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Running a paid newsletter with Simon Owens

Yaro Bagriy
Yaro Bagriy

About this episode: This week we have Simon Owens, a successful independent journalist running a paid newsletter on Substack. Simon also runs a popular podcast called The Business of Content, which is about how publishers create, distribute, and monetize digital content. In this episode we're going to dive into the pluses and minuses of publishing on Substack and when it makes sense to switch. We're also going to dive into the paid newsletter best practices and Simons weekly newsletter workflow.

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What is an SPF record?
I decided it was a good idea to make this a nice little continuation of the previous post in finer detail because we all know that deliverability is something that’s never static, it’s an ongoing process that involves more trial and error.

Show Notes & Insights:

  • If you're running a paid newsletter on Substack, it will eventually make sense to move off of it. The cut they're taking will eventually be significant enough. Why pay 10% to them when you could use that money to hire sometime?
  • If you're not technical and starting on Substack, it will also make sense to move off and use that 10% to hire someone to implement a cheaper tech stack for you. There are many options out there.
  • Use a service like Substack or Revue if you don't want to think about tech problems for more than 5 seconds per week.
  • The hardest part, other than getting someone to hand over their money when running a paid newsletter is the consistency. Paid newsletters are now bound to an official schedule for their paying subscribers. You can't skip an issue. They expect it.
  • If you're looking to start a paid subscription newsletter, start with a free version first. Flush it out and get traction with it. Then go paid.
  • What your newsletter is when you send out the 1st issue will not be the same when you send out your 100th issue.
  • Don't underestimate the time it takes to understand what is the value proposition of your paid newsletter.
  • The most optimistic projections on your paid newsletter won't pan out. Plan for that.
  • A solid weekly plan will decrease the time it takes to send your newsletter.
  • If you're sending out evergreen newsletters on a consistent basis, try and write as many as possible now. This will give you some cushion room if anything happens.
  • If you're a solo paid newsletter creator. Most of the subscribers are investing in you. They are rooting for you to succeed.
  • A podcast is an intimate form of communication that helps convert free subscribers to paid subscribers.
  • Encourage your free and paid newsletter subscribers to be evangelizing on your behalf.
  • Get your superfans to become your own personal marketing team.
  • Try leveraging paid Twitter ads and note the ROI on that channel. It's a low-cost investment that could pay off huge.

Newsletter + Guest Info:

Yaro Bagriy

Podcast host & community manager

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