Packy McCormick: A Tactical Masterclass in Online Writing

Packy McCormick is proof that writing online can attract real-world opportunities you never dreamed of. He went from 20 Substack subscribers to a $40 million venture fund - and he’s still growing. In this episode, we dive into the three main “how’s” of Packy’s growth.
First, he has a distinct, unforgettable style. His business-meets-memes newsletter, Not Boring, has amassed 220,000+ subscribers because his “funny finance guy” flair gives him an edge. Not to mention, it all started when he took the first-ever cohort of Write of Passage. (I may be biased, but seriously, that’s when it started.)
Next, Packy shares his domain expertise. He sees writing and investing as the perfect one-two punch. His goal? Share what he knows, and make a behind-the-scenes world accessible to the average audience.
And finally, Packy adds value to his readers. Relentlessly. Not by telling them what to think, but by trying to change the way they think. In a world filled with Beta content - cheap entertainment that disappears in 24 hours - Packy creates Alpha content - quality work that has long-term relevance.
Style. Expertise. Value. This is just a sneak-peek into our conversation. If you want to find your distinctiveness in a modern digital world, this episode is for you.
SPEAKER LINKS:
Website: www.packym.com/
Twitter: / packym
Newsletter: www.notboring.co/
WRITE OF PASSAGE:
Want to learn more about the next class Write of Passage?
writeofpassage.com/
PODCAST LINKS:
Website: writeofpassage.school/how-i-w...
Apple: podcasts.apple.com/us/podcast...
Spotify: open.spotify.com/show/2DjMSbo...
TIMESTAMPS:
00:00:00 Introduction
00:01:25 Writing titles and hooks
00:04:00 Writing introductions
00:06:30 Writing short vs long form
00:12:30 Cultivating your voice
00:19:15 Writing process
00:23:30 Writing on the weekends
00:28:00 Elon Musk
00:29:50 Flow
00:40:00 Writing with AI
00:44:30 Business model of writing
00:48:30 Writing and investing
00:53:25 Attracting audiences
00:57:15 Writing long form
00:59:30 Editing
01:02:50 Writing "The Great Online Game"
01:14:15 Where to find inspiration
ABOUT THE HOST:
I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible.

[@DavidPerellChannel]

*Episode Highlights* 1. Packy has published over 1 million words. There’s no substitute for practice, no matter how strong your Personal Monopoly. Put in the work. 2. Write your 1st draft while you're still excited. 3. Beta content vs. Alpha content: Beta content is designed for short-term engagement. It gets views but won’t make you any smarter. Alpha content is designed for long-term relevance and it comes from the writer’s unique experience and expertise. 4. Writing helps you discover who you really are because of the way it helps you stop lying to yourself. 5. Be fascinated about something, and explain to the reader why you’re fascinated with uncommon honesty. 6. Promoting your article: If you have a shocking chart or statistic, use it. It stops the scroll and makes people curious to know more. 7. If you don't know what to write about, there's opportunity in adding fun to topics that people usually approach with extreme seriousness. 8. Don't know what to write about? The thing you're nerdiest about is a good place to start. 9. In a rut? Try reading great writing. Might inspire you. 10. Packy’s reading strategy is to put as many interesting ideas in his brain as possible, have them bang into each other, and wait for original breakthroughs. 11. On the internet, you get points for being curious, sharing, and helping with no expectation of reciprocation. 12. A lot of writing is digging. People love when you uncover a gem for them. Look for a surprising source that throws new light on a common query, and you may have a viral post on your hands. 13. Writing is like skiing. Packy says writing something new is like skiing a path you’ve never skied before. You need to figure out your “line” ahead of time. Packy spends a long time on the first few paragraphs, figuring out the line ahead. Then the essay almost unfolds on its own. 14. When I met Packy, he had only the faintest clue what his niche would be, and he discovered it by publishing consistently. 15. Packy thrived by going all in on his Personal Monopoly. There were many business strategists around, and they had more connections, experience, and knowledge than him. But they lacked his quirky tone, the light touch, and the willingness to explore new angles. That became Packy’s value proposition and he named his newsletter Not Boring.

[@gbh2478]

Under 1k views is criminal. Excellent podcast.

[@leadgenjay]

Packy's approach to creating Alpha content is a game-changer for anyone looking to make an impact. For entrepreneurs, understanding the power of niche content can be pivotal. Instead of trying to appeal to everyone, focus on a specific audience and dive deep into that subject area. This strategy establishes you as an authority and fosters a more engaged and loyal following.

[@themgmtconsult]

Sh*****t!! Didn't know David was shilling so much quality on this KZbin channel. Just subscribed, binged on Howard Marks' episode and now this one. From an investing to a writing genius. Good job, sir 👍

[@JoeGannon]

Love any writer who brings their personality into their work

[@faheemkj7080]

Amazing talk, gives more knowledge on writing process and keep me attached to watch the full conversation.. It feels that writing is a difficult process but I like that and started finally….😊

[@makerphin]

Woaaa, 1h25! Brb, getting a coffee for this one

[@teddywilliams4112]

Been loving these episodes 👏

[@iAmWriting247]

Excited for this!

[@riccardocecco]

Amazing conversation guys! Thanks 🎉

[@Change_is_permanent]

Great content!

[@ryanmckennaonline]

So...many...yt.... ads....

[@Gustosales-zq9rb]

more lke this:)

[@peteweishaupt]

Great interview. a) have you considered a “Where are They Now” episode with Write of Passage alumni? b) I’m using the Packy M formula for ETA. Subscribe growth +80% can’t wait to see where it leads. c) do you have a list of Packy’s 100 ‘inspirational’ essays? d) interesting discussion writing what you’re curious about v. niche. e) still waiting on my OSV WoP scholarship ;) d) have a great rest of your week.

[@fischettif1972]

Classic Silicon Valley. A couple of noobs discuss a craft as though others haven't been grappling with the same challenges for hundreds of years. That said, these "noobs" are also pioneering a new business model whereby they're succeeding in capturing far more value for themselves than most journalists ever have. So, credit to them! Seriously! Still...these "challenges" are the same s**t every writer ever has dealt with. It's an "a$$ in chair business," as Nora Roberts said.