You had me at Hello (you better)



👋 Hi Reader,

As you know, I am a LinkedIn nut.

Since I have gone independent 6 years ago, 100% of my clientele came from LinkedIn. So naturally, everytime LI launched a new feature, I keep my eyes peeled on how it affects my target audience and my own content.

If you have missed it, LinkedIn has been rolling out ‘Report Your Content as AI Slop’ feature that has the entire network in rapture.

A lot of folks feel acknowledged that they finally have a way to cleanse their feed by reporting the wall of AI slop they see everyday.

But on the other hand, there are people like me who are delightfully unaware that their own hand-written content might come across as AI-generated too.

How? Let me explain.

I was showing one of my clients how I prepare these Letterstack issues by hand. He saw me write the whole thing and asked me innocuously to preview it on Pangram, an AI detection tool.

Suspecting nothing out of the ordinary, I pasted it there and….it reported the content as 80% AI generated :(

For the first five minutes, I was lost for words. And then I started researching around what ticks off these tools to mark them as AI generated.

Turns out like the good old pattern matching tools of the pre-GPT era, AI writing has a type.

Cory Doctorow named this behavior as enshittification. I couldn’t have come up with a better word to describe my grief.

But the real reason why this becomes a detectable pattern is because all AI writing algorithms takes the average of whatever content it sees, and then optimizes and flattens the specifics into a pattern-fitting content topic. If you would like to understand this better, Kyle Chayka writes in detail about this process in the article below and in his book ‘Filterworld’.

So my newsletter content is one click away for being marked as AI slop?

Terrifyingly yes.

​Sabreen Haziq, one of my favorite creators, appealed to her network to show some grace for the content people have been following for years pre-GPT, and use it as a discretionary method, instead of using it as a sledgehammer.

Welp. As if writing wasn't hard enough already. What do I do now?

There’s hope.

And that hope comes from revealing the details, warts and all.

The guiding principle would be as the writing legends put it:

You have been writing about the niche. Now you need to write from inside it.

Here’s a simple test to try out on every issue before you hit send:

Is there a painfully vivid detail that you are slightly embarrassed to include?

Turns out AI cannot be embarrassed. AI cannot admit and be ashamed by guilt.

So I would lean into it full-tilt. If your newsletter is about your lived experiences in a niche, I would share all the stories in gory detail, and how I ended up learning about something the hard way. The Pangram story above is a good starting point :)

Have you named the monster?

Turns out every newsletter niche has a villain and a monster, everybody inside the niche knows, but nobody calls it out loud. In the newsletter niche itself, open rates are one such example.

Name it, poke it in the eye, and run away back to the comfort zone of your ship as fast as you can.

(I am trying hard to shake away The Odyssey references, folks. Thank you for your grace in this important matter)

Make the hook look like a door slightly ajar

Every single subscriber knows the niche, but they don’t know all the hallways like the back of their hand. Your job is to make them aware that this is a new hallway that leads to a door halfway open, and make them peek inside….and ensnare them with your vivid content.

Keeps the human subscriber curious. Keeps the AI bot curiouser, because it has no idea how to summarize that email. Keep both of them guessing :)

Does that clarify your writing process? If you are still on the fence on how to escape the AI slop button, I would love to be a sounding board.

Let me know by hitting ‘Reply’ on this email, or send a note to marketing@letterstack.co.


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Renga from LetterStack

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