Infinite Loops Ep. 301

Guest: Packy McCormick
Host: Jim O'Shaughnessy
Date: February 12, 2026

Episode Overview

In this lively, insightful episode, Jim O’Shaughnessy welcomes Packy McCormick—creator of Not Boring—for a far-reaching conversation on how writing shapes companies, the power of optimism, cycles of innovation, and the virtues (and pitfalls) of technology-driven change. The pair reflect on Packy’s journey from struggling entrepreneur to influential writer, the psychological side of sharing ideas in public, scar tissue from setbacks, and why deep, structured writing still reigns amidst the rise of short-form and AI-generated content. Throughout, they champion curiosity, resilience, and authenticity in a rapidly evolving world.

Key Themes & Discussion Points

1. The Transformative Power of Writing

Timestamps: 01:37 – 10:00, 83:08 – 90:00

• Writing as Clarity and Strategy:
  Packy shares how recording ideas in writing was central to turning around a faltering startup, allowing clear communication and coordinated action.

  "Writing is thinking. Writing things out has killed more stupid ideas that I have had... it is only in the writing." – Jim (04:44)

• Not Boring’s Paid Product & Canon Documents:
  Packy discusses his pivot to a paid Substack model, designed not to lock ideas behind a paywall, but to encourage founders and domain experts to nail down their best, hardest-won ideas in deep-dive essays.

• Writing > Audio for Idea Longevity:
  The permanence and reusability of well-written essays stand in contrast to the fleeting absorption of ideas on podcasts and videos.

  "Any idea that I've said on this, at least personally, I would do a much better job expressing that idea in writing." – Packy (88:14)

• Advice for Hesitant Writers:
  Both stress that nobody remembers minor failures and that using writing to "think in public" leads to immense upside, far exceeding potential embarrassment.

  "People are nicer than you expect... The other is that people just don’t care. You have to fight for their attention." – Packy (18:25)

2. Building a Unique Voice and Audience

Timestamps: 09:18 – 13:03, 83:08 – 90:00

• Developing a “Personal Monopoly”:
  Packy describes how David Perell’s “Write of Passage” helped him overlap his interests to claim a unique niche—tech, pop culture, and even Philly sports—where he could stand out.

  "Pick a bunch of your different interests and overlap them until you find something that you’re the only person in the world who’s going to be good at writing..." – Packy (10:30)

• Navigating Audience Capture and Confidence Loss:
  Growth brings new pressures; Packy recounts periods of self-doubt and external criticism, especially after missteps during the crypto hype.

  “There was just a period…where I was way less confident. I’d try to write about things that I thought would do well… something changed…I do not care, [now] I just write what I find fascinating.” – Packy (11:46)

3. Scar Tissue, Resilience, and Advice for Creators

Timestamps: 13:11 – 20:25

• Surviving a Viral Internet Dunking:
  The low point: Packy details getting publicly ridiculed over a crypto gaffe while his son was in the hospital—an episode that shook his confidence, but ultimately gave him perspective and humility.

• Required Failure:
  Both Jim and Packy stress that getting publicly knocked builds the humility and perseverance required for long-term success.

  “If you don’t have scar tissue, you’re probably not going to make it… People are terrified to fail…but that’s the only road to succeed.” – Jim (17:25)

• Overcoming Fear:
  The major hurdle is not failure, but fear of being seen to fail. Both urge creators to act regardless:

  “People just don’t care… It is so asymmetric, the upside for the downside.” – Packy (18:25)

4. Optimism vs. Pessimism: Countercyclical Energy

Timestamps: 19:47 – 27:14, 90:00–92:00

• Being a Rational Optimist in a Cynical Era:
  Packy describes feeling countercyclical optimism during times of widespread doom-laden narratives, and credits proximity to founders and ongoing technological breakthroughs for his contagious forward-looking outlook.

  “I’m naturally optimistic… There’s just so much cool stuff coming down the pike… at least for our world, it’s hard to be too pessimistic right now.” – Packy (20:25 & 27:02)

• On Techno-Progress and Disconnection from Reality:
  The hosts cite tangible medical and energy breakthroughs as evidence the future is bright, despite headlines fixated on doom.

5. Cycles of Innovation & Elite Battles

Timestamps: 27:14 – 46:38

• The “ER Pattern” of Innovation Adoption:
  Jim’s AI analysis of history: Every new technology faces predictable skepticism, resistance from incumbents, and eventual acceptance—be it writing, printing, music, or AI.

  “What’s really happening is the prior regime that was really, really good at that particular skill gets nuked by innovation…” – Jim (29:04)

• The Printing Press as Case Study:
  Amusing stories abound—Gutenberg was a grifter funded by the Church for printed indulgences, only to see unintended second-order effects (e.g., Luther’s Reformation). The unpredictability and opportunism of innovation is a recurring motif.

  “Second-order effects of publishing created everything… the real history is so much more interesting than what we’ve been taught.” – Jim (37:11)

• Empire vs. Rebel Alliance Frame:
  Jim posits that the historic “elite” (World Economic Forum, legacy publishers) are now challenged by tech’s “Rebel Alliance” (A16Z, Packy), with surprising allegiances and implications for the speed at which industries can be disrupted.

  “The empire is levered to things staying exactly the same… the rebel alliance, to things getting better in the future.” – Packy (44:29)

6. Disrupting Publishing and Business Models

Timestamps: 46:38 – 52:14

• Reinventing Publishing for the Digital Age:
  Jim outlines how Infinite Books leverages technology and AI to empower authors, increase royalty transparency, eradicate “lanes,” and focus on the long tail of book marketing.

  “We look at the author and the reader. Those are our clients…Our internal mantra is, we only do win-win things.” – Jim (51:51)

• Counter-positioning for Competitive Advantage:
  Packy highlights that leveraging new workflows and technology, while recognizing where incumbents are “stuck,” is the holy grail for new ventures.

7. Venture Investing in “Hard” and Verticalized Companies

Timestamps: 53:58 – 59:04, 75:44 – 79:27

• What Excites Packy Now:
  He’s passionate about companies executing hard, verticalized, capital-intensive businesses—energy storage in Texas, full-stack ISPs in Colombia, mining automation in Australia.

• Why Focus There?:
  As software abstraction layers mature, opportunity moves into integrating software + hardware for physical world transformation.

  “I think people underestimate how quickly the largest companies in every industry can change and how much bigger those companies will become when they do.” – Packy (44:29)

• Global Perspective:
  Though primarily US-focused, Packy invests globally where execution is best.

8. AI, Hype Cycles, and Moats

Timestamps: 59:37 – 71:59

• On AI Startups & Hype Resilience:
  Candidly, Packy admits to skepticism about LLM wrapper startups—though plenty have defied expectations and reality-checks often arrive too late. He prefers comparative advantage by focusing on industries less crowded by attention.

• Comparisons Across Eras:
  Jim contrasts today’s AI startup explosion with the dot-com era: public markets, mass enthusiasm, and “information cascades” were more acute then; now there’s more skepticism, tooling complexity, and less straightforward public participation.

9. Filtering Startups and Seeking Edge

Timestamps: 73:39 – 75:44

• Deal Filtering:
  Packy drastically narrows his top of funnel, looking for truly unique, differentiated opportunities, eschewing “me too” ideas or those lacking a moat.

  “…A lot of small ideas go right into the trash. Anything that’s not differentiated for me goes into the trash. Differentiated, short term, structurally different… I want to invest in five companies I love this year.” – Packy (73:57)

• Exciting Boring Innovations:
  Anecdote: EarthAI—automated mineral discovery—mimics biotech’s platform model, leveraging vertical integration and proprietary data.

10. Co-writing and The Return of Deep Writing

Timestamps: 83:23 – 90:03

• Co-writing Experiments:
  Packy’s new paid model has him collaborating with experts; compelling ideas often emerge after refining beyond the surface-level “pitch.”

• Writing is Resilient:
  Despite the dominance of video and social, both maintain that writing is not dead but rather entering a deep-value phase—becoming a major differentiator for those who master it.

  "Writing...has just been so oversold. Video is great, podcasts are great... but writing doesn't feel like something that's going to go away." – Packy (89:39)
  “If I was giving advice to a young person today: learn how to write really, really well. Everyone else is doing TikTok. Go the other way.” – Jim (90:03)

11. Life Philosophy & Parting Advice

Timestamps: 91:41 – end

• Packy’s Two Incepted Global Truths:

  1. “Be you.”
  2. “Be joyful and energetic.”

  "There’s just differentiation in being unique and authentic... I’m really also just trying to be as joyful and energetic as I can be because the world just becomes more fun that way." – Packy (91:41)

  Jim echoes Oscar Wilde: “Be yourself; everyone else is taken,” and salutes the infectious optimism and authenticity that define Packy’s approach.

Notable Quotes & Memorable Moments

• On Writing as a Practice:
  "All of us have these ideas bumping around in our minds... if you just leave it there, you don't really know until you try to write it out."
  — Jim O'Shaughnessy (04:44)

• On the Power of Failure:
  "If you don’t have scar tissue, you’re probably not going to make it. You get scar tissue by just continuing to persevere and becoming a lot more humble."
  — Jim (17:25)

• On the Asymmetry of Public Creation:
  “It really is so asymmetric—the upside for the downside, because it is so hard to grab people's attention, positive or negative…”
  — Packy (19:06)

• On Optimism:
  "The people that we get to talk to every day are doing these unbelievable things that if 5% of them are right, the world is a much, much better place and nobody else knows about this stuff."
  — Packy (20:25, 27:02)

• On the Pattern of Innovation:
  “They change the playing field, and they stop talking about outcomes, and they start talking about process.”
  — Jim (30:59)

• On Learning from History:
  “There is so much alpha sitting in history books when you start seeing like these connections."
  — Jim (39:56)

• On Business Model Disruption:
  “If you can run fast at that weak spot, then that's the holy grail.”
  — Packy (51:51)

• On Filtering Investment Ideas:
  “If the fusion company that I invested in when I thought fusion was a completely uninvestable category... if I had studied for the rest of my life, I never would have come up with the idea that he had.”
  — Packy (73:57)

• On Life Advice:
  “Be you… be joyful and energetic… we’re so lucky to be in the situation that we’re in right now.”
  — Packy (91:41)

Highlights by Timestamp

| Time | Segment | Key Insight/Topic | |------------|------------------------------------|------------------------------------------------------------------------| | 01:37 | Writing as Strategic Tool | Why writing brings clarity and actionability inside companies | | 10:30 | Building Personal Monopoly | Using unique overlaps to stand out in writing | | 17:25 | The Gift of Failure | How getting “punched in the face” induces resilience & humility | | 20:25 | Rational Optimism | Being optimistic even in countercyclical times | | 29:04 | Patterns of Innovation | Each technological shift faces the same skepticism from incumbents | | 44:29 | Rebel Alliance vs. Empire | The intra-elite battle in business and ideas | | 51:51 | Redefining Publishing | How Infinite Books combines tech and win-win ethos for authors | | 59:37 | The AI Startup Landscape | Packy's skepticism and humility around LLM “wrappers” | | 73:57 | Filtering Dealflow | Packy’s higher bar for differentiation and uniqueness | | 83:08 | Co-writing as Content Model | Leading founders to deep, unexpected insights through writing | | 89:39 | Writing as a Deep Value Opportunity | Importance of writing amidst video/social/AI saturation | | 91:41 | Life Philosophy | Packy’s two messages: “Be you” and “Be joyful and energetic” |

Tone & Style

• Optimistic, candid, encouraging: Both speakers blend hard-won realism with infectious enthusiasm for new ideas, change, and human creativity.
• Conversational, open, witty: Spirited anecdotes (Gutenberg! Gold in hell!) and mutual ribbing make for an engaging, down-to-earth listen.
• Philosophical and practical: The talk moves fluidly from street-level tactics to 10,000-foot worldview.

For Further Discovery

• Not Boring (Packy's Newsletter & Paid Essays): Deep dives on tech, business models, and optimism.
• Infinite Books (Jim's publishing venture): Tech-enabled, win-win strategies for authors and readers.
• Historical References: Stories of Gutenberg, the Medici, Luther, Florence’s florin, and more.
• Key Concept: The “ER pattern of innovation”—how incumbents always resist, and then adopt, new tools.

Whether you’re a writer, builder, founder, investor, or simply someone ready to “be joyful and energetic,” this episode delivers richly across practical and philosophical lines, with wisdom rooted in history and a clear, optimistic gaze to the future.