Packy McCormick, writer of the Not Boring newsletter and former Write of Passage student, shares his tactical approach to online writing — from crafting titles and introductions to his chaotic weekly process, voice development, business model, and the interplay between writing and investing.
Titles, thumbnails, and first sentences
Packy treats titles as playful hooks — often puns or dad jokes — that convey the idea while catching attention; he sometimes starts with a title that sparks the piece itself.
Thumbnails matter less now that Twitter throttles links; he prefers a striking chart or shocking stat in the tweet itself rather than a polished title image.
He doesn’t consider himself strong at first sentences; instead, he pours time into the introduction to “plot the ski run” — framing the piece so the rest flows naturally.
Writing introductions
The introduction is where he establishes definitions, counters conventional wisdom, and maps the piece’s logic; once the frame is set, sections fall into place.
He aims to shift the reader’s mental model slightly — “shake something loose” — rather than maximize click-through with hyperbolic hooks.
He distinguishes “beta content” (generic takes like “AI will change everything”) from “alpha content” (novel framing that makes the reader smarter).
Short vs. long form: the barbell strategy
He adopts Sam Parr’s barbell: very short pieces (a few hundred words, screenshot-style) or definitive long-form deep dives (2,000+ words); the middle ground works poorly.
For company deep dives, his explicit goal: “the best piece ever written about this company” — so good that employees send it to their moms saying, “Finally she understands what I do.”
He positions himself as the “dumb guy” who learns alongside the reader, explaining complex topics in plain language — a deliberate counter-positioning against analysts like Ben Thompson.
Cultivating voice
The core insight from Write of Passage: find a “personal monopoly” at the intersection of things you care about (jokes, pop culture, business strategy, tech).
Early essays forced pop-culture analogies onto tech topics; over time he dropped the formula but kept the playful, accessible voice.
After publishing ~1M+ words, voice has grown more consistent but also more cautious — he feels the “caricature” of Packy (what readers expect) tugging against the evolving real person.
He admires Kevin Kelly’s advice: “Tell your story with uncommon honesty” — first uncover the truth for yourself, then put it on the page with courage.
Writing process: the weekly maze
Each essay is a week-long cycle: excitement → research → overwhelm → renewed excitement → writing → hitting walls → restarting from scratch (often 6–7 full drafts in new Google Docs).
He uses a “V0” doc to dump cut material; each fresh draft preserves the best sections but rewrites the rest to recapture flow.
Deadline pressure is essential: he routinely rewrites the entire piece 4:30–8:55 AM on send day (Tuesday), sometimes texting his ad manager to delay sponsors.
Before kids, he wrote all weekend; now he protects weekends and compresses stress into the final pre-dawn hours.
Flow state and voice transcription
Flow feels like “blacking out” and waking up to five good pages he didn’t consciously plan — discovered after the fact.
Typing causes physical discomfort (finger stiffness); he now uses Superwhisper for voice transcription while pacing or walking, doubling single-session output.
He accepts more editing in exchange for flow: “I’m not trying to make a statue, I just need marble.”
On walks, he starts with a one-sentence epiphany and a mental structure, talks it out repeatedly (compressing each time), then airdrops to the computer.
AI in the writing process
Uses LLMs (Claude, ChatGPT) as explainers: “Explain this phrase,” “Attack this argument,” “Is this right?” — good for sanity-checking and finding blind spots.
Both models are overly complimentary editors (“This is an A+ masterpiece”); he uses them partly for encouragement during slogs.
Best use case: a “bomb thesaurus” — paste a sentence, ask for 10 alternatives for a word with a specific emotional tenor.
DALL-E/Midjourney: used heavily early on, now sparingly; AI images look generic unless you develop a consistent visual style (like “techno Elysian”).
Business model: sponsorships, deep dives, and a fund
Three revenue streams: (1) regular newsletter sponsorships (simple, scalable), (2) sponsored deep dives — paid company profiles where he still aims for “best piece ever written,” (3) Not Boring Capital fund.
Sponsored deep dives: founders pay, give financial access, and trust him with their story; he filters heavily (20:1 request ratio) and only picks companies he genuinely finds interesting.
Example insight from a Ramp deep dive: they split engineers into “careful” (core payments) and “cracked competitive coders” (fast features) — a structural insight founders cite repeatedly.
The fund creates an information flywheel: writing attracts founders → investing grants access to founder memos/decks → those behind-the-scenes insights fuel better writing.
Writing and investing as mutual acceleration
Writing helps investing via access and signaling how he thinks; investing helps writing via privileged information flow (founders distill years of knowledge into memos for him).
He sees the internet’s best/worst as two sides of the same coin: loud opinions without expertise vs. loud opinions with deep expertise shared generously.
His mission (and Write of Passage’s): find people with “core ideas they’d bet their life on” and help them refine and publish — like Tyler Cowen’s Emergent Ventures, attracting the right people and repelling the rest.
Writing long form: from fellowship to weekly cadence
First long piece: “Conjuring Scenius” (11k words, 3 months, edited by Tom White in the Write of Passage fellowship).
Tom’s editing was transformative: specific, solution-oriented, framework-based (“stop doing these three things”) — made Packy feel supported, not crushed.
After that, the weekly cadence freed him: “It’s not the piece, it’s the practice” — lower stakes per piece, higher cumulative output.
Editing: the art of specific kindness
Great editing = telling the writer what to fix without making them feel bad, offering concrete alternatives, and synthesizing a simple framework for improvement.
Bad editing = vague labels (“unclear,” “confusing”) or holier-than-thou tone; the best editors (like Tom) make it feel like a shared mission.
”The Great Online Game” — the breakout piece
Written in one day (Sunday) after scrapping a Saturday draft; he didn’t expect it to spread.
It named a phenomenon everyone felt but hadn’t articulated: the internet as a serious game with real rewards — and gave readers a playbook.
Paradox: writing for the “stadium” fails; writing for one person (or himself) hits the stadium. His best writing often appears in private daily journals to a single friend.
Inspiration and information diet
Refreshes by crowdsourcing “favorite essays >2 years old” on Twitter, then rapid-fire reading 5–10 — resets his sense of what’s possible.
Favorite: “Becoming a Magician” by Autotranslucence — defines a magician as someone different “in kind, not quantity” (you could walk a trillion miles on their path and never arrive).
Reads widely (fiction, non-fiction, sci-fi); sci-fi’s value isn’t prose quality but “inhabiting a world where impossible things happened” — recalibrates his sense of what’s plausible near-term.
Gave up on memorization (unlike Ben Thompson/Byrne Hobart); instead stuffs brain with interesting/weird ideas and trusts collisions to spark novelty.
Self-knowledge through writing
Biggest irritation: lacks deeper technical depth — can explain the “what” and “why” but loses the thread three levels down.
Writing 200+ pieces forced surrender to his actual nature: optimist, eclectic, excitement-driven, bad at memorization, physically unable to sustain a fake persona weekly.
“You can lie to yourself for piece 1, 2, 3 — but by piece 200, writing about things you don’t care about sucks so much you have to be yourself.”
The only sustainable fuel: write the thing you’re most fascinated by this week, even if it confuses audience-building logic.
