Packy McCormick, writer of the newsletter Not Boring, discusses his approach to online writing, from packaging ideas to building a business around a weekly deep-dive essay. He explains how he develops voice, structures long-form pieces, uses AI tools, and balances writing with investing, all while navigating the tension between authenticity and audience expectations.
Packy’s Writing Philosophy and Goals
Core mission: Make business and technology writing fun, accessible, and genuinely interesting, treating topics like sci-fi drama rather than dry analysis.
Definitive deep dives: When writing about a company, his goal is to produce the best piece ever written about that company, often becoming the explainer that helps employees’ families understand what they do.
Writing for the “dumb guy”: He positions himself as someone who learns alongside the audience, making complex topics click for regular people rather than insiders.
Optimism as identity: His consistent thread is genuine optimism about technology and progress, which he leans into rather than fights, even when it draws criticism.
Packaging: Titles, Thumbnails, and First Sentences
Titles: He starts every piece with a title at the top of the doc, sometimes because the title itself is the reason he wants to write the piece. He favors puns and dad jokes that convey the idea while being fun and attention-grabbing.
Thumbnails: He spends less time on these now because Twitter throttles link previews. When he does use them, shocking stats or striking visuals work better than polished images.
First sentences and introductions: He doesn’t claim to be great at first sentences but invests heavily in the first few paragraphs. He thinks of it like skiing a fresh run: figuring out the line (the framing and structure) ahead of time makes the rest of the piece flow naturally.
Hyperlinks as respect: He uses hyperlinks to embed context without over-explaining, treating readers as smart and curious. This is a key advantage of online writing, letting writers reference things like “Romulus and Remus” without stopping to explain.
Voice and Style Development
Personal monopoly: From Write of Passage, he took the idea of finding the intersection of things he cares about: jokes, pop culture, business strategy, and technology.
Early approach: His first 10 essays explicitly paired pop culture analogies with business or tech topics (e.g., comparing creative destruction to the Mickey Mouse Club).
Evolution: Over time, he dropped the forced pop culture framing but kept the fun, fresh voice. He’s published over a million words, and his voice has developed through repetition.
The caricature problem: As an online writer grows, a caricature of themselves emerges, which can limit the real person’s evolution. He’s aware of this tension between “Packy on the internet” and “Packy in real life.”
Uncommon honesty: He values Kevin Kelly’s advice to “tell your story with uncommon honesty,” which means first figuring out what he actually thinks, then putting it on the page with courage.
Writing Process and Structure
Messy, iterative drafting: His process has gotten uglier over time. He writes multiple drafts (often six or seven), frequently starting completely fresh in a new document rather than editing the previous version. He keeps a “V0” doc where he dumps cut material.
Deadline pressure: He needs intense time pressure to finish. Recently, he’s been rewriting entire pieces from 4:30 AM to 8:55 AM on the morning of publication, racing against the clock.
Weekend writing: He used to write all weekend but has tried to remove stress from family time. He shifted from Monday to Tuesday sends to give himself more runway.
Research process: Each essay is roughly a week-long cycle of getting excited, researching, realizing the topic is bigger than expected, getting excited again, and writing. He’ll download books, dig into primary sources, and cross-reference data.
Flow state: For him, flow means writing several pages and then realizing afterward that what he wrote was better than anything he could have planned. It’s the Will Ferrell debate scene in Old School—black out and come to having said something great.
Voice transcription: He struggles to get into flow while typing (his fingers get tight and crackly). He’s started using voice transcription tools like Superwhisper, pacing around or going on walk-and-talk sessions, which has doubled his output per session despite requiring more editing.
Writing Long vs. Short
Barbell strategy: He follows Sam Parr’s insight that online writing works at two extremes—very short pieces (a few hundred words, screenshot-essay length) and definitive long-form pieces (2,000+ words). The middle ground doesn’t work as well.
Short pieces: Quick, compressed ideas, like Seth Godin or Chris Dixon’s three-paragraph essays.
Long pieces: Mic-drop definitive takes where he’s thought through something deeply. He aims for these when covering companies.
Research and Source Discovery
Eureka moments: Finding a single source that explains everything is one of the best feelings in writing. He gives the example of a leaked 2001 Boeing memo that predicted exactly what would go wrong with outsourcing.
Primary source digging: For a piece on Tencent, he spent two days on Chinese-language sites cross-referencing investment data into a spreadsheet. For a Sci-Fi Ideas project, he used ChatGPT and multiple Anthropic accounts to process a 3,000-entry list of sci-fi predictions.
Early founder interviews: He loves the genre of YouTube interviews with successful founders before they were successful—unhinged, desperate, singular. Examples include a blurry 2005 Stanford interview with Mark Zuckerberg and an early Jeff Bezos video.
Using AI in the Writing Process
Explaining things: He asks AI to explain phrases or topics in different ways, using it as a thinking partner.
Editor: He pastes drafts into ChatGPT or Claude for feedback. He admits he doesn’t take all the advice but uses it to sanity-check that he’s not crazy. Claude is extremely complimentary (“an A+, among the best things ever written”), while ChatGPT is more willing to cynically attack arguments.
Thesaurus: He uses AI as a “bomb thesaurus”—pasting a sentence and asking for 10 alternatives for a specific word, or leaving a blank and asking AI to fill it in based on the emotional tenor he’s going for.
Images: He used DALL-E heavily at first (5-6 AI images per piece) but has pulled back to maybe one per piece because AI-generated images tend to look generic. He now uses them only when out of time.
Business Model
Sponsorship: Regular sponsorships at the top of the newsletter are his baseline revenue. He chose sponsorship over subscriptions because he wanted to maximize growth and reach a large enough audience to sustain the business.
Sponsored deep dives: Companies pay him to write the kind of definitive essay he’d write anyway. He’s selective about which companies he works with (filtering happens at selection, not in the writing). These pieces often get the best feedback from founders because he gets unusual access to financials and internal thinking.
The fund: He runs an investment fund that feeds back into his writing. Investing gives him access to founders and behind-the-scenes memos that inform his essays. Writing gives him deal flow because founders read his newsletter and know how he thinks. He views the combination as his ideal life: writing, talking to smart people, and investing.
Attracting the Right Audience
Attract, don’t find: In the internet era, the key question isn’t how to find people with deep expertise but how to attract them. Tyler Cowen’s Emergent Ventures is a model—writing idiosyncratic content that attracts the right people and repels the wrong ones.
Repelling is important: At scale, repelling people who aren’t serious is as important as attracting those who are. He doesn’t want students who aren’t committed to writing something excellent.
Deep expertise over good writing: He believes people overestimate the importance of polished writing. What matters more is conviction, unique life experiences, and the work of synthesizing and clarifying ideas. Good editors can help with the rest.
Writing “The Great Online Game”
Unexpected viral hit: He wrote it in a single Sunday after scrapping a Saturday draft he didn’t like. He thought it was a throwaway piece.
Why it worked: It named something people had noticed but didn’t have words for, and it gave people something actionable—a game they could go play. It captured a moment when the internet felt both casual and seriously consequential.
Paradox of reach: He didn’t write it for a mass audience; he wrote it from a genuine place. The pieces that hit the stadium are the ones written for an individual, not the stadium itself.
Inspiration and Reading
Essay recommendations: When feeling stale, he tweets asking for favorite essays more than a few years old. Rapid-fire reading of great essays refreshes his sense of what’s possible in writing.
“Becoming a Magician” by Autotranslucence: A piece he returns to repeatedly. It defines a magician as someone different not in quantity but in kind—someone you could never reach by walking their path, no matter how far.
Reading approach: He has a terrible memory and has given up on memorizing. Instead, he floods his brain with interesting things and hopes they collide and produce new ideas.
Sci-fi reading: He reads sci-fi not for the prose (which is often bad) but for inhabiting worlds where impossible things have already happened. This helps him recognize when someone is building something from the future in the present.
Self-Awareness and Growth
Surrendering to who he is: He’s stopped fighting his nature—his optimism, his terrible memory, his wide-ranging curiosity. Writing 200+ pieces has made it impossible to pretend to be someone he’s not.
Biggest irk: He wishes he had more technical depth, the ability to go three levels deeper into how things work. He can track what’s important and explain it, but the next level of detail loses him.
Writing as self-discovery: Writing regularly forces you to uncover who you actually are. You can lie to yourself for piece one, two, and three, but by piece 200, you have to surrender to your actual interests and voice or you won’t be able to continue.
