Infinite Loops — Jimmy Soni: The Publishing System is Broken (EP. 295)

Date: January 1, 2026
Host: Jim O’Shaughnessy
Guest: Jimmy Soni (CEO & Editor-in-Chief, Infinite Books)

Overview

In this densely insightful episode, Jim O’Shaughnessy sits down with author and publisher Jimmy Soni for a deep-dive into why today’s publishing system is broken—and what Infinite Books is doing to reinvent it. Pulling from hard-won experiences with legacy publishers, innovative new experiments in editing, design, and marketing, and revealing stories behind his previous books, Jimmy shares a vision for a publishing world that is transparent, data-driven, and relentlessly author-first. The conversation explores everything from authorial power shifts and A/B testing book covers to creative collaboration, marketing at scale, and their new book projects. Both former “problem authors,” Jim and Jimmy candidly detail the tools, tactics, mistakes, and revelations shaping their disruptive approach.

Main Discussion Themes

• The Problems with Legacy Publishing: Lack of process innovation, risk aversion, opaque decision-making, and paternalistic author treatment.
• Infinite Books’ Approach: Author empowerment, data-driven decisions (A/B testing), proactive marketing, transparent processes, and openness to experimentation.
• Author-Publisher Collaboration: Breaking down old power dynamics, fostering developmental editing, and maximizing royalties.
• Reimagining Book Design & Marketing: Cover design processes, long-tail and targeted marketing, audience-centric mindset, technology leverage.
• Creative Experimentation: Writer’s rooms, AI integration, and genre-crossing for authors.
• Notable Upcoming Projects: Jimmy’s “The Dao of Kobe,” rescue/relaunch of overlooked books, and Jim’s new fiction work.
• Industry Trends: Rise of audiobooks and digital sales, global reach, and the importance of taste and authenticity.

Key Points & Insights

1. The Publishing System is Outdated and Resistant to Change

• Publishers are slow to adopt modern, data-driven practices. Feedback, A/B testing, and rapid iteration are rare or discouraged.

  “If you are in a big system where process improvements are frowned upon, it’s very hard to do them.” (Jimmy Soni, 07:58)

• Legacy houses treat authors as low-status, despite authors now often having larger direct audiences.
• Marketing is rushed, focused exclusively on massive advances or dictated by arbitrary two-week windows.

2. Cover Design by Data, Not Gut Feel: The Audience Knows Best

• Jimmy recounted his PayPal Mafia book cover standoff, where legacy process and stock images failed to represent the actual diversity of the story.

  “There were so many things that I did to make that book better that I now am like, well, we’ll just build that into our process.” (04:20)

• Both Jim & Jimmy have directly paid for (and A/B tested) their own covers, learning that iterative trials with real audiences win every time (see 09:56–15:44).

  “Mine won by a country mile… Simple process improvements can make a huge difference in how a book finishes up.” (Jimmy Soni, 00:27 & 15:05)

• Notable moment: Discussion of the “selfie cover” for Dispatches from Grief, dismissed by the team but winning audience tests repeatedly.

  “We ran seven different cover design tests… and every single test came back with the selfie cover winning… so we went against what our team wanted because we knew that's what the audience needed.” (Jimmy Soni, 15:06)

3. Authors: Demand More, Be a “Problem Author”

• Legacy systems label assertive writers as “problem authors”—but that’s how innovation happens.

  “The world needs more problem authors, right?” (Jimmy Soni, 16:46)

• Authors have more leverage and direct audience than most realize. They should challenge publisher assumptions and demand seat-at-the-table participation in key decisions.

  “Be a problem author, actually be the person that pushes your industry to rethink how it’s done things.” (Jimmy Soni, 95:07)

• Infinite Books makes A/B test data and process insights available to authors, encouraging collaborative, informed decision-making.

4. Marketing: Rethinking the “Two-Week Window” and Embracing Mass Customization

• Traditional publishers still operate under the “bookstores first” mindset, but 80-90%+ of book sales are now online, requiring radically different tactics (14:00).
• At Infinite Books:
  • Marketing is continuous, iterative (“no end date”).
  • Personalization: Outbound emails are tailored to the recipient’s demonstrated interests, not “spray and pray.”
  • Use of technology/AI to identify and reach micro-audiences at scale, vastly increasing open rates and positive engagement (48:14–51:29).

  “We are moving into an era of mass customization … if we discover it’s not [scalable], then it’s not. But our early tests suggest we’re knocking it out of the park.” (Jimmy Soni, 50:10)

Notable Marketing Story:
Jimmy’s “A Mind at Play” campaign—scraping 14,000 academic email addresses for ultra-targeted outreach—became an internal model for Infinite’s direct, relevant, “delighting” connections with prospective readers (45:04).

5. Creative Experimentation: Writer’s Rooms and AI as Force Multipliers

• Novel collaborative “writer’s rooms” (a film/TV import) are now part of Infinite Books’ editorial process, leveraging team input plus AI models (i.e., Notebook LM) for rapid, in-depth developmental feedback—done in-person for focus (32:31–43:27).

  “I was blown away, actually, by how amazing it was… and that will make a better book. Ultimately, we are just trying a bunch of tools and techniques to make the product better...” (Jimmy Soni, 36:28 & 41:35)

• Both fiction and non-fiction titles benefit from this collective, iterative approach.

6. Author Empowerment and Remaking Economic Terms

• Infinite Books splits royalties 70/30 in favor of authors, a dramatic break from legacy models (22:52, 86:23).
• Authors receive real-time dashboards for sales transparency and can see where/when their book is succeeding (54:27).
• Even agented authors are approaching Infinite, drawn by higher transparency and economic upside (85:09).

7. Reviving & Cross-Pollinating Books (and Authors)

• Infinite actively searches for overlooked gems—books that underperformed due to bad marketing or labeling—and “gut renovates” them with new titles, covers, or edits (77:21).
• Encouraging authors to break genre boundaries is core; publishers’ insistence on rigid “swim lanes” stifles creativity and leaves money/culture on the table (68:16).

Jimmy's Upcoming Book: The Dao of Kobe (55:17–67:45)

• The project was inspired by pandemic-era struggles; Kobe Bryant’s “super-nerd” mindset and creative ambition resonated deeply.
• Jimmy details his discovery process, uncovering little-known interviews, notes, and Kobe’s obsession with creativity, writing, and building Granity Studios.
• The book curates and synthesizes Kobe’s thinking, seeking to reveal him as a polymath-creative, not just a basketball legend.

  “He could always get a meeting because of his basketball accolades… but he wanted to work with people who saw him as Kobe Bryant, the creative.” (Jimmy Soni, 66:19)

• Modeled after Eric Jorgensen’s Almanac of Naval Ravikant, aiming to surface wisdom currently scattered across obscure media.

Memorable Kobe Example

“When I saw those flowers… I saw a metaphor for leadership. That season I had been too much like a bright sun, always on my team, never listening to them. ... When I saw those flowers, I said, oh, my sun has to disappear for a while, and then it has to come back. Who the hell speaks like that?” (Jimmy Soni, paraphrasing Kobe Bryant, 65:10)

Other Notable Quotes & Moments

• On self-publishing vs. team publishing:

  “It’s hard enough to write the book, let alone publish the book. Which is why we think there’s still room for a new publisher because many people want to be guided through this experience.” (Jimmy Soni, 31:00)

• On prestige blinding publishing to process improvements:

  “Prestige businesses… It becomes very hard to say, the emperor has no clothes...” (Jimmy Soni, 19:41)

• On continuous, data-driven publishing:

  “If we did fewer books that sold way better, the math works for us.” (Jimmy Soni, 82:26)

• On economic fairness:

  “Doing a book shouldn’t be a privilege reserved for a small clutch of people who can afford it.” (Jimmy Soni, 93:04)

• On empowering creators:

  “Our goal explicitly is to make millionaires out of our authors.” (Jimmy Soni, 90:39)

• On what he’d incept into the world:

  “Be the person that pushes your industry to rethink how it’s done things.” (95:07)
  “Think of the story you can’t shake. … Do something about the story you can’t shake.” (95:21)

Timestamps for Key Segments

| Time | Segment | |-------------|-------------------------------------------------------------------| | 00:00–03:40 | Jimmy’s “Founders” book journey and legacy publisher woes | | 04:00–08:30 | Infinite Books: process changes, author empowerment | | 09:56–15:44 | A/B testing covers, the “selfie cover” story | | 22:52–23:32 | Technology, royalties, and Infinite Books’ author-first model | | 32:31–43:27 | Writer’s rooms, AI collaboration in editing | | 45:04–48:14 | Proactive, hyper-targeted marketing stories | | 55:17–67:45 | The Dao of Kobe: origin, process, big revelations | | 68:16–71:18 | Breaking genre limits, supporting author pivots | | 77:21–80:15 | Reviving overlooked books, “gut renovations” | | 85:09–87:48 | Agents’ unexpected enthusiasm for Infinite Books | | 88:18–90:03 | Audiobooks, digital, and future experiments | | 90:39–93:44 | North Stars: author wealth, quality, internationalization | | 95:07–96:14 | Jimmy’s “emperor of the world” advice |

Conclusion

This episode is dense with practical wisdom for anyone interested in books, creation, and the future of ideas. If you’re an author (or aspiring one), a reader curious about the business behind the books you love, or a creative of any stripe, Jimmy and Jim’s conversation is a call to arms: don’t settle for the old ways, challenge them—or better yet, build the systems you always wished existed.

Listen if you want to hear:

• How two “problem authors” are becoming the publishers they always needed
• The story behind the cover of The Founders and why audience data always trumps team taste
• How to market your book (or project) long after launch
• Why every author should ask for more, push back, and demand transparency
• Why Kobe Bryant was a polymath creative, and what you can learn from him
• Why “the story you can’t shake” is the one you should pursue

Notable closing thought:

“Doing a book shouldn't be a privilege reserved for a small clutch of people who can afford it. ... Our goal explicitly is to make millionaires out of our authors. ... Be a problem author. ... Do something about the story you can’t shake.”
—Jimmy Soni (90:39–95:21)

(For more, visit newsletter.osv.llc for full transcripts and highlights.)