Paid newsletter best practices: Tried-and-tested tips from successful operators

Monetize Your List Newsletters
14 min read
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One thousand people. That’s all you need, according to the concept of 1,000 true fans (courtesy of Kevin Kelly).

The idea is simple: rather than focus on building an empire of millions of semi-enthusiastic fans, you only need to find a core of super-enthusiastic fans. A more profound connection with fewer people can be worth just much as a superficial connection with millions.

1,000 true fans is an alternative path to success other than stardom. Instead of trying to reach the narrow and unlikely peaks of platinum bestseller hits, blockbusters, and celebrity status, you can aim for direct connection with a thousand true fans.

— Kevin Kelly

“True” fans are your most valuable followers. And paid newsletters are a direct connection to them. In fact, newsletters even help you discover those core fans.

To build a successful paid newsletter, you don’t need a million people paying you. You only need a small, highly-charged group of people eager to hear what you have to say.

The problem? If you’re starting at zero, even achieving a thousand true fans sounds like climbing Mount Everest.

That’s why we asked some of the top paid newsletter creators what they can tell you about growing a list with your first paid newsletter. Here’s what they had to say.

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Treat your newsletter as a product

Michael Jones discovered his core of “true fans” by noticing a hole in the market.

Specifically, he saw a problem in ad-supported media. Working in magazine publishing as a fashion editor, he saw that two digital ad platforms—Facebook and Google—had created something of a duopoly.

In Jones’ opinion, digital and media focused too heavily on the interests of consumers or business leaders. Meanwhile, he felt the creative class was being ignored. “I saw an opportunity to elevate the creative class and add some perspective to the media we consume,” he said.

He discovered one solution to both problems: creating his own subscription newsletter. The result was Supercreator Daily.

Supercreator Daily covers the intersection of politics and creativity. Jones’ goal: Empowering creators with the knowledge to take action and make change, so their values are represented by the politicians they elect and the policies they’re governed by.

Jones identified his “true fans” by finding those who shared his beliefs that the goals of creatives were underserved in politics.

Though he doesn’t publicly disclose the size of his paid readership, he does point to high levels of engagement: Subscribers open his emails at a rate of up to 45%, more than double the industry average.

Paid newsletter example
Supercreator “AM” starts off with a brief introduction, then gets right to what matters most: what readers want to hear. Image via Supercreator.

Jones has learned plenty of lessons about paid digital media along the way. Here’s what he had to share.

It’s a product, not an email

Jones was able to grow his readership by focusing on the value each newsletter was delivering. For example, Supercreator Daily provides relevant, targeted content to a core group of people—people who know that every time they open an email, there’s going to be something for them.

It’s this value proposition that led to growth.

No one is paying you to send them more email. What they’re paying for is the value your newsletter delivers. And the best way to showcase that value is in a format that’s easy to create and consume issue after issue and does the heavy lifting of shaping your newsletter’s identity, expressing your voice, and keeping your readers interested over the long haul.

— Michael Jones, Supercreator Daily

Your newsletter isn’t about you

You don’t find your thousand true fans if you solely focus on what you want. A newsletter is ultimately about the reader.

“The best paid newsletters provide a service for subscribers,” he said. “Whether that’s to save time, inspire self-improvement, explain complex issues, or offer insights.”

Jones imagines a dream subscriber at whom he’s aiming his newsletter and then seeks to be at least one percent better than that dream subscriber’s next-best option. Write for the audience, not yourself.

Consistently ask what the reader is getting out of paying for your newsletter:

  • Are you really offering the best and most relevant content?
  • How can you be one percent better than the other paid options on the market?
  • What newsletter add-ons can you include with a newsletter to elevate the subscriber’s experience?
  • Can you add other elements, like private communities or audio recordings of the newsletter?

“Writing a newsletter is actually pretty unsexy work,” he said. “You’ll need skill, but it will also require you to master a level of consistency and mental well-being that will sustain you through the ordinary and extraordinary moments.”

Build your audience with a simple value proposition

If you’re starting out with zero true fans, the early stages can feel like a slog.

That was the case for Karmen Kendrick, who created Tips and Tacos—a paid newsletter that now has over 1,000 paid subscriptions at $6/month.

But Kendrick didn’t always have those one-thousand core fans. While she did have over 5,000 free subscribers on an existing list, “No one signed up the first time I made the [paid] offer,” she said. “But if you keep innovating and creating ways to showcase your value, the subscribers will come.”

The Tips and Tacos newsletter does have value built-in. With business, marketing, and design tips—not to mention a free giveaway taco to a lucky subscriber every Tuesday—it’s not hard to see why subscribers are willing to pay a small monthly fee for it.

Paid newsletter example
On the Tips and Tacos signup page, Kendrick offers incentives for customers to click “subscribe.” Image via Tips and Tacos.

But it wasn’t until Kendrick discovered the “Planet Fitness” model that she began to find her core paid fans.

“Planet Fitness charges a lower membership price than most gyms. The average person doesn’t miss the $10 coming out. So even if they don’t use it, most people are banking on the idea of ‘someday, I will,’” she said.

The idea isn’t to offer a low-value product but rather to keep your membership fee low enough where it doesn’t break your subscriber’s pockets. Being worth more than what you charge is one of the key newsletter best practices to keep in mind as you grow.

Eventually, fans will find you.

Start off with a free newsletter

“Build an audience,” Kendrick said. “It’s going to be pretty tough to sell a premium newsletter if no one knows who you are.”

She went on to recommend building a list of at least one thousand free email subscribers first. This introduces you to the “Planet Fitness” value proposition: delivering more value with each newsletter than you’re getting.

Learning the ropes of newsletter marketing created an excellent foundation for Kendrick. Eventually, it helped find her connection with her one thousand true fans…even if it didn’t pay off immediately.

Give them an incentive

Want another value proposition? When in doubt, give them free tacos.

Her strategy: use subscribers to help promote the newsletter. “I use a ‘click to Tweet’ in every newsletter I send out to my subscribers with a chance to win free tacos,” she said.

Sometimes, finding your true fans comes down to how many eyeballs you can get in front of your content. The “click to Tweet” feature (and tacos) incentivize subscribers to spread the word on behalf of the newsletter.

Want to do something similar with your newsletter? The SparkLoop Integration with ConvertKit helps you set up referral rewards. Once it’s set up, all you have to do is advertise it to your newsletter.

Remember the unique selling point—your community’s voice

In the original definition of 1,000 true fans, it’s pointed out that genuinely enthusiastic fans will buy just about any product a creator puts out to the world.

However, that enthusiasm only comes when you have a unique voice that resonates with readers.

For Britany Robinson of the newsletter One More Question, this means incorporating personality into the newsletter itself.

I strive to be personable and accessible in my newsletter. That might not always be possible as I continue to grow, but right now, my audience is a size that allows me to respond to all of my reader emails and develop some real relationships with those subscribers who are willing to reach out. Nurturing those relationships has been hugely rewarding, not only because readers are more likely to recommend my newsletter when they sense that genuine connection, but because I'm getting real relationships and conversation out of it, too.

— Britany Robinson, One More Question

One More Question has thousands of subscribers, 200 of whom are paid. That’s an impressive turnaround for a newsletter born just a few months ago. Robinson created a close-knit community by starting with herself, but she’s quick to point out that she loves highlighting other voices as well.

Paid newsletter example
At One More Question, Britany Robinson invites other voices to be part of the conversation, offering value for subscribers. Image via One More Question.

For Robinson, it’s an ongoing dialogue. Even her About page at One More Question features details on other writers, including highlighted tweets. She strives to expand the voices featured in her newsletter to create value for her readers.

“I’ve found it useful to introduce my audience to voices other than my own by way of Q&As,” she said. “Interviewees typically share the Q&A on social media, and I’m able to reach new subscribers that way…so these interviews expand the scope of my newsletter and its reach.”

Solve the problem your readers have

Despite the name, a newsletter doesn’t have to be all about news or updates. Sometimes, it’s as simple as solving your subscriber’s problem.

MC of Flow State discovered that by first exploring a problem he had himself: eliminating distractions and getting in tune with the work needed.

Flow State sprung out of that need. For $6 a month, the newsletter highlights two hours of music that are perfect for working—a musical mix specifically crafted to eliminate distractions, inspire energy, and get subscribers through two hours of rock-solid work.

Paid newsletter example
Flow State skips right to its main appeal: the music playlists its subscribers seek. Image via FlowState.

Although it’s not hard to see why this might be worth $6 per month, MC says the original idea came from needing the same thing:

Start with a problem you have yourself. This is classic product advice, and it applies to newsletters. If you want to create a newsletter whose readers make a habit of opening it, solve a recurring information problem for them. Think about what information needs to recur in your own life, and then imagine the newsletter that will recurrently solve them.

— MC, Flow State

If you’ve noticed a problem that your newsletter can solve, you have an instant connection with a potential audience. By treating your newsletter as a product, you’ll adopt the right mindset for monetizing it and identifying your core fans.

MC recommends getting very clear on the value your paid newsletter brings to the table. “Write a single sentence that clearly and compellingly conveys why someone should sign up,” he said. If this exercise is a struggle, you might want to consider launching a different paid newsletter.

However, he doesn’t recommend letting your connection with an audience do all the work.

Once you get a few people to sign up for your newsletter, ask them to share it. Explicitly say things in your newsletter, like, ‘We’re brand new, so if you enjoy our newsletter, consider telling your friends about us by sharing this link.’

— MC, Flow State

MC also made strategic use of discounts and promotions to expand readership. Brand-appropriate holidays, for example, can help create buzz and interest in a paid newsletter. At Flow State, MC offers deals on the birthdays of some of the newsletter’s favorite ambient artists.

Brian Eno’s birthday may not be what Black Friday is to retail. But to Flow State’s audience, it’s a neat reason to sign up. “A deal provides a good reason for someone to give your paid tier a try,” MC said.

Mix things up and build ultra-relevant content

Hustle Crew’s mission—to make tech more inclusive—isn’t solely focused on their paid newsletter. But the members-only side of its site at monthly fees of $15 features hundreds of people who have signed up for regular emails.

How did Hustle Crew find its true fans? According to its founder Abadesi Osunsade, her newsletter sign-up best practices can’t be narrowed down to just one critical insight:

  • Go ridiculously narrow to find your unique value proposition. Osunsade recommends imagining the exact person who opens your paid newsletter and devours all the content. Ask yourself who is a true fan? What enriches their lives? What can your newsletter offer them that no other newsletter can?
  • Gather feedback often. “We didn’t run our first feedback survey until six months in, which I really regret,” says Osunsade. “But just as important as gathering feedback is taking action to incorporate that feedback.” Had they acted earlier on that feedback, she believes they might have reduced churn in the early days of the newsletter.
  • Find relevant add-ons to your paid newsletter. “As an education company, it made sense for us to offer webinars and other training events,” Osunsade said. It was a natural fit: they built additional offerings into a referral engine. Meanwhile, the webinars themselves deliver plenty of value for people who don’t want to sign up just yet.

At Hustle Crew, the emphasis isn’t always on the paid side of their offerings. But for those who do pay, they get a VIP-like experience. That only comes from taking the time to build ultra-relevant content to your exact audience.

Hustle Crew doesn’t seek to be everything to everybody. But it does serve its 1,000 true fans.

How to increase newsletter subscribers when they’re paying

When your sign-ups don’t have to pay, it can sometimes feel easy to build a list. It’s when you start asking for money that you find out who your true fans really are.

In looking at the examples above, there are plenty of lessons you can glean as to how to grow newsletter subscribers with your own list:

  • Don’t give up. Even successful newsletters take a while to discover their 1,000 true fans. Karmen Kendrick had to start giving away free tacos to learn how many people were interested in her content.
  • Think product, not newsletter. Your newsletter shouldn’t be just another item to delete in the subscriber’s inbox. You’re charging people for delivering this product! Strive to create real value with every new issue. Build an ideal “subscriber profile” to learn what they want, and ask yourself how your newsletter can give it to them.

Ready to incorporate these paid newsletter best practices into your own newsletter? Grow your paid newsletter with ConvertKit today.

Build a loyal community with newsletters

With a ConvertKit Free account you can share what you love on a consistent basis with your newsletter to connect with your followers and grow your business.

Create your free newsletter

Kaleigh Moore

Kaleigh Moore is a freelance writer who works closely with SaaS companies and marketing teams for content creation.

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