3 Newsletter Mistakes That Scream 'Amateur Hour'

Your subscribers notice these more than you think

Your newsletter is the most important medium because that's where you generate sales.

The problem is that a lot of people actually screw things up.

I've been writing and sending newsletters for the past 13 years.

I probably made more mistakes than anyone else here.

Let me show you the three biggest mistakes that make your newsletter look like amateur hour.

Never start with these 2 words

"Hey everyone."

This greeting is the email equivalent of a telemarketer calling during dinner.

It screams mass email. It sounds like you're talking to a crowd, not a person.

Sure, people on your list know it's a mass email. But they can forget if you do it right.

Because when someone opens your email, they want to feel like you're talking directly to them. They want that one-on-one conversation feeling.

"Hey everyone" destroys that illusion instantly.

It's like walking into a coffee shop and the barista yells, "Welcome, customers!" instead of making eye contact and saying, "Hey, how's it going?"

The fix is simple: Just start talking.

Skip the greeting entirely. Jump straight into your story or point. Or if you must use a greeting, make it personal: "Hey there" or just "Hey [First Name]."

If you use the merge tag, don't screw it up, though. Because nothing says amateur like a broken personalization token.

#413

"Issue #413: How to grow your business" – who the hell cares that it's issue 413?

Your readers don't give a damn about your numbering system. They don't collect your emails like baseball cards. They're not keeping track of which issue they're on.

What makes people click is curiosity. It's talking to their fears, desires, and frustrations.

The subject line is prime real estate. It's the first thing people see. And you're wasting it on your Notion dashboard nonsense that means nothing to anyone except you.

Do you open "Issue #47: Facebook ads" or do you open "I lost $7,341.32 on Facebook ads (here's why)"?

The second one wins every time.

Your subject line should make people curious. It should hint at a story, a lesson, or a benefit. It should make them think, "I need to know what this is about."

Write like your writing gurus on Substack

Newsletters ain't blog posts.

The reader experience is different. People check their emails on their phone while checking Facebook, between Zoom meetings, or while sitting on the toilet.

They don't want to read War and Peace. They want quick, digestible insights they can consume and act on.

The solution? Write short emails. 200-300 words.

I used to write these long, essay-style newsletters. I'd spend hours crafting the perfect introduction, building up to my main point, and then wrapping it all up with a neat conclusion.

Hard to produce, hard to digest.

Your newsletter should look like an email – not a newsletter. It should feel conversational, not academic.

• Tell stories.

• Use bullet points.

• Break up your text.

• Make it easy to read on a phone screen.

A final word on writing profitable emails, fast

The moment you start treating your newsletter as a casual email that you send to a friend...

Not only are you going to sound more human...

But it will also make people open, read, click, and buy from you.