've done into different mediums.”

Steal thisMake long-form writing your single content source, then hire people to translate it into every channel.

Why book-of-the-month clubs are a brutal business

Ryan Holiday explains the book subscription box is hard: not many people read, logistics are tough, and even at best you only get books at 50% off the publisher, so a physical subscription ends up costing more than Netflix's unlimited content.

“Um, the problem with the business is, first off, not that many people read, right? Uh, unfortunately. Um, second, uh, the logistics of it are what is tough, right? So like, at the very best, you're going to be able to get those books from— like, let's say you're doing physical, right? At the very, very best, you're going to be able to get those books at 50% off from the publisher.”

Own the audience instead of running the book club

Rather than monetize a book-club subscription with all its fulfillment and customer-service overhead, Ryan Holiday built a 250k+ reading-recommendation newsletter and takes affiliate commissions when people buy through Amazon or his store. He'd rather own the list than service the box.

“But I'd much rather just have that list and that audience than try to monetize a book club itself, because the bundle of including the book, plus fulfilling the book, plus customer service and all that other stuff, it— I think, I think it's just hard to make the business itself work.”

Steal thisBuild the audience and earn affiliate revenue instead of taking on fulfillment and customer service.

It's almost easier to be great than to be good

After meeting world-class people like four-ring Hall-of-Famer Manu Ginobili, Ryan Holiday says he's become less impressed by rings and money and more by whether someone is a good parent, lives in reality, and can enjoy what they have. His goal: be world class AND a normal person.

“I think like to me, what the, the journey that I've tried to go on inspired by people like that is I want to be world class at what I do and, and like be somewhat of a normal person. Like who else? It's almost easier to be great than it is to be good. If that makes sense.”

Dov Charney and the danger of becoming a 'manifest cowboy'

Ryan Holiday, who worked directly under American Apparel founder Dov Charney, describes the entrepreneur's trap: you do the insane thing everyone said would fail, it works, and then you start seeing anyone who criticizes you as the enemy and ignore advice about operators, overexpansion and conduct, until you crash and burn.

“The dangerous thing you take from that is you now, as you said, see yourself as a person who does that, and you see people who tell you that you can't do it or shouldn't do it or criticize you for doing it, you see them as the enemy, right?”

Cerro Gordo's YouTube hit was built on skills learned for Daily Stoic

Ryan Holiday explains that Brent didn't randomly start the Ghost Town Living channel: he had built the Daily Stoic YouTube and podcast first, took Holiday's own camera to the ghost town, and used skills developed on the job. The lesson: people underestimate how long you develop baseline skills before the moment meets the man.

“Cerro Gordo was started with equipment that he had got for Daily Stoic and then used skills that he had developed, uh, with Daily Stoic that ultimately blew up into this thing that I don't think he— definitely not I would have predicted. But like, people often underestimate how long you have to spend developing like a baseline of skills before You know, sort of the man meets the moment, so to speak.”

Michael Lewis and the step-function career

Ryan Holiday uses Michael Lewis to illustrate how careers grow in step functions: a strong nonfiction writer for decades who became uniquely suited to write The Big Short when 2008 hit. The point is that working long enough positions you to capitalize when a once-in-a-generation moment arrives.

“And then 2008 happens and it's the most inexplicable but widespread financial event of, you know, since the Great Depression. And he is uniquely suited to write The Big Short, which was his big transformative, you know, huge book like Moneyball, The Blind Side, the other movies that come out.”

Success makes you more risk-averse, not more courageous

Ryan Holiday's counterintuitive observation: you'd expect security to make you bolder, but the rational response to having a lot is to become more risk-averse because you know how hard it was to build, creating a tension between pushing yourself and protecting what you have.

“Well, you, you think that being successful will make you more courageous because you are more secure, but it actually, the, the, the rational response to having a lot is to become more risk-averse because you know how hard it was to get it.”

Stop announcing your deal size: it only has downsides

Ryan Holiday stopped press-releasing how much his book deals sell for because publicizing the figure makes you a target, can read as selling out, and tips off competitors writing in the same niche to a multi-year project you're working on.

“I said, one, telling people how much money I made from it, it makes you a target, makes you weird. You know, it, it, it could. It could somehow be seen as selling out or something. But then the other part, I thought, I don't want people— this is an idea that's going to take me 4+ years to get to the end of. Why would I want to give people who might be writing in the same niche like a heads up about what I'm doing?”

Steal thisKeep deal figures private to avoid becoming a target and tipping off competitors.

Ryan Holiday's podcast crossed 100 million downloads

Ryan Holiday shares that his podcast (which he sold to Amazon's Wondery) crossed 100 million downloads and is getting close to being able to do that annually.

“Like I think we, we crossed 100 million downloads.”

A $10K Stoic boot camp — like Daily Stoic meets Wimp2Warrior

Sam points to Ryan Holiday's Daily Stoic empire ($25 coins, $19 email courses) and suggests the real opportunity is an intense, transformational boot camp: a month-long Stoic program charged at ~$10,000 that loads of people, himself included, would pay to attend.

“But I would imagine that if Ryan Holiday had like a Stoic boot camp for like a month and he charged like $10,000 and like it was around this mental fitness idea, I think loads and loads of people, including me, would pay to go.”

Steal thisTurn a low-priced info/content brand into a high-ticket, time-boxed, transformational in-person program.

Books are price-anchored: people will pay $26, not $32

Holiday notes a book represents two years and 60,000 words of work, yet readers have a fixed sense that a book should cost around $26 regardless of quality.

“But like that book is $26 and people, if that book was $32, people would be upset because there's like a sense of what a book should be, right? Like this is what people are willing to pay.”

Why Ryan Holiday refused t-shirts and invented the memento mori coin

Holiday rejected merch t-shirts as a low-margin, multi-SKU headache and instead created a single high-margin memento mori coin, manufactured by a Minnesota mint that invented the AA sobriety chip.

“So like bands become popular, people build a brand, the first thing they always think is t-shirts. But what I remember is just how fucking complicated t-shirts are. First off, 'cause you have to get someone to make them, But if you sell one t-shirt, that's already at a minimum 3 SKUs, right? Small, medium, large.”

Steal thisSkip multi-SKU apparel; build one high-margin physical product that embodies your idea.

Daily Stoic sells tens of thousands of memento mori coins a year

Holiday won't give an exact figure but says he sells tens of thousands of the coins annually, likely making him the mint's biggest customer.

“I, uh, I don't want to say exactly how many, but like tens of thousands. It's a lot of them.”

Daily Stoic sells tens of thousands of memento mori coins a year

Holiday won't give an exact figure but says he sells tens of thousands of the coins annually, likely making him the mint's biggest customer.

“I, uh, I don't want to say exactly how many, but like tens of thousands. It's a lot of them.”

Shopify will be the biggest company in the world

Holiday predicts Shopify becomes the biggest company in the world because it lets anyone turn an idea into a product, plug into third-party warehousing, and sell it — unlocking enormous untapped potential.

“This is why I think Shopify is going to be like the biggest company in the world, because they like let people do that.”

Trust Me, I'm Lying took 10 years to earn out its advance

Holiday's first book sold well and got huge attention, but its royalties will only cross from negative to positive on the advance ledger 10 years after publication, in July 2022.

“Like, by The, the, the— I'm— it's looking like the, the royalty statement I will get in July of 2022, which will be the 10-year anniversary of the book, it will finally go from, from negative to positive on the advance statement.”

Holiday doubled his announced book advance because nobody fact-checks press releases

His real advance for Trust Me, I'm Lying was about $200K, but he announced $500K to prove the book's own thesis that the media doesn't fact-check press releases. Nobody checked.

“I announced that it had been sold for $500,000 because I know— I knew people did. Nobody actually fact-checks press releases, so, uh, trust me. Yeah, so, so the whole point of the book was to prove that, like, uh, the problems I was talking about in the media system in the book were real. So I, I promptly, uh, doubled the advance when I announced it, and, and, uh, nobody, nobody checked.”

Write the book first to negotiate from a finished asset

Most nonfiction sells on a proposal, but Holiday left his job and wrote the whole manuscript first, so he negotiated his deal holding a finished 'piece of property' rather than a promise.

“Almost all nonfiction is sold, uh, with a proposal and then you go write the book. But I didn't, I didn't necessarily need to do that. So I wrote the book. So I had what was like, I had, I had a, it's like I had a good piece of property. Like I, I wrote something.”

Steal thisFinish the asset before you negotiate, so you're selling a finished thing, not a promise.

Most nonfiction authors make more from speaking than books

Ryan Holiday notes most nonfiction authors earn more from speaking than from their books — partly because speaking is lucrative, but mostly because most authors don't sell many books.

“it's most nonfiction authors make more money from speaking than from books. That's because speaking can be more lucrative, but it's also because most authors don't sell very many books, right?”

Almost all publishing income comes from the backlist

Ryan Holiday explains the front-list/back-list split: a frontlist title is its first year, after which it becomes backlist. Most books stop selling once they leave the frontlist, yet almost all of publishing's income is from the backlist — so he engineers a catalog of titles that sell every year.

“Front list is anything within one year. That, like, the year of release, that's considered a frontlist title, and then it becomes a backlist title after a year. So most titles stop selling when they leave the backlist— when they leave the frontlist and become on the backlist. But almost all of the income in publishing is from the backlist.”

Steal thisBuild a catalog of evergreen titles that sell every year (backlist), not one-hit frontlist books you must keep replacing.

Most nonfiction authors make more from speaking than from books

Holiday notes most nonfiction authors earn more from speaking than book sales, partly because speaking is lucrative and partly because most authors barely sell any books.

“most nonfiction authors make more money from speaking than from books. Um, that's because speaking can be more lucrative, but it's also because most authors don't sell very many books, right?”

Write the 'Christmas song' of your category for an annuity

Holiday's agent pushed him to write The Daily Stoic, a page-a-day book, promising it would be his best seller because it sells every New Year's. It worked — it sold more copies this January than last January, the publishing equivalent of a Mariah Carey Christmas annuity.

“And he was like, it will be your best-selling book. And I was like, there's no way, that doesn't make any sense. Every New Year's it will. He's like, it will. And he's right, the book sold, uh, more copies this— already this January than last January.”

Steal thisCreate a product tied to a recurring calendar moment (New Year's, holidays) so it re-sells itself every cycle as an annuity.

Backlist over frontlist: build a catalog that sells every year

In publishing, a title is 'frontlist' for its first year then becomes 'backlist.' Most books die on the backlist, but almost all publishing income comes from backlist titles, so Holiday engineers a catalog of evergreen books that sell every year rather than chasing new releases.

“Frontlist is anything, uh, within one year, uh, that like the year of release, that's considered a frontlist title. And then it becomes, uh, a backlist title after a year. Um, so most titles stop selling when they leave the backlist, when they leave the frontlist and become on the backlist, but almost all of the income in publishing is from the backlist.”

Steal thisBuild evergreen catalog titles that sell every year instead of chasing new launches.

Obstacle Is the Way got a $75K advance and outsold the $200K book many times over

Holiday's publisher was skeptical of an ancient-philosophy book and offered only $75,000 for The Obstacle Is the Way, which went on to sell many times more copies than his first book that earned a ~$200K advance.

“I got $75,000 for The Obstacle Is the Way. Um, which has sold, you know, many, many times more copies than Trust Me, I'm Lying.”

Treat your physical space as a content set, not a retail business

Holiday realized his bookstore's least important revenue stream is actually selling books; the property's real value ranks as office first, content/filming set second, real estate third, and retail last. The ghost town YouTube play works the same way.

“so opening the bookstore that like, that making money from selling books might be the third or fourth, like, least important revenue stream or, or use of the property, like the office being number one, uh, the space to film and make stuff like content being number two, and then like real estate being number three, and then, uh, you know, like the actual, uh, brick-and-mortar retail business being like four or five.”

Steal thisValue a physical space as a content set and asset first; treat retail revenue as the bonus.

One person made a TV-quality weekly show for a few thousand dollars a month

Holiday marvels that Brent, with a drone, a GoPro, and one Sony camera, put out a 45-minute, television-quality YouTube video every week for millions of viewers at a cost of a couple thousand dollars a month.

“he was at one point putting out like a 45-minute video a week. Like, he was putting like a television quality show out for millions of people, you know, for like a couple thousand dollars a month. It's crazy what you can do.”

Shoot in 30-60 second blocks to get 4+ bites at the apple per clip

Holiday films in 30-second-to-1-minute chunks so each clip can go on Twitter, Instagram Reels, Facebook, and TikTok, and then eight of those stack into an 8-minute YouTube video — many platforms from one shoot.

“so if I'm shooting in, you know, between 30-second and 1-minute chunks, okay, so that goes— content of that size can go on Twitter, Instagram as a reel, can be a Facebook video, and it can be TikTok. So you've got like 4 shot 4 bites of the apple there. Then that content can be packaged together to make videos on YouTube. So I'll take like 8 of those and that can become an 8-minute YouTube video.”

Steal thisFilm in 30-60s blocks so one clip serves Twitter, Reels, Facebook, TikTok, then stack into YouTube.

Audience capture: the algorithm seduces creators into telling fans what they want to hear

Holiday argues smart contrarians get trapped by audience capture — as relevance slips, the algorithm rewards controversy, so creators chasing the next 'blast from the past' hit spiral toward more extreme positions.

“I think there's, you know, what audience capture is, where you sort of get used to telling the audience what they want to hear. And so the algorithm is very seductive. It tends to reward, like, obviously controversial things. It rewards, you know, polarizing things.”