Ryan Holiday
Founder & Host, The Daily Stoic · 2 appearances on the record.
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Ryan Holiday is an author and former Director of Marketing at American Apparel who popularizes Stoic philosophy. He is best known for bestselling books including The Obstacle Is the Way and Ego Is the Enemy, as well as the Daily Stoic platform and podcast.
35statements → 11claims → 5claims resolved → 60%fully supported → 3.77/5average certainty → 1.94/5average debate potential → ≈4.0/5argument clarity, estimated → 64said about them ↓
3 supported 0 partly supported 2 contradicted 1 not yet assessed 5 not checkable as stated how the 11 claims stand · each chip opens the sources
3 predictions · 8 assertions · 4 opinions · 11 insights · 9 disclosures · every statement was checked. The predictions and assertions are the 11 claims: statements the public record can support or contradict. 5 are resolved, 1 is not yet assessed, and 5 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.
The record, in short
What the tape says about how Ryan argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.
Their most notable supported claim
Expressed certainty vs assessment result
weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet
How they sound: not measured why? →
We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Ryan Holiday on measured tape to publish a rate. This says nothing about how they speak.
Everything Ryan Holiday said on My First Million that made the record, most notable first. Filter by type, assessment or year in the ledger →
Holiday: Peter Thiel's obsessive drive leads to poor political bets
“The problem is if you're the kind of person who it's like, I'm going to spend 10 years chasing down this media outlet when everyone is telling me not to do that. You're also the kind of person who can get sucked into other things that I think are going to pay …”
Holiday: Shopify will become the biggest company in the world
“This is why I think Shopify is gonna be, like, the biggest company in the world, because they, like, let people do that.”
Ryan Holiday: Fox News programming exists to sell grifts to viewers
“There's an argument that Fox news basically exists for the sake of like reverse mortgages, gold coins. And other forms of grift. Like, if you watch Fox News, just the commercials, you get a sense of, like, Just how dumb the audience is to be perfectly honest.”
Holiday lied about his debut advance to expose media negligence
“It was, I think it was 200 with some incentives. Although when I announced it I announced that it had been sold for 500,000 dollars because I know, I knew people, nobody actually fact checks press releases. So yeah. So, so the whole point of the book was to pr…”
Holiday: Media mistreatment pushes figures into tribal contrarianism
“When you've been very mistreated by like, say the media or just like elite culture it's very hard for you to agree with those people, even when they're right. So you end up, going back to the contrarianism, you end up, like, going against things that ordinaril…”
Holiday: Bestseller lists do not meaningfully drive direct book sales
“There is, I think people tell themselves a story about how being on the list helps them sell more copies. 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 …”
Holiday: Releasing a book in paperback is a multimillion-dollar decision
“The distinction, the decision to put your book in paperback is actually a multimillion dollar decision for authors. And most authors have never even thought about this. So for instance, on a hardcover book the standard publishing contract and pretty much every…”
Holiday: Rigid, Grand Visions Lead to Disaster More Often Than Success
“All of these things start small and they build there when the person has this vision That they can clearly articulate that they know to be like that. To me, that leads to disaster more often than the prophecy comes true.”
Holiday: Achieving financial success makes you more risk averse, not courageous
“Well, you think that being successful will make you more courageous because you are more secure, but it actually, the rational response to having a lot is to become more risk averse because you know how hard it was to get it.”
Holiday: The Math Favors Traditional Book Publishing 90% of the Time
“90% of the time, you know, the math tends to go towards traditional publishing in my experience.”
Holiday: Elite performance with a normal life is harder than obsessive dedication
“Being really great at what you do and somehow managing to be, like, a somewhat normal person to me is actually, like, a rarer thing to do than to just be great at what you, like, I think if anyone decided to be, like, Tom Brady's Tom Brady, but there's a cost …”
Holiday: Self-prescribing psychotropics to heal trauma risks irreversible brain damage
“I don't think you should fuck with your brain the way some of these people are fucking with their brains, and I think it's gonna, I think we're starting to see some of the ramifications of it with some of the stuff we're talking about here, but I think this is…”
Holiday: BookScan excludes sales from author-owned bookstores
“The Wall Street Journal or BookScan, which is owned by Nielsen, just flat out told me they just don't include sales from stores owned by the author anymore”
Holiday: Business books confer more elite recognition than huge YouTube followings
“The interesting thing about books is that they sort of punch above their weight culturally. It's like the opera or something. Right. And so like you could be very famous on YouTube and your average billionaire might not know who you are, but if you write like …”
Holiday: Numerical sales goals place an unnecessary ceiling on creative success
“I don't have goals. Like, why would he, why would you even put a ceiling on it? Like what you should just try to sell as many copies as it's capable of selling.”
Holiday: Publicly disclosing deal numbers has no benefits and creates targets
“Telling people how much money I made from it. It makes you a target makes you weird. You know, 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 four plus years…”
Holiday: Most Nonfiction Authors Make More Money From Speaking Than Books
“Most nonfiction authors make more money from speaking than from books.”
Holiday: In Publishing, Almost All Money Comes from Long-Term Catalog IP
“Almost all the money is in the catalog in owning the intellectual property over the long term, but you can't do that if you are dependent, like you get paid as an author every six months.”
Holiday: Retail is the least important revenue stream for his bookstore property
“So opening the bookstore that like, that making money from selling books might be the third or fourth, like least important revenue stream or use of the property, like the office being number one The space to film and make stuff like content being number two, …”
Holiday: Discipline Is Destiny will sell over 40,000 copies in week one
“We'll probably come in a bit above 40,000 copies the first week. I would venture to guess could be higher if they keep trending this way.”
Ryan Holiday reveals he has sold five million copies of his books
“My books, I've sold five million copies.”
Holiday: Advance for 'The Obstacle Is The Way' was $75,000
“My advance on The Obstacle Is The Way was 75,000 dollars.”
Holiday: 'The Obstacle Is the Way' took 5 to 6 years to hit 1M copies
“I know it crossed the 100,000 copies mark within the first year, because there was a bonus attached to it. So it took, you know, 12 months to sell a 100,000 copies, but it probably took an additional four to five years before it crossed the one million copy ma…”
The other half of the tape: Ryan Holiday's own voice is left out of every number here. Other people bring the name up 58 times in 15 episodes on My First Million. 6 statements on the record name them. every mention, with the transcript →
Who brings them up most Sam Parr 33Shaan Puri 23Eric Glyman 1Andrew Wilkinson 1
Statements about Ryan Holiday, by other people (6)
Shaan Puri: Ryan Holiday sold $20 million of a single stoicism coin
“Like there's one skew, and I'm gonna sell, and I think he sold like twenty million dollars of this one skew. Over the years.”
Puri: People Pursuing Mindfulness and Stoicism Are Usually Still Seeking Calmness
“Usually when I find people who are gravitating towards things like meditation and stoicism and you know, micro dosing psychedelics, they feel like they're still on the search for that calmness. He felt like he found the calmness, and that was kind of the disti…”
Parr: Peter Thiel employed lawyers for a decade waiting to sue Gawker
“Peter Thiel basically employed this Three lawyers, big shot lawyers, and they're, and basically when he was outed as gay by Gawker, he employed, and this is a great book by Ryan holiday. I forget what it's called, but he employed these three lawyers and I forg…”
Puri: Ryan Holiday is the biggest customer of a major US mint
“And he also said that he works with some mint in the United States. And I guess it's one of the old famous coin mints. And he, I think he was like their biggest customer also. Like he's like, they're minting more of his momentum worry coin than they are anythi…”
Physical coins cost $1 to produce and retail for $25.
“And a coin is a great product to sell because it costs 25 bucks to sell. It costs like a dollar to make. It ships for whatever, a stamp, two stamps. So however much that is, 80 cents. There's no returns. There's no sizes. It's just like the easiest thing ever …”
Ryan Holiday makes more from Daily Stoic merch than book sales.
“Ryan Holiday wrote a book on stoicism. He's written six or seven now at this point, but he has this other property. It's a daily newsletter called the Daily Stoic, where they sell coins and merch and advertisements. He has told me that that has made more money…”
Every mention by year
tap a year for its mentions
2025 2 mentions in 2 episodes 1 per episode
2024 22 mentions in 3 episodes 7 per episode
2023 1 mention in 1 episode
2022 20 mentions in 4 episodes 5 per episode
- Is The Rock Going to Make $1B+ From Tequila? + Placebo Water, STR Update, and More
- This Guy Went From $0 to Billionaire By Starting A Toy Factory In China (#372)
- The 2022 Milly Awards (#401)
- 9 Business Ideas To Profit From The 2022 A.I. Gold Rush (Using Dall-E & GPT3) (#376)
- every mention in 2022, scene by scene →
2021 13 mentions in 5 episodes 3 per episode
- This Year's Best Twitter Accounts to Follow
- How to Make Millions by Unbundling Etsy | My First Million #207
- How Course Businesses Work & How Irish Pubs as a Service is Making Millions | My First Million #183
- How an Astrology App Makes $10m+ & Why a Boxing Announcer is Worth $400m | My First Million #182
- Unbundling Disney, Why CNN is Just Like the WWE, YouTube Creator Camps, and More
- every mention in 2021, scene by scene →
Appearances (2)
| Episode | Date | Speaking time |
|---|---|---|
| Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More | Oct 4, 2022 | 47m |
| Ryan Holiday On The Economics Of Book Publishing | Feb 8, 2022 | 38m |