Hey Reader — It's Doug.

I've been sending emails for 20+ years. Ran an email agency. Became Mailchimp's #1 global partner. Worked with 7,500+ brands.

And I still see the same newsletter mistakes. Every. Single. Week.

So here are six of them. With examples. And screenshots. Because nobody ever learnt anything from a wall of text.

Right. Let's go.

1. You let ChatGPT write it

Look, I use AI. Loads. It turns my video transcripts into outlines quicker than I can make a brew.

But you can spot an AI newsletter from across the pub:

Nobody talks like that. Not even people on LinkedIn.

Before: "In today's fast-paced world, building an audience has never been more important."

After: "LinkedIn could switch my account off tomorrow. 23,158 followers, gone. My email list? Still mine."

The first one could've come from anyone. The second could only come from me.

Rule: if anyone could've written it, nobody will read it.

Let AI be your sous chef. Let it chop the onions: transcripts, outlines, 20 subject line ideas. But you season the food.

2. You forgot why they subscribed

Nobody signs up to your newsletter thinking "ooh, I can't wait to be sold to."

They signed up for something. A tip. A shortcut. A laugh. Their reason, not yours.

Look at Morning Brew's sign-up headline:

Not "Subscribe to our newsletter". Not "Get our latest updates". Become smarter. In 5 minutes. That's the deal.

James Clear does the same thing:

3 ideas, 2 quotes, 1 question. Every Thursday. You know exactly what you're getting before you hand over your email address.

Before: "Subscribe to my newsletter for updates."

After: "One email tip every Tuesday. Nick it in 2 minutes."

Rule: every email has to pass the WIIFM test. What's In It For Me? ("Me" being them, not you.)

Your award, your office move, your new hire... nobody cares. Sorry.

3. You want it to work by Friday

Email isn't a scratchcard. It's a pension.

Morning Brew launched in 2015. Five years later, Insider bought a majority stake in a $75m deal.

Five years. Not five weeks.

Most people give up around issue 6. Opens are meh. Nobody replied. Sharon from accounts unsubscribed.

That's exactly when it starts working.

Rule: pick a day. Pick a time. Turn up every week. Consistency beats creativity, especially when nobody's reading (yet).

4. You're blasting, not chatting

Email is social media. Just slower and less shouty.

If all you post on LinkedIn is "BUY MY THING", you get tumbleweed. Same in the inbox.

Ann Handley doesn't obsess over clicks. She tracks her "Open-to-Write-Back Rate": how many readers actually hit reply.

Her line: "Size is a byproduct, not a goal."

My rule of thumb is 80% value, 20% sales. Earn the right to pitch.

Before: "Last chance!!! Click here to buy now."

After: "Quick one. What's stopping you sending every week? Hit reply. I read every one."

The replies are gold. You learn what people actually want. And inbox providers like it when people reply to you.

5. Your lead magnet is a 60-page ebook

Nobody wants your 200-page ebook. They want the 10 pages that fix their problem today.

High value. Low time. Low friction.

My best ever lead magnet wasn't a PDF. It was a free email preview tool. It pulled in 30–50 new subscribers a day.

Formats that work: checklists, templates, swipe files, a 5-day email course, a little tool or calculator.

And only ask for first name and email. Every extra field means fewer sign-ups.

6. You know nothing about your subscribers

A list of email addresses isn't an audience. It's a spreadsheet.

Lead magnets do double duty. They pull in new subscribers AND tell you about the ones you've already got. Someone grabs your cold email checklist? They just put their hand up. Tag them.

Here's a cheeky one I nicked from Andrew King at EmailLove. Don't know someone's name? Don't hide it. Point at it.

Playful. Obvious. And people actually fill it in.

Then in email 3 of your welcome sequence, ask one question. Just one. "What are you struggling with right now?"

Rule: small asks, often. Not a 20-question survey on day one.

Bonus: how it all fits together

Funnels leak. Flywheels spin.

This is my 4 Cs Flywheel:

1. Content. You post where people already hang out (LinkedIn for me). That audience is rented. You don't own it.
2. Community. You move them onto your newsletter. Now they're yours.
3. Commerce. They trust you, so they buy something.
4. Customer. They love it, become your case study and send their mates. That case study becomes content. Back to step 1.

Your newsletter sits right in the middle. It's where followers turn into people you actually know.

That's it. Six mistakes. I've made most of them. Some twice.

Hit reply and tell me which one you're guilty of. I won't tell anyone.

Cheers,

Doug

P.S. I'm building something called Noosletter. That's all I'm saying for now.

P.P.S. Know someone whose newsletter is guilty of all six? Forward this to them. Don't tell them it was from me.