The Anti-AI Writing Style Guide
Your readers can smell AI copy in two sentences. Here’s how to avoid it.
The 25 Banned Phrases
If any of these appear in your newsletter, delete them immediately:
- “Delve” / “delve into”
- “Landscape” (as in “the AI landscape”)
- “Tapestry”
- “It’s worth noting”
- “In conclusion”
- “Let’s dive in”
- “Game-changer”
- “Revolutionize”
- “Leverage” (as a verb)
- “Synergy”
- “In today’s rapidly evolving”
- “At the forefront”
- “In the realm of”
- “It is important to”
- “Cutting-edge”
- “Groundbreaking”
- “Seamlessly”
- “Robust”
- “Holistic”
- “Unlock the power”
- “Harness the potential”
- “Take it to the next level”
- “Furthermore”
- “Navigate” (as in “navigate the complexities”)
- “Paramount”
The 6 Writers to Study
Your voice should be the intersection of these people:
Paul Graham (Essays)
- Steal: Short sentences. Strong opinions. Contrarian takes.
- Example: “The most dangerous thing about bad investors is not the money they burn, but the time.”
- Rule: If you can say it in 5 words, don’t use 15.
Packy McCormick (Not Boring)
- Steal: Conversational tone. Analogies from unexpected places. Builds excitement without hype.
- Example: “Stripe is basically doing to financial infrastructure what AWS did to computing infrastructure, except financial infrastructure is a much bigger market.”
- Rule: Make complex topics feel like a story you can’t put down.
Lenny Rachitsky (Lenny’s Newsletter)
- Steal: Direct. Opinionated. Data-backed. No filler.
- Example: “The #1 mistake PMs make is building features nobody asked for.”
- Rule: Every sentence earns its place. If it doesn’t add value, cut it.
Ben Thompson (Stratechery)
- Steal: Analytical frameworks. Connects dots others miss.
- Example: “The Internet transformed distribution. AI transforms creation. They are complementary, not competitive.”
- Rule: Have a unique lens. Don’t just report — explain why it matters.
Trung Phan (SatPost)
- Steal: Witty. Pop culture references. Makes business fun.
- Example: “Mark Zuckerberg’s pivot to the metaverse was like Blockbuster launching a streaming service in 2010 — right idea, wrong execution, wrong time.”
- Rule: Humor makes dense topics accessible.
Simon Willison (Blog)
- Steal: Hands-on. “I tried this and here’s what happened.”
- Example: “I ran this prompt against Claude, GPT-4, and Gemini. Here’s what each got wrong.”
- Rule: Show, don’t tell. Credibility comes from doing, not theorizing.
The Formula
Every article summary in your newsletter should follow this structure:
- Hook — One sentence that makes them stop scrolling
- Context — What is this, specifically? (Not vague)
- So what? — Why should a builder care?
- Edge — What do you know that they don’t?
- Action — What should they do about it?
Example (Bad — AI Slop)
“In today’s rapidly evolving AI landscape, a groundbreaking new framework has emerged that promises to revolutionize how developers leverage large language models. It’s worth noting that this cutting-edge tool seamlessly integrates with existing infrastructure.”
Example (Good — Human)
“GitAgent packages AI agents into portable containers — like Docker but for agents. If you’re shipping agents to customers and tired of ‘works on my machine,’ this is the fix. LangChain and CrewAI agents both work. Try it before your competitors do.”
Same information. One sounds like a robot. The other sounds like a friend who just found something useful.
The Structural Tells (What Detection Tools Actually Measure)
AI text gets flagged on two metrics: perplexity (how predictable each word is) and burstiness (how much sentence length varies). Here’s how to beat both:
Sentence Structure
- Never start two consecutive sentences with the same word
- Mix 4-word sentences with 25-word ones. Three sentences of similar length in a row = AI flag
- Use fragments. For emphasis. Like this.
- Start sentences with “And” or “But” sometimes. AI never does
- Stop ending sentences with ”, hoping to…” or ”, making it…” (participial phrases). AI does this 2-5x more than humans
- Don’t do three-part parallel lists (“fast, efficient, and reliable”) more than once per section
Paragraph Structure
- Vary paragraph length wildly. One-sentence paragraphs exist. Use them.
- Don’t follow topic-sentence > evidence > summary for every paragraph. Lead with the example sometimes. Let the point come last.
- Never write a conclusion that restates what you said. End on a detail, a question, or just stop.
Punctuation
- NEVER use em dashes. AI uses them 10x more than modern human writers. They are the #1 punctuation-level AI tell.
- Semicolons: max one per 500 words
- Don’t bold random words. Don’t use emoji in prose. Don’t use arrows or decorative unicode.
Tone
- Don’t hedge everything. “Try this” beats “it may be advisable to consider implementing”
- Say things are bad when they’re bad. AI is relentlessly positive. Genuine negative opinions signal humanity.
- Mix contractions inconsistently. Sometimes “it’s,” sometimes “it is” in the same piece. Humans do this naturally.
- Include specific names, numbers, dates, dollar amounts. AI writes in plausible generalities.
The Test
Read every sentence out loud. If you wouldn’t say it to a friend over coffee, rewrite it. If a sentence could appear in any article on any topic, it’s too generic. Kill it.