What it takes for me to upgrade to paid

I write about how I make the decision to go paid, and I share my thinking along these lines.

a man opening his wallet to buy a service

I am probably an “Ideal” consumer of newsletters here on Substack. I have pretty wide ranging interests, I have ample resources to subscribe and pay for ‘stacks, and I am not hesitant to push the button to “upgrade to paid” … if I am convinced.

Since the powers that be at Substack are constantly “nudging” me to add paid subscription offers to this one¹, I thought I would share my thinking and what gets me to mash the “Upgrade to Paid”.

At the moment, I am subscribed to 96 Substack newsletters, and I am a paying subscriber to 19 of them. Given that the average cost is abut $50 a year, I am probably spending $500 a year give-or-take annually on various ‘stacks.

As such, there are several reasons why I do go paid:

First is if I find the content interesting, and that the author(s) are doing really good work. In this case I want to continue to support good or interesting writing. Usually, these authors do not put much if anything behind a paywall.

Examples are Jeff Tiedrich’s “Everybody is Entitled to My Opinion”, and Judd Legum’s “Popular Information”, and many many more. I pay them not because I have to, but because I want them to be able to continue to prodigiously post (Jeff), or to continue to do cutting edge journalism (Judd).

Second is usually smaller stacks, where I have established a rapport and (quasi) friendship with the author(s). Here I put offers like “Susan Speaks” and “Alicia’s Substack” to damn fine people who I just adore when they post and I want to toss a few bucks their way to fund coffee (or beer).

Some of these stacks, I even open my wallet further and upgrade to “Founder” tier. Again, it is because I want to support them as people, as much as as authors,

Fourth are stacks where there is a mix of paid and free posts, and I want access to the good stuff, but also because I believe in their mission. Lyz Lenz’s “Men Yell at Me” is an example, and even though she doesn’t put the Friday staple “Dingus of the Week” behind the paywall, I pay to help support her, as she makes a large portion of her living from Substack. There are many of my 19 paid ‘stacks that fall into this space, and I am glad to be able to contribute to their bottom line. I enjoy their writing, and I can afford to pay, so I do.

Fifth (and last) are newsletters that are actively in the fight. Here there are two golden examples, the first being Jessica Valenti’s “Abortion Every Day”, where she does yeoman’s work tracking the fuckery of Republican states and their douche-nozzle pols who really hate women. Another example is Rick Wilson’s "The Rick Wilson’s Substack”, because he is taking the fight to Trump, and doing it with delight! Plus he (and The Lincoln Project) is really good at getting into Trump’s head. Delish!

What pretty much assures you that I will NOT pay

Whilst the above are the reasons that I open my wallet and pay, there are plenty of newsletters that I will not subscribe and pay for.

If you have too aggressive “paywall” turned on. That is, I can see like one paragraph and then you cut me off. Unless I can get a feel for what you are writing about, and how I “value” it, I am likely to just unsubscribe and move on.

If you post infrequently. Look, there are a couple of newsletters that I pay for where the frequency of posting is low, but when they do post, it is always a BANGER (example” Catherynne Valente’s “Welcome to Garbagetown”. I not only pay for her newsletter, but I also have upped it to “Founding” tier, because when she tears into a subject, it is with a gusto and vigor that is to be savored.

But many people who have payments turned on², post less than once a month. I have paid for some of these, and then cancelled due to almost no posts.

That is mostly it though.

Do you have any criteria for when you push the button to go paid? Share below in the comments, I would be delighted to hear your thoughts.

1. Don’t worry, I plan to keep this free forever. Even if I woke up one day with 3M readers, I would not turn on payments.

2. I suspect this is not conscious on the author’s part, Substack really pesters new writers to get a Stripe account and to connect it to Substack at the beginning. I feel this is a mistake for most authors.

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