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Every Piece of Newsletter Advice I Have to Give as I Approach 200,000 Email Subscribers

by | Dec 11, 2023 | Writing

“Build your email list or don’t write.”

That’s what my mentor said to me at the start of my writing journey. Thanks to him he’s saved my writing life.

If I’d ignored him and focused on useless followers or pandering to platforms, I’d be broke as a joke, begging my former bank bosses for a job again.

If you’re an entrepreneur, creator, or writer then an email list is your lifeblood. Without it, your career dies.

It’s been one hell of a journey and I’m about to hit 200,000 email subscribers. Here’s every piece of advice I have for anyone with fewer than that number of subscribers (learn from the best, ignore the rest).

1. Killer subject line or no one opens

You live and die based on your email subject line.

It’s the same as headlines on social media. One data point I have is when I get fancy and become unclear in email subject lines, no one reads. I may as well not have sent the email.

Use the principles of good essay headlines in your email subject line.

  • Clear not clever
  • Feature a benefit
  • Use proven headline templates
  • Don’t make the headline too long or it’ll get cut off

2. Send your newsletter at this exact frequency

This one confuses people.

Sending daily newsletters is a pain in the butt. This isn’t social media after all. The magic frequency is a weekly newsletter. If you publish less than that, then people forget who you are and unsubscribe.

If you publish more than that, your emails can be deemed spam and get an unsubscribe slap from a reader’s hand.

If you want to post more often, then you use mass social media platforms to write short-form content that leads to your newsletter.

3. A newsletter without the help of social media is useless

I can’t tell you how many times writers send me links to their Substack newsletters. They’re so proud of it.

They publish their gorgeous little newsletter and go “see, I’ve got the writing habit so watch out for my New York Times Best Selling Book.”

This is a lie.

Being prolific as a writer isn’t enough.

A newsletter needs distribution. It needs a way for new readers to find it and subscribe to it. You cannot successfully run a newsletter without social media, sorry.

The strategy is simple:

1) Choose your poison (social media app)
2) Post short-form daily
3) Reply to your post with a link to the newsletter

You can literally make 7-figures with this newsletter strategy, yet most won’t because they overcomplicate it.

4. Have fun

Wait, what?

Yep, too many writers turn their newsletter into a boring job.

They write about their precious niche like it’s going to win them the lottery. As a result, they chase trends and topics they’re NOT obsessed with and eventually give up.

The strategy is to have fun and write about what you’re interested in. The niche is your worldview, not a topic. We are not one-topic people who can never escape the constraints of a niche to read about a field like medicine (that we don’t have a degree for).

I’ve had so much fun writing my newsletter. I’ve gone from what’s happening on Wall Street, to life advice, to productivity, and even quote posts from controversial figures.

Because I have fun my newsletter doesn’t feel like work.

That effortless feeling makes it 10x easier to write and that’s why people show up to read it.

When you’re interested, the reader is interested.

5. Remove the filter

A lot of online writing makes me fall asleep while reading it at the traffic lights. I’m surprised I haven’t slammed into another car yet (joking).

The reason is everyone is taught in their jobs to write with this corporate wanky tone that tries to sound smart and please everybody. It makes me vomit in my mouth.

It’s why 99% of newsletters sound like press releases instead of writing people want to read.

That’s why I called my Substack “Unfiltered.” It’s a daily reminder to remove the corporate banking filter I acquired in my 9–5 life and write like I speak so people don’t fall asleep.

I occasionally swear. I sometimes use Aussie slang. I don’t give a flying hot potato about grammar or commas.

There’s not much editing either. I write the newsletter, edit once, chuck it in Grammarly, then hit publish.

Is it perfect? Nope. Do I give a f*ck? Nope.

  • Remove the gaffer tape from your mouth and your newsletter will come alive.
  • Use a nickname to begin with if you’re afraid of the work bosses.

6. Not too many links

A podcast between Tim Ferriss and James Clear a few months back changed my thinking on newsletters.

James said people open newsletters to click links. But people don’t listen to podcasts to hear links then enter them into their phones.

That’s why I love newsletters.

You can insert links to resources. You can softly insert links to your products or services. You can link to your other content and social media to create a flywheel. Or you can quietly put in affiliate links and earn a commission without feeling sleazy.

Where creators stuff up is they insert so many links, you feel like you’re at the car dealership and the car salesperson is trying to add in the tint, paint protection, bigger tires, and fluffy dice.

The power of newsletter links is to use them sparingly.

I often only ever have one link in my newsletter, that way the reader isn’t confused about what they can do after reading.

7. Don’t sell too much

Most newsletters are a salesfest.

You feel like you’re at a FX trading seminar and the guy’s trying to upsell you every coaching program in finance history.

Sales is a subtle art. If you sell too much you come across as needy. And needy creators make pennies and starve. If you sell occasionally, ethically, and with good intent to be helpful, people don’t mind it.

Your newsletter isn’t a sales letter. Read that again.

Most of you shouldn’t be selling at all in the beginning.

8. Tell stories

Too many newsletters have just become lazy curation.

They’re full of other people’s work and they’re put together 10 mins before it goes out while sitting on the crapper dropping last night’s dinner. Yuck.

The way to stand out — yes, you’ve heard it a million times — is to have stories in your newsletter. My best newsletter editions always start with a story. And it’s not one that takes 5 hours to read and needs a degree.

The best newsletter writers are observers. They see the world and all the stories within it, then write about it.

Fewer facts, more stories.

9. Double down on your best editions

If I was famous and had a fan club it’d be called “Data-Driven Writers.”

The worst thing you can do with newsletters is guess. I’m a dumb-dumb and didn’t study English, so I believe the readers are smarter than me.

When I see a newsletter edition do well, I do more of it. Early on in my Substack journey, I noticed when I did lists of quotes from controversial leaders, people loved them.

So I repeated this idea many times.

Now, every few weeks, I do a deep dive on a controversial leader and dare to see the good and the bad in their life. I would never have discovered this unusual topic if I didn’t experiment and pay attention to the data.

Stop guessing. Ask readers what they want. Pay attention to reader engagement. Then double down on what works without joining the jerks.

An unexpected and controversial ending

I don’t want to grow my newsletter much more.

Yep. Bombshell. The reason is because of an article I read by Tim Ferriss about fame. I fear if I keep building this huge newsletter, I may become famous and that means losing my privacy.

This journey has taught me to focus less on vanity metrics and more on building deeper relationships. It’s one of the reasons some of my newsletters are now behind a paywall.

You think you want millions of email subscribers until a stalker shows up at your door and wants to make love with your blender.

So build your email list. Just find a number that’s enough, then double down on monetization.

God bless the famous people who cop all the attention so the rest of us can live in quiet peace.

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