3 Myths about Paid Subscriptions

How successful creators kill them

Newsletter Circle is the newsletter all about newsletters for indie creators.

👉 Every Sunday, you will read the unique journey of a different newsletter creator and learn more about how to start, grow and monetize your own newsletter.

👉 Every Wednesday, you will read articles and the list of curated resources to level up your newsletter business.

Hey, all newsletter enthusiasts!

Welcome to the “Wednesday Issues” by Newsletter Circle.

Today, we’ll talk about three myths about paid subscriptions and some lessons to take from real-life cases killing these myths.

Before starting, here are some juicy finds of the week.

🔎5 Handpicked Reads about Newsletters

💡“I was wrong about newsletters” - by Scott Oldford

🔎 “Still Bullish on Newsletter Businesses - by Richard Patey in response to Scott Oldford

🎯 What happens if you create content for 1037 days in a row

⚒ Who is good at building digital products?


Revenews is a newsletter dedicated to helping you monetize your newsletter.

Why you should subscribe - As the former head of sales at two large, successful newsletter companies, Dan Barry has expertise in newsletter monetization. He teaches both strategy and execution.

I find it significant that he focuses only on monetization, which helps him explore any topic in depth. A Guide to Bigger Deals is a great example.

I’ve been a subscriber since Day 1 and learning a lot from him. Join me.

Three Myths About Paid Subscriptions

Myth 1: “The only way to provide value is to send a subscriber-only issue.”

Katie Hawkins Gaar has been writing My Sweet Dumb Brain since Sep, 2015.

She has over 13,000 subscribers, of which hundreds are paid ones.

However, it didn’t become easy to land in her current successful model.

Katie started a paid subscription one year after the launch.

She published two newsletters a week for over a year: The Tuesday essay for all readers, plus a subscriber-only issue on Fridays, which were essentially a round-up of reader responses to the Tuesday essay.

The workload stressed her, but she was sure there was no way to provide value to her paying subscribers.

Well, actually… there was.

The survey she conducted in October 2021 revealed that:

  • Many of her free readers weren’t becoming paid subscribers specifically because they didn’t want another email to read each week!

  • Her paying subscribers could take or leave the Friday issues.

  • What everyone wanted was the Tuesday essay that went out to all readers!

Based on these, she added paid subscriber extras to the end of Tuesday essays and only sends out one newsletter a week

Result was a win-win: Much more manageable process and a boost in the number of paying subscribers.

"Sometimes doing less really is more!”

Katie Hawkins Gaar

Read hereHow Katie Hawkins Gaar built My Sweet Dumb Brain

Myth 2: “My readers are ready to pay if I share more content.

Jeff Matlow launched a paid version of By Title Only in 2021 just after Substack had become a rising star and made paid subscriptions popular.

He had 5,000 subscribers at the time of the launch.

His initial assumptions:

  • Paid subscription fits every newsletter and doesn’t require a huge work

  • Easy to convert 7-10% of free subscribers just because they want more of what he writes

  • If I let people pay me, they will pay for more content

He started by doing an extra subscriber-only article every week, and got about 100 paid subscribers quickly but couldn’t reach 500 as he planned.

After a while, he decided that it was a bad decision because he:

  • realized he didn’t have enough time to create a compelling offering for those subscribers

  • couldn’t define a clear strategy about how to differentiate the content for free and paid subscribers

“I found myself wanting to make sure it was good quality, but not TOO good that I’d be annoyed it was only read by a small group of people.”

Jeff Matlow

After seven months, he canceled the paid version and refunded the subscribers.

Jeff Matlow is a fearless creator experimenting with diverse strategies and capable of pivoting when needed, as he did with paid subscriptions.

His attempts and learnings are inspiring.

Read hereHow Jeff Matlow built By Title Only

Myth 3: “I need to focus on converting free readers.”

Hanna Raskin is a successful food journalist and the mastermind behind the multiple-award-winning publication “The Food Section”, covering food and drink across the American South.

Since then, she reached over 8,000 subscribers, with hundreds of paid subscribers.

Hanna Raskin offered a paid subscription from Day 1.

In the beginning, she focused on how it could be possible to turn free readers into paid ones, as many newsletter creators do.

However, she found an interesting fact when she zoomed into her data:

If readers don’t pay up in the first 72 hours, they are unlikely to ever pay.

In the interview with Dan Oshinsky, she brought a meaningful explanation unique to her case:

“I think part of [the reason for all the conversions in the first 72 hours] is because I’ve been fortunate to have publicity, so people know what they’re getting into. We don’t really have that getting-to-know-each-other process I think many other publications do.

So people pay in anticipation of what they’re going to get instead of gratification for what they did.

They’re like, “Sign me up, let’s do it. I’m giving you my money.” And if they don’t, they won’t.”

Hanna Raskin

Since she realized that it was useless to focus on conversion, she found a controversial way to increase the number of paid subscribers.

She sent a message to her list saying that she would randomly remove 15% of the free subscriber list and that the only way to prevent it was to subscribe.

Thanks to the surveys she had previously conducted, she knew her readers quite well, so she felt that this strategy would resonate with them.

The result was quite positive, which led to an immediate increase in subscriptions and continued growth.

Read hereHow Hanna Raskin built The Food Section

 3 Lessons to take:

  1. Focus on Offering Unique Content, Not Quantity: Readers pay more attention to the value you provide than to how frequently you publish. Remember, more content doesn’t necessarily mean more value. Instead of sending more, focus on delivering unique and valuable content. As Katie says, "Sometimes less is more."

  2. Know Your Audience: While it's a cliché, the essence of a successful newsletter business lies in understanding your audience. Conduct surveys, engage with your subscribers, and gather feedback. Any investment in understanding your audience is an investment in building a sustainable business. Both Katie Hawkins Gaar and Hanna Raskin emphasize the importance of knowing their audience through surveys and data analysis.

  3. Keep Experimenting: There's no one-size-fits-all recipe for success in paid subscriptions. Factors like timing, pricing, acquisition source, and content type may vary depending on your content and audience. Start somewhere, gather feedback, and keep experimenting. As long as you're confident in the value you offer, don't be afraid to take risks.

ICYMI - The Latest Newsletter Circle Interviews

👉 Sponsor Newsletter Circle to reach 1,600+ newsletter creators & enthusiasts.

*Disclaimer: Affiliate link. I only recommend resources/platforms that I genuinely find useful.

Join the conversation

or to participate.