How to Tell Captivating Stories in 103 Minutes – Nat Eliason

How I Write 1h41 5 min #43
How to Tell Captivating Stories in 103 Minutes – Nat Eliason
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Summary

  • Nat Eliason spent two years reinventing his writing style—from concise how-to internet articles to emotionally rich, narrative-driven books—culminating in Crypto Confidential, a non-fiction book about the wild world of cryptocurrency told through personal stories, high stakes, and literary craft.
    • He realized that to truly captivate readers and spread ideas widely, he needed to master storytelling, not just information delivery.
    • This shift was driven by the insight that most people don’t read short manuals—they read stories, and stories are what endure culturally.
    • His journey involved studying great writers, rethinking audience, embracing vulnerability, and developing practical frameworks for compelling narrative.

Learning to write with emotional honesty

  • Nat was deeply influenced by David Foster Wallace’s willingness to expose raw, painful emotions—especially around addiction, despair, and suicide—without holding back.
    • Wallace’s power comes from honesty: he makes readers feel they’re not alone in their anxieties or inner turmoil.
    • Nat applied this to Crypto Confidential, writing scenes so emotionally intense he couldn’t reread them or even read them aloud without breaking down.
    • He credits a mutual friend, Nathan Bos, with pushing him to add more interiority—what he was thinking and feeling—not just action.
      • Example: A scene where his team debates launching a risky token. Originally flat, it became powerful when he added his internal conflict after receiving a brutal message from a crypto figure telling them to “quit being a pussy and ship it.”
      • That tension—between reckless industry norms and real human consequences—came alive only after he showed his hesitation and moral discomfort.

The Grammarly problem: preserving voice vs. conforming to rules

  • Nat warns against over-editing and relying too heavily on tools like Grammarly, which strip away stylistic uniqueness in favor of generic “correctness.”
    • Great writing often breaks rules deliberately: long sentences, missing dialogue tags, fragmented structure—all used to create mood or urgency.
    • Example: In Crypto Confidential, he wrote entire sections with no dialogue or setting tags—just rapid-fire quotes—to mirror the manic, chaotic energy of crypto trading.
    • He argues that hiring too many editors or following formulaic advice (like private equity optimizing a company) kills artistic distinctiveness.
      • Pop music analogy: some artists engineer hits; others prioritize authenticity. You must choose which you want.

Writing for multiple audiences

  • Nat wrote Crypto Confidential for three distinct groups:
    1. Crypto insiders – who lived through the events and wanted to feel seen.
    2. Partners of crypto enthusiasts (mostly women) – who were bored or confused by the obsession.
    3. Parents – who feared their kids were wasting their education on speculative tech.
    • He took feedback from non-crypto readers (especially women like his wife Cosette and sister) far more seriously than from experts, because they revealed where the story was confusing or dull.
    • This helped him balance technical depth with narrative excitement, using structural tricks inspired by Anthony Bourdain’s Kitchen Confidential: embed explanations in side chapters so they don’t slow the main story.

Promise, Progress, Payoff: the core of captivating stories

  • Nat adopted Brandon Sanderson’s framework: every good story has a promise (what the reader will experience), progress (movement toward resolution), and payoff (a satisfying conclusion).
    • The promise must be compelling immediately—or readers quit.
      • Example: Atlas Shrugged opens with “Who is John Galt?”—a mystery that sustains 1,000 pages despite weak dialogue.
      • Contrast: Dune had a slow, unclear promise; many readers dropped it early, though fans later evangelized it.
    • You can get away with a mediocre payoff or slow progress—but never a weak opening promise.

Creating stakes without melodrama

  • Stakes don’t require earthquakes or death—they can be psychological, relational, or existential.
    • The number one reason people stop reading is they don’t care about the conflict.
    • Nat opened Crypto Confidential with: “I’m getting thrown out of bed… my baby is crying… I’m about to lose $100 million of other people’s money.”
      • This creates multiple forms of “death”: financial ruin, loss of identity, relationship breakdown.
    • Even mundane situations can have stakes if something meaningful is at risk of ending—identity, trust, community.

Crafting effective dialogue

  • Good dialogue isn’t realistic—it’s purposeful.
    • Real conversation is 80% filler; story dialogue must advance conflict or reveal character.
    • Key techniques:
      • Tension: Characters should disagree or challenge each other—even friends.
      • Redirection: Instead of yes/no answers, surprise the reader (“We already scheduled two hours!”).
      • Non-verbal responses: A character leaving without speaking can be more powerful than any rebuttal.
    • Every scene should follow intention + obstacle: what the character wants vs. what blocks them.
      • Scenes end in “yes, but…” (success with a catch) or “no, and…” (failure with added consequences), raising stakes each time.

Braiding: the mark of advanced writing

  • Great writers weave together four elements seamlessly:
    1. Action – what happens
    2. Dialogue – what’s said
    3. Description – sensory details of the environment
    4. Interiority – thoughts and feelings
  • Bad writers use only one or two (e.g., action + dialogue in a “white box”).
  • Example of braiding: noticing the fridge’s organization while getting water, hearing records on the wall, thinking about sparkling vs. still—all in half-sentences woven into conversation.
  • Editors see braiding as a key differentiator between good and great writers.

Using AI as a writing partner—not a replacement

  • Nat uses Novelcrafter, an AI fiction tool, but emphasizes: out-of-the-box AI writing is bad.
    • Success depends on detailed prompting: feeding in plot synopses, character bios, 30,000 words of his best writing as a style sample, and a custom checklist of rules (e.g., “never use adverbs,” “show don’t tell,” “avoid ‘he said loudly’—use ‘he shouted’”).
    • AI helps most when he’s stuck: generating descriptions (his weakness), suggesting plot turns, or offering alternatives he can react to.
    • Analogy: Like Miranda Priestley in The Devil Wears Prada—AI doesn’t create; it presents options for a skilled editor (the writer) to accept, reject, or refine.
    • Over time, using AI this way helps close the “taste gap”—you absorb better techniques by seeing them applied in your voice.

The taste gap and the long game

  • Nat references Ira Glass’s “taste gap”: beginners know what good work looks like but can’t yet produce it—a painful but necessary phase.
    • He admits he’s still in it: he sees flaws in his work that others don’t notice.
    • Danger: if the gap stays open too long, it can destroy you (as it did David Foster Wallace).
    • Healthier mindset: “It’s good and it can be better”—not “it’s bad.”
  • Mastery takes decades:
    • Steinbeck called East of Eden the book he’d prepared for his entire life—Grapes of Wrath was just a warm-up.
    • Seinfeld is 70 and still improving; Cormac McCarthy published his final book a month before dying.
    • Nat has only been writing books seriously for two years—he’s okay with Crypto Confidential not being perfect, because he’s playing the long game.

Overcoming isolation in long-form writing

  • Moving from instant-feedback internet writing (tweets, newsletters) to a two-year book project was psychologically brutal.
    • No dopamine hits, no reader reactions, constant self-doubt.
    • He coped by building a TikTok following (reaching 100k+) to get validation—but eventually quit because it distracted from writing.
    • Solution: built a simple writing tracker app (like Strava for writers) to log daily word counts and share progress socially—giving small wins without publishing prematurely.

Final insecurity: will anyone care?

  • Despite finishing both Crypto Confidential and a sci-fi novel, Nat’s biggest fear is silence—not bad reviews.
    • A confusing Publishers Weekly review stung, but he reframed it: being reviewed at all is an achievement.
    • He accepts that most books aren’t finished by readers—and that’s normal.
    • His goal isn’t instant success, but continuous improvement: each book better than the last, reaching wider audiences over time.
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