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My First Million5 Genius Business Tactics Turning Broke Authors Into Millionaires
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Ryan Holiday’s Daily Stoic: turning a book idea into a high-margin merch business
Sam kicks off with Ryan Holiday as an example of an author whose biggest earnings come from extensions beyond book sales. They discuss how The Daily Stoic newsletter and simple products—especially a coin—can out-earn the books that made the author famous.
- •Sam recounts Ryan Holiday’s comment that many authors claim speaking pays more than books because they didn’t sell many books
- •Sam says Ryan’s non-book businesses (The Daily Stoic newsletter, ads, merch) have made more than his book sales
- •They break down why a coin is an unusually “easy” product: low cost to make, simple shipping, no sizing/returns
- •Shaan recalls Ryan saying he worked with a U.S. mint and implied huge volume for the coin
James Patterson as a scalable “brand author” built for volume
Sam introduces James Patterson as an author whose output and economics look more like a company than a solitary writer. The key idea: scale book production through process, co-authors, and a focus on quantity.
- •Shaan doesn’t recognize James Patterson, prompting Sam to frame him as a massive bestseller-level hitmaker
- •Sam sets up Patterson’s extreme publishing pace (averaging multiple books per year and later far more)
- •The core question becomes how Patterson can publish at that volume, especially later in life
- •The episode positions Patterson as an example of making authoring work like a scalable business
The Stratemeyer-style “hit factory” model and Patterson’s co-author system
Sam explains a historical template for formula-driven publishing, then shows how Patterson modernized it with teams and co-authors. Shaan highlights how this approach breaks traditional “prestige author” norms by productizing the craft.
- •Sam describes the Stratemeyer Syndicate model: series rules, chapter structures, and consistent “house author” branding
- •Sam explains Patterson’s workflow: outlines/frameworks, co-authors drafting, Patterson editing with notes like a script review
- •Sam claims Patterson has written only a portion of the books credited to him and uses high-profile co-author pairings
- •Shaan frames the strategy as rejecting preciousness: formulaic writing, hiring help, and stacking singles/doubles over time
Jack Carr’s brand-heavy fiction and affiliate commerce layer
Sam spotlights Jack Carr’s thrillers as a new kind of monetization: heavy product naming inside the story that funnels readers to purchase pages. They discuss how book characters can drive demand for the exact gear described in the narrative.
- •Sam describes noticing constant brand and product naming inside Carr’s books (weapons, coolers, gear)
- •Sam finds Carr’s website with curated “gear guides” that include affiliate links
- •Sam notes Carr also sells products directly, including an item featured prominently in the story
- •Shaan reacts that book-based product placement can mirror how it works in movies and influencer commerce
Steve Rinella and Meateater: content-to-commerce at $100M revenue scale
Sam shifts to Steve Rinella as the clearest example of turning authorship and media into a large commerce business. Shaan connects it to a broader “content to commerce” investment thesis and explains why niche lifestyle audiences can be extremely valuable.
- •Sam traces Rinella from outdoor journalism to books (foraging/Thanksgiving concept and American Buffalo) to Meateater
- •Sam describes Meateater expanding into podcasts, newsletters, and acquiring product brands (e.g., duck calls, clothing)
- •Sam cites Meateater’s announced 2023 revenue figure of $100 million from product sales
- •Shaan explains the “content to commerce” idea: re-rate media businesses by attaching commerce to the audience
What authors really earn: tiers from ‘no money’ to blockbuster status
After the case studies, they zoom out to talk about the economics of being an author and why writing purely for money is usually a mistake. Shaan outlines tiers of author success, from most making nothing to the rare mainstream phenomenon.
- •Sam asks whether these examples change Shaan’s thinking about becoming an author
- •Shaan argues writing a book ‘to make money’ is misguided and there are easier ways to earn
- •Shaan describes the distribution of outcomes as extremely uneven, with most authors making little or nothing
- •They identify a top tier where authors become mainstream canon and get major adaptations and cultural permanence
The magic of invented universes: the JK Rowling detour
They briefly detour into awe about how a writer can create an entire universe that becomes part of everyday culture. The conversation becomes playful, reflecting on how believable a richly built fictional world can feel.
- •Sam marvels at the idea of inventing a universe with enduring concepts and language
- •Shaan says he frequently thinks about the fictional places and worldbuilding details
- •They joke about the feeling that a world might be ‘real’ and the listener might just be outside it
- •The segment reinforces how rare true cultural-scale authorship is
The “big single book” tier: Atomic Habits, Goggins, Ferriss, and scale comparisons
Shaan compares notable modern non-fiction hits by their apparent sales trajectories and implied economics. They react to how massive one runaway bestseller can become relative to books that feel culturally huge but sold fewer copies.
- •Shaan places James Clear, David Goggins, and Mark Manson in a tier of extremely high-earning single-book authors
- •Shaan describes James Clear’s reported year-over-year growth pattern and claims very large cumulative sales
- •Sam reacts with surprise at the scale and notes James Clear felt like a normal blogger before the breakout
- •Shaan contrasts this with Tim Ferriss’ The 4-Hour Workweek selling fewer copies than he expected and discusses Goggins’ publishing economics
The Navalmanack: packaging someone else’s fragmented wisdom into a product
Shaan tells the story of The Navalmanack as an “open source” curation play rather than original authorship. They discuss why organizing and distributing existing ideas can create significant value—and potentially significant income.
- •Shaan explains the concept: compiling and packaging Naval’s scattered ideas into a cohesive, usable book
- •He estimates the creator’s earnings range and expresses high confidence it exceeded $1M
- •They discuss whether Naval receives money, with Shaan emphasizing the distribution benefits as the main payoff
- •Shaan frames it as a ‘genius’ move: choose the content people already want, then make it accessible
Hugh Howey’s ‘Wool’: self-publishing momentum, guerrilla marketing, and community building
Shaan recounts Hugh Howey’s path from broke and underemployed to a breakout self-publishing success through rapid iteration and direct-to-reader tactics. The story emphasizes speed, compounding momentum, and treating books like startup products.
- •Shaan describes Howey starting broke, publishing a first attempt that sold under $1,000, then persisting
- •He tells how Howey chose a low-intensity job for maximum writing time and wrote Wool quickly
- •Howey priced low, built a small enthusiastic audience, quickly released sequels, then bundled the series at a higher price
- •Shaan lists distribution tactics: sending to Goodreads reviewers, doing a long Reddit AMA, encouraging fan fiction/art, recruiting beta readers from diehard fans
- •He describes Howey resisting traditional publishing offers due to already having distribution, and selling film rights separately
James Clear’s habit app and Andrew Wilkinson’s partnership playbook
They return to the present-day catalyst: James Clear launching a habits app built in partnership with Andrew Wilkinson’s company. Shaan argues this is a repeatable model for building businesses with trusted experts who have direct audience relationships.
- •Shaan introduces the new app launch and Sam cites the ownership split described in Andrew Wilkinson’s tweet
- •They discuss why a habits app is a natural fit for James Clear’s brand and audience trust
- •Shaan compares the strategy to earlier content-to-commerce models, but focused on partnering with authorities to build products
- •Sam predicts it may be cooler than other businesses but questions whether it will out-earn Wilkinson’s more “boring” holdings
Super-networking tactics: turning relationships into real businesses (Wilkinson, Sacca, and ‘playing offense’)
The episode closes with a deep dive into how Andrew Wilkinson and Chris Sacca build networks that compound into deals. The hosts contrast casual networking with intentional value creation—using assets like an agency or a destination home to create deeper time together.
- •Shaan describes Wilkinson’s ability to meet specific people he admires and convert those connections into tangible outcomes
- •They argue Wilkinson approaches networking in a mutually beneficial way by bringing real value (e.g., agency capabilities)
- •Sam suggests having an agency or a compelling “hosting” asset can create an excuse for deeper relationship-building
- •Shaan recounts Chris Sacca’s approach of moving to Truckee to ‘play offense’ and hosting founders for weekends instead of coffee meetings
Publisher timestamps
- 0:00Intro
- 3:00James Patterson's hit-making formula
- 12:30Jack Carr's shameless product placement
- 18:00Steve Rinella's $100M content to commerce play
- 23:30Other $20M - $50M authors
- 27:00The genius of the Navalmanack
- 30:00How Hugh Howey became self-publishing's unlikely hero
- 39:30James Clear's new habit app
- 44:00The super networking tactics of Andrew Wilkinson
