CopyThat Copywriting Challenges

A 14-PDF copywriting course from CopyThat, covering foundational techniques through annotated real-world examples. Each challenge dissects a famous piece of copy and extracts the pattern behind it.

These patterns are directly applicable to Sanity Check content, launch copywriting, and our broader open knowledge sharing approach.

Challenge 1: Louis CK — Sales Page Simplicity

Technique: Write sales copy like a human conversation, not a pitch.

Louis CK’s “Live at the Video Store” sales page reads at a Grade 2 level with 11 words per sentence. It sells a comedy special without any sales language.

Key patterns:

• Start at the beginning. Don’t overthink the opening. Louis literally starts with “I developed and prepared this material over the last year or so.” It grabs attention because it’s so straightforward.
• Long sentence, then short. Breaking up rhythm keeps the reader engaged.
• Parenthetical humor. Fun phrases in parentheses humanize the writer and make them more likable. Most people don’t write this way, so doing it makes you stand out.
• The rhythm trick. End the story, then keep going. Like writing a short message with a long PS containing the bulk of the content.
• Forgotten text is content. Welcome emails, unsubscribe pages, copyright messages — most companies leave these as boilerplate. Making them fun is a differentiation opportunity.
• Zero jargon. Use human language to describe what most companies describe with jargon.
• AIDA in action. The opt-out options (“No, leave me alone forever, you fat idiot”) are a perfect example of a clear, fun “Action” step.

Challenge 2: Gary Halbert — The AIDA Letter

Technique: AIDA — Attention, Interest, Desire, Action.

A letter from legendary direct mail copywriter Gary Halbert to his son Bond, teaching the AIDA formula through a real estate investment sales letter example.

Key patterns:

• Attention must be relevant. Halbert attached physical objects (coins, sand in a baggie) to direct mail — but the gimmick had to tie naturally into the letter’s story.
• Interest through facts. Feed the reader interesting, specific details — cubic tons of sand, specific fish you can catch, how many pretty girls are around.
• Desire through benefits visualization. Help the reader picture the benefits: new car, nice house, peace of mind, vacations, leisure time. Even the obvious benefits need to be spelled out.
• Action must be explicit. Tell them where the order coupon is. Tell them to fill it out. Tell them to enclose payment. Tell them how much. Tell them to do it NOW.
• Asking questions breaks up flow. A wonderful way to create rhythm and keep the reader engaged.
• Devote serious space to closing. Halbert devoted 25% or more of entire ads to the close.
• Handwrite great copy. Halbert’s assignment: copy a great ad by hand to internalize the patterns.

Challenge 3: Joel Spolsky — The 12-Step Blog Post

Technique: Building hype and slippery slope to keep readers falling forward.

Joel’s blog post “12 Steps to Better Code” is a masterclass in the Attention and Interest portions of AIDA, using anticipation and tension to pull readers through.

Key patterns:

• Attention grabber for the right person. “Have you ever heard of SEMA?” — this immediately filters for the target audience while creating curiosity.
• Italics, bold, capitalization. These transfer the emotion in your head to the reader’s head. When you read italics, you raise the voice in your head.
• Build expectations. Plant seeds for what’s coming. Tony Robbins is famous for this technique.
• Create fear and FOMO. “A score of 12 is perfect, 11 is tolerable, but 10 or lower and you’ve got serious problems” — fear and FOMO are the most powerful emotions for keeping a reader reading.
• Use the least words needed. This doesn’t mean always use short. Joel used the perfect amount to build hype. The goal is the minimum needed to achieve your purpose.

Challenge 4.1: Scott Adams (Dilbert) — The Day You Became a Better Writer

Technique: Radical simplicity in writing. Grade 2 readability, 8 words per sentence.

Scott Adams distills good writing into a blog post that practices exactly what it preaches.

Key patterns:

• Simple writing is persuasive. Five good sentences sway more people than a hundred brilliant ones.
• Prune extra words. Don’t write “He was very happy” when “He was happy” works. “Very” adds nothing.
• First sentence must grab. Adams rewrote his opening a dozen times. It makes you curious — that’s the key.
• Replace commas with periods. You can often turn one sentence into two. This keeps sentences short and punchy.
• Subject before action. “The boy hit the ball” is faster to process than “The ball was hit by the boy.” All brains work this way.
• Parenthetical asides add personality. Even when not strictly necessary, they make writing feel human.
• Humor writing = business writing + better word choices. Don’t say “drink” when you can say “swill.”

This connects directly to Perell’s writing principles — simplicity and clarity as the foundation of all good writing.

Challenge 4.2: Stephen King — The Writer’s Toolbox

Technique: Kill passive voice and adverbs. Active, muscular prose.

An excerpt from Stephen King’s On Writing about the craft mechanics that separate weak writing from strong.

Key patterns:

• Active voice always. “The meeting’s at seven” not “The meeting will be held at seven o’clock.” The passive voice is the voice of timid writers.
• Adverbs are not your friend. They signal the writer is afraid they aren’t expressing themselves clearly. If the verb is right, the adverb is unnecessary.
• Break complex thoughts into shorter sentences. Readers understand “My romance with Shayna began with our first kiss. I’ll never forget it” better than one tortuous passive construction.
• The reader is your main concern. Without Constant Reader, you’re just a voice quacking in the void.
• Most business writing is bad. Two pages of passive voice — any business document ever written — makes King want to scream. This applies directly to us.
• Creative metaphors over cliches. King’s language itself is a slippery slope — you keep reading because his prose sings.

Pairs well with the creativity faucet — King’s toolbox is the craft discipline that makes the faucet’s output publishable.

Challenge 5: The Wall Street Journal — The Most Famous Sales Letter Ever Written

Technique: Story-driven selling. Open with a narrative, let the product emerge naturally.

This letter ran for decades and generated over $2 billion in subscriptions. Grade 8 readability, 15 words per sentence.

Key patterns:

• Start with a story. Two college graduates, same background, same company — but 25 years later, one is a department manager and the other is president. What made the difference?
• Beginning, middle, end. The story has complete structure. It draws you in before any selling begins.
• The sell emerges from the story. “The difference lies in what each person knows and how he or she makes use of that knowledge. And that is why I am writing to you about The Wall Street Journal.”
• Slippery slope through curiosity. Each paragraph creates a question that the next paragraph answers.
• Super clear action. “Simply fill out the enclosed order card and mail it in the postage-paid envelope provided.”
• Casual selling. Like Louis CK — what’s a little money amongst friends?
• Circle back to the opening. The letter ends by returning to the two classmates. “Knowledge. Useful knowledge. And its application.”
• Release tension at the end. The PS about tax deductibility is a gentle, practical close.

Challenge 6: HEY Homepage — Love Letter Copy

Technique: Manifesto-style copy that sells through shared values, not features.

Jason Fried’s HEY email homepage reads at Grade 2 with 8 words per sentence. It’s a love letter to email itself.

Key patterns:

• Colloquial opening. “Hey everyone—” immediately sets a casual, approachable tone.
• Simple word choices. “Stuff” instead of more formal alternatives. Write like you speak.
• Start sentences with conjunctions. “And,” “And yet,” “So” — these create slippery slope momentum.
• Rhythm through parallel structure. “Something you fall behind on. Something you clear out, not cherish. Rather than delight in it, you deal with it.”
• Name the enemy. “Gmail, Outlook, Yahoo, and Apple just let it happen.” Bold, specific, and it creates trust.
• Address objections. HEY charges while Gmail is free. Addressing this on the sales page is critical. (CopyThat notes this is the one area they might improve.)
• End with a signature. ”— Jason Fried” personalizes the entire page as a letter from a real person.

Challenge 7.1: Rolex — The Matterhorn (Expertise as Selling)

Technique: Explain industry-standard processes as if they’re extraordinary.

Grade 7 readability, 15 words per sentence. A short-form ad that sells through manufacturing detail.

Key patterns:

• Open with a vivid, specific image. “We built the Rolex Explorer because there isn’t any watch repair shop on top of the Matterhorn.”
• Explain the obvious. Every watchmaker probably tests for temperature and pressure. But Rolex describes it in a way that makes it feel exceptional.
• If you’re an expert, remember others aren’t. Even if something is common in your industry, explaining it in cool ways can be a great way to sell.
• Sequential build. Carved from a single block, tested at extremes, certified by an institute — “Then, and only then, do we sell it.”

Challenge 7.2: Rolex — The Oyster Case (Proof Through Destruction)

Technique: Demonstrate product quality by showing its limits — and showing it still wins.

Grade 2 readability, 9 words per sentence. The simplest Rolex ad in the series.

Key patterns:

• Challenge the reader’s assumptions. “Next time somebody tells you they have an amazing, new waterproof watch… tell them about the crushed Oyster.”
• Narrative tension through incremental testing. 1,000 feet — nothing. 1,500 feet — nothing. 1,700 feet — crystal bends. 2,000 feet — severely bent. But still watertight.
• Fun, casual tone from a luxury brand. Rolex uses simple, casual language. Luxury doesn’t require pretension.
• Let the product speak. No adjectives needed. The facts are the selling point.

Challenge 7.3: Rolex — James Bond (Aspirational Identity)

Technique: Sell the lifestyle, not the watch. Associate with an aspirational identity.

Grade 2 readability, 10 words per sentence.

Key patterns:

• Lead with credentials, then pivot. Opens with the Submariner’s 660-foot rating, then: “It seems to work pretty well at any level.”
• Mystery as selling. “How come it’s seen so much where the wettest thing around is a dry Martini? Who knows.”
• Flirtatious tone. “Ask her. Maybe she knows.” — playful, confident, aspirational.
• Close with identity. “When a man has a world in his hands, you expect to find a Rolex on his wrist.” The product becomes a signal of who you are.

Challenge 8.1: The Hustle — Welcome Email

Technique: Make transactional moments feel like celebrations. Turn a welcome email into a story.

Grade 3 readability, 13 words per sentence. Sam Parr’s welcome email for The Hustle newsletter.

Key patterns:

• Treat the signup as a big deal. “I assure you, we don’t take what just happened lightly.”
• Paint a vivid, funny picture. A buzzer goes off in the office. The office manager golf-claps. The ops guy does a pushup. Greg runs outside and hugs an old lady.
• Real-time unfolding. The email feels like events are happening as you read it. “Is she pouring another one? Ah crap, I gotta go and stop her.”
• Forgotten copy matters. Welcome emails are usually afterthoughts. Making them memorable creates an immediate emotional bond.
• Include a share mechanism and PS. The PS links to an ambassador program — more forgotten copy turned into a conversion point.

Directly applicable to Sanity Check’s launch sequence — the welcome email is a huge opportunity.

Challenge 8.2: Tactile Turn — About Us Page as Story

Technique: Origin story that embodies the brand’s values. The founder IS the product.

Grade 9 readability, 17 words per sentence.

Key patterns:

• Start with a person, not a company. “Meet Will Hodges.” Immediately personal.
• Universal need, specific frustration. “Everybody needs a pen. Will was frustrated with how disconnected we are from the things we buy.”
• Concrete origin details. WWII-era lathe, 160 sq ft corner of a friend’s workshop, first 1,000 pens by hand. These details create credibility.
• Show growth without losing soul. New 9,000 sq ft workshop, state-of-the-art machines — but still hand-machined in Garland, Texas.
• Parenthetical personality. “(although they do have an aerospace engineer on staff)” — you can hear them saying it.
• Define your customer. “People who sweat the small stuff, yet stay remarkably cool under pressure. People who measure twice and cut once.”

This pattern connects to Nathan Barry’s authority positioning — the founder story as proof of expertise.

Challenge 9: Notion Mastery — Sales Page

Technique: Problem-agitation-solution with a personal founder letter.

Grade 8 readability, 16 words per sentence. Marie Poulin’s course sales page.

Key patterns:

• Social proof opener. A quote from Notion’s CEO calling Marie “one of the most knowledgeable Notion users in the world.” Instant credibility.
• Agitate the specific pain. “You binge-watched how-to videos on YouTube for hours instead of writing those blog posts you had planned.” Painfully relatable.
• Templates ≠ A System. A sharp distinction that elevates the product above free alternatives.
• Bullet-point pain list. “Any of these sound familiar?” followed by a list of exact frustrations the reader has experienced.
• The “HOWEVER” pivot. After presenting Notion as the solution: “If you don’t already have well-established systems, you’ll simply recreate the same dysfunctional patterns.” This creates need for the course specifically.
• Founder letter with vulnerability. Marie shares her ADHD diagnosis and how Notion became a life-changing tool. Authentic, not performative.
• Bridge the gap. “The only tool I’ve found that truly enabled me to bridge the gap between bigger long-term goals and day-to-day actions.”

Challenge 10: Hint Water — Advertorial (The Hustle)

Technique: Hero’s Journey advertorial. Native advertising that reads like editorial content.

Grade 6 readability, 14 words per sentence. A sponsored post for Hint Water in The Hustle newsletter.

Key patterns:

• Hero’s Journey structure. Hero starts ambitious journey, hits adversity, improves, overcomes. Most TV shows use this. Most copy should too.
• Headline as hook. “Getting called ‘Sweetie’ Helped this Entrepreneur Create a Multi-Million-Dollar Business” — curiosity gap that demands a click.
• Dialogue adds emotion. Direct quotes from the Coke executive and Kara Goldin make the story feel real and immediate.
• Multiple tension/resolution cycles. Create tension, resolve it, create more tension, resolve it again — multiple times in a single piece.
• Turn naysayers into fuel. “Listen to your naysayers… not because they’re right, but because it’s fuel.”
• Seamless product integration. The CTA (“Get a bundle of their top flavors for 40% off”) feels like a natural extension of the story, not an interruption.
• Team endorsement. “The Hustle team tried all the flavors and watermelon is our favorite.” Social proof embedded casually.

Pattern Library: Quick Reference

Craft Rules (recurring across all challenges)

1. Readability matters. Most of these pieces score Grade 2-8. None exceed Grade 9.
2. Rhythm is everything. Long sentence, then short. Comma becomes period. Conjunctions start sentences.
3. Parenthetical asides humanize. Multiple challenges highlight this as a standout technique.
4. Forgotten copy is an opportunity. Welcome emails, unsubscribe pages, error messages, copyright text — make them all great.
5. Write like you speak. Use “stuff,” start with “and,” be colloquial. Formality kills connection.
6. The close deserves 25% of the space. Be explicit. Tell them exactly what to do, step by step.
7. Stories beat arguments. The WSJ letter, the Hint advertorial, the Tactile Turn about page — narrative wins every time.

Open Questions

• Which of these patterns should we prioritize for the Sanity Check revival? The welcome email (Challenge 8.1) and manifesto copy (Challenge 6) feel like immediate wins.
• Can we build a “conversational sales” template for Sanity Check landing page copy, modeled on Louis CK’s approach?
• How do the Rolex ads (Challenges 7.1-7.3) apply to positioning data/analytics expertise? Explaining common processes as extraordinary maps directly to open knowledge sharing.
• The Hero’s Journey advertorial (Challenge 10) could be a format for sponsored content or case studies. Worth testing?
• Stephen King’s passive voice and adverb rules (Challenge 4.2) should become a checklist for all published writing, pairing with the creativity faucet for draft-then-edit workflow.
• The AIDA formula (Challenge 2) and Scott Adams’ simplicity rules (Challenge 4.1) together form a complete writing system. Can we codify this as a writing standard for Ray Data Co content?