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Write a Newsletter for 52 Weeks in a Row, and Watch It Change Your Life

by | Apr 11, 2022 | Writing


The best ideas are so stupidly simple.

A newsletter doesn’t seem smart. Anyone can create one. Email is nothing new. Yet a small number of us have unlocked the secret of why newsletters are so powerful.

One of those is Dickie Bush. His mentor Khe Hy said to him while working a dead-end job at financial services company Blackrock, “Write a newsletter for 52 weeks in a row, and watch it change your life.” It did.

My newsletter now has more than 50,000 subscribers.

I wish I’d known these simple strategies at the start of my newsletter journey. Steal them.

No one is looking for more emails. Sorry.

Quit thinking your newsletter is better than hot sex.

The only two ways to succeed with a newsletter is to:

  1. Write the best newsletter on a topic
  2. Curate the best content

If you can do one of these you’ll be wildly successful.

Use discount bias

One option to make money from a newsletter is to charge for a subscription to it using a platform such as Substack.

One of the best newsletter writers in the world, Polina Marinova, came up with a genius strategy.

$10 a month…

Or $50 a year.

Our brains are biased towards discounts. If something is cheaper then logic takes over. Everyone who buys a subscription from Polina goes for the yearly option as it’s more than 50% cheaper than monthly.

Readers get great value. As the newsletter owner you get a subscriber for more than a year.

Once someone’s read your work for a year, they’ll probably stick with you long-term. But a subscriber who only commits for a month can easily love ya and leave ya.

A newsletter that costs money to subscribe to grows painfully slow

Asking for payment is one of the biggest decisions you’ll make with a newsletter.

Recently, I got a crash course from a guy on Twitter. He said to me, “Tim, you’re a freaking idiot, you know that?”

“Paywalled content isn’t shareable.”

Think about it. I share an article with you via email. You click it. It takes you to a page and asks you for a credit card before you can read it. Most people will close the tab. Too much friction. Not enough information. No idea if the link is worth the money. And there’s so much good free content anyway.

Always start with a free newsletter.

It tests your skill and allows it to easily be shared online. As people share it, your subscriber numbers grow quickly.

There’s a way around the asking for money problem

Once you’ve had some time in the game, there is a way to go premium yet still have people share your newsletter.

The formula I’ve found is this:

For every 6 editions of your newsletter, make 4 free and only 2 able to be seen if a user pays the subscription.

Free does the marketing. Premium pays your bills. Marketing problem solved.

Two other ways to make money from a newsletter

1. Sell one ad at the top of each edition

2. Place affiliate links in the email

Newsletter ads have exploded since Apple destroyed Facebook ads by asking users to opt in to being tracked.

With the success of Facebook and Instagram ads falling off a cliff, businesses need a way to access audiences.

An ad in a newsletter now gives them better ROI. If you own a newsletter, then guess what? The ball is now squarely in your court. This is a huge opportunity.

If you manage to get an advertiser, take it to the next level. See if you can get a share of the revenue from every sale of a product/service that happens from the link in your newsletter. Boom!

Growing a newsletter isn’t obvious

The hardest part with a newsletter is finding an audience.

My friend Jack Raines taught me a cool technique. Do what early bloggers in the 2000s did: guest post in other newsletters.

Find a newsletter you love, guest post in it, then link back to your newsletter at the top of the edition. The newsletter owner can then post in yours and link to theirs.

Plus readers that are already trained to love newsletters are better than regular readers on social media who don’t appreciate the art of a well-written email as much.

The main way a Substack newsletter grows

Casey Newton has lit the newsletter industry on fire with his publication Platformer.

He says most Substack newsletters only grow through tweets.

Polina Marinova says if you want to grow a newsletter it’s best to do it through Tweet Threads — a series of tweets from an article with the last tweet being a link to the full story on Substack/Ghost/Beehiiv. (Example here)

Change the labels

Don’t call it a newsletter. Don’t call people subscribers.

If it sounds generic then we’ll ignore it.

The big newsletter opportunity no one saw coming

Web3 expert Balaji Srinivasan opened my eyes to another slept on opportunity. He says every company now realizes they need a newsletter, just like they learned five years ago to have a blog.

Every company will eventually have a newsletter. But business is lazy AF. They won’t start newsletters. Nope.

They’ll acquire them.

If you have a great newsletter already then there’s a good chance it can be acquired for a nice amount of cashola. You’ll likely get offered a role to stay on as editor-in-chief doing what you do best.

SaaS companies will likely bundle their software with a free newsletter. The goal will be to turn customers into readers, because readers become part of the community then.

Community is where future profits lie. Your newsletter can be a bridge between customer disloyalty and the new world of community loyalty.

What stops us starting newsletters…

We think our newsletter has to be unique or special. No way.

A powerful newsletter that people can’t resist delivers commentary with real style and personality. Anyone can do that. Even you.

The coolest part about a newsletter that will change your life in 52 weeks

The title made a big promise. Let me deliver. Ready?

The coolest part about a newsletter isn’t the money you can make. It’s the accountability it creates.

Readers will depend on you to show up. That builds an unstoppable writing habit. A writing habit will change your life in 52 weeks or less.

Maybe it’ll be the newsletter that creates your future success. Or perhaps a newsletter becomes the seed of your success. A newsletter allows you to be around what you’re passionate about. It’s forced learning. It involves free networking as part of the process.

A writing habit can change your life. Get leverage.

Publish a newsletter for 52 weeks in a row and become Dickie Bush or Khe Hy.

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