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My First MillionThe 3-Step Writing Framework That Helped Us Build +$10M Newsletters
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CHAPTERS
- 0:00 – 2:38
Promise, Credibility, and the Subscribe Ask
Shaan Puri promises listeners will become better writers by the end of the episode and explains the listener question behind it. He and Sam Parr lay out their credentials in newsletters, email sales and writing courses, and ask for a YouTube subscribe.
- •The episode answers a listener request for the 80/20 of writing
- •Sam says they are not necessarily great writers but have been great at getting results
- •Both have built and sold newsletter businesses for tens of millions
- •Shaan cites roughly $20M in email-driven e-commerce sales and a top-rated Maven class
- •The only ask is a subscribe, which they call the gentleman's agreement
- 2:38 – 3:59
Why Writing Matters: Persuasion at Scale
Sam explains why people should care about writing, starting with persuasion at scale, drawing on his move from selling hot dogs one-to-one to copywriting. Shaan adds that nearly anything you want to make happen requires persuading people.
- •Writing is persuasion in its most scalable form
- •Sam moved from one-to-one street-meat sales to copywriting that scales to unlimited people
- •Writing covers everything from blog posts to recruiting to Tinder messages
- •Shaan says anyone trying to make something happen needs to persuade partners, customers and hires
- 3:59 – 8:42
Clear Writing Means Clear Thinking
Shaan argues that writing is a forcing function for clear thinking and an idea generator, citing Paul Graham. Sam explains why long-form writing exposes bad thinking, and Shaan describes Bezos banning PowerPoint for written memos.
- •Struggling with writing usually means the idea isn't clear yet
- •Writing generates new ideas rather than only communicating existing ones
- •Long-form writing can't hide bad thinking the way a PowerPoint can
- •Sam cites Paul Graham's point that much of your writing will be bad and has to be cut down
- •Shaan describes Jeff Bezos replacing PowerPoint with narrative memos
- 8:42 – 14:11
Begin With the End in Mind: Emotion, Action, Headline
Shaan shares the pre-writing questions he learned from Chris Quigley's viral-video agency: pick the emotion, the action and the one line to remember. Sam adds that he starts with a headline and subheadline instead of an outline, and both say to unlearn school writing habits.
- •Chris Quigley's agency worked backwards from an emotion to make videos go viral
- •Shaan asks what reaction he wants, what action he wants, and what one line should be remembered
- •Sam replaces outlines with a single subheadline sentence
- •School rewards word counts and fancy vocabulary; the internet rewards concise, simple writing
- •Tools like Hemingway check reading level
- 14:11 – 17:07
Warm Up With Copywork
Sam and Shaan describe copywork, copying admired writing word for word by hand, as a warmup before writing. They give examples of pieces they copy and compare it to covering songs or following recipes.
- •Sam did copywork about two hours a day for eight months and still does 10 minutes before important pieces
- •Copy word for word without improving it, ideally by hand
- •Shaan uses one of Sam's posts for persuasive copy and the Slack CEO's memo for serious business writing
- •The analogy to musicians playing covers or cooks following recipes before making their own
- 17:07 – 21:03
Draft Fast, Incubate, Then Edit
Sam lays out the draft, incubate, edit sequence, arguing that a draft should be quick and ugly and that editing is where the value is. Shaan explains how adding a break of 90 minutes or more between drafting and editing improved his process.
- •Drafting is where you're supposed to look stupid; bang it out fast
- •Incubation, such as walks or showers, lets passive thinking improve the idea
- •Sam quotes David Ogilvy: a lousy writer but a good editor
- •Shaan stopped over-polishing drafts and now edits with high energy after a break
- •Sam jots sentences in his phone and returns to them later
- 21:03 – 22:48
Build a Swipe File
Shaan and Sam explain that a swipe file of great phrases, headlines, openers and closers gives you inspiration ready before you write. Shaan keeps separate openers and closers files because awkward starts were his blocker.
- •A swipe file is a stash of well-done examples you collect over time
- •Shaan keeps files for phrases, headlines, connecting words, openers and closers
- •Sam writes down phrases that grab his attention, such as 'it doesn't get any better than this'
- •People scroll through thousands of articles, so lines that stop you are valuable
- 22:48 – 26:48
Don't Bury the Lead and Create a Curiosity Gap
Shaan names burying the lead as the first common mistake and uses Sam's Soylent post as a model opener. They cover the cover-the-text test, the curiosity gap, and the idea that a sensational headline isn't clickbait if it pays off.
- •Put the most important or provocative sentence first
- •The Soylent opener creates curiosity right away
- •Sam suggests cutting everything but the last couple of sentences of an opener, rather than a school-style thesis paragraph
- •Shaan's test: cover all but the first two sentences and ask whether you'd need to read the next one
- •It isn't clickbait if you deliver on the promise quickly
- 26:48 – 32:31
Write Like You Talk and the Voice Memo Test
Shaan says 'I'm not a good writer' often means 'I'm not a good thinker' and recommends writing what you would say aloud. He describes training Milk Road writers with 60-second voice memos, and Sam adds tips like writing to one person and avoiding jargon.
- •If you can't explain it out loud, you're not ready to write it
- •Avoid LinkedIn-style jargon like 'utilize'; Stephen King says any word you hunt in a thesaurus is wrong
- •Louis C.K.'s plain-language landing page is an example of writing like you talk
- •Shaan's voice memo test: if you wouldn't tell a friend about it, don't write about it
- •Sam tells writers to write to one person
- 32:31 – 33:17
Write Simply: Lower the Reading Level
Sam recommends targeting roughly a sixth to eighth grade reading level and compares sources. He notes that Warren Buffett's writing falls in that range too, and that the Hemingway App can check it.
- •Aim for around sixth to eighth grade, and as low as fourth is fine
- •Sam says USA News is around fourth grade and the New York Times around seventh
- •Warren Buffett's insurance writing tests at about the same levels
- •Tactics include avoiding adverbs and keeping sentences short
- 33:17 – 40:24
How to Tell a Great Story: Intention, Obstacle, Stakes
Sam shares the Hint Water 'sweetie' story he wrote, which Hint ended up promoting. Shaan explains Aaron Sorkin's intention-and-obstacle framework and the art of high emotional stakes in low-stakes situations, with examples from his HOA story and Larry David.
- •Sam's Hint article about Kara Goldin drove significant sales when the company promoted it
- •Shaan notes the story works because it triggers outrage
- •A story is someone wanting something with an obstacle in the way
- •You should be able to pause any moment and name what the character wants and what's in the way
- •High-stakes emotion in a low-stakes situation gives you endless stories
- 40:24 – 44:53
Short Sentences and Writing With Rhythm
Sam argues for short sentences, citing Buffett's shareholder letters getting shorter and simpler over time and the Hey.com CEO letter. Shaan reads the 'great writing has rhythm' passage and explains varying sentence length, and Sam adds small tactics for rhythm.
- •Buffett's words per sentence dropped from 17 to 13 and reading level fell from 10th to fourth grade over the period analyzed
- •Simple sentences work even on complicated topics, as in the Hey.com CEO letter
- •Great writing varies short, medium and occasional long sentences
- •Sam's tactics: swap commas for periods, start sentences with 'and' or 'but', voice the reader's internal dialogue
- •Shaan says copywork on rhythmic writing primes him to write with variety
- 44:53 – 53:21
Resources, Comedians, and Being Yourself
Sam and Shaan share the resources that influence them, from Stephen King's On Writing to Theo Von, comedians and true crime podcasts. Shaan highlights Louis C.K.'s and Dave Chappelle's storytelling, and both end on writing as yourself with content that is you pushed out.
- •Sam recommends On Writing by Stephen King, split between biography and toolkit
- •Theo Von, comedians and true crime podcasts are sources for phrasing, timing and tension
- •Shaan studies Louis C.K.'s return show and Chappelle's Netflix routine as storytelling for persuasion
- •Sam likes Joel on Software and top Hacker News posts
- •Shaan says the best content is you pushed out, a personal monopoly
- 53:21 – 56:43
Next Episode and Where to Learn More
The hosts preview the next Questionable Advice episode on planning before starting a business. They plug Shaan's Power Writing course on Maven and Sam's Copy That site, and note the course waitlist.
- •Next episode covers what planning they do before starting a business
- •Shaan's course teaches through principles, examples and practice
- •Shaan's Power Writing waitlist has about 8,000 people and he may run one more cohort
- •Sam's copythat.com offers pieces to copy by hand with breakdowns
- •Links will go in the show notes
