[Guest post] How Substack Became Milquetoast

If this all sounds overly theoretical and not at all applicable to your lived experience, then fine. But how often have you gone back to read an old edition of your favorite newsletter? Why bother when you’ll have a new one tomorrow?

having someone who is not your spouse feed their thoughts to you 5-days-a-week, thoughts that they themselves have only had a day to work on, thoughts which would likely go refined or unexpressed in a publication with longer-time horizons, is probably not good for your brain.

In the language of Ben Thompson, Substack has two choices. It can become a full fledged aggregator, build network effects and community, personalized content and so forth, but risk the moral purity of being one of the last ad-free algorithm-free corners of the internet, or it can become a platform, provide valuable infrastructure and flexible prici... See more

I said earlier that the biggest risk to Substack is archives, but that’s only true in the existential sense. With regards to future growth, the biggest risk is that the mainstream population continues to read mainstream journals, and Substack never crosses the chasm.

My rough rule is that I’d like to write stuff that will still be worth reading in five years, and ideally stuff that will be more relevant a year from now. Because of the way news site algorithms currently work, that’s the opposite of what everybody who writes for a living does.

Much of the day-to-day thinking involved in creative work is simply lost, like sand castles in the tide. Ephemerality can actually be useful in low-fidelity thought, but it’s simply an accidental property in many cases. We should do our serious thinking in the form of Evergreen notes so that the thinking accumulates.

The biggest risk to Substack isn’t that Gmail changes its algorithm or that readers set up automatic forwarding and share accounts. It’s that years from now, each author will have built up so much content that a reader can pay a 1 month subscription, download the archive, and be set on reading material.

In the past, you might have spent 10 hours reading a book that took 4 years to research and write, a 3500x multiple on time! Today, a newsletter that publishes M-F and takes 30 minutes to read only provides a 67x multiple.