How to start a Paid Newsletter Business

Paid newsletters are growing quickly and can be a great way to generate income. Learn how paid newsletters work and how to get started

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Parthi Loganathan

Dec 17 2020

11 mins read

Why paid newsletter subscriptions are increasingly popular

"Why would someone pay for a newsletter when so many of them are free?"

Paid newsletters bring a lot to the table. The rise of paid content and subscriptions on platforms like YouTube, Twitch, and others, shows that people are willing to pay for premium content. And a paid newsletter is one of the best ways to promote premium content.

In this post, we'll go over why paid newsletters are useful, how to start your paid newsletter, and which services can help you get started. 

What is a paid newsletter?

Paid newsletters are email newsletters with a paywall that gates some or all content. You may have heard of popular ones such as Stratechery by Ben Thompson. These newsletters charge a subscription fee for access to content targeted at a specific audience.

Why create a paid newsletter?

A newsletter can be a great way to combine your interests, build an audience, and an income stream. The most successful newsletter writers make over $1 million annually. Paid newsletters are not only a source of potential income but also a creative outlet. It’s a great way to share content about a topic you’re passionate about and to build a community of readers. It does require work to come up with useful or entertaining content on a regular basis and market it, but it can be very rewarding if executed correctly. Newsletters are typically sent out on a weekly basis, but daily and monthly are popular publishing frequencies too.

To set up a paid newsletter business, all you need is a computer, an internet connection, and publishing software to format and send out your newsletter to your readers.

Free vs. paid newsletters

Free newsletters are great for audience building, but they do take up your time. It’s a good idea to figure out how to make your writing sustainable by turning it into an income stream. As soon as your audience gets to a certain size, around 1000 subscribers, you can start publishing your content behind a paywall. The paid newsletter content can contain exclusive, and unique content that is carefully curated by writers for a specific audience. For example, if you're a stock trader with a successful track record, you might create an exclusive newsletter in which people can learn about the trades you make so they can follow along given your expertise.

Free newsletters have an obvious appeal and making all of your content publicly available increases your reach. But ultimately, to make it sustainable, you need to monetize. A paid newsletter lets you offer your audience greater value and financially worth your while. They are often combined with other benefits like access to an exclusive community, events, and services. For example, our hypothetical stock trader can discuss recent events in the stock market with their readers or offer financial consulting with their newfound audience.

How to start a newsletter business

If starting a newsletters business sounds appealing, here’s how to go about starting one:

Find your niche or area of focus

Newsletters are versatile. They can contain interviews, podcasts, lecture notes, market reports on trends, personalized advice, and long-form essays.

As long as your content is original, creative, informative, and has a clear value proposition, it’s sure to garner a loyal following over time. This is why it's crucial to write about something you're passionate about. This will stop you from losing motivation. The keys to eventually building a successful newsletter are consistency and listening to feedback from your early readers to understand what resonates with them. You also need to determine if the cadence will be a daily, weekly, or monthly newsletter.

Find your target audience

After deciding the content of your newsletter, you should find the audience who might be interested in your content. Who are you writing for? Who might enjoy reading it and why? These are important questions that you need to answer. You’ll iterate on this over time as you write more and learn which of your early readers are most engaged with your content. Once you understand your niche, it’s just a matter of getting in front of more people like them.

Pick your newsletter software

You know what to write. You have an idea for who will read it. Picking the right software will allow you to get started with minimal friction and will help you scale as you grow your readership. You need something that gives you SEO optimized posts that are discoverable on Google and other search engines. You also need the ability to collect email addresses, to reliably send email, to provide insight into your readers. The tool must also have marketing tools to grow your audience, the ability to set up paywalls to accept payments, and enough customizability to make your newsletter feel like your own brand.

If you’re looking for The One, we’d like to introduce ourselves. Letterdrop can help you with all of the above. You can get your first post out in less than 5 minutes. It’s free to get started, is affordable, has advanced growth and marketing practices built-in, and is flexible enough to scale should you decide to launch a full-blown media business. Letterdrop puts your brand first and operates quietly behind the scenes.

Determine your pricing model

Paid newsletters typically charge between $5-20 per month. You want to pick a price with your target audience in mind.  However, you don’t want to scare away potential readers by charging too much. You also want to make this a sustainable revenue stream. For example, if you write a newsletter targeted at businesses, you can charge a lot more as your readers will likely expense it.  $15 is the magic number where most people in America would pay for something without thinking too hard about it. Check what other newsletters in your niche are charging to get an idea for a baseline.

Start writing your newsletter

After you’ve settled on the pricing, all that’s left is to get writing. Simple enough, right? Once you begin writing, you can get a better sense of how long it’ll take to write posts and your expected cadence for future posts. The important thing is to make it a habit and establish healthy writing practices.

Promote your newsletter to grow your subscriber base

Once your content is ready, it’s time to start promoting it. Start setting up social media pages on your audience’s preferred platforms to encourage reader engagement. Finding your target audience also streamlines your marketing methods, such as which platforms to promote your newsletter on. Figure out where they hang out on the internet and in-person - Facebook Groups, Reddit, Twitter, private forums, Slack or Discord communities and other social networks. While you don't have to leverage advertising to help grow your newsletter, ads can be a way to increase your subscriber base if you have the funds for it.

Entice your target audience by offering examples or exclusive previews of what your newsletter has to offer. This helps build your mailing list and can increase loyalty.

Keep writing

This is probably the hardest part. Consistency is important. For whatever frequency you’ve chosen to publish, give yourself enough time to write, edit, review and then publish the material. Your existing fanbase will come to depend on your consistency and once you earn their trust, your readers will share your newsletter with potential new subscribers. Organic growth through referrals is the most reliable way to get more readers.

Examples of paid newsletters

Not sure what a good newsletter subscription looks like? There are plenty of ways to create a newsletter and here’s some examples of paid newsletter subscriptions:

Cleaning the Glass

Cleaning the Glass is written for hardcore basketball junkies by a former analyst for NBA teams. After 8 years working for NBA teams, Ben Falk wanted a venue to research and discuss interesting basketball topics. He brings what he learned from working inside the league to its remarkably smart, sophisticated, and savvy fans.


Stratechery provides an analysis of the strategy and business side of technology and media, and the impact of technology on society. Weekly Articles are free, while three Daily Updates a week are for paid subscribers only.

The Daily Coding Problem

What better way to polish your coding skills than by practicing every day? The Daily Coding Problem began as a practice among friends and grew into an entire community (you can read about it in their welcome email). Free subscribers get daily coding problems while paid subscribers get all the features, plus tricks and guides to coding problems.

Start a newsletter with Letterdrop

Interested in becoming a newsletter writer, but not quite sure where to start? The Letterdrop team is here to help!

Getting your first post out is a piece of cake 

We bake in the best practices so you can get your first post out in five minutes without worrying about your emails ending up in spam folders or not getting discovered on Google. With minimal setup and a powerful clean editor, you can focus on the writing. We’ll take care of warming up your beautiful posts in the oven with a comments section, dark mode, heading highlights, custom colors, fonts, buttons and more.


With Letterdrop, you’re in control of your newsletter. We want to be your secret sauce taking care of your technology needs so that the flavor of your content can really shine and get you as many subscribers as possible.

You can host a blog of your newsletter posts on your own custom domain so that you get all the SEO benefits. You can email users from an email address on your domain so that you build a relationship directly with the reader. 

Marketing tools and analytics

We’ve talked to hundreds of newsletter creators and built-in marketing tools to help your newsletter reach as many readers as possible. Set up a referral program with only one simple click and join the likes of Morning Brew and The Hustle, both of which grew their subscriber base by 30% through referrals alone.

We also provide you with more insight into your audience than anyone else. When a reader signs up with their email, we can find their Twitter and Linkedin so you can understand who your readers are, and use this data (safely) when talking to prospective sponsors.


Letterdrop integrates with Zapier and has an API, so you can enable automated workflows when a user signs up, stops reading your emails, or refers a friend. You can also automatically invite your readers to platforms like Slack, Circle, Mighty Networks and Discord to build a community attached to your newsletter.

Earn from paid memberships

Letterdrop supports payments backed by Stripe. It’s super simple to create custom paid plans for your newsletter and add a paywall to access your paid content. Hook readers in with your best free writing and then earn by sharing exclusive insights to paid members.

Newsletter publishing FAQ

Here are some popular newsletter related questions people have. If you are seriously considering starting a business for yourself, then these answers may help!

How do I start a newsletter business?

To start a newsletter business, you need a way to receive payments, reliable newsletter software, and your own creativity! There are many tools out there, but we made Letterdrop to be both comprehensive and user-friendly, perfect for the first-time writer serious about getting into the newsletter business.

Can you make money from a newsletter?

Yes! Successful newsletter writers make more than  $1 million a year.

How much should I charge for a newsletter?

Newsletter writers can charge between $5 and $99 for a subscription. To narrow things down, consider the nature of your content, and how much value it offers your readers. Some ways to evaluate that are: 

  • How exclusive is your content?
  • Does it provide business value or help your readers make more money? (You can charge more if so!)
  • Can your readers expense it on a corporate card?
  • Do your free posts contain content valuable enough to drive paid readers? 
  • How does your content differentiate itself from its competitors?  If you’re not the first, then how are you going to write in a way that’s different from the first, second, or 67th writer in that niche? 

It’s also a good idea to look at what your potential competitors are charging, or to take advice from fellow writers/entrepreneurs! 


Paid newsletters are a great way to offer high-quality, unique content to a specific audience while generating income if you’re creative and consistent. It’s easy to get started, especially with a tool like Letterdrop., We can help you grow from 0 to tens of thousands of subscribers (nearly hundreds of dollars in revenue) in a few months. 

Ready to start your own paid newsletter? Sign up for Letterdrop - it’s free to get started!

Thanks to Taran and Piyali for this piece.

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