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This is my bi-weekly “newsletter” delivered straight to your inbox with at least one guaranteed typo I’ll catch after hitting send! If email collectors’ items aren’t your thing, don’t hesitate to switch to the RSS feed or just bookmark loudpoet.com and check in now and then. You do you!

NOTE: I was in Puerto Rico last week, on a relatively casual vacation that somehow also involved driving more than 600 miles around the island, because we apparently don’t understand how to just relax in one place for a week! It was our first time back in 10 years and we had a good time exploring the west and southwest sides of the island, but it left me with a range of mixed emotions, too. That’s a complicated, nuanced subject for another time, though.

_ONE

The Rise and Fall of FOLIO: A Mirror for the Magazine Industry | BoSacks

The death of FOLIO: isn’t just about a single magazine; it’s about a collapsed ecosystem. You simply cannot have a truly thriving trade publication without a thriving trade to cover and serve. And when that trade becomes smaller, more concentrated, and less relational, what happens to the connective tissue that binds it?

FOLIO: Magazine was an industry bible early in my publishing career, one of the first trade publications I ever subscribed to and devoured every month. I even almost worked for them during a major restructuring when I worked at Primedia Business back in 2001, sparked by a wave of consolidations that turned out to be an early warning sign of troubles ahead. Eventually writing for them a few times was a major professional milestone, too.

Sacks’ insightful retrospective is a bittersweet reminder of what we’ve lost, and most of it was absolutely NOT inevitable.

__TWO

The Media’s Pivot to AI Is Not Real and Not Going to Work | Jason Koebler

AI is a tool (sorry!) that people who are bad at their jobs will use badly and that people who are good at their jobs will maybe, possibly find some uses for. People who are terrible at their jobs (many executives), will tell their employees that they “need” to use AI, that their jobs depend on it, that they must become more productive, and that becoming an AI-first company is the strategy that will save them from the old failed strategy, which itself was the new strategy after other failed business models.

Every time I read something about another media company embracing “AI” (usually in some vaguely defined way that will lead to vaguely defined productivity and efficiency gains), or signing licensing deals to “legally” feed their content to one of the robotic parrots, I remember all of the previous objectively bad technology decisions media executives have made over the years. Sadly, in many cases, it’s the same dudes with resumes full of failures by most rational metrics — except most business metrics for “success” are anything but rational.

Koebler doesn’t pull any punches here, presenting numerous examples, and will surely be dismissed in certain circles as a disgruntled Luddite who simply doesn’t get it. Which, of course, means I wholeheartedly agree with him!

If you’re still drinking the “AI” Kool-Aid in August 2025 and are in a position to make decisions that will impact the livelihoods of others, I assume you’re either personally invested in making AI “inevitable”, or you’re just another sycophant hoping to fail upwards like the mentors you’ve chosen to follow. Or, maybe, you’re just bad at your job and believe 10xing yourself will change that fact?

___THREE

Why Substack’s new valuation means a monopoly is brewing | Lex Roman

In short, Substack may not be generating enough actual capital, but they have scammed their way to a significant amount of cultural and political capital. This new valuation is betting they can turn that cultural capital into a massive payout for their investors.

At least twice a week I get annoyed by Publishers Weekly‘s newsletter promoting Substack like it’s an editorial peer rather than just another platform some notable writers use to host their writing. In the old days, you had to pay for that kind of “free” exposure, but so many media organizations do it for Substack on a regular basis without them paying for a single ad or even hosting an industry party.

Of course, this is partly the fault of the many writers who have willingly elevated Substack’s brand over their own, particularly the ones Substack isn’t directly invested in supporting (which is most of them). Roman does a great job unpacking that problematic aspect without ever mentioning the Nazi Bar situation, which also continues to be problematic but is somehow still not a deal-breaker for people who should know better by now.

Meanwhile, if you’re reading this via email or RSS, be sure to check out my WordPress! #cmonson

____FOUR

Fell in a hole, got out. | Tony Stubblebine

I’m not sure if a company is allowed to be this blunt about how bad things were. But it’s very much of the Medium ethos that if something interesting happened to you, then you should write it up and share it.

Medium hasn’t been on my radar much in recent years, but I’ve been intrigued by Stubblebine’s candor ever since he took over as CEO a few years ago, particularly because the story of a power user taking over a company he loves *without ruining it* is arguably an outlier, especially in tech-adjacent media. Or media-adjacent tech?  ¯\_ (?)_/¯

Medium has always been an intriguing platform with potential, but Evan Williams’ hyperbolic aspirations and multiple pivots were never aligned, and they pulled the rug from under writers and publishers so many times over the years, it’s a miracle it still exists at all. Stubblebine is apparently that miracle, and there are several great insights here about startups, finance, and being mission-driven.

It made me want to give Medium another look, to understand how its turnaround has affected who is writing there these days, and more importantly, who is reading and sharing what’s being published there. I nuked my original account years ago, but I updated my profile and posted something there earlier this week out of curiosity and will be poking around off and on to see what I find.

I definitely don’t see it as an alternative to WordPress or even Ghost, but maybe it’s ready to fulfill its potential for writers who just want somewhere simple to post longer writing that includes links to other people’s writing, a throwback to the early days of blogging but with the benefit of many lessons (hopefully) learned since then?

_____FIVE

Medium versus Substack: Six reasons writers pick Medium | Zulie Rane

Successful content creators on Substack tend to have to “brandify” their Substack publication and stick to a single niche with their content creation, since they’re going deep on expertise to sell a Substack subscription to a paying audience. On Medium, enjoy the freedom to show the full breadth of who you are, with all the interests and ideas that you’re passionate about.

One of the arguments I hear from writers for Substack is that it’s free, an important factor for those who haven’t built up an audience yet, especially not one willing to pay for a newsletter. Managing a whole website can be a pain in the ass and more than many writers need, and Substack’s early appeal was its simplicity.

Of course, Substack has aggressively moved beyond its original positioning as a simple newsletter platform and is trying to become a closed garden of its own as quickly as possible; one where “free” newsletters are simply a growth hack to build an audience they can monetize beyond paid subscriptions. (If you think ads aren’t coming soon, this must be your first rodeo.)

Rane does an admirable job of positioning Medium for a certain type of writer at a time where it desperately needs a clear identity, and doesn’t shy away from calling out Substack’s refusal to moderate hate speech. I’m not convinced about Medium’s ability to attract and drive audiences themselves, whether through their own efforts or SEO, but that’s what I’ll be looking at as a reader over the next few weeks while I give them a shot to convince me otherwise.

______BONUS

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