Insights From Not Boring’s Hypergrowth

Packy McCormick’s Not Boring ad-supported newsletter growth has been meteoric. Packy reflected on the first year in a refreshingly transparent way. I encourage you to read it in entirety.

A Not Boring Adventure, One Year In (Link)

I re-factored it a bit for future reference.


  1. Make room for hobbies, even just a few hours a week.
  2. Don’t be afraid to admit that something you thought was a good idea turned out to be a bad idea. You’ll know it in your gut. Trust that instinct and cut bait.
    • One of the problems with being good at writing is that you can convince people that bad ideas are good. You can even convince yourself.
    • [My observation]: Packy embodies Not be the best. Be the only.

      I realized that I could write about the things that I liked writing about — strategy, finance, economics, and tech — even though they were crowded, as long as I wrote about it with my own, unique voice.

      [I encourage people by reminding them that everything is a remix but there are so many people who “hear” differently and your voice might be the one that resonates. There are no adults. Ask for forgiveness not permission. However you want to put it…get unstuck and move. Motion creates motion]

  3. Sustainable growth comes from a consistently quality product that people want to share. Growth hacking doesn’t work long-term, but it does help to kick things off.
    • Growth

      We decided the best path was to come up with a list of 100 growth ideas. We got to eleven, and did maybe three of them. I’m not a growth hack person.

      • Not Boring has grown through a series of fortunate events, and a lot of help from friends and internet strangers.
      • Asking People to Share and Launching Not Boring
      • Setting up a landing page on Product Hunt
      • Referral program
    • Luck  [Me: Seemed inevitable because of 2 things: hard work & focus on customer]
      • Packy mentions how much luck he had but I’d say the amount of work and thought meant that good luck was inevitable. The magnitude can be debated.
      • Responding to reader’s desires

      I spend a lot of time on Twitter and talking to people to figure out the most interesting companies and things going on that people don’t quite understand, and then I try to understand and translate.

  4. Subs vs Sponsors (ie ads)
    • Subscriptions
      • Pro: generate predictable cashflows
      • Pro: allow writers to focus on writing quality content for their core audience instead of optimizing for clicks (the argument goes)
      • Pro: subscription-based writers aren’t beholden to their advertisers and can therefore write whatever they want without fear of retribution
      • Con: Harder to grow because content is behind a paywall
      • Con: People will only pay for so many subscriptions
      • Con: When someone subscribes for a year, you need to write for a year

    Good for: Topics with a clear focus, especially work-related ones that can be expensed

    • Advertising
      • Pro: Free content means readers can share and drive growth
      • Pro: Makes content more broadly accessible. Another way to look at it is that advertisers are paying for everyone’s subscription
      • Pro: Writers can experiment and dance around more since people didn’t pay for a particular type of content
      • Pro: Optionality

      • Con: Need to spend time doing ad sales and writing ad copy
      • Con: Ads take space that people need to read before getting to the meat

    Good for: More general content with wider appeal

    • Why sponsors were a better fit for Not Boring:
      • Product/Content: It’s not focused on a particular niche.
      • Growth: Not Boring grows mainly through word of mouth. Putting the best content behind a paywall means that people can’t share the best stuff.

[A fast growing letter with a large possible audience seems to be better suited to ads.]

    • Getting sponsors
      • Making a pitch deck

        I surveyed Not Boring readers to learn more about their backgrounds, professions, and preferences, and with examples of previous sponsorships in hand, put together a rough sponsorship deck. Instead of doing outbound sales, because I hate selling, once I had the deck, I decided to tweet it out into the universe

Broader Lessons

  • Flywheels work even if accidental

The Not Boring Flywheel

Writing —> Not Boring Investing Syndicate —> Attracts growing companies —> Loop

  • [In my words: You can’t please everyone. Own that. ]

The only things I’m not optimistic about are cynics and “well, actually…” people. It’s easy to dunk. It’s easy to look smart saying why things aren’t going to work. But those people are not our people. [emphasis on this negative screen is mine]. Not Boring is for the optimists, and for the people trying to make crazy things happen. I’m definitely going to be biased. I’m going to have the backs of the companies in which we invest, and the companies that support Not Boring.

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