Ideas and Validation April 17, 2020

💌 Trends #0011 — Paid Newsletters


I just published a report on paid newsletters at And thought you might be interested.

Some have said that email is dying. Not true. It’s evolving.

Would love to know what you think. Especially ways to improve these reports. Thanks! 😆

🔍 Problem

Advertising alters incentives.

💡 Solution

Write for your readers. Not advertisers.

🏁 Players

Paid Newsletters


🔮 Predictions

  • New types of newsletters will be created. Need an example? Flow State sends you music every weekday.
  • Substack will help writers extract more value (and commissions) from their audience. Their incentives are aligned.
  • It will be hard to cancel writers. Paid newsletters make you accountable to your audience. Not sponsors or their stakeholders.
  • More writers will hold events. Sam Parr held a small meetup at his Airbnb with subscribers. Fintech Today hosts virtual events.
  • Newsletter fellowships will become common. Substack CEO, Chris Best, described the Substack Fellowship as a "mini-YC" for writers.
  • Most writers will add products to their offering. Paid content is a simple way to monetize. But this leaves money on the table.
  • We will see more newsletter bundles. Bundling newsletters can lead to more revenue and lower reader acquisition costs.

☁️ Opportunties

  • Build a community on top of your newsletter. Use your platform to connect people. Courtland AllenPieter Levels and Jack Butcher used this content-to-community playbook.
  • Reach 1,000 free subscribers then monetize. The founders of Substack estimate a 10% free-to-paid conversion rate if you have:
    1. At least 1,000 subscribers
    2. At least a 50% open rate
    3. Good feedback from your readers
  • Start a podcast. You'll reach a new audience that prefers to listen. Make money from podcast memberships.
  • Build a SaaS for your audience. Jane Portman has UserlistPaul Jarvis has Fathom AnalyticsJustin Jackson has Audience-first works.
  • Use your newsletter as a funnel for books, courses, events and consulting.

😠 Haters

"Reader acquisition costs is a made up term."
Everything is made up. Stay woke.

🔗 Links

  1. How Newsletters Make Money for Writers with Hamish McKenzie of Substack — Hamish McKenzie, Co-founder of Substack, drops tactical knowledge bombs. Find out what he has learned from thousands of paid publications. And why he recommends charging general audiences $5+/mo and professional audiences $10+/mo.
  2. How to Build a Six-Figure Newsletter Without Anyone Knowing — Glen Allsopp shares the stories of several six-figure newsletters. Great, in-depth writing. High signal-noise ratio.
  3. This indie newsletter generated over 10,000 paying subscribers — Robert Cottrell founded The Browser. He shares what he has learned so far. And how he uses an algorithm to find some of his content.
  4. 1 Company, 1 Employee: Tearing Down Stratechery's Pricing — Patrick Campbell, founder of ProfitWell, explains why Stratechery is priced too low. With data from 1,411 current, former and prospective customers. Spoiler alert: Some would be willing to pay $18.40 per month or $201.39 per year.
  5. How My Newsletter for Developers Generates Subscription Revenue — Adam Roberts shares how he went from ads to subscriptions.

You can also check out other trends 🙂

Thanks for checking it out!

  • Any thoughts?
  • What did you like?
  • How can this be improved?
  1. 4

    Thank you for sharing this Dru! The two side-projects I'm currently focused on are email-based. Some days I wake up thinking: "perhaps it wasn't a great idea to shape them as a newsletter", as I'm finding it tricky to get new subscribers, but posts like this are a great push!

    1. 3

      Thanks great to hear Elies! Have you thought about making tweetstorms or tagging people mentioned in your newsletter?

      Here's an example:

      1. 2

        Thank you for the tip Dru! I'm afraid the type of content of both newsletters might not be ideal for this method, but I will definitely take it into account :)

        1. 2

          NP! And you're right. Everything depends on context. If the content is music related. One thing to consider before writing it off:

          1. 2

            Cool, thanks! I'll keep an eye on them, I can see they are doing a great job!

  2. 4

    Another amazing walkthrough. I love the way these flow and just how much valuable info you pack into each one. It's like a perfectly balanced 5 course meal AND a cooking lesson all in one 🙌🏾.

    1. 1

      Love this analogy!!! Thanks Gill

  3. 3

    These are gold @dru_riley. If you are looking for inspiration or just want to be able to quickly understand an emerging or growing trend. These are a must read.

    1. 1

      Thanks Vik! Happy to know these are resonating. 🙌

  4. 3

    Every time I read your trends report, I learn ten new things! Keep it up 🙌

    1. 1

      Thanks Whit! Will do 🙂

  5. 2

    I really love these. Found this thread from elsewhere where you talked about how little you were able to monetise in your time as a maker. Given the quality of these I’m surprised. If you don’t work in a hedge fund or IB you won’t have access to your own research desk and I love the consumable, “bite size” feel of these.

    Just wanted to tell you to keep pushing forward as I do think you have a quality product here.

    1. 1

      Made my day. Thanks so much!

      1. 1

        You’re welcome!

        I mean for comparison In my day job I’m in b2b sales with investment banks and financial services firms and we have clients who pays thousands of £/$ for admittedly longer form but considerably less insightful research. Just need to find the right audience and monetisation strategy and you could be onto a winner.

        I think if you focus on building community with these the monetisation angles will emerge.

        1. 1

          💯Great points

          • The plan is to raise prices over the next few months
          • I'm with you on community
  6. 2

    Just found out about these!! @dru_riley These are fantastic! You got yourself a new subscriber here. Keep it up!

    1. 1

      Thanks for checking them out Benas! And subscribing 😀

  7. 2

    The value in these are amazing by the way!

    1. 1

      Thanks Yaro! 👊😄

  8. 2

    This is really interesting. In my experience the difficult part is trying to strike a balance between having enough free content to attract new subscribers and having enough gated content to justify paying the price.

    This is an interview with one of the most successful Substack writers that I've found interesting.

    PS Ghost is a player too.

    1. 1

      Thanks for checking it out Andrea!

      I agree. That balance is hard to strike. It's something that I'm thinking about right now.

      Ben Thompson has a high cadence. Weekdays. I think it's easier for him than others.

      If your schedule is weekly. Then what do you do? Let me know if you have any ideas.

      I'll add Ghost to the report. And adding Judd's interview to the queue.

      1. 2

        Yeah it's a good question and one I'm thinking about too. At the moment my best answer is to keep the weekly one free, introduce a subscription as a way to support the writer's work (Patreon style) and try to come up with an interesting perk for the premium subscribers (additional content, community, weekly AMAs...).

        1. 1

          Would like to follow how you solve it. This made me think about a report where I wrote about Tim Ferriss:

          When he didn't gate content. But offered things, such as Q&A, aside it.

          1. 2

            I sent you a DM on Twitter

  9. 2

    Each week, I am inspired by your clarity, consistency and presentation of the report! Great job again, Dru. Keep going. Can't wait for this to one of the all-time great newsletters about trends in tech.

    1. 1

      Thanks so much KP! I appreciate all of your feedback and encouragement! 🙏🙏🙏

  10. 2

    @pmmjehan might be interested in this.

    1. 2

      This is a neat and tidy newsletter @dru_riley Nice work!

      Thanks for the recommendation @Lakebed_io

      1. 1

        Thanks Jehan and Simon! 👊

    2. 1

      Thanks for sharing Simon 🙂

  11. 2

    Thanks for putting this together, Dru. I run a side-project and a newsletter, so seeing this instills some motivation in me to keep going.

    1. 1

      Thanks for checking it out Darshan! Is it

      1. 2

        Yup, that's right. Been running it for almost 3 years and I launched the version 2.0 on Product Hunt this week.

        1. 2

          Nice. Just subscribed a few podcasts from Product Disrupt. Thanks for sharing.

          1. 0

            Definitely start a podcast. Use this link for a walkthrough (sorry I'm late to the game).

  12. 2

    Shameless plug, My product is fully newsletter based :)

    1. 1

      Looks great Abinaya! How long have you been building Remote Leaf?

      1. 2

        I had this idea for years, but actively working on it for the past 6 months :)

        1. 1

          Nice! And remote is a great niche.

            1. 1

              NP! Just followed. Super interested in where you take this.

  13. 2

    Another brilliant category worth diving into. Looking forward to reading these every week. Thanks Dru 🙌

    1. 1

      Thanks for checking it out Ash! 😃

  14. 1

    This comment was deleted 10 months ago.

  15. 1

    This comment was deleted 10 months ago.

    1. 1

      Hey Sebastien! Thanks for checking it out.

      You can subscribe here:

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