How to Be the One Well-Loved Substack People Pay For

“There are many Substacks about Substack. This one is the OG.”

—Gregg Easterbrook

Part 1 and part 2 are special bonuses for you as a free subscriber. I so appreciate having you. Get the full 2026 Pathway to Earning an Income on Substack by upgrading to paid.

This is the only guidance based on real data—four years of pattern recognition across my work with 1000+ private clients. I will save you from wasting time and energy spinning on Substack, taking random advice, and trying to figure out what works.

Okay, so I did some digging to see if there really is a crisis in paid subscriptions on Substack (and newsletters generally). ICYMI, someone wrote a viral article that stoked a lot of fear about the future of paid subscriptions on Substack.

The feelings are real—the worry—but the reality…might surprise you:

• It has always been hard to get paid subscribers.

• The rhetoric that Substack’s subscription model will never work has been around for half a decade, possibly since the platform’s inception in 2017. It might not, but the talk is nothing new.

• The data doesn’t support the idea that something has suddenly happened foretelling a grim reality and terrible future with paid subscriptions on Substack.

Fueling the worry are five (deadly) paid-subscriber assumptions:

1. The economy is terrible, and people won’t pay.

2. Subscription fatigue is driving a downturn in paid subscriptions.

3. There’s a “subscription pie” we have to compete for a slice of.

4. Bundling newsletters is the solution.

5. Making Substack into a platform of Dollar Stores is the answer.

These simply aren’t supported by the data.

But they did lead me to the five things you can do right now to be the one well-loved Substack people pay for.

And avoid the 5 (deadly) paid subscriber assumptions