What Really Happens When You Turn on Substack Payments

Karen Cherry
12 min readDec 14, 2021

All the details you can’t find out from Substack

All screenshots by Author

You’ve got a Substack newsletter, you’re publishing regularly and you know your way around the platform. Now you want to know exactly how to monetize without accidentally upsetting your current subscribers. You’ve come to the right place! Read on.

Substack provides creators with information about how to turn on payments, but their content doesn’t answer every nitty-gritty detail about what you and your subscribers will experience when you go paid with Substack.

Substack monetization is optimized for creators who want to send different content to free and paying subscribers. For example, a common model is to send three free posts per week, plus one special post just for paying subscribers.

But what if you want to send similar content to everyone at the same time? For example, you might want to add an audio embed and a small critical incidents section for paying subscribers, but otherwise want free subscribers to get the same experience as paying subscribers.

Is that possible in Substack? And what else happens when you enable payments? I wanted answers. So I ran an experiment to find out.

The Experiment

I created a test Substack newsletter and enabled payments with the aim of answering the five questions below.

  • Can I send similar newsletters to free and paid subscribers without creating (almost) duplicate content in the archives?
  • Will my free subscribers be constantly badgered by Substack for money? — and how much control do I have over that process?
  • Will my subscribers (who are predominantly business professionals) be able to easily expense their subscriptions?
  • Can I connect my existing Stripe account or should I make a new one?
  • How much money exactly will I get into my (non-US) bank account for each subscription?

The Method

  1. I made a payment-enabled Substack and subscribed myself using two different email addresses.
  2. I made a ‘free post’ with a paywall and sent it to everyone.
Karen Cherry

Substack writer. Secret tree hugger. Aussie business owner with >$13K revenue on Substack. Refusing to dumb it down.