Coffee With Cole: The Digital Writing Podcast

How to Start and Sell a Paid Newsletter That Works

41 snips
Mar 18, 2025
Discover how to successfully launch a paid newsletter by first building demand with free content. Learn why knowing what people are willing to pay for is crucial—it's about insights, not just information. Experiment with one-time products to gauge interest before committing to a subscription model. Understand the challenges of retaining subscribers and how to turn popular material, like books, into engaging newsletters. This discussion is packed with strategies for turning your writing into a profitable venture.
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INSIGHT

Free vs. Paid Content

  • Free content attracts a different audience than paid content.
  • What compels free consumption isn't always what justifies payment.
INSIGHT

Value of Paid Content

  • People pay for insights, perspectives, and personal experiences, not just news.
  • Paid content thrives on personality and unique viewpoints.
ANECDOTE

NYT Example

  • The New York Times struggles to get subscribers for more than $1/month.
  • This is because they try to monetize commoditized news.
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