Not Boring

Not Boring grew from a 20-subscriber class assignment into long weekly essays. Packy McCormick started in the first Write of Passage cohort, with an assignment to get 20 subscribers, and built that into weekly essays of 5,000 to 10,000 words.

David Perell watched him grow from his first published piece, back when Perell taught the course from his bedroom. McCormick has since published over a million words.

How I Write

Ads and sponsored deep dives fund it, with no paywall. Revenue comes from advertising plus sponsored company deep dives. About 20 companies ask for a deep dive for every one he writes.

Sponsored deep dives give him access to financials and inside detail he could not get otherwise. His brother Dan works with him on sponsor timing.

How I Write

Writing opens doors and investing shows how founders think. Founders who read Not Boring already know how McCormick thinks, which gave him access to founders and a venture fund. Investing in turn teaches him how founders condense everything they know into a pitch.

He has moved from an outsider writing about strangers to writing about founders he knows and invests in, which he says changes the voice.

How I Write

Change how readers think instead of adding another common take. McCormick calls crowded takes like "AI is going to change the world" beta content, since another one makes nobody smarter. He aims for alpha content that shifts how someone sees an idea, even if they forget the details.

He avoids hyperbole and hooky openings because they embarrass him. "Maybe it'll just shake something loose in your brain."

How I Write▶ 5:37

Each company deep dive aims to be the best piece ever written on it. His Stripe piece set out to be the definitive one, and Stripe gave it to new employees. The common reaction from founders is "Finally, my mom understands what I do."

He sees his role as the "dumb guy" who learns alongside the audience, since someone deep in an industry struggles to explain it. Early on he wrote about public companies through metaphors because he could not out-analyze the analysts.

How I Write

Write very short or definitively long, not in the middle. He follows Sam Parr's barbell: pieces of a few hundred words, like Seth Godin's or Chris Dixon's, or pieces over 2,000 words that become the reference. The middle works less well.

Hyperlinks let him skip explanations and treat readers as smart. Sometimes the most clicked link is a 2,000-word explainer deep in the piece, showing readers are still engaged that far in.

How I Write

The Great Online Game spread because it named something people already sensed. He wrote it in one day after scrapping a weak Saturday draft. It went out to fewer than 50,000 subscribers and is still his most cited piece.

He thinks it worked because it gave readers a name for what they had noticed and something to go and do. He did not expect it to take off, and says conviction and lived experience matter more than wordsmithing.

How I Write▶ 1:03:38

He built a distinct voice by positioning against Ben Thompson. McCormick chose to be what Ben Thompson never would: silly, comparing creative destruction to the Mickey Mouse Club. His first 10 essays paired a pop culture idea with business strategy.

The idea came from Write of Passage's personal monopoly, at the intersection of jokes, pop culture, business strategy and technology. Some tech ideas had no good pop culture analogy, so he dropped the formula but kept the playful voice.

How I Write

Write what fascinates you, because readers and you will notice by piece 200. He hops from biotech to space week to week, breaking audience-building advice, because he picks whatever fascinates him most. Perell's point is that you can fake interest in piece one but not piece 200.

Switching topics also keeps him from becoming the caricature his audience expects. "When you try to write for the individual, you're so much more likely to hit the stadium."

How I Write▶ 1:20:39

Overthinking and sounding smart make his prose flat. When he over-intellectualizes or tries to sound smarter than he is, the writing comes across flat, so he tries to get his original excitement onto the page.

Perell adds Kevin Kelly's advice to tell your story with uncommon honesty. Being dunked on, as with a Twitter account mocking his phrase "cost physics", adds a defensiveness he wants to remove, and he plans to reread old pieces to recover early freshness.

How I Write▶ 18:32

The title comes first and the image comes last. He types a title at the top of the doc with "Title image" in brackets below it, and sometimes the title is the reason to write the piece. The image is a last-minute job, hand drawn or made in DALL-E.

He likes a good pun. Because Twitter throttles links, a striking number or bar chart now does more work than a thumbnail.

How I Write

Most of the time goes into the introduction, which sets the route. He compares the first few paragraphs to picking a line on a fresh ski run: once the framing is set, the definitions and the old view to knock down fall into place.

He admits he is weak at first sentences and hooks. His test is the most interesting way to tell a story nobody has told.

How I Write▶ 3:52

He restarts in a fresh doc rather than editing a bad draft. He drafts while excited, researches the gaps, then starts a new doc keeping only good sections, through about six versions over four to seven days.

A file called V0 holds everything cut from later versions. Each restart leaves him understanding the topic a little better.

How I Write▶ 20:39

A send-morning deadline forces the final rewrite. For roughly his last ten essays he rewrote from 4:30 to 8:55 AM on send day while texting his brother about the sponsor slot. He is unsure whether the rush makes essays better or worse but needs the pressure.

Weekend writing stress spilled into family time, so he asked his wife Pooja for one six-hour block ("My golf is writing") and moved sending from Monday to Tuesday. For deep dives the angle is fixed a couple of days early so the last day is only editing.

How I Write▶ 22:03