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My First MillionRyan Holiday Reveals How Much Best Selling Authors Make, Crazy Peter Thiel Stories & More (#370)
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New book launch, first-week sales expectations, and why bestseller lists matter less
Sam and Ryan open with Ryan’s new release and immediate early sales indicators. Ryan explains why selling through his own bookstore can exclude him from certain bestseller lists and why he’s stopped caring about the status of list placement.
- •Ryan shares that his new book is "Discipline Is Destiny" and discusses early momentum.
- •He estimates first-week sales and notes audiobook numbers take longer to fully see.
- •Ryan explains his own bookstore sales can keep him off the Wall Street Journal list and makes the New York Times list uncertain.
- •He describes how bestseller lists may flag bulk sales and why some lists exclude author-owned stores entirely.
- •Ryan says he now prioritizes actual readership and total sales over list recognition.
Do bestseller lists actually drive sales? How readers discover books
Sam asks whether list placement helps sell more books. Ryan breaks down the major national lists and argues that most readers don’t buy because of the lists, and many don’t even know where to find them.
- •Ryan names the three national bestseller lists: New York Times, Wall Street Journal, and USA Today.
- •He says people often believe list placement boosts sales, but he’s never heard of someone buying due to a list.
- •Sam frames the conversation around the perception that the book business is weak versus evidence of big author wealth.
- •Ryan emphasizes the fundamental goal of book writing is to be read, not to collect status markers.
Publishing economics: industry size, royalties, and the hardcover vs. paperback decision
Ryan argues publishing is a large business and walks through how revenue flows from retail price to author royalties. He explains standard royalty structures and why format choices—especially paperback timing—can be a major financial lever for authors.
- •Ryan cites publishing as a large industry and names major players like HarperCollins and Penguin Random House.
- •He uses his own five million copies sold to illustrate gross revenue versus what authors actually earn.
- •Ryan explains wholesale pricing and middlemen reduce revenue before royalties.
- •He details standard hardcover royalties and contrasts them with paperback royalties and pricing.
- •He says deciding when to go paperback can be a multimillion-dollar decision and gives examples of long-lived hardcover titles.
Audiobooks, ebooks, international sales, and why copy totals don’t equal cash
The conversation shifts to audio and ebook royalties, then to how international publishing complicates earnings. Ryan explains that lower transparency, different deals, and even lack of copyright enforcement can make global sales less lucrative than they appear.
- •Ryan says ebook and audiobook royalties are higher percentages but on lower price points.
- •He estimates earnings per book across formats often land in a few dollars.
- •Ryan notes international popularity can reduce earnings compared to domestic standard royalties.
- •He shares an example of an unauthorized Persian edition and explains he won’t earn from it.
- •Ryan cautions against multiplying total copies sold by a single royalty rate to estimate an author’s cash.
Books vs. scalable wealth: investing, checks that beat royalties, and cultural leverage
Sam asks whether Ryan’s books might become small compared to other income streams, like investments. Ryan acknowledges investing can produce outsized returns with less work, but he also explains how books confer cultural influence and access, especially among wealthy readers.
- •Sam compares book income to wealth from investing and asks if Ryan’s path will mirror that model.
- •Ryan describes receiving investment-related checks that would require selling many books to match.
- •He says this can make publishing economics feel less compelling, even if they’re good.
- •Ryan argues books “punch above their weight” culturally and can create elite-group name recognition.
- •He notes many very successful businesspeople still want to write books, highlighting the non-financial appeal.
How Ryan produces so much: enjoying the work, steady success, and avoiding the post-hit trap
Sam marvels at Ryan’s output across newsletters, books, podcasts, and YouTube. Ryan explains he likes making things and believes quantity and quality can reinforce each other; he also reflects on why slow-and-steady success can be easier to live with than a massive breakout hit.
- •Sam lists Ryan’s multiple channels of output and asks how it’s possible to sustain high quality.
- •Ryan says he’s energized by the work itself and often has more ideas than distribution “pipes.”
- •He agrees that quantity and quality don’t have to be opposed and that doing more increases odds of something great.
- •Ryan describes how hard it can be to follow a massive hit, referencing the pressure on breakout authors.
- •He contrasts his steady growth with sudden mega-success and says operating in a big niche can be a good place to be.
Systems and discipline for daily publishing: batching, workflows, and skepticism of “quality takes time”
Ryan explains how he schedules Daily Stoic and Daily Dad content far in advance and how batching makes daily publishing feasible. He also challenges the idea that taking a long time automatically produces better work, arguing many creators hide procrastination inside “quality.”
- •Ryan says he writes the vast majority of Daily Stoic and Daily Dad emails, with limited team help on drafts.
- •He describes a tracking system that keeps newsletters scheduled weeks or months ahead.
- •Ryan explains how short writing sessions can produce multiple emails at once.
- •He argues “quality over quantity” often doesn’t show up in the finished work and reflects inefficiency.
- •He contrasts that with writers whose long timelines are evident in the depth and research of the final product.
YouTube production approach and team size behind Daily Stoic, The Painted Porch, and more
Ryan explains how different YouTube formats are created, from compilations to scripted history/biography-style videos. He describes how book writing supplies the core material across formats and shares the size of the team supporting his work, including the bookstore.
- •Ryan outlines YouTube formats: compilations of short clips versus more structured explanatory videos.
- •He says some videos start from team outlines combined with material he’s written elsewhere.
- •Ryan describes translating book ideas into other mediums with help from his team.
- •He confirms he mostly uses Google Docs.
- •Ryan says the team is roughly around 10 people, including the bookstore staff, and fewer than 15 total.
Why book clubs are hard businesses: margins, logistics, and reader behavior
Sam asks about book-of-the-month style subscription businesses. Ryan explains why the model is challenging: limited readership overall, thin margins on physical books, and the heavy operational burden of fulfillment and customer service.
- •Sam references established book subscription brands and asks if Ryan has explored the model.
- •Ryan explains publishers’ discounts cap margins and subscriptions compete with cheaper entertainment alternatives.
- •He says not many people read, which constrains market size.
- •Ryan describes his long-running book recommendation newsletter and why he prefers audience-building over operating a club.
- •He says servicing subscribers with logistics and support makes scaling a physical book club difficult.
Vinyl Me, Please comparison and chart exclusions: discovery works differently for music
Ryan and Sam compare book clubs with Vinyl Me, Please, discussing discovery dynamics and repeat consumption. They also return to the theme of rankings excluding bulk or subscription-driven purchases, paralleling bestseller list quirks.
- •Ryan mentions Vinyl Me, Please as a larger business than many would assume.
- •Sam recalls chart recognition issues where subscription volume wasn’t counted for rankings.
- •Ryan connects this to bestseller list exclusions and how rankings can “skunk” legitimate volume.
- •They discuss how music is consumed more passively and repeatedly, supporting subscription discovery.
- •Ryan suggests book discovery is constrained because readers have limited “room” for new books.
Admiring grounded excellence: athletes, fame, and being world-class without losing normal life
Sam asks who Ryan admires among people he’s met. Ryan talks about being more impressed by groundedness—good parenting, living in reality, enjoying life—than by raw achievement, and shares experiences with elite athletes and a highly successful musician.
- •Ryan describes having lunch with Manu Ginóbili and being struck by his normalcy alongside elite achievement.
- •He contrasts the stereotype of greatness requiring imbalance with examples of high performance and stability.
- •Ryan says he now evaluates success by realities like family relationships, groundedness, and enjoying the present.
- •He discusses Chris Bosh as similarly admirable and notes how competitors can remain personally separate.
- •Ryan tells a story about visiting a musician’s home via helicopter and admiring long-term family stability and rootedness despite extreme success.
Peter Thiel stories and revenge logic: power, resentment, and reality distortion fields
Sam brings up Ryan’s reporting on Peter Thiel and asks what Thiel was like. Ryan explains how revenge can feel understandable at high levels of power while warning that believing you can bend the world to your will can spill into irrational bets, including political ones.
- •Sam references Thiel’s long-term strategy against Gawker and other intense security/escape details.
- •Ryan explains why feelings of humiliation and impotence can motivate a decade-long campaign.
- •He distinguishes understandable revenge impulses from the broader danger of believing rules don’t apply to you.
- •Ryan discusses how that mindset can lead to questionable political bets and overconfidence.
- •He uses Dov Charney as an example of entrepreneurial success feeding a destructive “reality-bending” self-concept.
Cerro Gordo and Ghost Town Living: the non-obvious path to a viral success
Sam asks about Cerro Gordo and the plan, crediting the YouTube channel with helping him during the pandemic. Ryan explains the messy reality behind the story: early struggles, financial losses, shifting plans, and how Brent’s behind-the-scenes apprenticeship made the channel possible.
- •Sam describes the appeal of Ghost Town Living and asks how it got so good so fast.
- •Ryan says one mine goes 900 feet down and emphasizes how extreme the work is.
- •He explains the original plan was a hotel/luxury concept that didn’t work for years and the project lost money initially.
- •Ryan shares that Brent previously interned for him and built systems for Daily Stoic, developing production skills over time.
- •He explains the channel started using Daily Stoic equipment and that long skill-building preceded the “moment” that went viral.
Apprenticeship, step-function growth, and long-term creative ambition
They reflect on how apparent “overnight” success often rests on years of preparation, and how careers can jump in sudden steps. Ryan discusses the idea that his body of work may be training for a future, uniquely suited project while still feeling satisfied with his current career.
- •Ryan asks Sam whether his current work is an apprenticeship for a larger future company; Sam agrees strongly.
- •Sam argues step-function growth is real but usually requires years of skill-building before the jump.
- •Ryan cites Michael Lewis as an example of a long career that became newly essential at the right historical moment.
- •Ryan says he’s satisfied beyond what he once imagined, yet still hopes for a future “book at the moment.”
- •They discuss how ambition persists, how goalposts move, and Ryan’s preference for pursuing ceilings-free output over fixed numeric goals.
Future projects, risk aversion after success, and why Ryan doesn’t share deal numbers
Ryan outlines his current professional mountain—a four-book interlocking series—and hints at wanting to write a major biography someday. He and Sam also discuss how success can increase risk aversion, and Ryan explains why he avoids publicizing financial figures and deal sizes, including a podcast deal.
- •Ryan says his main focus is completing the four-book series on an ambitious timeline.
- •He says he’d like to attempt a large biography someday but won’t name the subject to avoid idea theft.
- •Ryan and Sam discuss the tension between having “house money” and becoming more protective and risk-averse.
- •Ryan explains he stopped announcing deal amounts because it can make you a target and offers little upside.
- •He reveals he did a podcast deal with Amazon Wondery, notes the podcast’s scale, and both discuss YouTube growth as a major opportunity; they close with where to buy the new book for Ryan’s best economics.
