Oct 4, 2022 · 1h 13m · my-first-million
Ryan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More (#370)
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Author Ryan Holiday joins host Sam Parr to break down the real financial economics of book publishing, scalable content creation systems, and how applying Stoic principles helps creators balance extreme ambition with a grounded life.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 28% of the talking time here. How this is scored →
The hosts as informed peer 4.3 Guest teaching 5.3 Guest disagreement 2.2 The hosts pushing back 2.2
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 48:16 Ryan dismisses the 'manifest cowboy' reality-distortion mindset
Ryan directly challenges Sam's claim that strong-willed operators can bend reality at will, arguing that hubris destroyed figures like American Apparel founder Dov Charney.
Hardest push from the hosts ▶ 1:07:07 Sam presses Ryan on contradicting his own fisherman parableSam catches Ryan saying he hopes to reach a place where money does not matter before writing a biography, forcing Ryan to explain why he is not already living by his own advice.
Biggest teaching moment ▶ 7:15 Ryan reveals the multimillion-dollar impact of paperback contract clausesRyan educates Sam on publishing contract mechanics, explaining why authors like Tim Ferriss avoid paperback editions due to drastic royalty drops on MSRP.
The host holds their own ▶ 1:01:04 Sam asserts the reality of step-function career growthSam draws upon his direct experience building and selling The Hustle to prove that rapid step-function breakthroughs are legitimate when built upon deliberate skill apprenticeship.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Discipline Is Destiny Launch and Bestseller List Realities | 3 | 6 | 2 | 1 | Sam opens by asking about the mechanics of the bestseller lists and whether owning a bookstore skews numbers. Ryan educates Sam on BookScan anti-fraud rules and why industry lists do not actually drive consumer buying behavior. | |
| The Financial Economics of Book Publishing and Royalty Contracts | 4 | 8 | 2 | 2 | Sam is curious about author earnings after seeing Mark Manson's real estate purchases. Ryan delivers a comprehensive masterclass on publishing economics, detailing standard hardcover 15 percent royalties, paperback trade-offs, and international copyright leakages. | |
| Venture Wealth, Creative Fulfillment, and the Fisherman's Parable | 4 | 5 | 1 | 1 | Sam compares author income to venture investing windfalls like Tim Ferriss's angel investments. Ryan agrees that investing scales faster, but explains the cultural prestige of books and shares the parable of the fisherman to highlight misplaced financial goals. | |
| Internalizing Philosophy versus Managing Daily Emotions | 2 | 4 | 1 | 1 | Sam asks whether writing philosophy enables Ryan to absorb his own advice better than readers. Ryan candidly admits he understands macro philosophical questions but still struggles with everyday emotional management. | |
| The Quantity versus Quality Debate and Content Systems | 5 | 6 | 3 | 2 | Sam and Ryan align on the idea that quality versus quantity is a false dichotomy in content creation. Ryan details his rigorous drafting workflows and challenges creators who hide behind long timelines without delivering commensurate quality. | |
| Commercial Break: HubSpot CRM | 5 | 5 | 1 | 2 | Following the mid-roll ad, Sam proposes book subscription clubs and cites his personal connection to Vinyl Me Please. Ryan breaks down the unfavorable logistics and low margins of physical book fulfillment compared to newsletter audience monetization. | |
| Balancing Elite Performance with Family and Normalcy | 3 | 6 | 2 | 1 | Sam asks Ryan about role models among the high performers he meets. Ryan contrasts single-minded, out-of-balance icons with grounded figures like Manu Ginobili and an unnamed rock star who maintained long-term family stability. | |
| Peter Thiel, Gawker, and the Dangers of Hubris | 6 | 7 | 6 | 6 | Sam embraces Peter Thiel's vengeance against Gawker and describes himself as an intoxicating 'manifest cowboy' who bends reality to his will. Ryan firmly pushes back, citing Dov Charney and political hubris to demonstrate how believing one can bend reality inevitably leads to catastrophic ruin. | |
| The True Story of Cerro Gordo and Brent Underwood | 4 | 6 | 2 | 1 | Sam inquires about the viral ghost town project Cerro Gordo. Ryan demystifies the overnight success narrative by detailing Brent Underwood's decade-long apprenticeship building Daily Stoic media channels before the ghost town succeeded. | |
| Apprenticeship, Step Functions, and Career Longevity | 6 | 4 | 3 | 4 | Sam shares how Robert Greene's Mastery shaped his acquisition of copywriting skills prior to selling The Hustle, while arguing that growth step functions are real. Ryan acknowledges this but contextualizes it with Michael Lewis's multi-decade trajectory. | |
| Long-Term Creative Ambitions and Playing with House Money | 5 | 3 | 2 | 4 | Ryan discusses his long-term ambitions to write a major biography while playing with house money. Sam smartly calls back to the fisherman story from earlier, questioning why Ryan does not already feel financially unconstrained, which Ryan clarifies is a creative scheduling issue. | |
| Deal Privacy, Podcast Reach, and the Power of YouTube | 5 | 4 | 1 | 1 | Ryan explains why he avoids publicizing exact deal numbers, and both share metrics on their respective media properties, agreeing on the massive distribution power of YouTube before ending on warm mutual appreciation. |
Statements from this episode (21)
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.”
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: 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 …”
Ryan Holiday reveals he has sold five million copies of his books
“My books, I've sold five million copies.”
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: Advance for 'The Obstacle Is The Way' was $75,000
“My advance on The Obstacle Is The Way was 75,000 dollars.”
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: '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…”
Holiday: My entire media brand and bookstore operate with under 15 employees
“I'm saying that I probably have 10 employees, maybe, maybe 11 or 12, but less than 15.”
Holiday: Publishers Cap Subscription Book Discounts at 50%
“At the very, very best, you're gonna be able to get those books at 50% off from the publisher.”
Holiday: Prefers Book Newsletter Over Subscription Club Due to Margins
“I just prefer to like, look, if you want to buy the book from my bookstore, I make a little bit of money doing that. If you buy it from Amazon, I get the commission, but I'd much rather just have that list in that audience than try to monetize a book club itse…”
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: 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: Cerro Gordo lost money rapidly before Brent Underwood moved there
“Brent's idea was buy this place, find, build a hotel on the site and make it some sort of like luxury resort thing that, that, that they failed to do for like two years, maybe even three years. He had no intention of living up there. It was losing money hand o…”
Sam Parr: The Hustle sold for tens of millions when I was 30
“So the hustle we sold for, let's say tens of millions of dollars, which is like, I think by most people, if you do, I think I was 3130 when we sold it, which is so like, that's six that I would say it's objectively successful, but compared to others, like it's…”
Holiday: Mark Manson built an audience for a decade before his book
“To give Mark credit though, Mark doesn't hit the lottery. I mean, Mark was an online copywriter and marketer and had a platform for a decade before he writes a book, right?”
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: 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: 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: Daily Stoic Podcast Crossed 100 Million Downloads
“Like I think we crossed a hundred million downloads.”
Sam Parr: My First Million generates 2M to 5M monthly impressions
“Our monthly downloads on the podcast are, Range between 1.5 and two or 1.3 and two million. And then the pod, the, and then the YouTube episode views are another one or two million. So we're in the range of two to five on any given month.”