8 Top Creators Pricing Strategies: Winners vs. Losers

My Exclusive Pricing Analysis of 8 Leaderboard Publications And Lessons Learned

Pricing a newsletter on Substack is one of the most agonizing decisions creators face. Should you compete on price with others in your space or base it on your unique value? What's too high and scares people away? What's too low and kills your revenue potential? When should you even start charging?

These questions keep creators second-guessing themselves, and often drastically underpricing their expertise.

I just spent days analyzing the pricing strategies of 8 top newsletter creators with audiences from 11K to 113K subscribers to answer these exact questions. What I found will shock you: the majority are dramatically undervaluing their expertise, leaving between $50K and $300K on the table every year.

Today you're getting my complete breakdown of their exact pricing, what's working, what's failing, and the proven framework that separates the winners from the losers.

The $2.4 Million Revenue Gap

I analyzed 8 creators across business strategy, journalism, productivity, AI/tech, finance, and education. For each, I documented their complete pricing structure, value propositions, and revenue potential. The results reveal clear patterns about what drives revenue—and where most creators are making expensive mistakes.

The Breakdown: Who's Winning and Who's Losing

The Undervalued (Leaving Money on the Table):

Dan Koe (113K subscribers): Charges $150/year base, $300 premium with vague "other perks."

Could easily charge $300-500 for base tier given his authority. Missing $180K+ annually.

Lenny Rachitsky (Top business leaderboard): Only $200/year base, $300 premium for the #1 position.

Should be charging $400-600 premium. Missing $250K+ annually.

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