👋 Hi {{first_name}},
Asking people to pay you for your writing always feels…wrong? Of all people, I should know.
I started my marketing career wanting to learn how to write effectively. And this is after 15 years in tech, having built a considerable career in building software products.
Still, asking for money for putting my expertise in words always came with a share of guilt. And uncertainty. 7 years on, the guilt and the uncertainty comes back every time a newsletter creator asks me:
Should I make my newsletter paid?
At which point, I send them the article from Defector.
Sponsored Ad section start
Find what’s slowing your GTM.
Most GTM problems aren’t one big failure. They’re one or two weak spots quietly dragging down the rest.
The free GTM Audit scores your go-to-market across four dimensions, then sequences a 90-day roadmap for your stage.
Drop your URL. Get your score in about 10 minutes.
Sponsored Ad section end
Make them pay
Lex Roman is one of my favorite independent media publishers to follow in this space. They have been observant of every change this fast-moving space makes. So naturally, when Lex pointed out the slew of paid newsletter offerings from the Ringer on their LinkedIn post, I had to take notice.
Among the many vague moves that Lex points out, like the newsletter platform spread across beehiiv and Substack, the most glaring move might be the most telling too:
Why go paid in the first place?
Media brands cutting across platforms is not new at all. I spoke with Danya Henninger from Technical.ly on the LetterStack podcast, where she spoke about their plans to introduce more journalist-centric content on beehiiv, in addition to their brand newsletters on their own bespoke platform.
So where’s the rub?
The rub is to clarify when and why you decide to monetize your newsletter writing to your audience. Your audience might be all across the spectrum, with a majority still wanting to consume free content, and a small portion of them happy to shell out their monies.
How do you find out who’s ready to pay, and at what point in their dialogue with you?
Here’s where Lex’s resources come into play. And although there is no shortage of resources online, the reason I come back to Lex is because of their reader-funded model with Revenue Rulebreaker.
Revenue Rulebreaker continues to be the only example I know where the majority of the revenue comes from the reader. We have an episode coming up, where Lex describes their thesis behind the model. But the part that’s very refreshing to me, is the clarity in the thought process to go paid.
To that end, Lex also documented their thinking in their Paid Newsletter Playbook, which I believe, is the only article you need to read, print, and stamp on your desk, so you know exactly when to go down the paid route for your newsletter.
So if you are wondering when to go paid on your writing, I hope Lex’s resource is a compelling start to help you decide.
While you are at it, Lex’s Legends community is worth signing up too. I have been there for a year now, and I only wish I had joined in earlier.
If you still have questions, I would be happy to be your sounding board. Let me know by hitting ‘Reply’ on this email, or send a note to [email protected].
Make Sure You See Our Emails!
To ensure our emails land in your main inbox, follow these easy steps:
Find this email in your Promotions tab.
Drag it to the Primary tab.
When Gmail asks, click "Yes" to get our future emails in your main inbox.
You can also add us to your contacts to stay updated!
We Value Your Feedback
Your feedback means the world to us! Just hit reply and share your thoughts on this edition - we're always looking to improve. You could also reach out to us on [email protected].
Cheers,
Renga from LetterStack
Was this email forwarded to you by a friend? Sign up here to get content like this directly in your inbox.



