Your Newsletter Is Ready to Make Money (Even If You Don't Think So)

The complete guide to newsletter monetization for small audiences: when to start charging, how much to ask for, and why 50 engaged subscribers is enough to build a profitable newsletter business.

This edition of 9-To-Thrive is dedicated to

Meadow Grace

who asked me if she should start monetizing at 54 subscribers. Here’s the answer to that question.

Here's what I'd tell someone with 50 engaged subscribers: Start monetizing immediately, but do it strategically. You don't need 1,000 or 10,000 subscribers to begin charging. You need the right mindset, approach, and pricing strategy.

Why 50 Subscribers Is Actually Perfect for Starting

The "Small Audience Advantage"

• Direct feedback loop: You can personally engage with every subscriber

• Lower pressure: Easier to test and iterate without massive audience scrutiny

• Higher engagement rates: Smaller lists typically have 2-3x higher engagement

• Personal relationships: You likely know many of your subscribers personally

• Faster iteration: Can pivot pricing/offerings quickly based on immediate feedback

Real Success Examples at Small Scale

Many successful newsletters started monetizing with fewer than 100 subscribers:

• Lenny's Newsletter: Started charging at ~200 subscribers

• Not Boring: Began paid tier with ~500 subscribers

• The Generalist: Launched premium at ~300 subscribers

The 50-Subscriber Monetization Strategy