What You Can Learn from The Internet’s Most Successful Newsletters

And how you can apply them to grow and monetize your own newsletter.

What You Can Learn from The Internet’s Most Successful Newsletters
Photo by Amelia Bartlett on Unsplash

And how you can apply them to grow and monetize your own newsletter.

A newsletter is the most underrated business opportunity for writers.

Don’t believe me?

The top 27 most profitable newsletters on Substack generate over $22 million annually.

Image by SingleGrain from Turning Inboxes into Gold: Newsletters as a Profitable Business

Even if you don’t want to monetize your newsletter immediately, starting one today can pave the way for your future success. A few benefits of having a newsletter: 

  1. It’s platform-agnostic. You can reach your readers directly through their emails.
  2. You’re 100% in control of what, when, and how you publish content.
  3. You can use it to sell sponsorships, build communities, and establish other side hustles that will eventually generate passive income.

All benefits aside, starting a newsletter can feel intimidating, especially if you’re a new writer.

I’ve spent the past 30 days studying 50 of the most successful newsletters on the internet. In this article, I’m dissecting the four most powerful lessons I learned from my analysis.

Read on, and make sure to take notes as you go. They’ll come in handy when you finally decide to launch your own newsletter.

1. Have a catchy name 

When it comes to books or articles, the reader that’s casually passing by will always be more inclined to pick the one has the catchier title — something that has shock value and isn’t what one would normally expect.

A newsletter is no different. 

In today's time of short attention spans and an ever-increasing number of distractions all around, it’s important to have a catchy name. 

Learning from some successful newsletters around the world, here are some tips to write a catchy title:

1.1 Make sure it conveys the purpose of your newsletter

Imagine there’s a reader who’s just skimming through the internet and lands on your landing page. 

How do you convey to them what your newsletter is about without expecting them to read the 3000-word copy you’d written for newsletter subscribers?

You have a name that conveys the exact value proposition of your newsletter. Make it catchy and as straight-to-the-point as you can. Some examples are:

  • Tim Ferris’s weekly newsletter, 5-Bullet Friday where he shares five coolest things he’s found or explored that week.
  • James Clear’s 3–2–1 Newsletter where he shares 3 short ideas, 2 quotes from others, and 1 question for the reader to ponder.

1.2 It should be tied to how people otherwise know you

  • Mark Manson, famous on the internet as the author of The Subtle Art of Not Giving A F*ck has a newsletter titled Mindf*ck Monthly.
  • Music critic Bob Lefsetz writes an eponymous monthly newsletter called the Lefsetz Letter.

2. Make people WANT to sign up

You have a catchy name and have already planned the content for the next four newsletters.

That’s cool, but how do you get people to read your work?

The trick is to develop a hook so intriguing, that people are tempted to share their emails with you. Let’s take a look at how some of the most-subscribed newsletters around the world are taking care of this.

2.1 Offer a freebie

  • Bestselling author of You Are A Badass, Jen Sincero offers a free download “10 Secrets to Being a Badass” for every person who signs up for her newsletter.
  • New York Times bestselling author, Gabby Bernstein offers a free 3-part “Judgment Detox Mini-Course” as a freebie for signing up to her weekly newsletter. 

2.2 Play to their emotions

Humans make emotional decisions all the time. 

As a writer, you can utilize this to get more email subscribers. Some examples:

  • James Altucher doesn’t ask people to simply “sign up” to his newsletter. He asks them a question “Will you choose yourself?”, and anyone who clicks on the bright blue button saying “Yes, I will,” is lead to the newsletter signup page.

2.3 Incentivize people who want to reach you

People who sign up to your email list usually do it because they found your work inspirational and want to feel more connected to you. 

You can incentivize them further by giving them much more in addition to your weekly emails. Some examples:

3. Pick a frequency that suits you

The publishing frequency depends on the content you’re sending and the industry trends in your niche. 

Ultimately, your newsletter should solve a genuine problem the readers have. Your publishing cadence should match with how often they want such solutions in their email inboxes. 

Here are some examples of newsletters from different niches to help you decide on a frequency:

  • If you write about news items, it’s best to send a daily newsletter. For example, Morning Brew, the newsletter with market reports and the day’s most pressing news sends emails every morning to its subscribers.
  • If you’re writing fiction through a newsletter, you can take a leaf out of Elle Griffin’s book and publish one chapter a week, just like she’s serializing her first novel, Obscurity with one new chapter released every week.
  • If you’re creating awareness around and sharing job opportunities, you can choose to publish every fortnightly, weekly, or even more frequently depending on your audience’s demands. For example, Austin Kleon’s newsletter contains inspirational tips for creative freelancers and is sent out every Friday. 
  • On the other hand, Hayley McGuire sends detailed how-tos for freelancers and her research-heavy newsletter only comes out once a month.

Lessons from the Internet’s Most Successful Newsletters: TL;DR

Writing a newsletter can be your ticket to converting your online writing into a business and generating some passive income on the side.

Based on my study of the internet’s most successful newsletters, here’s everything you need to know before starting your own newsletter:

  1. Have a catchy name that conveys what your newsletter is about, and/or makes it evident it’s written by you.
  2. Get people to sign up by offering them something of value in return. Simply asking people to “Sign up for my newsletter” rarely works.
  3. Based on what you’re writing about, your newsletter can be sent daily, weekly, or monthly. Choose whatever frequency works for you and stick to it for a year or two to see real traction.

I’ve used my newsletter to sell courses, do product launches, carry out affiliate marketing deals, and more. Collectively, the 5000+ subscribers on my two newsletters have made me more than $50,000 in three years.

If I can monetize my writing, so can you.

So, what are you waiting for? Start planning your newsletter today.

I just launched Freelance Superheroes: A training program for writers who want to earn from writing online without leaving their job, attract gigs outside Upwork/Fiverr, and become irreplaceable. Get it today!

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