What to do if your marketing sucks 📉

How one company became “cool” by doing these 3 moves.

Oct 16, 2025

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What to do if your marketing sucks 📉

I stood in line for 2 hours last weekend.

For a hat.

A hat that says “thinking” on it.

The line went around the entire block in NYC. I talked to probably 30 people while waiting. Founders from Austin. Marketers from LA. Developers from Brooklyn.

Everyone wanted this hat.

It was Anthropic’s viral coffee shop popup (they make Claude AI).

But their marketing used to be absolutely terrible.

One year ago, I saw their ads at Times Square: “Move your work up and to the Claude”.

I remember staring at it and thinking “what does that even mean?”

Then, in 2025, they made a bet. Went the opposite direction of everyone else. And it worked.

I’m going to show you exactly what they did because you can copy this for your own brand.

Here’s everything you need to know.

Safe marketing is just slow death 💀

Anthropic ran these “safe” ads for two years:

I’ve been doing marketing for over a decade, and I think I know what happened here: Some agency got paid $200K to write that copy. Everyone in the boardroom nodded. It sounded professional. So they approved.

It was garbage.

Then September 2025 happened.

OpenAI launches Sora 2. It generates AI videos. Everyone in tech got excited. Then people realize what this enables: mass-produced AI content. Low-quality videos made purely for engagement and ad revenue. Twitter had a new word for it: “slop”.

That’s when Anthropic saw an opportunity.

They hired a new growth marketing lead and tried something new.

They launched their “Keep Thinking” campaign and popup coffee shop. The entire positioning became anti-slop. Against AI-generated garbage. For actual human thinking. Keep thinking.

The contrast was perfect.

While OpenAI is making more AI content, Anthropic is positioning against all of it.

Where 99% of marketers go wrong ❌

Let me give you a test.

You’re running marketing for Claude in 2024. Your product is great for writing, coding, analyzing data - basically any work that requires thinking.

How do you position this?

Be honest. What would you write?

Most marketers would write traditional enterprise copy:

“Make better business decisions with Claude”
“The AI for business productivity”
“Work smarter with AI”

It’s wrong. ❌

You just made it sound like every other B2B software: Business-focused, work-focused, and most of all, boring.

Anthropic did something way smarter:

They said Claude is for ANYONE who thinks. ✅

Not businesses. Not productivity seekers. Just people who think.

Now everyone uses Claude - artists, writers, lawyers, students, etc.

One billboard says: “There has never been a better time to have a problem.”

I read that and thought “damn, that’s good.”

They’re not saying “we solve problems fast.” They’re celebrating the fact that you HAVE problems. Because having problems means you’re doing real work.

The frame changed from “productivity tool” to “thinking tool.”

That opened everything up.

The 3 bold moves they made

I studied everything they did, and it breaks down to 3 specific moves:

Move #1: Full opposite direction 🌀

They had the courage to say the opposite of what their competitors are saying.

🪫 Everyone in AI: Automate everything! Replace humans! Go faster!
🔋 Anthropic: Think more! Enhance humans! Go deeper!

That’s not slightly different… It’s completely opposite.

Move #2: Made it physical 🧢

They opened the coffee shop I mentioned for one weekend.

Free coffee & hats. The hat says “thinking” (a play on “put on your thinking cap”)

Wearing that hat signals you use Claude. It makes you look smart. Like you’re someone who values deep thinking over quick answers.

Move #3: Celebrated the person, not the product 🎉

Their ads don’t say “Claude is smart”. They say “YOU think. We help”. That’s the entire difference.

Why the hat itself is actually genius 🧠

Most company merch has SALESFORCE or HUBSPOT in giant letters. You wear it once if you work there.

The “thinking” hat is different.

When you wear it you’re saying: I value deep work. I’m against slop. I make real things.

It’s identity, not advertising.

That’s why I waited 2 hours.

Remember: People don’t buy products. They buy membership in tribes.

That hat is a badge that says “I’m in the anti-slop movement”.

Your marketing sucks because you’re selling features. Features are boring. Tribes are magnetic.

The Anti-Positioning Playbook (a.k.a. how to fix marketing you hate) 📕

This is the framework Anthropic used. I’m calling it the “Anti-Positioning Playbook”.

If you hate your current marketing - this is how you fix it:

Open a doc. Write down what your top 3 competitors say on their homepage. I bet they’re all saying the same thing.
Check what they’re actually running right now. Use Meta Ad Library, TikTok Ad Library, LinkedIn Ad Library. Here’s my guide on tracking competitors.
Find the pattern. When I did this for AI companies: automation, speed, efficiency. For productivity tools: do more, move faster. What’s your industry’s echo chamber?
Write what your product is actually good at. Be honest.
Write what people in your industry are exhausted by. What are they tired of hearing?
👉 Find where those two overlap. Anthropic’s product helps you think through problems. People were tired of mindless automation. Boom - “thinking tool” not “work tool”
Or ask: what makes your product “slower” or “harder” than competitors? That might be your strength. Anthropic could’ve hidden that Claude takes time. Instead: “Keep thinking”.
Pick your opposite stance. Write it as a belief (not a feature). Anthropic: “We’re for thinking, not automating.”
Make something physical. One thing. A popup. Merch. An event. Something people can touch or attend. Budget doesn’t matter - just make it real.
Make it about them, not you. That “thinking” hat doesn’t say CLAUDE. It says what kind of person you are.
Finish this sentence: “People who use [your product] are the kind of people who ___________” If you can’t → you don’t have positioning yet.
Write the reason someone gives when asked “why do you use this?” Again, it should be a belief, not a feature. “I’m against AI slop” is repeatable. “It has better context windows” isn’t.
Now make that the center of everything you say. Rewrite your homepage around it. Change your ad copy to it. Train your team to say it. This is your new positioning - let it replace all the feature talk.
Launch it all at once. Don’t test. Don’t phase it in. Change everything the same day. Half-committed positioning is bad positioning.

Safe = invisible 🌫️

Your boss will 100% push back on this playbook.

Someone else will say it’s too risky, or too different, or too likely to alienate customers.

That’s why your marketing doesn’t work now.

Because safe is invisible.

Look at what actually breaks through:

DuckDuckGo makes $0 from selling user data when Google’s entire model is tracking everything. Their privacy tribe grew to 100M daily searches.
Notion spreads bottom-up through individuals when enterprise software is usually sold top-down to CXOs. Their tribe created 100,000+ templates for each other.
Oatly makes F*ck Oatly - a website documenting every negative thing about their company. All the hate comments. All the boycotts. All the lawsuits. Their board probably thought they were crazy. It became their most shared marketing asset.

The pattern of all of them: Pick a side. Make enemies. Build a tribe.

Anthropic probably heard “don’t position against the entire AI industry” 100 times.

They did it anyway. Look where they are now. They win.

Your move 💣

This is the Anti-Positioning Playbook.

Use it when your marketing sucks and you hate looking at your own ads.

The playbook is right here: Pick your side. Make enemies. Give people a tribe to join. Anthropic went from cringe to viral in 90 days by doing exactly that.

The safe zone is where you disappear.