I was scared to send newsletters.

So this morning, while sipping my third cup of coffee (don’t judge, you know how it is), I caught Tyler Morin, who is also a client of ours, on the LetterLand podcast.

Btw, Tyler runs a newsletter called The Water Coolest, which has over 100,000 subscribers, and he also writes the dankest jokes. (even better than me)

Enough about Tyler, I want this to be about me because you know… I’m a narcissist. 🌚

Tyler said something about AI and newsletters that caught my attention.

He was talking about how everyone and their uncle is suddenly obsessed with whether newsletters are dead or if AI is going to take all the wind out of our sails.

If you run a brand or business, you’ve probably had the same nagging thought: “Are my newsletters even landing, or are they just lost in a cluttered, AI-summarized inbox?”

Here’s the thing: I get that worry. Back when I was building out our first real mailing list for God Block, my NFT company, I was terrified. I’d send out these carefully crafted emails, cross my fingers, and then…wake up the next day to a handful of opens and maybe a stray reply.

Nothing kills motivation faster than no one caring.

But a couple of weeks ago, a client came to me with a burning problem: their expertly written newsletters weren’t moving the needle. People were skimming and bouncing.

Worse, a few told them straight up that their inboxes were getting “AI digest” versions instead of the real newsletter!

I realized then, as Tyler echoed on the podcast, that we’re not fighting against AI; we’re fighting for attention. And that’s actually good news.

Let me tell you how we flipped things around. Instead of blasting “top tips” or generic wisdom, we got real. Every email started with a true story from the founder.

Winning moments. Ugly losses. What went sideways and what actually worked. Suddenly people replied to that. Here’s what else we did, step by step:

• Shorter, punchier emails. Three scrolls or less.

• One story, one lesson, and one ask per email. No more “everything and the kitchen sink.”

• Brutal honesty. If something flopped, we owned it.

• We asked readers to hit reply and share their take or challenge. And we actually wrote back.

• When we referenced data, it was our own. No recycled stats or random predictions.
  

Not going to lie, there were misfires at first. But whenever we led with a true behind-the-scenes fail (like that time I accidentally sent sent the wrong link to the entire list — yikes), the replies rolled in.

Why does this matter now? Because newsletters aren’t about info, they’re about having a real voice in someone’s day. AI can summarize, but it can’t replace the awkward, funny, and flat-out human parts that make your story stick.

So next time you sit down to write your newsletter, ditch the best practices list. Think of a conversation you had this week that made you laugh or pause.

Tell that, and tie it back to something practical your reader can use right away. Keep it messy if you have to, but keep it real.

If all this sounds like the sort of thing you want more of — or you want someone to help you build, grow, and actually scale a newsletter that breaks through the noise — check out The Newsletter Company.

That’s my team’s jam: building newsletters that feel like they’re written by humans, for humans.

Hit reply if you want to swap stories or see some examples. If nothing else, let me know one thing you wish landed better in your inbox.

Catch you later,
— Shashank

P.S.

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