More people than I anticipated have reached out about this weirdo article comparing City Council Members to Queer Ultimatum contestants.

Happy Pride Month!

Since this has already been a *high-volume* Queer Ultimatum content week with both a personality quiz and a niche municipal explainer, I figured, why not send one more email?

I wanted to talk about the future of media, my own insecurities about *niche political content* and then, at the very end, make an ask.

So I’m sending you one more email this week as an experiment, not dissimilar to the elaborate scientific experiments of the Lacheys.

What’s Up With Newsletters Right Now?

Many people starting newsletters today, especially ones that are similar to mine in… weirdness, tend to already have large platforms and decent lists.

At the very least, they have some clarity on who reads their work and why.

These writers built their list through partnerships with other people doing similar work, by building a platform on social media, or through tenure at media outlets reaching many many people.

This is sort of the classic Substack model, what we think of when we think of “having a Substack” — you write a bunch of stuff, the people who like it pay for that stuff.

Honestly, as is so often the case, the normative model is also the hardest one to sustain.

The writers with successful Substacks using this model (which simply means they make over $30,000, by the way) are very rare: it often requires a large platform, to begin with.

Just like in book sales, well-known names who already have a platform will sell more books (Substack subscriptions) than low-profile authors will — because a lot of people already know who they are.

Of course, lots of people maintain email lists and promote their work online without having hundreds of thousands of readers.

These people tend to use their lists to build a larger income beyond Substack: they do training, they consult about their industry expertise, or they use their email list as leverage in their day jobs.

I’m consistently surprised by how even the weirdest influencers have figured out a path toward financial sustainability, from selling merch to whatever is going on with that TikTok barista guy.

Even though I wanted to write another 1500 words about Ray Lopez and his dogs in that last piece, I can’t justify it without more certainty that the people who actually want to read about Ray Lopez’s weird texts to Lightfoot will see it.

Thanks a lot, Elon Musk.

What’s Up With This Newsletter Right Now?

Unlike the many newsletter writers out there getting started, my list is pretty small.

This is 70% intentional and 30% long-standing self-sabotage.

Part of my rationale for never building a list, beyond (I was scared) — until very recently, social media was far less algorithmically directive.

I felt confident that if I shared something really good about Alder Ray Lopez, it was likely the 13 people who cared would see it, even though my social media followings (and email list) were relatively small.

Social media stayed more or less democratic in this way, even after it started rewarding paid content and rage engagement, as long as you follow certain rules — not linking outside of the platform, trying to figure out Reels, whatever.

So — with that in mind, my list not being very large didn’t really matter, IMO, as long I made things people were interested in.

Doing almost anything online without death threats is a luxury that very few well-known trans writers have.

And this choice was also protective: having a small list of people I knew in real life and cared about, without focusing on a clear “beat” or tone meant I could write about my dead friends and Mary Shelley and the weird marketing tactics erotica authors use without getting death threats.

What’s Up With Social Media Right Now?

But lately, this kind of reach has dramatically fallen on almost every platform.

I hear from people with followings of all sizes that the only way to really get traction on Twitter right now is to align with what Musk wants to see from Twitter — which, you know. Yikes.

So, with Twitter the way it is now, it really doesn’t matter if I make good Niche Chicago City Council Content, because the 18 people who want to see it — don't.

(You’re probably one of those 18 people. I love you.)

This means, with every social media algorithm on the fritz, it’s harder and harder to grow a bigger list.

That uncertainty about reach matters.

I like writing out or exploring the history of the CTU, but when I’m not sure if people will see it at all, and it’s hard to reuse or share with others, it’s harder to justify.

While I’m job + PR contract hunting, I try to limit time spent on articles like these to about 10 hours (plus promotion), which also doesn’t count the time spent turning these pieces into Twitter threads, videos, plus curating and managing social in general so the algorithm doesn’t suppress my reach when I do make content.

But after years of consulting (and obsessively stalking those using this newsletter model well), three things feel very clear:

1. This path is highly unpredictable and constantly changing — what works one day might not work the next, and that directly impacts your income.

2. The newsletter model is not SO different from the gig economy because it incentivizes individualized platform-based media — when people are reading your work for your voice, your hot take, and your intel, it’s harder to break from that norm, to attract new readers with different types of content, or think outside of the niche audience you serve. This also incentivizes “solopreneurship” — the type of work where you do everything all the time to cut costs.

I still think newsletters can be an exciting step towards more coop-based media — but as the recent Autostraddle challenges show us, we’re not going to automatically get to a place of media utopia in the way writers like Hamilton Nolan have posited.

And right now is one of the HARDEST times I’ve seen to build a sustainable media list, primarily because of changes to social media.

Okay, What’s the Ask Though?

Since I’ve been so sweaty in my job hunt, I’ve had many people ask me if I’ve ever considered monetizing this newsletter.

In many ways, though I’ve had this list for 7 years, it is almost explicitly designed to be un-monetizable.

But writing this kind of stuff in an emotional and financially sustainable way is hard to picture until I have a bigger list, far beyond any questions of *monetization* — because I want to make stuff that people actually benefit from.

That’s a lot of marketing rambling — here’s the ask.

There’s only one way around these issues: for people like you to share these articles with your friends, on social media, or with anyone you think would enjoy it.

Remember, this ask is part of an experiment, just like the Queer Ultimatum itself.

My goal is to get 25 new people signed up for these emails this weekend — partially as an incentive, but also because it helps me understand what’s actually useful for the people I like out here in this wild weird internet.

Also, if you have thoughts on any of this, always please comment or send me a note — I genuinely want to know what you think. Have a good weekend!

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