Surprise Saturday drop.

Every now and then, I’ll drop something off-cycle when it matters — and I think this one does.

Last week I had a call with a prospective client in the financial media space. 

After we got off, I got curious and did a little sleuthing online. 

Among other things, I searched for “CFO newsletters” and landed on one of those typical SEO-driven, affiliate-laced, aggregator pieces:  17 CFO Newsletters You Need to Read in 2025. 

My first thought was, seventeen must-read newsletters… for CFOs?

Holy shit this space is crowded. 

And those are just the musts. I could probably find five more listicles with fifty more options, each claiming to be indispensable.

It reminded me how absurdly crowded the media landscape has gotten — especially since the 2020/2021 exits of The Morning Brew and The Hustle (my crew!).

But even more so since the launch and wild proliferation of AI.

These days, anyone can spin up a newsletter on Substack or Beehiiv in an afternoon. 

It’s great for frictionless publishing. It’s great for accessibility. Dare I say, it’s great for democratizing ideas and distribution.

You know what it’s not great for?

Reading.

Because the truth is: 99.9% of what crosses my feed these days gets filtered out immediately. 

Not because I’m ‘better than it’ — but because I can tell when something was made to check a box or strikethrough a notion list. 

I can’t always prove it was AI-generated, but…

It’s not that hard to tell. 

I was talking to my biz coach the other day about this — how the media space is both the best and the worst it’s ever been.

(If you want to geek out on it, here’s the full write-up my coach shared.)

How replicating or summarizing can seem more approachable (and monetizable) than the sometimes onerous process of actually creating. 

When the world’s this flooded with content, it can feel like your only options are to:

And if you take Ben Thompson of Stratechery at his word - that content is now completely commoditized as the last piece of the content value chain is unbundled - then, f*ck, maybe we should truly give up...

This stuff messes with your head, especially if you make stuff for a living, if you do something for the love of it, or if you just actually like reading good shit.

But, the conversation I had the other day did actually help me re-anchor.

Because when I look back on the last few months of my own writing — after deciding to jettison my 20-year startup career  — the stuff that has actually resonated with readers wasn’t overly clever, it wasn’t heavily optimized, it wasn’t keyword-driven, and it definitely wasn’t AI-generated.

Do I use AI for occasional idea generation, for banter? Yes.

Do I use it for grammar and editing? Of course, I’m not a donkey.

But the ideas, the urgency, the voice? 

That shit is all me. 

Here are a few good illustrations of why it matters: 

You know what absolutely bombs? When I write about stuff I don’t actually care about.

➡ Case in point: I posted on LinkedIn about agentic commerce (a legit interesting concept that piqued my interest for all of 20 minutes)… and it tanked. 😭 900 impressions.

And it wasn’t because the idea sucked. Let’s not go blaming agentic commerce!

It was because I didn’t actually feel anything about it. 

I wasn’t pulled to write it. It didn’t wake me up in the morning. It didn’t keep me up at night.

And people can tell.

Between creating because you have to, versus creating because you can.

It’s the difference between creative output and mechanical output. 

One is born from urgency, emotion, and a shit ton of lived experience. 

The other’s built to optimize. 

One makes you feel something. The other fills an empty slot.

When people read something clearly generated by AI — or worse, regurgitated by a human acting like one — the relationship to that content is fundamentally different. 

It’s transactional. It’s disposable.

Technically, it may be right — but emotionally, it’s flat.

To be fair, this didn’t start with ChatGPT. 

This shift began years ago, as SEO, keyword targeting, and “content calendars” began to replace actual voice, an actual point of view. 

It’s one of the reasons The Hustle worked as a business newsletter -- the writing actually had personality. It had voice. The writers had opinions. 

The whole thing had some f*king teeth.

Real creativity starts with a felt impulse.

You can use reminders and organizing software and productivity tools, fine. 

But don’t create because your Notion jawn says “Post Tuesday”. 

Create because there’s something gnawing at you - and the only way to make it stop is to get that shit down on paper. 

And the work that comes from that place - it’s different. 

It makes someone think, “Shit… yeah, I’ve felt that, too”. 

That is what having a relationship with your audience is all about. 

Synthetic work rarely does that. 

It’s not built to do that - it’s mostly built to just replicate structure.

Here’s a quote I’m going to leave you animals with:

F*ck yes. I love love love that line. 

So if you're writing, building, making anything right now — don’t just aim for scale, don’t just aim for reach, or even usefulness. 

Start by aiming for what’s actually true to you.

Don’t outsource the part that makes it real:

Your attention.
Your creativity.
Your emotion.
Your taste.
Your voice.

That’s the only thing these snitches can’t fake.

And it’s the only thing we’ll still care about years from now.

Enjoy your Saturday.

Love yous.

Jordan

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