Got annoyed last week.

Every now and then, I’ll see a post or podcast talking about the demise of content marketing.

Why does this poke my buttons? It’s not just because of the obvious clickbait labeling, but that every one I’ve bothered to check out says “naw, just joshing, but I sucked ya in with that headline!” and/or “yet it survives in this brand-new consulting service we just launched combining [insert trend du jour here] and content.”

Reminds me of all the social apps in 2000 saying that “we’re going to kill email” while relying on email to verify users and log-in to those very same apps.

Like most hot takes; this one is always wrong. Content marketing has been building trust and informing audiences across at least three centuries; 130 years (at least) – and counting – of effective marketing.

While I believe newsletters are a critical, must-have content marketing pillar for businesses, I don’t want to mislead that they’re the only vehicle. So I had the thought of compiling a quick list (which then led to a second list about newsletters) of how content marketing delivery platforms have changed over the years while the basic strategy remains.

Here’s the timeline. Note/mini-AI-use example, I used Claude to compile this list based on my initial thoughts – I missed soap operas, Guinness, and Red Bull. This list is lightly edited because a total rewrite doesn’t change the information.

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1895 — The Furrow. John Deere launches a magazine that teaches farmers how to farm better. Actual useful information for the people they wanted as customers. It’s still publishing today. The Furrow has outlived radio’s golden age, broadcast TV’s dominance, AOL, MySpace, and whatever platform died while you were reading this sentence. Ink on dead trees remains a viable way to reach an audience (of course, especially when deliver is also pixels on a screen). Hell, you can squint and look at a newsletter as a single feature delivered via (most often) email.

1900 — The Michelin Guide. A French tire company publishes a free guide to restaurants and hotels. Why? So people would drive more. Driving wears out tires. That’s the origin of the stars chefs aspire to claim. A century later, the content is more famous than the product — chefs weep over Michelin stars, and most of them probably don’t know a Michelin from a Firestone tire.

1904 — Jell-O recipe books. Jell-O was a flop. So salesmen went door to door handing out free recipe books — here’s what you make with it. Jell-O became a household staple because somebody answered the question “okay, but what do I DO with this?”

1921 — Betty Crocker. General Mills’ predecessor invents a woman. Betty Crocker answered baking questions by mail, then on the radio, for decades. She wasn’t real, but the trust was. Millions of American home cooks had a relationship with a fictional person because the advice was good.

1930s — Soap operas. Procter & Gamble funds radio dramas to sell Oxydol soap to housewives. Shows like Ma Perkins worked so well that we named an entire genre of entertainment after the sponsor’s product. I sometimes think this teeters on the edge of advertising, but I love this story too much to drop it.

1955 — The Guinness Book of Records. The managing director of Guinness gets into a bar argument about the fastest game bird in Europe and realizes there’s no reference book to settle it. So the beer company makes one — a promotional item to spark pub debates and keep people in the pub. The giveaway became a global institution that’s outsold nearly everything except the Bible. So the next time you’re enjoying bar trivia night, raise a pint to Sir Hugh Beaver’s argumentative nature.

1983–84 — Afternoon Cartoons. He-Man, G.I. Joe, Transformers — 22-minute toy commercials disguised as entertainment. G.I. Joe even ended every episode with a little PSA — “Now you know. And knowing is half the battle.” A toy ad, teaching kids not to play with downed power lines. Content marketing with a merit badge – and huge sales.

2002 — Seth Godin starts blogging daily. One post. Every day. For 24 years and counting. No hacks, no funnels, no growth loops. Just showing up. That consistency has made Godin, for folks like me, hugely influential and a trusted authority on marketing.

2012 — Red Bull Stratos. An energy drink company puts a man in a capsule, lifts him to the edge of space, and he jumps. Millions watch live. Red Bull isn’t a beverage company that does marketing — it’s a media company that sells caffeine. The content IS the brand. I still kinda regret not checking out Flugtag when it was in Baltimore in 2006.

2014 — The LEGO Movie. Basically a two-hour toy commercial that made hundreds of millions of dollars. AND boosted LEGO sales and profits over multiple years.

2009 — Marcus Sheridan’s pool post. I saved this one for last even though it’s out of order, because it’s the one you can actually copy. After the 2008 crash gutted his pool business, Sheridan wrote a blog post answering the one question every customer asked and every competitor dodged: “How much does a fiberglass pool cost?” One honest answer. That single post generated over $2 million in tracked sales within a few years — Sheridan says the lifetime number is far higher. It saved his company.

But, Uh, What About Newsletters?

Fair question. This is a newsletter, written by a guy who builds newsletters for a living. You’d think I’d have led with them.

Here’s why I didn’t: newsletters are OLD. We thrive on information, newsletters (and proto-newsletters) having been helping us separate noise from signal for 4,000 years; give or take a few. I also used Claude to compile this list, while I had a suspicion proto-newsletters existed before I started writing and delivering DOC.1 via fax in 1996, I had no idea how far back the history went.

~1900 BC — The Kanesh tablets. Assyrian merchants running trade routes across what’s now Turkey left behind 23,000 clay tablets — much of it business correspondence. Prices. Shipments. Warnings about the market in the next city over. Four thousand years ago, somebody was pressing “what’s the tin market doing?” into wet clay.

51 BC — Cicero’s news feed. When Cicero got shipped off to govern a Roman province, he set up his buddy Caelius to send him regular dispatches from Rome. The first delivery promised “the Senate’s decrees, the edicts, the gossip, the rumors.” A subscription newsletter wrapped in a toga.

876 AD — The dibao (and its Indian cousins). Imperial China ran court newsletters for over a thousand years — edicts, promotions, palace news — hand-copied and couriered to officials across the empire. The oldest surviving issue on the planet, from 876 AD, sits in a library in Paris right now. Various empires in India did the same thing for nobles and provincial governors. Two empires basically sending out an internal company newsletter.

Mid-1400s — Venice. Now it’s a newsletter you’d recognize: paying subscribers, handwritten letters twice a week, merchants tracking exchange rates and business news. [CLAUDE – what was the name of this]

1704 — The Boston News-Letter. America’s first. Ran 72 years, then became a newspaper. Which is what newsletters kept doing, by the way. The newspaper is the newsletter’s kid. Not the other way around.

1904 / 1923 — Babson and Kiplinger. The paid expertise newsletter becomes a modern business model. The Kiplinger Letter is still publishing a century later (there are now four of them).

1990s — Enter Email. The examples you need here are in your inbox.

We desire information. For 4,000 years, people have gone to serious effort for newsletters. For at least the past 500 years, they’ve rewarded that effort with cash.

While I’m not convinced Edison was first, it’s the first example I can find without a DEEP dive into the Internet rabbit hole. In 1882 The Edison Electric Light Co. Bulletin decided to give away their newsletter. It was content marketing, complete with testimonials, reports from neutral observers about the company’s efforts, and, my favorite as a fish aquarium fan, a story about lighting (under water) the trout tanks at a Fulton Market fish stall.

I’d almost bet money the folks at John Deere paid attention.

Educate or Entertain

Look at the list again. A farm magazine, a restaurant guide, recipe books, a fake woman, radio dramas, a bar-bet settler, cartoons, a blog, a space jump, a movie, a pool post.

Three centuries. Different media. Same thing: figure out what your customer actually wants/needs to know or be entertained by, give it to them, and then keep doing that until it’s no longer effective.

Delivery methods die, to lean in to our John Deere example, fields go fallow over time; the strategy doesn’t. Print circulation collapsed. Radio drama died. Blogs were declared dead a decade ago (which I continue to find hilarious given this site is a blog site with built-in distribution).

The content marketing strategy isn’t about the medium. It’s about answering real questions and delivering real value so people trust you (and buy your product/service; it’s equally important to remember this isn’t entirely altruistic).

That’s the 130-year lesson for content marketing, supported by 3,900 years of “we need our newsletters” too. Be useful. Be consistent. Own the connection.

I’ll take a 4,000-ish year track record of success over the bleatings of pundits grasping at relevance.

And now you know. And knowing is half the battle.

Comments, criticisms, and witticisms welcomed.

P.S. — Michelin made a restaurant guide to sell tires. You just have to make a newsletter to sell what you already sell. Considerably easier. I'll build it with you. See how here or skip it and let’s see how I can help you (bryant@simplyusefulmarketing.co).

If you’ve never had to suffer through a G.I. Joe episode; my brother and cousin LOVED it; that was the tagline of their end-of-episode PSA. It got burned into my brain so deeply during my high school years, I STILL say it.

And now to pass the pain, er, knowledge on to you. Here’s all of them if you’d like to torture yourself.

9:55 last Tuesday, “Let me double-check the time for tomorrow’s webinar starts.”

25 minutes later I was in a different town in a different parent’s house.

Here’s what happened.

About 2 months ago, the lovely and talented Laura Wolff asked me to give a short presentation about the value of newsletters to her clients. We’ve been in each other’s online orbit for . . . a year? Two? After being in an online cohort together a while back.

I was flattered, yet terrified (hate speaking in front of groups), but as I was in a “say yes/confront fears” week. I said yes.

From there, a few mistakes on my part led to my last minute parent-to-parent dash.

The Original Sin

Me and dates have a nodding relationship — I often have to think about my birthdays (and my daughters’).

Despite having the right day in my Google calendar from the beginning, I got it into my head that the webinar was on a Wednesday and was at 1 or 2.

In my defense, I co-created and hosted a webinar program (over 100 webinars) that was on a Wednesday at 2 eastern so there’s some hard-wiring in my brain.

This wouldn’t have been an issue had I bothered to actually check the date at any point and time. But, I KNEW it was Wednesday at 1. Had told my Dad and my Mama when I first drove down here the first week of June I’d be staying at my Mama’s that Tuesday (June 23) night to talk on Wednesday.

It was also a good thing my paper planner was out of reach at the time, because I had even put it on the wrong day/time there. How? NFC.

So when I looked at Laura’s email with the date and time I confirmed for her (and my online calendar), I did the opposite of the advice in Hitchhiker’s Guide to the Galaxy and panicked for about 30 seconds

Webbed Feet Furiously Paddle

After loudly yelling “FUCKFUCKFUCKFUCK” a few times (my Dad and Benny-Benny, my stepmom, can confirm); threw a set of clothes into a bag, packed my laptop, and sprinted out the house.

You might be wondering why I needed to move houses. I mentioned the 100 plus webinars. In about 1/3 to a quarter of those, Murphy meddled to one degree or another. You learn early to remove as many moving parts that can break as possible – the moving part here is a weak Internet connection at my Dad’s (a bad thing for an online presentation).

Out of the house here in Sulphur by around 10:05 or so. It’s about 20/25 minutes to my Mama’s in Lake Charles. Made that in about 15.

10:20. Grab chair and put in bedroom that has the desk. (Say hello to Mama and my brother.)

10:25. Try to print notes.

10:35. Give up. Send to my brother’s Gmail on my Mama’s laptop. Try to print from there.

10:45. Give up. Decide that I’ll just have that laptop open with my notes on it.

10:46. I had already pulled a draft set of slide text with Claude. Had Claude create that as a PPT.

10:47. Save.

10:47 to 11. Stop sweating. Change shirt. Attempt to brush too-long hair. Bio break. Pour a glass of water.

11 to 11:05. Log in. Realize I had forgotten my external camera so the entire presentation would be me in what looks like those shadowed interviews with criminal informers. Then learned that Zoom hated my headphones, which, luckily a simple plug and unplug worked to fix (this time!).

11:05 to 12:30ish. Presentation and Q&A, which everyone enjoyed (even me).

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What I Did Right — GenAI and Experience Helped

The presentation probably ended up better, in some ways, than if I had had the extra 24 hours to have a smoother slide deck as well as get the flow down.

A combo of lingering professionalism from habits formed during my webinar days and how friendly Laura and her folks are made it work though.

I had shared my initial thoughts on what I was going to cover and the general flow of the presentation with Laura a week or so before. Good to go there.

The week before, I had jotted down essential points I wanted to make in a notebook, pulled a presentation from my existing content using Claude (one benefit of having a body of work to pull from), and pulled a draft slide deck to edit.

Plus, I know this stuff.

So, planning:

1. Good outline

2. Talk track/notes

3. Presentation draft

4. Topic knowledge from living it

This is where genAI is a fantastic assistant.

The presentation itself was about the basic value of newsletters for businesses today. I’ve written about those topics across multiple posts:

1. I wasn’t going to be saying anything new

2. I pointed Claude at my relevant posts (about a dozen or so here) and, based on my outline, had the pattern matching machine pattern match

3. I could have spent 30 minutes flipping through the text and pulling out slide content or do what I did – tell Claude to pull a slide deck of talking points from the presentation notes content only.

   1. This is also where “assistant” is the key word here. Because you do not want to simply use unedited/un-reviewed genAI-generated content, even if pulling directly from your own work (because genAI will make things up – read that again and internalize it).

      1. The only thing I wish I could have done differently or had slightly more time for would have been to smooth out the slides so they sounded 100% like me.

The Lesson: Screw Up and Keep Paddling

I did think in those first 30 seconds of calling Laura, apologizing profusely, and rescheduling. But that would’ve been shitty. So I pulled on my big boy pants and scrambled.

1. I knew I had the basics down and, worst case, could give a good presentation via my phone and my notes

2. I knew, barring an accident on I-10, I had enough time to drive, setup, and still breath for a minute or two before starting.

3. I knew I could use genAI (Claude) to spit out a basic set of slides in minutes.

Writing this, it hit me that while there is a LOT of truth in “fake it until you make it” advice; a baseline of experience and knowledge helps you pull it off. A looming webinar disaster didn’t faze me because I’ve been through that before. Fake it till you make it gets easier when you know, deep down, that you can make mistakes and still muddle through (I think this is true even when the mistake is a new one in new endeavor). I didn’t need a great deck, my talk track, or a decent camera; I knew I could do this presentation with just my notes and what’s between my ears.

As I was trying to get my mic to work, there was a conversation about not telling folks you’ve made a mistake because they won’t know. I do think in some situations that is 100% golden advice.

But as I sat there trying to get Zoom to acknowledge my mic existed, it didn’t feel right. So I quickly shared my mad scramble to get ready. And decided to use the slides to point out how genAI can be so, so wrong, but also so, so right.

I think the honesty was appreciated. Plus it gave me the opportunity to poke fun at both my writing style and how genAI sometimes poorly attempts to recreate my writing style.

As I went through I pointed out how Claude almostbutnotquite got wording right, but also, especially on the last slide (below), also gets it right. The line here is pretty good. At the same time, I would have cut “That’s the whole pitch” because that line makes my skin crawl a little.

By being honest about the last-minute scramble (and using genAI), I was able to point out pros/cons of the tool and turn a potential mistake into presentation material.

I know it’s easy to look at the folks who are doing spectacularly well here (and there and everywhere) and just feel like you’ll never get there.

Not me today, but once upon a time I was a medium fish in a smaller pond. It always amazed me that people would read the magazine (which was excellent) and then assume that I had my shit totally together — those things met less regularly then than they do now!

We’re all experimenting and trying new things and succeeding and failing and flailing and sometimes catching a ledge to pull up and sometimes falling into the abyss.

So, I guess, as I wrap this mess up, we all know we live in a mostly-curated social bubble. You don’t feel like you have it all together. That goes for about everyone, so don’t judge yourself too harshly by mistaking the front someone shows to the world as, necessarily, the reality. And be kind to each other.

And give yourself a break too. I hadn’t had to scramble like that in quite a while. It sucked, but was also reassuring to know I can still pull a rabbit out of my buttockal region.

Or, to tie into the title, can still swim relatively smoothly even as I paddle like mad beneath the water.

One last thing, make sure you have the day/time right for anything with a deadline! (Still don’t know how I manage this at least once a year.)

Scrambling with your newsletter? My Newsletter-in-a-Box service will let you paddle a little less furiously because you’ll have one less thing to worry about. Let’s talk and see if we’re a fit: bryant@simplyusefulmarketing.co.

And it’s not a webinar, I don’t miss publication dates!

Music Festival

Had a little Blackberry Smoke mix in the background as I popped this into here. One of my favorites of theirs.

My relationship theme song! Maybe the next time it’ll end up being this. And see Stapleton in concert. He’s great.

I had the privilege of being asked by Laura Wolff to share my thoughts on the value of newsletters with her clients this Tuesday. Give her a follow, she regularly shares great advice about leaning into yourself.

After totally getting the date wrong, and a frantic drive from my Dad’s in Sulphur to my Mom’s in Lake Charles about 45 minutes before the start (that’s in Louisiana; WhoDat and pass me dat boudin, sha) for her more stable Internet connection, it went well. Probably better than if I had time to “plan” more (fritter away time, worry, and not really improve anything).

My emphasis on getting the intention right by thinking of a newsletter as first a trust-building tool (but also one that should lead to revenue) and then a few pieces of practical advice for a simple start was well-received.

Better yet were the questions. We had, I think 15 folks online. I’ve moderated webinars with 1,000-plus folks listening live and gotten fewer questions. That was fantastic!

Here they are, asked and answered, and lightly edited for readability and added context in a few spots where my brain shorted out in real time.

For context, this post might help.

Segmentation — what’s the strategy, and how much does it matter?

Until you actually have a list, it doesn’t — so I’ll start there. My whole career has either been small-scale, like I am now, or larger-scale at AIIM, which was a national trade association with about 60,000 members [this feels low, but it was over a decade ago and I have no access to numbers]. So I’ve either been at the 300-person scale or a much larger scale. [I did spend 4 years doing inbound marketing as a HubSpot agency for copier dealers, but none of them paid for the segmentation tier. We did segment by splitting lists based on purchases and interests, but it wasn’t as sophisticated as we could have done for them and their 4,000 to 10,000 customers/leads.]

The one tool I really know is HubSpot. The basic buckets are intent and interest. On intent, it’s tofu, mofu, bofu — top, middle, bottom of funnel. Someone new is top of funnel. Someone in the decision or interest stage is middle. Someone ready to buy is bottom. The other way you split is by interest — so for you, that’d be fasting, the courses, and so on.

[I misspoke here. By interest, I was thinking topic – document imaging, records management, standards, workflow, etc. to use examples from my AIIM time. What I said out loud was segmentation by product, which is a third way to segment your audience.]

Say you had four segments with a few thousand names each. You’d only send the fasting course to people who signed up for the fasting lead magnet — you segment them out instead of blasting everyone. It does boost revenue, but you have to get to that point before it matters. I wouldn’t trust my word on the exact number, but 500 feels about right to start, if you’ve got two main product lines. Beyond that you get into “these people bought these three ebooks and not these five,” and you start upselling and cross-selling. That’s structured thinking, which is not what I do well. I know just enough to be dangerous — I get inside a tool and poke buttons until it happens.

[The poking buttons is true, but with a little more planning and intent behind it. I’ve done some lightweight segmentation work for email campaigns. Once you have more than one thing to sell, segmentation becomes a possibility:

1. These folks have bought thing 1, so let’s not send messages about buying thing 1 to them.

2. But, let’s send emails to the purchasers of thing 1 to see if they would also like thing 2.

From there, it starts to get complicated.]

How long should a newsletter be?

My rule of thumb: shoot for 500 words. That’s about enough to cover one topic or introduce a couple. But the real answer is write until you’re done. I think it was Strunk and White — write until you’ve said what you wanted to say, then stop. [Actually, I think this was Mr. White, my sophomore high school English teacher. “Friends are like shoes. You get ‘me, use ‘em.” was another expression of his.]

A newsletter is a container word, like “book.” What goes inside can be anything. It could be a single 2,000-word piece. There’s one I get — Newser or something like that — where the guy pulls ten bits of news, writes a short bit up top, tweaks the headlines and decks, and links out to the original source. Nearly pure curation (he makes revenue from sponsorships/ads). [Others add commentary to each item then link to the source.] I still think of newsletters like a magazine because I did that so long — features, departments, an agony column like Irma Kurtz’s in Cosmo. It can be whatever you want.

And you mix and match. Over time you run experiments — sometimes short is what your audience wants, sometimes long. Nobody knows until you start doing it. I used to make fun of consultants for saying “it depends.” Then I became a pseudo-consultant, and yeah — it really does depend.

I’ve written about this in detail in these two posts, I only touch on length in the 22 tips piece, but I think the advice is relevant for you if you’re reading this and having a hard time starting.

Substack vs. my own email list — how do these interact, and do I need both?

[I didn’t quite grasp the “why are you doing the same thing for a slightly different audience” nature of this question at first though a question later got us there.]

I probably wouldn’t run both long-term. You could absolutely just use Substack as your newsletter platform because it has the discovery features. But Substack has no real email campaign or management capability — even the most basic email platform beats it. You can send a one-off email to your subscribers in Substack, so it’s bare-bones email marketing, but if you’re doing anything complicated, keep them separate.

If you’re trying to simplify, ask yourself: is your activity on Substack growing the list and bringing in customers? If it is, keep leaning on Substack. If your own self-contained list is doing well and people are finding you and you’re getting business, why drive yourself crazy running both?

On video — YouTube is one of the top sites in the world, so being there is good, but you still have to make the video somewhere. The way I want to use mine: shoot on my phone, drop it on YouTube as a holding place and where it can be found, embed that video in the Substack article it came from, then put it up on LinkedIn, since video does well there for B2B. One thing, distributed multiple places. I think of YouTube as just my video hosting platform that also happens to be one of the largest search engines. It’s not my “home” online; that’s Substack. Figure out where your one home is, then point everything else at it.

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Is it ethical to invite my Substack subscribers onto my main newsletter list?

I’m pretty sure this is fine — I get queasy about sketchy stuff, and this feels okay. Check my work though! These are people already actively hearing from you who said yes to you. You’ve got this other thing over here. So send an email: “Thanks for being a subscriber — I do this other stuff over here too, are you interested?” Let people say yes or no.

It’s close to a re-qualification campaign — like when you’ve got a dead list of names you don’t want to just dump. I did this for a company a couple years back. They had three or four thousand names from trade shows they’d never touched. We set up a short sequence: “Thanks for being here, haven’t heard from you in a while, still interested?” As long as you don’t keep emailing the people who never reply, you’re fine. And always, ALWAYS, have an easy unsubscribe process.

Why would I have both a Substack and a newsletter — and if I do, do I copy one to the other? [This is a continuation from the question earlier]

If you’re just starting out with nothing, go to Substack. Why keep ramming your head into a wall when there’s an option with built-in findability? A WordPress blog just sits out there alone — Substack has the discovery, the Notes, the built-in network. I’d ditch the standalone newsletter, import your list, and run it on Substack. Most of us hit the first friction point and quit. Substack is dead easy, works on your phone, and removes some of that friction.

On copying one to the other: if it’s the same content going to two different lists, you’re just making work for yourself — combine them, pick one. From the reader’s end, nobody cares whether it came from MailChimp, Kit, or Substack. That part is irrelevant. The only real exception is a launch sequence — schedule a masterclass, reminder email, sell-sell-sell, then close. You can’t really automate that in Substack; you’d have to send each one manually. I half suspect Substack will eventually bolt on some light email-management tool and charge for it.

[This also gets at name confusion, which I talked about in the presentation – is Substack a newsletter? An email? A Twitter-esque feed/micro-blog ? A blog? Yeah, it’s all of those. I wrote specifically about what a newsletter is here to get folks thinking about the content, not the container, as the important thing.]

You said a CTA in every newsletter — but isn’t that just selling?

Yes, a CTA in every one. And yes — it is selling. It absolutely is. You have to hold two things in your head at once – you need to use your newsletter to build trust by sharing helpful/useful information AND you need to sell your services/products. Kinda like propaganda and marketing are flip sides of the same coin — same mechanics, the intent is what’s different.

So if you coach people-pleasers: write a post that says “stop doing that,” and your CTA is a class — “I can teach you how not to do that.” That’s sales, and that’s fine. I put a CTA in every newsletter for Newsletter in a Box. I can’t think of a single newsletter on Substack that’s serious about using it to market/sell what they do that doesn’t have at least one CTA per issue. Some people put it at the top; I do a middle one and a PS at the bottom.

So 80% helpful, 20% sell?

I’ve seen people do that. Mine is more — some are like, you would have like 95%, you’d have a very tiny CTA or message at the end. I’ve seen others, you have maybe a 1500 word post, and then they’ll have a three or four hundred word description of an upcoming whatever they’re doing, like a cohort or what have you. A CTA is a container word like “newsletter” — it can be a buy-now button, a simple subscribe button, a short description with a link, or a half-page description of your service with a button or link.

You said you’ve spent eight years thinking you had to send eight purely helpful issues and then one with a CTA. It took me a couple years to get past that too. Ask for the money in every one. You are a business. It’s OK to ask for the sale. Don’t be a jerk about it, don’t be pushy — but tell people you can help them. Selling is helping. When you truly believe that, you realize you’re doing people a disservice by not making the offer.

And, yes, I still feel that awkwardness too, but all it does is hold you back from succeeding. Work to overcome it without becoming the stereotypical used car salesman.

A random thought here to your point about the eight and then one. I think there is space every now and again to just be like, “Hey, I do this. Here’s what I do. Here’s how I help.” as your newsletter issue. I’ve not done it because it feels a little bit weird, but I have thought about the idea of writing a “here’s how I work with you” sort of thing, which is basically an entire sales post semi-hidden behind a “hey, this is complicated, you SURE you want to do it yourself” type post. It’s a pure sales pitch and I haven’t brought myself to do one (yet).

What’s the actual difference between a newsletter and email marketing?

Think of your newsletter as your asset — the thing people love. Email marketing is what happens when someone clicks on a CTA (possibly, depending on the offer in the CTA) and kicks off an automated email campaign. Say you’ve got a CTA in your newsletter — “interested in my slumber party this weekend, we’re having slushies?” That CTA feeds into an email marketing campaign, maybe four emails.

First: “Thanks for your interest, here’s what’s happening.”

Second: more detail — who’s coming, who’s already pitched in. Each one has a harder sell at the bottom.

Third: Hey, register now and we’ll give you a free pillow so you’re not unarmed in the pillow fights!

Fourth: I think of this as the shit or get off the post email: “Last time we’re asking and buh-bye for now if you’re not interested.”

The newsletter builds the trust; the email campaign does the direct selling off the back of it.

I’m going to build a webinar off of this presentation. It won’t be a goo-roo pitch of 15 minutes of content surrounded by 45 minutes of “Buy my services.” In fact, here’s the pitch I’ll include (because you do need to ask for the sale and I like a good scotch now and then): hey, I do this stuff. Need help? Let’s talk. Details are on the last slide and you know how to find me on Substack.

If you’re interested, drop your name below and I’ll make sure you get the details as soon as I figure them out.

PS — Got a question I didn't cover here? Ask away. And if the answer is "I just want someone to handle all of this," that's Newsletter in a Box, send me an email: bryant@simplyusefulmarketing.co.

Musical fun.

Can’t pass up the opportunity to share one of my favorite sitcom intros! The full song follows for a double-dose of nostalgia.

That, of course, kicked off a stream of 70s-era tunes, here’s the one I picked out, which I’ve always thought is the definition of melancholy wistfullness.

If you’re reading this, you already know why you need one (if not, short reading list for you at the end, before the).

A few months ago, I wrote up a list of 18 things people obsess over instead of starting their newsletter. This is the other half — the short list of what you need to do, in order, to get a first issue out the door. Note that I’m writing from a B2B background and this is focused on newsletters used to market a business (that includes all the businesses of one out there). The advice is similar for paid newsletters where the newsletter is the product, but there are some differences.

Think you’re too late? You’re wrong. Sure, the best time to start was last year. Second best is now.

It’s not rocket science. You can do this.

1. Understand why you’re doing this — and who it’s for

Before you touch a tool or pick a name, you need to know two things::

• Why you’re doing this

• Who it’s for

You don’t need a 12-month strategy. A sentence or two will do.

Not to get too guru or granola-eating, tree huggerish*, but you need to set the right intention to build on from the beginning.

Help your customers solve a problem and make their lives easier. Use your newsletter to deliver useful, helpful information to your customers that builds trust over time. Trust builds businesses.

This also helps you stay top of mind and can bring in new, potential customers.

You know your customers. Pick one or two and have them in mind while writing. I did this with the second newsletter I did with AIIM. By then, I had met many of the readers during my time as magazine editor. I always had a rotating cast of real people in my mind as I put each issue together.

It made me want to do a good job for them because I knew and liked them, which also made the newsletter better.

Of course, the big, underlying “WHY” of a newsletter is that it’s the one relationship you own online, not one dependent on an algorithm than might change (again) tomorrow.

*I’m a child of the 80s, this is how we explained new aged thinking back in the day. The current nomenclature seems to be “woo woo thinking.”

2. Pick a platform

This is where people disappear for three weeks comparing feature charts. Don’t.

Every platform does the same three things: collect emails, send emails, and let you export both if you ever want to leave. That’s all you need. Mailchimp, Kit, Beehiiv, Ghost, Substack — any of them will work.

For most people starting from zero, I’d point you at Substack. It’s free, it takes about ten minutes to set up, and it comes with built-in discovery — other writers and readers can find you through Notes and recommendations, which a standalone email tool won’t give you. You can start today and worry about nothing else.

The exception: if you already have a real customer list — people who’ve bought from you, with new ones coming in steadily — an email-first tool like Kit or MailerLite may serve you better. Those are built for working a list you already own: tagging people by what they bought, sending different messages to different groups, tying a send to a sale. Substack is great for building an audience from scratch. Email-first tools are great when you already have one and want to put it to work.

You can import an existing list into Substack, so it still could be the right choice, but you need to take a little more time to think through the pros and cons, but no longer than a few hours.

Either way, pick one this week. You can move later — that’s what the export button is for. The tool has never been the thing standing between you and a published newsletter.

3. Handle the boring setup

Give this an afternoon, not a week.

Name it. “[Business Name] Notes” or “[Business Name] Updates” is fine. Nobody subscribes — or unsubscribes — over the name. Pick one and move on.

Set the “From” name to your actual name, or your name plus the business. People open emails from humans, not from “Marketing Department.”

Start in plain text. A clean email with a few links and a little bold beats a fancy template you fussed over for hours. Add design later if it helps your readers — not your ego. If you’re like me, you have plenty of text-only newsletters in your inbox now.

Write one or two sentences saying who it’s for, what they’ll get, and how often. That’s your description. Done.

Subscribe now

4. Decide how often — and be honest about it

Pick a cadence you can keep for three months without starting to hate your life.

Monthly is fine. Twice a month if you’ve got it in you. Weekly if you’re sure — but be sure.

Consistency beats frequency every time. One solid issue a month, every month, beats four issues in three weeks followed by silence for the next three and the accompanying vague sense of shame.

The fastest way to kill a newsletter is to promise weekly and deliver “whenever.” Promise less. Deliver it every time

5. Figure out what to write (and you already have it)

This is the step where most people freeze. The blank page. What the hell do I even say every month?

Relax. You already have the content. You’ve just been giving it away one customer at a time.

You answer questions all day. How does this work? What does it cost? How often should I do this? Which option is right for me? Every one of those is an issue.

Marcus Sheridan — a guy who installed fiberglass pools, not a writer — saved his company during the 2008 recession by answering customer questions on his blog. He traced $2 million in sales to a single post about what a pool costs. His book, They Ask, You Answer, is a great practical read of writing content to help your customers (not a ready, he gives away the whole thing in the title). He’s now a successful content marketing consultant; and he still owns the pool company.

Here’s the exercise to get unstuck:

Write down the three questions customers ask you most. Pick one. Answer it the way you would in person — like you’re talking to a customer you actually like. Stop when you’ve answered it. That might be 200 words. It might be 800. Don’t pad it. Don’t stop too soon because it’s “too long.”

That’s your first issue.

No list of questions handy? Email your last 20 customers two questions: “What’s the one thing you wish you understood better about [your thing]?” and “What do you keep asking us?” Or pick up the phone and call a dozen. You’ll have months of topics by Friday.

6. Put signup forms everywhere

Once people have a place to sign up, put the link everywhere they might run into you:

• Your email signature

• Your LinkedIn bio — and the occasional post

• Your website header and footer, not buried on a “blog” page

• The end of every piece of content you publish

And give people a reason. “Subscribe for updates” is not a reason. “A short monthly email on [the specific thing you help with] — one useful idea, no spam” is. Tell them what they get.

One more: every issue needs a CTA. That’s marketing-speak for “ask the reader to do one thing” — reply, book a call, buy the thing. You’re running a business, not a hobby blog. Make the ask, keep it relevant to the issue, and don’t cram five of them in. I do two an issue – the one immediately preceding this and a PS at the end.

7. Get your first subscribers — you start at zero, everyone does

The threshold to start a newsletter is zero subscribers. Don’t wait for “enough.” Enough is a moving target that never arrives.

If you have customers or even an older list, start there. These are people who have already raised their hand and you have permission to email — customers, past clients, the folks who’ve done business with you or asked to hear from you. Import them and send. One caveat: that means people with a real connection to you, not a list you bought or scraped off LinkedIn. Emailing strangers is how you land in spam folders and torch your reputation before you’ve built one.

Then tell people you have a newsletter and keep telling them.

Build from there, one issue at a time. A small list of people who want to hear from you beats a big list that doesn’t.

8. Write issue one and hit send

This is the step that matters, and it’s the one people skip by perfecting steps one through seven forever.

Draft your first issue. Make it sound like you — like you’re talking to a customer you like, because you are. Read it out loud (I sound like I’m talking to myself when editing; sometimes I even startle my co-worker, Knox); if you trip over a sentence, your reader will too. Fix it.

Then send it. Not after one more edit. Now.

It will not be perfect. Mine aren’t. You’ll learn more from one published issue — who opens it, what they click, who replies — than from another month planning the perfect one that never leaves your hard drive.

Lather, rinse, repeat.

9. Write a welcome message and a welcome email.

When you send your first issue, include a message explaining what you’re doing. Something like:

Welcome to Kooking for Kats, our first newsletter from Katzatopia. You’re reading this because you’re a customer. Thank you! While we hope you’ll love the tips for healthier and happier kats you’ll receive every other week in this newsletter, we know how full inboxes are. You can unsubscribe by clicking here.

A welcome email is sent to new subscribers when they subscribe. Over time, the welcome email can also be used as a sales tool. BUT THAT’S FOR LATER. Keep your first one simple. Tell them thank you, what to expect frequency-wise, and a little bit about what you’ll be sharing.

None of this is complicated, though it is easy to over-complicate it.

Planning, research, and thinking about each of these steps feels like research and work. Mostly it’s just procrastination in disguise.

Or fear.

Focus. Decide. Act. Send your newsletter.

As you grow, the decisions do become more complex and require more research based on your goals and what has been working.

But you ain’t getting nowhere if you allow fear and pointless concern over “what do I do with 5,000 subscribers” when you have a list of 15 people and haven’t sent them a single issue.

P.S. — If you’d rather not learn all this the slow way like I did, I take on a handful of Newsletter-in-a-Box clients at a time. Reply here or hit me at bryant@simplyusefulmarketing.co and I’ll tell you straight whether it’s a fit.

Short reading list, for those interesting, music below the list.

Musical Fun

For anyone who’s ever had a crap job; sing it loud and with feeling!

One of my many favorite Johnny Cash songs, love this version. He loved that woman something fierce.

I don’t generally like gospel, but Cash can take me to church most days.

Let’s start off with the title.

Not write.

Not create.

Generate.

Not in the “create” or “beget” sense of the word; that implies originality.

In the more straightforward “produce” way.

There are already too many people already using generative AI as a crutch and shortcut. That’s a bad idea for a multitude of reasons:

1. Writing is thinking. When you don’t struggle through the false steps, deleting 500 words only to realize about 200 of them worked, trying to find just the right word to say what you want to say; you’re cheating yourself. And, if you care, your audience. Also, everyone says this because it’s true.

2. “Writing” with genAI isn’t original. All you’re doing is recombining what already exists. These aren’t thinking engines; they’re prediction machines.

By all means, use AI to edit and spellcheck (what do you think Grammarly is?). Use it to outline. Use it to point out logic holes and gaps in your reasoning AFTER you write. Use it as a research assistant to find research (for you to read) to support your arguments.

Don’t use it to write your original content. It is impossible for a generative AI tool, which “writes” by predicting which word goes next based on your prompt and relying on the massive volume of content hoovered up by the genAI engine to pull the next word from, to create something original.

It’s a gigantic plagiarism machine.

Now, that said. Generating content from genAI is a different animal – but one with the same frenetic energy and all-out-drumming of The Muppet’s Animal.

When you turn Claude or ChatGPT loose on your own body of work, you can find a goldmine of extra content, insights hidden in plain sight, and, occasionally, a reflection of your thinking back to you that makes you think either “Damn, I’m smart” or “How the hell did I miss that!”

You can’t plagiarize yourself.

You can repurpose the hell out of your own content.

Take a seat on grandpa’s knee and let me tell you a quick story. Way back in the olden days of social media (LinkedIn 2003, Facebook 2004, and Twitter 2006), marketers, as they do, took to the new platforms to drive traffic back to their websites.

While it was blessedly easy back then to simply paste in a title and then the link and you’d have a good chance of boosting people visiting your website (”Web traffic” in marketing terms); most of us were manually and laboriously cracking open our various blogs, whitepapers, webinars, ebooks, and infographics to extract interesting nuggets to share.

I would have shivved my Mama for access to genAI back then (well, maybe not my Mama, but definitely a random stranger . . . fine, maybe given someone a rude shove).

GenAI takes this process from hours to minutes. It’s wonderful. Anyone who tells you different is a Luddite or doesn’t know what they’re talking about.

Here’s why. The tool is looking for patterns. The prediction aspect of genAI is predicated on the fact that the underlying engines are also pattern matching entities. So when you turn your genAI tool loose on your content, asking it to find patterns and common themes across your work, you’re asking it to do what it’s designed for — look for potential trends across huge volumes of data/information.

I will admit that the first few times I did this it felt like cheating.

Like somehow I wasn’t “doing the work.”

It took some time and self-reflection to get to the point of understanding that I had ALREADY done the work. And, as mentioned already, all I’m doing is automating a process I was doing manually before in a fraction of the time.

Is it 100% as good as what I would pull myself?

No, not always.

But 95% of as-good as I could do myself, but it took 15 minutes (including editing and posting time) rather than 2 hours?

I’ll take that exchange every damn time. You should too. Plus, now and then, the 1s and 0s rub themselves and deliver up an angle that you hadn’t considered before.

Before we get into how I’ve used it, a quick thought on terminology because I think it matters.

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Why I Use “GenAI” Rather Than AI

Because “artificial intelligence” doesn’t exist.

At least in the sense of what the majority of folks who hear “AI” default to — an autonomous machine capable of independent thought.

Here’s a basic explanation of artificial intelligence.

The 4 types by capability — what it can do:

• Reactive — responds to inputs, no memory, no learning. Chess computers.

• Limited Memory — learns from past data to make better decisions. Everything you use today.

• Theory of Mind — understands human emotions and intent. Doesn’t exist yet.

• Self-Aware — has consciousness and a sense of self. Science fiction for now.

The 3 levels by scope — how broadly it can think:

• Narrow AI / ANI — does one thing well. Every AI product on the market.

• General AI / AGI — thinks and reasons like a human across any task. Not here yet.

• Super AI / ASI — smarter than all humans at everything. Theoretical.

Put bluntly: there’s no such thing as artificial general intelligence. We’re still at the first level — a dumb prediction engine rubbing ones and zeros together really, really, really fast that gives the illusion of intelligence. It’s extremely useful, as limited as it is. But it doesn’t — and can’t — think for you. It’s a server in a rack . . . somewhere.

Repurposing Yourself for Fun and Profit

Here’s what that actually looks like in practice. Every one of these started (and starts) with content I’d already made.

Condense long into short. A 1,500-word newsletter becomes five LinkedIn posts and a half-dozen Substack Notes. Going in the other direction hasn’t worked as well for me.

Combine pieces into something new. Ask Claude or GPT to analyze multiple pieces of content to look for common ideas and themes; then pull those into standalone pieces for LinkedIn or Notes. Please note: YOU HAVE TO EDIT THESE, but edit time is still less than doing this from scratch time.

Pull the threads out of a brain dump. I dumped 30 years of stories into a chat — jobs, marriages, life, the webinar program I built that grossed millions and the $2,000 bonus I got for it. What came back was a through-line I’d never said out loud: I’d spent three decades building for everyone but myself. I didn’t write that sentence, but it smacked me straight in the face.

I literally grunted and sat back in my chair after reading that, along with a few of the half-obscured and half-felt linkages Kim Doyal’s genius series of prompts unveiled: You’re Sitting on a Lifetime of Stories (And a Blank Page Keeps Proving It).

Turn old posts into a sellable PDF. I have . . . a bunch of articles, blog posts, and draft ideas. A hefty chunk of this stuff is evergreen advice. All of my most recent pieces are in Claude. The first two PDFs for sale I created were largely pulled from existing content. Both were all there, spread across multiple published newsletters (and emails I had sent). I simply used Claude to pull MY content into a single piece, made slight edits, then used Designrr.io to make the PDFs.

You can buy either/both ebooks here:

• Marketing Writing for Non-Marketers

• What to Write When You Don’t Know What to Write: 12 Ways to Listen to Your Customers

Mine the archive for beliefs. Twenty-five marketing beliefs. Five marketing truths I can’t stop harping on. None of it was new thinking. It was already scattered across years of posts — I just needed it gathered in one place.

Repurpose one idea into every format. A newsletter becomes a LinkedIn post, a carousel, a 60-second video script, a chapter in an ebook. One idea, several avenues to spread the idea.

Generate titles and decks on demand. I sporadically practice writing 10 titles each day. It is truly a great habit that will improve your writing. Still. Titles are hard. I get stuck. Asking for five to 10 title options in ten seconds gets me unstuck. Extra tip: I’ve been honing titles with Sharethrough for at least a decade. It’s a great, free tool. Give it a look.

Write CTAs. Mid-story hook and a PS. I think of these as my mini house ads. I know the structure cold; but I get stuck (yes, I get stuck often). Having a line to respond to is infinitely better than spinning your wheels for 30 minutes. Now, yeah, I know, you can read this as slightly contradictory to the “writing is thinking” I opened with. But, there’s also reality and deadlines and only 24 hours in a day. Sometimes you need the jump start.

Draft the sales and outreach copy. Landing pages, launch posts, the first ugly version of a cold email. The core of what I want to say exists in my current writing in these cases, but often scattered. I rewrite all of it in my voice. But a bad first draft I can fix beats a blank page I can’t.

When I do outreach to someone entirely new or in a new industry, I dump out an ugly first draft, then massage with genAI.

Newsletter/Blog post. I generated The AI Revolution Has a Foundation Problem from a 2014 ebook I compiled, multiple Claude and GPT chats, back and forth prompting, and, of course, a bit of editing. I explained how I put it together, follow the link above and scroll to the end (the article itself is looooongg).

So, Whaddya Do?

Look, do what you want — use genAI, don’t use AI; that’s a decision you need to make for yourself.

Obviously, I encourage you to use it. Not as a crutch or to write for you, but as another tool that allows you to create supporting marketing content, help you with ideas, strategic direction, and so much more.

There are really only two reasons to say no.

One: you’ve got a legitimate concern about the output — quality, accuracy, whatever. That’s a real problem, and it’s a fixable one. Edits and rewrites. Try it. And if the output still isn’t good enough after that, fine — give it a skip.

Two: you don’t want to use it because . . . well, because. It feels icky. Or like cheating. Or a bastardization of your life’s work. I get it. I felt it too. But this isn’t original analysis. It’s marketing — marketing that recombines YOUR existing words and insights into something useful. If that’s the concern, well . . . get over yourselves.

Use the tool. Get more done. Or get the same amount done faster and then go outside and touch grass, or stay inside and touch yourself, or, consensually, someone else.

P.S. You can't repurpose what you never made. If you're looking at an empty folder instead of a full one, that's the front-end problem — and it's what Newsletter-in-a-Box is built for. Reply "NIB" (bryant@simplyusefulmarketing.co) and I'll send the details.

Musical Interlude

Finished and edited to one of my favorite feel-good soundtracks, Curious George.

You don’t need to be printing ink on dead trees to be a publisher.

If you have a newsletter, you’re a publisher. If you’re using content to market your business, you’re a publisher.

Act like one.

Or don’t. Be a hobbyist. Dabble. Dip your toes in the newsletter waters and never go deeper. That’s fine — no judgment. If you’re doing this for fun, for shits and giggles, have a blast. I run a just-for-fun newsletter (Absolutely Useless). I’d like to get it on a schedule eventually. Maybe it turns into something. Probably not. Either way, it’s the last thing on my list because it’s a pleasant diversion for me.

This — Simply Useful Marketing — is my business.

Publishing here isn’t optional. It’s the support beam for everything I’m doing. And I haven’t treated it that way, at least not with action, even though I know better.

Act Like a Publisher — What Does That Even Mean?

Here’s something I didn’t know until a few minutes ago: “publish” comes from the Latin publicare — to make public. That’s it. To publish is to take something private and put it where people can see it. A deliberate act, not an accident.

If you’re using an online platform to share information with an audience in pursuit of income (directly from paid subscriptions or indirectly from leads), that’s a business. Want it to make money? Be a business.

That means —

1. Have a schedule. There’s no hard and fast rule for how often you have to publish to succeed. My goal right now is two to three posts a week. Once I hold that for a few months, I’ll evaluate. Can I sustain it? Should I vary the topics and lengths? Are the calls to action working? And of course — more subscribers, more leads, more customers?

2. Stick to the schedule. You won’t hit a wall by publishing a day early or a day late. You will fall off a cliff and disappear if you’re not visible regularly.

3. Ask for what you want. Put calls to action everywhere. Subscribe buttons, sure — but point to your products and services too. Make the sale.

4. This isn’t for fun. It might BE fun — I usually enjoy stringing words together until they say what I mean. But take it seriously.

Know you should publish on a schedule but can’t make it stick? That’s what my Newsletter-in-a-Box service is for — I build it so you can’t fall off the cliff.

Publish or Perish — Not Just for Academics

The data backs the potential peril. One analysis of more than a million email campaigns found that sending on an irregular schedule pushed the unsubscribe rate 125% higher than sending consistently. Not sending more — sending predictably. The rhythm itself is the variable.

Orbit Media’s annual blogger survey says the same thing from the other side: the bloggers who report strong results are overwhelmingly the consistent ones, not the occasional ones — and the more they publish, and the deeper they go, the better those results get. Meanwhile, 92% of marketers in HubSpot’s latest blogging report say it still drives measurable traffic and leads.

There’s no magic number for everyone. There is one for you. It’s the behavior here that’s important to pay attention to: show up, on a schedule, on purpose.

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The Mental Part Matters

There’s science behind this. I don’t know the mechanism. What I do know: when you treat something as important, you’re far more likely to act like it’s important.

There’s a dismissive attitude around publishing content — at least among people who don’t do it for a living — that it’s “just writing.” Not that hard. And who needs to write anymore with generative AI, right? (NO. But that’s a diatribe for another day.)

Buy into that mentality and your newsletter drifts. It never arrives anywhere except by accident.

You can do better.

So do it.

P.S. Still got “newsletter” filed under the last thing on your list? My Newsletter-in-a-Box services moves it to the top.

I have an editing and writing process. I rarely think about it. But I did last Friday.

Last Thursday I published Wyatt Earp on Gunfighting: 6 Marketing Lessons.

I was (and am) happy with it. The idea behind it was simple: my hamster was still spinning his wheel slowly. I needed a quick, easy idea to ease me back into thinking after 3 weeks of creeping crud. It’s sometimes easier to react to an idea than to create one out of nothing, so as I skimmed my list o’ “these should be quick” ideas; gunfighting advice screamed “pick me, pick me.”

I work with Michael Kaye, The Business Coach, who has done yeoman’s work steadily helping me reverse some business-related cranial-rectal inversion. (Check him out, he’s awesome. Full disclosure: I help him with his newsletter.)

So Michael calls me Friday as I’m just beginning my drive down to Sulphur, Louisiana. “Bryant, read the latest article – Enjoyed it! I was a huge Wyatt Earp fan growing up! But . . .”

I knew that “but” was coming.

“I almost didn’t read it at 13 minutes and did you need to lead with the negativity of him being anything other than a hero?”

After a little back and forth, I said something awkward that lead to this post: I know I could’ve strengthened it by making it shorter, but I didn’t have time.

Which Michael rightly pointed out as a contradiction.

Between dodging 3 accidents that had me taking detours; I started writing this (it’s a long drive, my throat gets sore singing over 19 hours, not much to do but think). Like a grain of sand in an oyster, my response to Michael kept aggravating me. Now, I don’t know that what follows is a pearl, but here’s a look at how this editor/writer made writing and editing decisions on his newsletter piece

Topic Selection

I believe in structured, but open, planning on topics. I transitioned into a content marketing role a year after over a decade editing a magazine (the year in the middle was online content/building AIIM’s online community from scratch).

Planning and scheduling content is natural to me. It also helps you stay on schedule.

But slavish devotion to a list of topics can cause you to get stuck. While there’s a lot to be said about “just freaking write it” (especially when deadlines are involved), sometimes you just get stuck on a post or you look at the next two topics and your brain rebels.

Or, like for this one, you just need something fairly easy to write.

That’s when you’ll want to:

1. Skip ahead.

2. Look at the draft topics you haven’t added to the calendar yet (keep an idea journal – an actual journal, notebook, index cards, document, etc. – to pull from when you’re stuck).

3. Work on the random, fun idea you just had yesterday that you’re excited about writing.

4. And then go back to your list, you created it for a reason. Do the work.

I have a list of topics (adding deadlines this week, finally). I ignored it for an idea I really wanted to write about and that would be easy.

First Draft

To get the ideas flowing, I started off by listening to a YouTube video of Earp’s advice being read as I made tea. Tea in hand, pulled up the PDF of the advice and started typing in headers, along with quick brain dumps of what I was thinking, marketing lesson-wise.

I tried to use as many quotes as I could, but that didn’t always work, so started light rewrites of the advice for the headers.

Realized that looked . . . odd to me, so went back and changed some of the headers so it would be a “quote/marketing lesson.”

I wrote the intro and then bounced between the lessons until I was happy-ish.

Parked it for an hour.

Review – Enter the GenAI

For a longer piece, I’ll reread and jot down where I think it’s weak, what I want to change. For this one, I did that in my head — it’s tight here, weak there, this seems out of order.

I have a standard review process in Claude, so popped the first draft into a new chat in “My Work” project (all my writing is in there) and prompted the review.

Claude flagged the same things I had (seems to run about 50/50 — half the time it’s reinforcing my thoughts; even after prompts to “not give me what I want to hear”; the other half, I’ll get an “oh, I shoulda noticed that/damn, I’m not sure I would’ve noticed that” suggestion/insight).

1. It was long.

2. It lead with the weakest section.

3. Headers were inconsistent.

4. Quotes and lessons that were dupes or reaching for what wasn’t there.

From here, there are two basic choices:

1. Rewrite yourself.

2. Use your genAI tool of choice.

Too many things needed to be changed for me to be comfortable with a genAI edit. If the piece had just needed some slight smoothing, I would’ve had Claude rewrite while tracking changes (to keep, ignore, change).

Second Draft – Rewrite

Here are the revisions I made:

• Trimmed the intro by 150ish words.

• I had a “5 Rounds Chambered” lesson that was redundant with the “Two Pistols” subhead.

  • Killed the “5 rounds” section and moved a relevant paragraph to “Two Pistols.”

  • I had fallen in love with both pieces of gunfighting advice, but they just didn’t work independently.

• Changed the headers so they all matched; marketing lesson/Earp quote or point (this was a flip from the quote/lesson order I had in the draft; I think it works better).

• I was making two, contradictory points with “notched pistols.” Deleted the secondary point about still needing to shout and left it at the “focus on your customer” advice.

• Moved “Take Marketing Seriously” from first to last and rewrote it entirely to serve as a solid close rather than a weak open.

• “Substance Over Flash” is the best section, moved it from 2^nd to last section to first.

• I had a few asides within the piece that were distracting, including one about my hatred for Buc-ee’s, so changed the reference to Royal Farms. Though, yeah, I despise Buc-ee’s.

• Tightened in general — cut 300 to 400 words.

One key point about using genAI as an editing assistant — they will often make assumptions about the goal of the article that are wrong. Now, you CAN avoid this by adding all of your context up front. I find this tedious and dull because I know what I want more often than not.

One of Claude’s main points was that the advice was basic. This I already knew and was the point of the post — make basic marketing points using an odd analogy. So I simply ignored this advice as irrelevant here.

GenAI is the tool. You make the decisions. Don’t. Get. That. Backwards.

Decisions and Michael’s Feedback

I could have taken the gunfighting article in multiple directions.

1. Added research. There is plenty of available research to support all of these points. Adding would have made this longer than I wanted. It felt like a clunky bolt-on rather than a smooth support to the simple points I wanted to make. I LOVE research-based posts; this one just wasn’t a fit. Even if I had been inclined, adding that detail would have taken more time than I had.

2. Streamlined about 20% word count by cutting the history. I could have deleted most of the explanatory history from each point and let the headers do the lifting for the analogy. I decided not to:

   1. I thought folks might find it interesting.

   2. I indulged my inner history nerd.

3. Mentioning the other aspects of Earp’s life in the deck. Unlike the famous line from Liberty Valence (another great movie, much less Western —Jimmy Stewart, John Wayne, Jack Palance), I find the nuanced, actual history more fascinating than “print the legend.” And I figured everyone would make the “OK Corral” association anyway, so why not add the more interesting nuance?

Regarding length, the final word count was 1,395 words. Long-ish? Maybe. Too long? Hard to say. Michael and I have gone back and forth over length for over a year now (I even wrote about it here: The Goldilocks Content Problem: What the Hell Is “Just Right”?)

He likes short and punchy. My response is always “you aren’t writing for you.” Fact is, no one knows what “too long” or “too short” is (I explain this in the “Goldilocks” article).

That said, for marketing newsletters like mine; I believe a mix is better than a one-tone-note. You’ll see a mix of short (500 to 800), long (2,000+), and medium from me over the rest of this year (and as long as I keep doing this).

Circling back to that “grain of sand” I mentioned about “not having time.”

There is a point where you start making changes to a post that are just changes. They aren’t better. Or worse. Just different. At some point, editing becomes wasting time. Perfection is the absolute enemy of the good (and published). Good enough IS good (and, barring a piece being truly awful, infinitely better than never published).

On the other hand, if I had wanted this piece to be different — longer, with more marketing lessons and/or supported by research; I would have taken the time.

And while I could have edited further for length, I intentionally made the decision to keep the gunfighting lessons background. Was it the right decision? I don’t know. But I enjoyed it and I didn’t receive fewer likes than normal, so at least it wasn’t an awful choice.

I knew all of these decisions and trade-offs I was making, but didn’t convey them well enough to Michael. Especially the length point, as I never explained the draft was about 500 words longer than the end result. This is a matter of perspective — I knew I had already cut it and it gets harder and harder to condense your own work as you do so (at least in my experience). Michael likes a sub-1,000 word read.

The upshot is this: The article does what I want it too by combining a, let’s face it, random topic to illustrate basic marketing principles. I could have condensed it, focusing entirely on the marketing points, but I chose not to.

And apologies to Michael for, I think, making a childhood hero human.

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Final Edits

Once I finished my updates, I ran it quickly through Claude again to double-check I caught the mistakes and changes I wanted to make; as well as ensuring all of my headings were in the correct order (using genAI to check for this sort of consistency is very good thing).

Once I confirmed I had covered my bases, I did a final spell check in LibreOffice and then the last thing I do for everything I publish: a final pass to remove any double spaces.

I then used ChatGPT to create images, pasted into Substack, did a final line spacing and obvious typo scan, and published.

That Was Harder Than Expected

I have always been an intuitive writer. Usually when it feels right; I’ve been right.

Taking the time to think about and now write this out was harder than I thought it would be. I’ve said a variation of this before related to the “good enough” concept I mentioned earlier: at some point when you’re writing, you’ll just know — it’s too long, or too short, or needs something, or is off somehow, etc. — but to get to that point, you have to put in the time and write.

I might try to do more of this in the future — pulling out the specific thinking that I do intuitively. Until then, write, publish, repeat.

PS: If you’re having a hard time with that, I created my Newsletter-in-a-Box service (read about it here) for you. A newsletter remains the only controlled, one-to-one mass communication marketing vehicle you can own as a business. Everyone should be using newsletters to build customer trust because trust builds businesses. Let’s talk and see how I can help: bryant@simplyusefulmarketing.co.

The title is a play on George Jones’s Choices, which might be tied for White Lightning as my favorite George Jones song. Since Choices played while I was thinking about this on the road, it worked it’s way into the title.

I have loved a good Western movie and “Wild West” history since I was a kid. I spent a lot of time reading about men like trapper Jim Bridger, the Texas Rangers, Red Cloud, Geronimo, etc.

A scene from Eastwood’s “Unforgiven” tugged at a memory when I rewatched it a few weeks ago. There’s a scene when Gene Hackman’s sheriff character, Little Bill, is explaining real gunfights to the dime store novelist traveling with the Duke of Death.

The memory is Wyatt Earp’s gunfighting advice, which contradicts most of what you see in many westerns – speed, shooting from the hip, shooting two guns at once, etc.

After finding and reading it again (I’ve embedded it below), I found myself making marketing analogies. So, without further ado, marketing lessons channeled from Wyatt Earp’s gunfighting knowledge.

Substance Over Flash - “Pull the Trigger Once.”

We’ve all seen the Western, the quick draw and shooting from the hip. The real proficient gunfighters looked down on the hip shooters and gun fanners: “what could happen to him in a gunfight was pretty close to murder.”

The trick of gun fanning was impressive, someone good at it could fire five shots and it was so fast it would sound like one. But in a real fight it would also get you killed.

There are always flashing tricks and bright lights in marketing. They’re usually a lot of heat and noise. The basics almost always win.

Wild Bill Hickock (a truly fascinating figure of the Old West, reading a book about him at the moment) was an incredible marksman and trick shooter. He never used those tricks in a gunfight, instead he was cool, calm, and deliberate at speed.

There are always BRAND NEW and EXCITING NEW WAYS to marketing. They’re usually not. Every social media goo-roo is following the basic content marketing playbook laid out by John Deere’s The Furrow Magazine in 1895 or The Michelin Guide in 1900 (originally an enticement to get people to drive for good food so Michelin could sell more tires).

The basics of marketing haven’t changed in hundreds of years; maybe never. Make a good product/service. Know your customers. Provide them great service. Find out where they are and talk to them. Share information about how you can help improve their lives.

That’s pretty much it. Of course the tactics change (though both of those 100 plus year old publications are still going strong) as the technology does.

But the fundamental of servicing YOUR customer never will.

Be Fast, But Don’t Rush - The Winner of Gunplay was usually the man who took his time.

This doesn’t mean move slow. To the contrary, speed IS essential and important. But too much speed, too much hurry, would get you killed That fraction of a second to aim to make sure you were going to hit the target could be the difference between having your next whiskey or being laid out in a pine box.

Your marketing should likewise be quick, but deliberate. You don’t want to launch without taking the time to understand your customers/audience and how you can best help them. Pulling the trigger and firing in all directions isn’t going to help you.

Multiple Tactics Can Work, But Start With One at a Time - Carry Two Guns, Shoot One at a Time

There’s a scene in Silverado (highly recommend – Danny Glover, Scott Glenn, Kevin Kline, Jeff Goldbloom, John Cleese, Linda Hunt; great cast, very underrated Western from 1985) where Kevin Costner’s cocky kid gunslinger’s character stands at a street intersection and shoots two men simultaneously (see the image). Looks cool in a Western movie, but it wasn’t reality.

Gunfighters would carry 2 pistols and often draw them at the same time, but would shoot them one at a time.

Stop trying to hit every target at once. Have multiple options in your marketing arsenal, but “shoot” them one at a time --- especially if you’re a small business. Calm focus will get you farther than frenetic action that both misses that target and burns you out.

There are more marketing tactics and things you “could” do than you have time for. That’s especially true for us solo/small teams types.

You can’t do it all. YouTube AND Instagram AND TikTok AND Facebook AND Substack Live AND LinkedIn Live is a recipe for being reduced to a gibbering husk, babbling in a corner.

Pick your platform. Pick your tactics (and newsletter is ALWAYS a good one!).

And focus.

As Wyatt put it, “I remember quite of a few of these so-called two-gun men who tried to operate everything at once, but like the fanners, they didn’t last long in proficient company.”

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Competence Over Show – Don’t Notch Your Pistol

Wyatt noted that the men who killed for the “sake of brag” sometimes notched their pistols. Reputable peace officers didn’t. For the men who tamed the West, it was a job. A task. While some of them certainly enjoyed others’ elevated opinions of them, they were primarily focused on the job at hand. Not like Texas Red in The Marty Robbins song, “the notches on his pistol number one and 19 more.”

The gun was tool and using it a vital skill to stay alive – not for ostentatious show. There are so many websites and company marketing materials that are focused on themselves as opposed to the actual reason to have a website – attracting and gaining the trust of potential customers that remind me of the “wild crew” who notched their weapons.

Details Matter – Thumb the Entire Trigger

I found this fascinating. You would think you’d use the ball of your thumb to cock a pistol, but any moisture from sweat or rain could cause your thumb to slip. And an uncocked gun in a gunfight is not a good thing. Instead, they would use the entire thumb joint as they were drawing to cock the pistol.

Small details like this can make a huge difference. For marketing, pay attention to the details. Do you have alt-text for all of your photos? Do your links work? Are you cross-linking your content (I’ll be doing this for older pieces next week myself)? Is the copyright date on your website correct? Is there a CTA on every post? How’s your grammar and spelling (this doesn’t have to be perfect, but at least master subject-verb agreement and common you/you’re type misspellings)?

Attention to the small details is a good sign that someone has a good grip on the bigger picture too.

Take Marketing Seriously - “Shooting, to them, was considerably more than aiming at a mark and pulling a trigger.”

This one is so basic, I nearly didn’t include it. But. Many companies continue to ignore or give lip service to the value of marketing. That’s a mistake.

Early in his life, Earp spent time with Tom Speers and had first-hand insights from men who survived because they understood the gun was an essential tool that kept them alive. Cheyenne warriors or bandits were ready to take their lives because of encroachment or greed. There weren’t Royal Farms around for buckets of fried chicken. Knowing how to use a gun kept you safe and fed.

Marketing is an essential tool that keeps your business alive. You don’t market? How will people know you exist? Word of mouth. Excellence. Both great things, but your marketing – whether a simple newsletter, your presence on one or more of the various social platforms, email marketing, etc. are essential to keep you in front of customers and potential customers.

I hope you enjoyed this even a little bit as much as I enjoyed writing it.

Are you tired of shooting in all directions? Or being afraid to pull the trigger at all? One of the best, most effective marketing tools for any business is a newsletter. Let me help you with yours. Check out my Newsletter-in-a-Box service or just go ahead and drop me a line: bryant@simplyusefulmarketing.co.

Note on Historical Accuracy: The shoulda-been history major in me has to say that while the advice from Wyatt Earp I shared here is broadly accurate; there’s no way to guarantee that Earp said exactly what is quoted in “Wyatt Earp: Frontier Marshall” by Stuart N. Lake. It’s widely suspected that he was . . . liberal on his quotation policy.

Still, I’ve read enough history of the “Wild West” to have seen various aspects of this advice attributed to different historical figures. So are these 100% Earp’s words? Probably not. Is the advice true and amalgamation of effective gunfighting? Yes.

W Earp On Gunfighting

608KB ∙ PDF file

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Here’s the scene from Unforgiven.

And Big Iron, the Marty Robbins song where I pulled the “notches” quote from.

Deathstalker. A muscle-bound barbarian is sent by a witch to track down a magic sword, a chalice, and an amulet before an evil sorcerer can grab them — and along the way, falls in lust, rescues a monster/man and a princess, and returns a kingdom to the people.

This is the quintessential pulp movie. On one hand, chef’s kiss.

OTOH, it is an absolutely horrible movie. Don’t watch it. I honestly wish I hadn’t. It’s barely coherent, it’s got zero redeeming value, and while it might be a cult classic for nostalgia purposes, it comes loaded with the 80s issues of casual misogyny and women existing at the disposal of men because they’re women and men are manly and all of that.

Even when I was younger, I always had an issue with the non-consent issues in these movies, as much as I enjoyed (fine, still enjoy) the gratuitous female nudity. Not trying to make grand social commentary here, simply giving fair warning about what you’re getting into if you watch this one.

Anyway, since I did watch it; here are a few marketing lessons.

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Be Who You Are

From the beginning, you know what you’re getting with this movie. The credits open with vaguely threatening, propulsive synth and drums — cheesy-ass 80s music. Menacing figures run along in the background, then jump out and attack someone the second the credits end, along with a touch of gratuitous nudity. It opens in a way that tells you exactly what’s coming.

Some Days, You Just Get the Shit Stick

That group of figures leaps off the screen and attacks a guy who’s obviously a thief — he’s got loot and a bound woman in his camp. About 20 of them, one of him. He runs. And runs. Then he sees a horse and thinks he’s saved. He turns a corner and there’s Deathstalker, staring at him. The thief does the math — one, I saw a horse, I’m saved; two, Deathstalker, hey, maybe I won’t die. Deathstalker kills the entire group. Then he kills the thief too, because Deathstalker isn’t a nice guy either.

“This Just Isn’t Your Day, Is It?” he says over the corpse.

Some days you’re swimming uphill during an avalanche. Every small thing goes sideways. There’s no marketing fix for that, because there’s nothing to fix — the day was just shit. Absorb it. Let it pass through you. Accept it. Move on. There will be better days, and a string of bad ones doesn’t predict them. Don’t quit the newsletter, torch the plan, or rewrite the strategy on the strength of one rotten day. Take the shit stick, set it down, and show up tomorrow.

Tits Ahoy! Know your audience.

The boobs fly early and often, aimed straight at the acne-covered, never-touched-a-girl D&D demographic still living off the high of accidental side-boob contact with Sister Mary Jo Rottenkrotsch at the church dance two years ago. The audience likes boobs, so the director gave them boobs. When Kaira shows up, she’s in a robe, starts a sword fight, and her bosoms flop out — because apparently that’s what all women sword fighters did. Fought naked, no armor, just a harness under the boobs. Ludicrous. But again, it’s pandering to the audience.

What’s this mean for your marketing? At some level, give the people what they want. I used to run editorial surveys — ask for replies, then build the next year’s articles around direct customer feedback. Doesn’t have to be complicated. When you know your audience, you know what to give them. In this case, it’s boobies.

Here’s the catch: most people never ask. They guess at what their audience wants, guess wrong, and then wonder why nobody opens the email. A newsletter is the cheapest, most direct way to actually hear from the people you’re trying to reach — but only if you’ve got one running. If staring at a blank screen every week is the thing keeping you from starting, that’s the exact problem my Newsletter-in-a-Box service exists to solve.

“I steal and kill to stay alive, not for the luxury of glory.”

Deathstalker at least knows who he is. Focus on what moves your business — not your ego.

Power Unearned Isn’t Power

Scars make us human. The immortal sorcerer holds power he never earned — borrowed, taken, never sweated for.

You can’t plug expertise in. This isn’t The Matrix — nobody loads “I know kung fu” into your head and suddenly you can fight. GenAI will hand you the output fast and clean, but it can’t hand you the understanding underneath it. Skip the reps and you don’t actually own the thing. You can’t feel where it shaky, can’t tell when it’s wrong, can’t defend it when someone pushes back.

You bought the answer. You didn’t earn discernment.

Use the tool. Just don’t mistake what it gives you for what you’d know if you’d done the work.

From He-Man to Deathstalker

I literally laughed out loud at the sword pose lifted straight from the cartoon. Everyone borrows from everyone else — there’s nothing new under the sun, and pretending otherwise is just a fancy way to procrastinate. Extending someone else’s work is original. Combining two old things into one new thing is original. It’s your spin — your fold, spindle, and mutilate — that makes it yours.

I looked at the dates just before I hit publish. This might just be a sword and sorcery sword-position trope I’ve never noticed before given Deathstalker came out a year or so before He-Man.

Times Change

If I’d seen this at 12, I’d have loved it — hello, boobies! A little older (most days) and it’s just not good. The boobs-as-scenery, the women-as-furniture was standard in 1983. Honestly made me cringe a bit watching this week.

Times change. The fundamentals don’t — useful beats clever, trust beats hype, same as it ever was. But the surface does. Tone, references, what your audience will sit still for — that shifts under you. Don’t run 1983’s playbook in 2026 and wonder why it falls flat.

And, yes, boobs as scenery still exists — Game of Thrones fans will remember the mini-uproar over the “sexplanation” scenes from Littlefinger’s whorehouse.

Own Your Power

One of the small moments of empowerment for women in the movie: Kaira sits down. She moves a woman who’s seated below Deathstalker and claims that place next to him — not where the other woman was sitting, two steps down, but right next to him, as an equal.

You have products and services people want to buy that will help them own that. There’s nothing more powerful than knowing who you are, knowing your power, and using it.

Never Trust the Evil Sorcerer

The immortal ruler of the land is holding a tournament to pick the strongest person in the realm as his successor. Of course, an immortal sorcerer doesn’t need a successor — he’s immortal. The obvious answer: he’s pulling everyone in so they kill each other off, and then he kills whoever’s left standing. That’s the evil sorcerer’s plan.

Look around and you’ll see hustle bros trying to separate you from your money with false scarcity, fake time limits, and fear. There’s an element of truth in some of their language — scarcity and urgency are viable marketing tools when used judiciously, with the intent of helping rather than scaring. But getting your audience to buy because they’re too afraid not to is just propaganda.

Biggest Takeaway

Do your weird thing. If this godawful piece of shit can become a hidden cult classic and inspire loyalty 40-odd years later, then the weird thing in your head — the one that’s probably not horrible, doesn’t treat women like objects, and might actually be coherent — has at least an equal shot at getting picked up and loved.

There’s no guarantee. Other than the guarantee that if you don’t do it, you won’t be found, you won’t be loved, you won’t be turned into a cult classic. Someone else may have the same idea. It might be worse than yours. But they’ll reap the rewards because they did it and you didn’t.

Closing Thought

So go make your weird thing. It might be bad. It might be a cult classic. It might be both! Or it might be great and beloved or universally hated. You don’t get to find out until it exists — and a barely-coherent 1983 disaster with a director hiding behind a fake name is proof that made and loved is better than unmade and “perfect.”

PS — If your weird thing is a newsletter you’ve been not-starting for a year, that’s a solvable problem. Newsletter-in-a-Box gets it built and out the door with you, so the thing finally exists instead of living in your head. Reply to this one and tell me what you’d like to write about — bryant@simplyusefulmarketing.co.

Musical Interlude

Edited while listening to one of Humano Studio’s playlists. If you’re looking for background music, give ‘em a try.

You should repurpose your content.

That advice is so common, and common sense, that too many practitioners (like me) gloss over it without explaining what we mean.

With my publishing background, I am guilty of this. Over the years, I’ve developed a built-in idea filter for everything I publish. It goes in two directions:

1. Can I bundle these small things together into a big thing?

2. Wrote a long thing, how can I break it down into smaller pieces?

You can develop that filter, but it takes time. Keep reading, and I hope we’ll jumpstart creating your filter as I share this example from earlier in my career.

I’m going to share how I created an ebook that did two things:

1. Was generally useful and informative for everyone in my existing audience while also a lead magnet (a lead magnet is the name for a piece of free content given in exchange for name, email address, etc.)

2. Directly brought in sales for the 2014 AIIM Conference.

I’ll also share a few other examples I’ve created.

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What Is Repurposing

Before diving in, I figured a definition might could be helpful here.

Repurposing is taking something you already wrote (or spoke) — a blog post, a newsletter, a podcast episode, a keynote presentation, webinar, etc. — and reshaping it for a different format, channel, or audience.

The point: you did the hard work once. Research, thinking, writing, getting the argument right. Repurposing is making that work pull a second, third, and fourth shift instead of letting it die in the archive after one publish.

What it looks like:

• A blog post becomes a newsletter (by itself or combined with others), then a LinkedIn post, then a short video, then a slide in a deck.

• A podcast transcript becomes three articles and a dozen quote graphics.

• An evergreen post gets updated with new examples and republished a year later.

• Multiple short posts (Substack, LinkedIn, Twitter, etc.) can be combined into blog post/newsletter; maybe even an ebook if you have that many.

What it isn’t: copying the same words into five different boxes and calling it a strategy. Each format has its own rhythm. A 1,200-word essay does not survive the trip to LinkedIn untouched. Adapt it or skip it.

Repurposing Content for Event Marketing – Blogs Into an Ebook

Events are a GOLDMINE of content marketing content, especially if your organization is putting on the event.

AIIM (where I spent the first 20 years of my work life) has an annual conference. In 2014, I suggested we use the event content to raise exposure and create leads.

I decided we’d publish blogs from speakers as well as the event sponsors as content marketing in two ways:

1. 1. Each blog posted online

   1. to the AIIM community site with a call to action for readers to register for the event

   2. AIIM’s president had his own blog (a vanity project that would have been better for AIIM had it been ON the AIIM site, but that’s a post for another day). The vendor “Hot Seat” posts would go there.

2. We’d create an ebook from all of this blog content.

At the time, part of my job was to manage the member community, which included a roster of expert bloggers. Asking people to write was part of my daily work. I had previously had some success increasing our webinar registrations by having both the sponsor and the speaker write a short, 500 word or so blog post around their topic. My instructions were always simple: don’t tell them what you’re going to talk about, share an actually useful/insightful bit of information – the reverse of the cow/milk dating philosophy. “Show a little leg” is how I like to describe it.

So it was natural to go down the list of speakers (I knew at least half of them already, which made it even easier) to ask them to write a blog post about their session.

While there was a LOT of content, the process was simple. OK, you might look at the list, see the number of steps, and think “Is THIS what you call SIMPLE!??!?!” Yes. Why? Because these are no shortcuts. Just because the list is long doesn’t make it complicated.

1. Ask the speakers and sponsors to contribute – mostly email, a few phone calls.

2. Interviewed each of the keynote speakers via email. Based on their keynote topics, created a short list of questions and sent to the four keynote speakers to answer that way. I knew John, Alan, and Thornton already. I didn’t know Johnny Lee, I think I may have interviewed him over the phone or Skype/Zoom, but given I have to think about what I had for breakfast, just don’t remember.

3. Edit and post each piece of content to the AIIM Community blog as noted above, each with a CTA (tracked in HubSpot, the CRM, customer relationship management system) to register for the conference.

4. Shared each post on social media multiple times — Twitter and LinkedIn (and of course asked everyone to share on their personal channels).

5. Pulled session descriptions from the event materials to include with each post.

6. To save time, we started the design before I had every single piece of content in. We did this for a few reasons:

   1. There was no guarantee everyone would contribute — our speakers already had jobs and were doing this voluntarily. Waiting for a few stragglers before doing the layout would have given us less time for this ebook to do work for us.

   2. By having the pages designed already, it was easy to simply drop in the handful of speaker posts that came in late.

7. John handled all of the sponsor submissions to his blog.

8. Created a single document for the designer with all content in order from the cover to the final “About Us” page (along with a few placeholders for the blogs that were late).

   1. This was a tedious, copy-paste exercise almost certainly done in an evening with a glass of whiskey at hand.

   2. More tedious was copying and pasting the Hot Seat pieces.

   3. Once everything was in one document, I went through and did a final spell check, made sure all of the headings matched (upper case, bold), that the sponsors were in alphabetical order by contributor name (there was a reason we did it that way, damned if I can remember it), formatting, deleted extra lines between paragraphs, and made sure instructions to the designer were clear – including sketching out the page layout (I knew what I wanted it to look like, just didn’t – still don’t – have the chops to pull it off myself).

   d. This was, and is, the most tedious part of ebook layout, but taking time here will save you time once the designer goes to work.

   e. If you’ve never done this before, recommend doing it on paper. You’ll notice things you could miss if you edit on your laptop.

9. Designer created the first draft.

10. I printed it out and edited only for typos, spacing, and other design/look and feel things. By this point, everything had already been edited for content and accuracy (though I did find a few typos anyway) so this went faster than if I had also been editing for meaning.

11. Designer updated the document with my edits and returned it.

12. This is why I edited on paper — I went through each of my edits to ensure they were made. Caught the few that the designer missed and had those corrected.

13. Gave it to. . . someone else for a final look over as by this point someone else needed to point out the handful of typos I had seen and already missed 3 or 4 times. Whenever possible, always have someone else do a review! You WILL miss things.

14. Sent back to the designer with the final edits and, after one more round of review to ensure those changes were made, we had a final document.

After that, it was the basic marketing block and tackling of loading the file into HubSpot, creating the landing page, sent the ebook to registered attendees to get them excited about the event (a simple “Thank you for registering, here’s something extra for you” message via email with a link to download), and then blasting it about our social accounts and newsletter. This paragraph could be a future post.

Design

I cannot recall if we used our internal designer for this or outsourced it, but the ebook was created by a designer. With this many moving parts, even today, with easy-to-use tools, I would do the same.

As a marketing piece for the Conference, it needed to be thematically identical. So we didn’t overthink it:

1. Reused speaker headshots and session descriptions from the Conference page

2. Used the color scheme and art elements within the ebook for color, chapter divisions, and CTA design

3. We decided to leave white space because we were pressed for time and adding images would have sucked up more time than we had. Plus, the extra step and time wouldn’t have made the final product that much better.

4. Decided on one CTA to use for the entire thing — which we also used online.

5. The chapters matched the Conference tracks, so anyone interested in a particular topic could get an idea for where to spend their time at the event.

The only part of the design I regret is the social share icons. Mostly because I was the one who had to hyperlink every single one of those — draw the outline over the box, insert the link, save, next. Tedious. Two hours of my life I’d still like back.

If you’re reading this thinking “cool story, but I haven’t written 40 of anything” — fair. Repurposing only works if you’ve got something to repurpose. That’s the thing nobody tells you. Newsletter-in-a-Box is how you get to the part where you actually have an archive to mine — the writing rhythm, the system, the spine. Then everything in this post becomes available to you.

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RESULTS

While I don’t have access to the actual statistics any longer, this piece of content was a success in a few ways:

1. Downloaded a few thousand times.

   a. for existing contacts, progressive fields in HubSpot allowed us to collect more information about potential leads

   b. Brought in at least hundreds of new leads

2. Kept the event in front of our audience for months afterwards. After the event, we replaced the “preview” language, tweaked the landing page, and keep it online as a lead magnet through the summer and into the fall.

3. At least six sales. Attribution wasn’t set up properly in HubSpot, but we managed to identify at least six conference pass sales from the ebook. That’s about $9,000 in direct ROI.

4. Our audience liked it.

Other Examples

I’ve been repurposing content for decades, going back to the most basic of basic “repurposing” of putting print magazine articles onto a website.

Here are a few other examples.

Sexy Copiers

This was for a copier client (duh, I know). They were beginning to sell document management as a Laserfiche reseller (if you’re an SMB or larger in need of DM, give Laserfiche a look; solid company). The concept was new to most of their customers. We created a mini-campaign:

1. Series of blog posts.

2. Turn those into an ebook to use as a lead magnet.

3. Created a CTA for the ebook and then inserted those into the existing blog posts.

After I wrote the posts, we created the cover, I wrote a short introduction, and we added the call to action page at the end. While I can’t confirm it led to sales (their internal attribution process was a mess), I do know it created leads, client meetings, and sales opportunities.

The Basics Of Dm

1.49MB ∙ PDF file

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InfoChaos Infographic

This one was a distillation of an AIIM thought leadership whitepaper. The goal with this one was two-fold:

1. Provide value by itself

2. Generate interest and downloads in the whitepaper

Unlike the copier ebook above, this took more time – about 30 hours distilling the whitepaper to it’s most important points, deciding on layout designs and then working with the designer on the best one, and then the usual process of back and forth editing,

Because we produced the infographic and the whitepaper at the same time, we also repurposed art from the infographic in the whitepaper.

FWIW, I think both this infographic and the whitepaper nailed the central challenge of business today – how to control and use the information in their business. Too many are still failing at it (which is also why AI implementations are going to fail in large numbers – AI relies on accurate content; companies don’t know which part of their content is accurate. Anyway, I digress.).

Information Chaos - Infographic

512KB ∙ PDF file

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Video Scripts – Simply Useful Marketing Minute

My goal is to convert every one of my blog posts into at least one short video. I’m in the midst of revamping this, but embedded an older one below. It’s a wee bit ugly.

It’s a straightforward repurpose:

1. I’ll draft a short script or have Claude generate one and then tweak.

2. Record it on my phone.

3. Edit and publish to YouTube.

4. Embed the video directly into LinkedIn (LinkedIn video content often does well at attracting an audience).

5. Embed the video in the relevant post.

I find it faster to do these in batches of 4 to 8. This allows you to get into a good groove editing and putting the videos together.

LinkedIn Carousels

These streamlined, ebook-ish assets are doing really well on LinkedIn for engagement. For one client, I’m getting 70% plus click throughs on their carousels.

I think of these as Cliff’s Notes ebooks. Provide some quick, actionable knowledge or insights in 6 to 12 pages. I use Canva for this at the moment because it’s free, relatively easy, and “good enough.” I will be investigating Karen Spinner’s Carouselbot (you can read about it versus Claude here) soon though.

If you have a long blog/newsletter, you can create a carousel from a single piece of content. You can also point your genAI weapon of choice at multiple blogs, ebooks, notes, etc. and ask for common themes.

I’m still getting to grips with what creating these, but:

1. Short.

2. Simple.

3. Streamlined.

4. Minimal design/easy to read.

Regardless of topic, keep those four points in mind and you’ll succeed without driving yourself (too) crazy. Here’s a simple one I did from my Marketing Advent Calendar last year. I’ll also probably tweak this in the next few weeks to be something like “The 25 Marketing Fundamentals I Think Are Needed for Successful Marketing.” Oofah, that’s long, but you get the idea.

Marketing Advent Calendar

68.3MB ∙ PDF file

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What I believe to be true about the fundamental principles of marketing.

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Quick Note on Generative AI and Repurposing

I’ll revisit using genAI to repurpose content in the future, so just a few quick thoughts here.

First, let’s get this out of the way:

No, genAI shouldn’t do your writing for you.

But genAI is PERFECT for extracting short pieces, recombining existing content, finding similar themes across dozens to hundreds of articles, newsletters, social media posts; and using that to extend the life and value of what you have written.

Closing Thoughts

None of this is clever. It’s mostly copy, paste, and trusting that work you did three years ago still has more to give. The clever part is just not throwing it away and knowing what, when, and how to combine and recombine.

PS — You can’t repurpose until you have some content. One way to begin stacking up words that can be reused in the future (as well as building trust with your customers and potential customers) is a regular newsletter. My Newsletter-in-a-Box service does both. Hit the link here for more details or contact me now at bryant@simplyusefulmarketing.co.

It’s Cinco de Mayo. In the US., that mostly translates to “drink a margarita.” Fine by me.

Most of us slurp margaritas poured from the slushie machine behind the bar at our local Mexican joint. Sugar, ice, and a vague rumor of tequila. It’s easy to forget that a real margarita needs only 3 ingredients:

• Good tequila

• Fresh-squeezed lime juice

• Cointreau, fresh orange juice, or agave nectar (there’s a spirited — ha — debate about which. Some recipes call for both. Research is the only way to know. Recipes at the end. Salud.)

That’s it.

If you’ve ever had a real, 3-ingredient margarita, you know it’s a simple yet elegant cocktail that blows the doors off of the slushie version.

What’s this got to do with content marketing?

A lot of content marketing is the slushie. Sweet, easy to drink, hopefully you get a little tequila. Empty calories that resemble the real thing in name only.

Real content marketing — the kind that builds a business — has three ingredients.

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3 Ingredients of Content Marketing That Actually Works

Tools aren’t ingredients. Substack, Mailchimp, Canva, LinkedIn, ChatGPT, whatever you’re using this week — they make life easier. They don’t make the marketing.

Your marketing needs a soul.

Here’s the recipe:

• 2 ounces of patience

• 1 ounce of belief

• 1 ounce of trust

Shake with a little TLC. Pour.

Tequila: Patience

Content marketing takes time. I write about this constantly because people keep refusing to hear it.

Months. Not weeks. Here’s what the work actually looks like:

You figure out who you’re writing for. Not “small business owners” — an actual person, with an actual problem, who you can name. You talk to a few of them. You listen.

Then you build a strategy — what you’re going to write about, how often, where it lives, what it leads to. Then you write. Then you write again. Then you write a third thing because the first two weren’t as good as you thought.

Then Google has to index it. Your audience has to find it. Some of them have to read it. A smaller number have to subscribe. A smaller number than that have to keep opening. A smaller number than THAT have to eventually buy.

Meanwhile you’re building landing pages, writing the welcome sequence, figuring out what your offer actually is and/or how best to frame it, learning how to talk about it without sounding like every other vendor in your space, and cleaning your email list because half the people who signed up six months ago aren’t opening anything.

Expect 6 to 12 months before things start clicking. That’s not me dragging out a retainer. That’s how it actually works. [Yes, I know there are a few “instant successes” here on Substack, which almost always involves bringing an existing audience from elsewhere into this new platform.]

The folks who succeed are still showing up at month nine. The ones who quit at month three are now doing the same thing on TikTok and complaining nothing works.

Patience isn’t passive. It’s the discipline to keep going when the numbers say you shouldn’t.

Lime: Belief

Content marketing is both a strategy and tactics. Most importantly, it needs to be based on a belief system.

The belief? You have to believe that helping people is the way to earn their business. That answering their actual questions matters more than shouting your features. That doing the work of being useful — over and over, for months, years, decades (John Deere has been producing The Furrow since 1895 for content marketing) — pays off.

If you don’t believe that, content marketing won’t work for you. Not because it’s broken. Because the moment it asks you to choose between being helpful and sharing how wonderful you are, you’ll choose you (not your customers), and the whole thing collapses.

While the various hustlebros are annoying; they also believe in content marketing. All of them have a variation of a traditional content/inbound marketing funnel — an asset to grab an email address, nurturing email workflows, landing pages, blogs, etc. Now, I don’t think most of them give a shit about their customers, but that’s a different post.

Look at what they actually publish. The “I used to be broke, sleeping on my mom’s couch, eating ramen” origin story — recycled monthly, sometimes weekly, by the same guy who’s now selling a $2,000 course on how you can escape the couch too. The fake vulnerability post that’s actually a flex. The screenshot of a Stripe notification. The “most people won’t read this but” hook that 40,000 people read. There’s no belief underneath it — just mechanics. They’re using the vocabulary of help while running the same old school interruption playbook in a longer format.

That’s why their audiences eventually tune them out. The mechanics work for a while. Then people figure out there’s nobody home.

Belief is what keeps you writing the post that helps a customer make a decision — even when the decision is “not yet” or “not you.” A “not yet” who trusts you is worth ten “right nows” who don’t.

Cointreau: Trust

Trust is the flip side of belief. Belief is what you bring. Trust is what they give back, eventually, if you do the work long enough to earn it.

Trust compounds. One useful piece doesn’t move the needle. A hundred useful pieces, over 6 months or 2 years, builds something competitors can’t copy.

Reach goes up and down with whatever the algorithm is doing this week. Trust just keeps building. It’s what makes someone open your email when they don’t have time. It’s what makes them tell a colleague to subscribe. It’s the engine running underneath everything else you do.

Trust is also fragile. Once you have it, every piece you publish either reinforces it or undermines it.

And TLC

One more thing, that little something extra – lagniappe as we say at home in SW Louisiana. A little tender loving care. To be blunt: Give a damn about your customer beyond the revenue line.

Content marketing is about leads and sales. Of course it is. It’s also about being useful to people who will never buy from you, and being useful to the ones who will.

If you don’t actually care, your customers will sniff it out over time; you can’t fake it forever. They’ve been marketed to their entire life. They know what insincere “helpful” content looks like. It looks like 90% of LinkedIn.

If you don’t give a damn about they, your customers won’t give a damn about you either.

Patience is the ingredient most small businesses run out of first. Not because they don't believe in the work — because the writing, the schedule, the offer, the list, the welcome sequence, the everything-else piles up and the newsletter slides off the calendar. That's what Newsletter-in-a-Box is built to fix. I run the system so you can show up at month nine instead of quitting at month three. Hit me at bryant@simplyusefulmarketing.co.

And the Recipes

I don’t often make margaritas — I’ve been more of a whiskey guy the past few years — but when I do, I use one of these two recipes.

1. My Favorite

Ingredients

• 2 oz blanco tequila

• 1 oz fresh lime juice

• ½ oz orange liqueur

• ½ oz agave syrup

• Salt rim, optional

• Lime wheel

Method

Shake hard with ice and strain over fresh ice.

2. Original Cointreau margarita

Use this when you want a dead-simple 2:1:1 formula. Easy to remember. Hard to screw up.

Ingredients

• 2 oz blanco tequila

• 1 oz Cointreau

• 1 oz fresh lime juice

• Ice

• Salt, optional

• Orange slice, optional

Method

Shake with ice and strain into a salt-rimmed glass over ice.

Notes: Either version is great straight up in a martini glass. If you like ice, go for bigger blocks — less dilution, more nummy margarita flavor longer while staying chilled. For on the rocks, I like a small glass tumbler (or plastic if outside).

Salud.

And, of course:

Marketing is, on one level, a seduction. How do I turn a stranger into a customer?

The marketing process for this is called a funnel. It’s a dull, boring word to describe the process of pulling new people into your world and nudging (nurturing is the marketing word) them to become a customer.

There’s nothing wrong or nefarious about this process. A few weeks ago I wrote about why funnels aren’t the enemy — why the folks telling you to “drop the funnel” all have one, they’re just calling it something else.

When I heard George Strait’s song, “The Chair” a few days ago, it struck me that he kinda sorta outlines the funnel process in a tight 2 and a half minutes.

The piece of content that sits at the top of your funnel can be whatever you want. Newsletter signup. Free guide. Educational email course. Webinar. A checklist. A demo. Free access to the product (especially apps/software). Doesn’t matter. Someone gives you their email because you offered them something useful. Then you build the relationship from there.

A funnel is a funnel is a funnel.

One of my favorite explanations of old-school, interruption marketing came from Gary V — back when his first few books were genuinely good and before he became whatever he is now. He described it as buying someone a drink in a bar and then asking them to go to bed with you immediately after.

A little more seduction is in order. Before getting to the song, here’s a quick explanation of what a funnel is and why they matter.

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Funnel: Quick Explanation

A funnel is the path from “who are you?” to “shut up and take my money.” Wide at the top because lots of people kinda-sorta know you exist, narrower the further down you go because most of them peel off along the way.

Stages, in plain English: they notice you, they consider you, they buy (or don’t), they come back, they tell their friends. That’s it. The last two get skipped a lot, which is dumb — keeping a customer is cheaper than finding a new one. [FYI, MOFU, middle of funnel, is my favorite marketing acronym and never fails to crack me up.]

The point of the funnel isn’t the shape. It’s that it makes you count things. How many came in. How many made it to the next step. Where you’re leaking. Numbers instead of vibes.

Caveat: nobody actually moves through it in a straight line. People lurk for six months, ignore you, then buy on a Tuesday because their coworker mentioned you in Slack. This is the “messy middle,” or, as I like to call it, reality. The funnel is useful as a framework — just don’t mistake the diagram for how humans actually behave.

Alright, let’s learn from George!

The Chair

So here we go, an inbound/content marketing funnel explained via a country song.

“Well excuse me, but I think you’ve got my chair, No that one’s not taken, I don’t mind if you sit here, I’ll be glad to share.”

Ah, the website (your newsletter site here is a website) — your chair. A nice, inviting website that answers customer’s and potential customer’s questions will make strangers come in, have a seat, and look for the bartender.

“Yea it’s usually, packed here on Friday nights, Oh if you don’t mind could I talk you out of a light?”

At this point, most guys are “Woohoo! She half-smiled, I am a stud!” Settle down there, buckaroo. Start a conversation small and slowly, with a question that’s likely to get you a yes. Circling back to Gary V, “let’s fuck” probably isn’t going to work out for you — either in a bar or selling your service. (Usually, there’s a story at the end of this post.)

For content marketing, this could be useful/entertaining/valuable/interesting content that’s relevant to the person now on your website. Good information that’s just there and requires no commitment. Think of this as your blog content. Or your LinkedIn posts. Or your Substack Notes. Or your newsletter (if it’s for marketing and not the product itself). Whatever channel gets you in front of them.

“Well thank you, could I drink you a buy?”

We all stumble and make mistakes. You will have typos. You will create and use email subject lines or blog titles that suck. Don’t freak out. Just acknowledge the slip-up and move on.

“Oh listen to me, what I mean is can I buy you a drink? Anything you please.”

Here’s your landing page with something useful on the other side of an email address — a free guide, a checklist, a short email course, a newsletter signup, a webinar, whatever fits. It should be something they actually want and is useful.

“Oh you’re welcome, well I don’t think I caught your name, Are you waiting for someone to meet you here? Well that makes two of us, glad you came.”

They filled in your landing page form, downloaded the asset, and you know their name and email address.

Now say “Thank you.” Keep the conversation going with a thank-you page pointing to related, helpful content. And start using email to build the relationship — not to blast them with 14 reasons to buy from you right now.

“No I don’t know the name of the band but they’re good, Aren’t they, would you like to dance?”

Start to develop the relationship. This is a bit of a leap from the song lyric, but as you begin to understand their problems and where you can help, you can really begin to understand them and ease them through your funnel.

“Yea I like this song too, it reminds me of you and me baby Do you think there’s a chance? That later on, I could drive you home?”

It’s a 2-minute song, so George had to move quickly — faster than you need to. The buyer journey usually takes longer than this. Keep showing up with useful information. Keep earning the right to ask for a little more.

“No I don’t mind at all.”

And now you’ve got a customer.

That’s the whole flow — chair, light, drink, name, dance, drive home. If your version is missing a few of the middle steps — no real lead magnet, no landing page, nothing useful going out after someone signs up — that’s what Newsletter in a Box is for. Click here to ask me about it.

“Oh I like you too and to tell you the truth That wasn’t my chair after all.

I guess George just wasn’t thinking of me writing this post when he sang this back in 1985, so this is where the analogy ends. I’d never recommend faking it, lying, or even “shading the truth” when attracting customers (or a date). If you see someone in a bar, use whatever opening line you can think of that might let you sit down and attempt a conversation. Well, any line that’s not, “You must be tired because you’ve been running through my mind all night” or is an outright lie.

Definitely not that.

Also, if you’re humming Amarillo By Morning now, you’re welcome.

A True Bar Story

In the 80s and 90s, Miss Kitty’s was the main meat market in Lake Charles, La. South of town, so was . . . huh, kinda Roadhouse-ish now I think about it . . . with shitkickers from south of town (cattle, farms, horses, oil workers) and preppies from the “big city.” Probably went 20 or so times, pretty sure there was a fight each time.

Anyway, when I was in high school, remember talking to my buddy Clyde’s brother. Somehow or other the conversation turned to Kitty’s and he told us he had used this pickup line: Let’s breed.

He got slapped once.

It worked once. Every now and then a cold call or an immediate “gimme money” request will work. But it’s not a long-term strategy.

Pretty sure the success rate would have gone down if he hadn’t started dating his future wife shortly after using it. Given my vague memory of her and the fact that she wanted a dry reception after the wedding, 99.9% sure he didn’t try it on her. And the reception was dry, except for me and Clyde’s table.

P.S. The song ends when she says yes. That’s where the actual relationship starts — and where most newsletters quit. Newsletter in a Box is what you send on the second date. Click here to ask me about it.

Musical Coda

Egads. Truly horrible video. I do like the song though!

One of my all-time favorite songs. Had no idea there was an official video until just now.

The future of work was, is, and always will be about content — creating it, managing it, and protecting it for business use.

I’ve always loved prediction season because predictions are fun.

They feel like work, but allow you to indulge in a bit of whimsy and speculation without having to worry about being wrong.

They’re even better when you get them right!

12 years ago, a Gartner analyst I know (Hanns Kohler-Kruner) invited a large number of folks in the ECM* (enterprise content management) industry to make predictions about the future of work for research Gartner was conducting at the time (never read that research).

Doing some overdue spring dead-heading of old content on LinkedIn (along with seeing if anything is worth refreshing) and started reading the short essay I wrote in response to Hanns’ request.

Much to my surprise, I was actually mostly right. And while we’re still too early for 2027 prediction season, I thought I’d share anyway.

Below is my original post, along with combined responses from Claude and ChatGPT for accuracy and my grade (and no, I didn’t tell them to grade on a curve!). The stuff from the robots is in brackets.

The Future of Work – All About Content

Unlike George Jetson, I’m pretty sure we won’t be able to fly our car to the office, push a red button, and then relax until it’s quitting time (barring our blustering boss pushing HIS button to yell at us). Work will still be work. How we get it done . . . that might be a lot cooler.

Two things first off. One, half of everything everyone writes will be collectively wrong — I’m still waiting on my flying car. Two, we should be clear that we’re focused on office/knowledge work. While technology will of course affect tracking, assigning, etc. other work; digging a ditch is still digging a ditch.

[Holds up. Software wraps around more work now, but the ditch is still a ditch.] Me again: I will add here that robots work autonomously in warehouses and I do think that there’s potential for automating manual work outdoors with robots as technology continues to improve.

The future of work will be reliant upon effective creation and maintenance and then distribution of content/information/documents/data (pick a word). The companies that take this fire hose of information and point it in the right direction will be the ones that win.

[Arguably more true now than in 2014. Every shiny AI demo is still sitting on top of content, data, documents, workflow, and retrieval. The model isn’t the moat. The plumbing is. Sadly, nobody wants to talk about the plumbing.]

I’m going to assume that we’ll get the maintenance and storage of content mostly right going forward, otherwise, we should all buy stock in storage companies now.

[Partial credit. Storage got cheap and abundant. Findability, governance, and basic “where did we save that” remain a mess in most organizations.]

I think we’ll get to a heads up display for work, which will make the “office” even more portable than now. To interface with this HUD, we’ll have some combination of input from eye tracking or direct “jacking” into brain waves.

[Directionally correct, early on timing. Apple Vision Pro ships with eye tracking and is pitched at productivity; Meta’s Orion points the same direction. Brain-wave input remains clinical and experimental, not something anyone uses to clear their inbox. Call it right in concept, a decade optimistic on adoption.]

I think from a marketing standpoint; companies will be able to slice and dice a huge amount of data from customer interactions to pinpoint and deliver targeted ads/offers (whatever you want to call them) to consumers at point of sale/point of looking in the aisle (if you have your mobile device/embedded chip turned on); geographically or online.

[Full marks. Retail media is its own category now. Every major grocery chain runs an ad network. Transaction, loyalty, and behavior data drive targeting at the moment of intent. The embedded-chip line reads less like a joke than it did in 2014.] Me again: This was inspired by a conversation I had had with the guy who created the software that spat out those personalized ads/coupons on the back of your grocery store receipt.

I think Facebook and/or Google will be less about “the Web” and more about delivering that customer data to advertisers.

[Right in substance. Alphabet closed 2025 at $402.8 billion in revenue, most of it still advertising; Meta’s revenue is overwhelmingly ad-driven. “Less about the Web” is the part that needs a tweak — Search is still the cash register — but both companies are fundamentally ad and data businesses with products as the delivery mechanism.]

[Note: this might be more today than the future.] Unlike the other brackets, this was an original aside.

[Accurate self-catch. This was already underway in 2014.]

I think we’ll stop worrying about the bullshit divide between work and personal and finally acknowledge that because the office is so portable, office hours really don’t mean much beyond some basic, core ability to be able to meet with your team at a mutually convenient time. There will be times when 9 to 5 is needed. Other times, the ability to be untethered to a cubicle but still connected will unleash a huge wave of productivity — and maybe even decrease the amount of time we all spend in rush hour (a productivity saving all by itself).

[The most optimistic paragraph in the piece, and where it misses hardest. Portability happened — roughly a quarter of US. paid workdays are remote — but the divide didn’t dissolve. It collapsed into always-on. Late-night meetings are up, cross-time-zone work expanded, and the boundary is worried about more now, not less. Right on the technology. Wrong on what humans would do with it.]

Despite 1 and 4, the value of face-to-face, real-time meetings (virtually or IRL) will continue to be a powerful way to collaborate.

[Correct. Hybrid won. Pure async didn’t.]

Paper — or at least some sort of digital paper — will continue to be with us. People like to write stuff down.

[Right. Quocirca survey data still puts printing as necessary for a clear majority of SMBs, and paper note-taking remains stubbornly popular among the people supposedly living in the future.] Me again: Recent AIIM research shows about 50% of all business processes run on paper. The supply chain industry remains almost entirely paper-based; and with something like 100 documents for a single container and with the average container ship ferrying 10,000 – 20,000 containers . . . that’s a LOT of paper, ripe for automation.

Cultural issues will hold productivity back more than technology. Dilbert’s Pointy-Haired Boss (hmmmm, any resemblance to Cosmo Spacely?) will still be with us and not all companies will be able to be truly creative as C-level continues to focus on productivity measures that just don’t matter.

[The piece’s most durable prediction. Gallup’s 2026 report shows global employee engagement dropped to 20% in 2025, the lowest since 2020, with disengagement pegged at roughly $10 trillion in lost productivity in 2024. Technology keeps improving. Management keeps underperforming. The culture lag is the real bottleneck, and it has been for decades.]

And, as Gregg Easterbrook says in his brilliant Tuesday Morning Quarterback column: All predictions wrong or your money back.

[Not all wrong. No refund issued.] I am delighted to just now discover that he still writes the column here; and I just subscribed. Now just need football season to hurry up and get here! WhoDat!

Roughly 7 right, 2 half-right, 1 early.

Final grade: B+. Strongest on ad-tech targeting, paper not dying, the primacy of culture over technology, and the portability of office work. Weakest on assuming portability would feel like freedom rather than a longer leash. Would be an A- with slightly less cheerful naivete about what humans do with always-on tools.

Your turn. Dig up something you wrote 5, 10, 12 years ago. Read it. Grade it. You’ll probably be more right than you remember — and wrong in ways that are useful to notice. Hit reply and tell me what you found. Love to see what y’all come up with.

Thanks for reading, comments, criticisms, and witticisms welcomed.

Nobody knows.

That’s the answer. I’ve been comfortable saying that for decades even though as an editor and content marketing pro it always feels like people think I’m being glib when I do.

Nobody — not the guru with the $997 course, not the algorithm whisperer on LinkedIn, not the marketing professor with a shelf full of textbooks — knows what “just right” is for your content. Not precisely anyway. The honest ones will say it anyway rather than trying to tap-dance their way through an impressive 2 minute discourse that boils down to “I don’t know for sure.”

The fear that you’ll get it wrong — too long, too short, too often, too infrequent, too much, not enough — is one of the most effective forms of procrastination I’ve ever seen. Researching can look like strategy. It feels like diligence. But it’s just paralysis by analysis.

I’ve written about pieces of this before — the “great” trap, the goldfish myth, the barking problem – but not altogether.

Here’s how they fit. Let’s go.

The “Too Long” Myth Is Still Bullshit

Let’s start with length, because this is the one that won’t die.

“Keep it short. People don’t read anymore. Attention spans are shrinking.”

No. People don’t read your shitty, self-involved content that serves you and not them. That’s a different problem entirely.

I’ve been watching content performance metrics since me, the mail room guy (now a successful Web designer), and my managing editor built our first website together in 1998. Longer content that’s actually useful consistently outperforms shorter content on time-on-site, engagement, and conversions.

And the data keeps backing this up. Long-form content of 3,000+ words performs 2.5 times better than shorter pieces. The average content length for the top 10 Google search results is approximately 2,200 words. Posts over 2,000 words generate three times more backlinks and shares than shorter ones. Content Marketing Institute data shows long-form articles get 75% more time-on-page than short pieces.

On the other hand, the average blog post length actually shrank in 2025 — down to about 1,350 words, decreasing for the second year in a row. So the average is getting shorter while the best-performing content is getting longer.

Why? Because AI is pumping out short, mediocre content at industrial scale. The floor is flooded with machine-generated filler, and it’s pulling averages down. Meanwhile, the stuff that actually works — the content people read, share, link to, and act on — keeps getting longer and more substantial.

While I remain dubious that anyone can always tell if something is created by GenAI, we all at least say we want human content. Stats show that human-generated content receives 5.44 times more traffic than AI-generated content.

The competitive advantage of writing something real and useful and long enough to actually help someone is widening, not shrinking. There’s less competition at the top because fewer people are willing to do the work.

Meanwhile, 60% of adults binge-watch TV regularly. I once turned on the first episode of Cobra Kai around 9 on a Friday night and looked up at 4 a.m. having finished the entire first season.

We pay attention to things we find interesting. That’s it. That’s the whole secret.

If it’s short and shitty, people won’t read it. If it’s long and good, they might. Length is not the problem. Usefulness is the variable.

But There ARE Broad Targets

I’m not saying anything goes. There are general guidelines that work across platforms, and if you’re just getting started, they’re worth knowing — not because they’re sacred, but because they get you unstuck.

For blog posts, 500 words is enough to make a single point. I’ve been telling people that for over two decades and it still holds. It’s short enough to write quickly but long enough to actually say something. For meatier pieces that you want to perform in search and get shared, the research points to 1,600 to 3,000 words — but that’s not every post you write. Though one effective strategy is to only write long, well-researched posts. Yeah, it really does depend on your goals, time, budget, skills, market, and so on.

For newsletters, one useful idea per issue. That’s the bar. “Here’s one question we get all the time. Here’s the cleanest answer I have. Here’s what to do if you need more help.” Done.

For social posts, shorter tends to win because you’re fighting a feed, not a reader’s attention span. But even there — a longer LinkedIn post that tells a real story will outperform a punchy one-liner with nothing behind it. One interesting wrinkle: LinkedIn carousels — the PDF-style posts — earn a median engagement rate of 21.77%, which is 196% higher than video and 585% higher than text posts. Highest of any format on any platform in a recent Buffer analysis of 45 million+ posts. That’s a format thing, not a length thing — which is exactly the point. The “rules” are platform-specific and format-specific, not universal.

For video, I recommend a length ladder: 7–10 seconds for a teaser, 20–30 seconds to answer one question, 60–90 seconds for a full explainer. Record once, cut three ways, and let the audience tell you which one they actually watch. Full disclosure: I give this advice but haven’t mastered the multi-cut workflow myself yet. I’m still learning. But the principle is sound — and it’s supported by the data. Videos under two minutes have a 70% higher completion rate than videos over five minutes.

These are starting points. Guardrails. Training wheels. They exist to get you moving without running into a ditch, not to define or limit you. In time, you’ll be riding in the ditch and jumping the guardrails – but you have to start first.

Frequency: The Other Goldilocks Problem

How often should you publish? The honest answer: I don’t know. Neither do you. Neither does anyone — until you start.

There is a “that’s just too much” level every newsletter reaches. But no one knows where that line is until they cross it. Your audience might want to hear from you more than you think. Don’t limit your reach voluntarily.

Start monthly. Twice a month if you can sustain it. Stick to that for three months. Then pay attention. Are people opening? Clicking? Replying? Unsubscribing in unusual numbers?

Increase the frequency until more folks than normal unsubscribe from an issue. Congratulations — you’ve found “too much.” Dial it back one notch. That’s your Goldilocks zone. For now.

Because it moves.

Here’s what the data actually says, and it’s worth knowing: MailerLite analyzed over 12 billion emails in 2025 and found that sending frequency has less impact on unsubscribes than sending irregularly. Sending less than once a month was the biggest driver of unsubscribes — not sending too often. More frequent senders (weekly, twice a week, even daily) actually had lower unsubscribe rates.

Separately, Campaign Monitor’s research shows newsletters should land somewhere between once a month and twice a week, and there isn’t much difference in open rates across that entire range. Brands sending 4–8 emails per month tend to hit the best balance.

You don’t need to worry about frequency until you actually publish one. Then another and another. Create a cadence you can stick with. Give yourself deadlines. Meet those deadlines. Publish.

If you get to the point that you really need to worry about sending “too much,” congratulations, you’re kicking ass and taking names.

Again: Be. Consistent.

If you’re reading this and realizing your newsletter is one of those things you keep meaning to start — or restart — but the “just right” question keeps freezing you up, that’s exactly the problem I built Newsletter in a Box to solve. I handle the writing, the strategy, and the showing up on schedule so you can stop agonizing and start publishing. Hit reply (bryant@simplyusefulmarketing.co) if you want to know how it works

Volume: The Barking Problem

Volume in content marketing has two meanings: output and promotion.

So let’s tackle output first. We just covered frequency for newsletters, but this applies to everything. Blog posts, social posts, videos, all of it. There’s a middle ground between publishing nothing and flooding every channel like a bot high on Red Bull and Sour Patch Kids with a quota. Brands published an average of 9.5 posts per day across all networks in 2024. The resulting saturation sets up a vicious cycle of doing more than your competitors who then do more than you and then you . . . until customers start to tune you out or hit block and unsubscribe.

But most small businesses and solopreneurs are nowhere near that problem. They’re not posting too much. They’re barely posting at all. If you’re agonizing over whether three LinkedIn posts a week is “too many” or if two newsletters a month is “spamming,” you’re worried about a problem you don’t have.

The second meaning is promotion — how loudly and how often you share what you’ve already made. This is where most people I talk to fall down (including folks who know better). They publish something, share it once, and move on. They want the work to speak for itself. I operated that way for years. It doesn’t work. You have to share your content more than feels comfortable. You have to ask for the sale or the meeting. You have to bark.

Not like an over-caffeinated chihuahua barking or the bot on a sugar high. But you do have to open your mouth.

The Goldilocks zone here isn’t about finding a magic posting schedule. It’s about whether you have something worth saying each time you show up. “Post with purpose” sounds like a bumper sticker, but it’s the actual answer. One thoughtful post beats three that exist because someone told you to post daily.

Rule of thumb: share at least one thing daily, even if it’s engaging with someone else’s content. And when you publish something you’re proud of, share it more than once. I promise that there are more people who would be interested in seeing it than already saw it.

Quality: The Trap That Eats Everything

And then there’s the “great” problem.

A lot of writing and marketing advice tells you to create “great content.” I’m all for great content. I’d love to write one great thing. But trying to be great before you’ve published a damn thing is how you end up frozen.

I’ve been there. When I took over as editor of a professional magazine at 26, I wanted every issue to be perfect. I had to figure out how to get out of my own way. And when I moved into content marketing years later, the same problem came back.

The truth is that even the greats aren’t always great. Drew Brees won games with 37 seconds on the clock and also threw interceptions that ended seasons. The Eagles have some incredible songs and some you skip every time. As my favorite greatest hits album title — from Primus — says: They Can’t All Be Zingers.

Focus on being useful and you might get to great on the way.

The AI flood actually makes this argument stronger than it was a year ago. As one analysis put it: the more machines produce fast, standardized, context-free content, the more humans crave analysis, experience, and deep thinking. Long-form, human-written content is becoming a marker of expertise — not because long is inherently better, but because anything real stands out (reinforcing the “longer can be better” point I made earlier).

One sobering note worth sitting with: the average bounce rate for content pages in 2026 is 45%. Nearly half of visitors leave without engaging. Quality alone doesn’t guarantee attention — distribution and trust still matter. But that’s not an argument against quality. It’s an argument that you need both: something worth reading AND the willingness to put it in front of people.

The Goldilocks zone for quality isn’t a fixed standard. It’s “better than the bots, and actually helpful to a real person.” That bar keeps moving, but it’s achievable for anyone willing to do the work.

Two Contradictory Things That Are Both True

Here’s where it gets uncomfortable, because I need you to hold two ideas in your head at the same time.

First: Follow the broad guidelines. They exist to get you started and unstuck. Don’t overthink. Don’t wait for perfect. Just do it — and over time, you’ll develop a feel for what works. You’ll build a filter. “This is me” on one side, “this isn’t me” on the other.

I can’t tell you exactly how that filter develops.

There’s no secret. Do it. Do it again. Evaluate. Tweak. Revise. At some point you’ll be writing and you’ll just know if it’s right or wrong.

Second: When that filter tells you to break the guidelines — break them. Want to write something longer than the “best practices” say you should? If you believe in it and you believe your audience will get something from it — do it. No one knows your audience better than you do.

Slavish devotion to rules is as bad as having no rules at all. The guidelines are there to remove the fear, not to replace your judgment.

Mini Content Lesson

Before letting you go, a quick mini-lesson in content creation. I noted in the intro that I’ve touched on each of the topics above, but not as a single post to have them all in context. NEVER think of a piece of content in isolation. Note that this is a reflexive skill/habit built over 30 years and I still get it wrong at times; so be kind to yourself if you’re just beginning to create content.

You can bundle pieces together to build something new (Notes into a newsletter post for example). Or take something large and pull it apart (a webinar could turn into a blog post, a series of social posts, a Q&A post – with each Q&A as its own Note or Tweet; you could also bundle the content from a webinar series into a larger ebook or whitepaper).

For instance, this newsletter could turn into:

1. Each section as a standalone post on LinkedIn

2. Shorter snippets to share on Notes

3. A short, Simply Useful Marketing Minute video

4. A chapter in an ebook on online writing advice

5. Go deeper into each section and create more in-depth posts

6. Compile those posts with a bit of connection tissue and it’s a short ebook.

It’s not always effective or worthwhile to pursue every permutation of what you can do, but it is a good idea to think of how you can use/reuse what you publish.

So What the Hell Is “Just Right”?

It’s a moving target. Sometimes it doesn’t exist at all. And the search for it — the endless calibrating, the reading one more article about optimal post length, the tweaking before you’ve even shipped anything — is itself a form of procrastination.

The only way to find your version of “just right” is to publish, pay attention, and adjust. Over time, patterns emerge. You’ll notice what your audience responds to. You’ll develop instincts you can’t fully explain but learn to trust.

That’s the Goldilocks zone. It’s a feel, not a number.

And the only way to create that feeling is to start publishing and pay attention to what happens. You’ll never find “just right” by reading “just one more” article about it.

P.S. If this whole piece made you think “I know I need a newsletter, I just don’t have time to figure all this out” — that’s literally why Newsletter in a Box exists. One conversation and I can tell you if it’s a fit. Email me at bryant@simplyusefulmarketing.co and we’ll talk.

No music today, just one of the innumerable Justice League Chicago Fire SVU shows in background (I’m at my Mama’s). Though here are a few sources for further reading.

Sources for content length

• https://www.averi.ai/how-to/10-content-marketing-trends-for-2026-(and-what-they-mean-for-startups)

• https://www.georgescifo.com/2025/10/the-definitive-guide-to-content-length-best-practices-for-2026/

• https://www.content-managers.com/insights/how-to-measure-content-performance/

• https://www.amraandelma.com/top-long-form-vs-short-form-content-statistics/

Frequency Sources

• https://www.mailerlite.com/blog/email-cadence-and-frequency-best-practices

• https://blog-origin.mediashower.com/blog/how-often-should-i-send-newsletters/

• https://nucleusmarketing.org/mastering-newsletter-timing-best-practices-for-frequency-timing-and-performance-benchmarks/]

In Greek mythology, the Moirai — the three Fates — controlled every mortal life. Clotho spun the thread. Lachesis measured it. Atropos cut it. Even Zeus couldn’t overrule them.

It’s a fun story if you’re inclined to enjoy mythology. However, waiting on fate is a terrible marketing strategy.

If you’re waiting for customers to find you — waiting for the right person to stumble across your website, or hoping your name comes up in conversation at the right moment — you’re handing your business plan to three fickle goddesses with a pair of shears. To market your business, you need a plan. Whether that’s a complex strategy with ad spend, multiplatform outreach, and a website that converts — or something simpler, like a clear offer on a landing page and a newsletter that builds trust (and an audience) over time — the common denominator is action.

Not hope.

Not fate.

Action.

I don’t believe in fate. Or “meant to be.” I think that belief leads to a learned powerlessness — an excuse to stop doing the work because the universe will sort things out.

But I do think we massively underestimate the role of chance. Not fate. Not manifestation. Just the plain, dumb reality that small random events can bend the entire arc of a life.

There’s science behind this. In 2018, a team of Italian researchers simulated a thousand careers over 40 years and found that the most successful people weren’t the most talented — they were moderately talented people who encountered the most lucky random events. Talent did play a role; in that a talented individual is better equipped to take advantage of a fortuitous event; but it wasn’t close to a guarantee of success. Their takeaway: we miss a critical piece of the success picture when we focus only on personal ability. FYI, it’s a fascinating article Read it here: Scientific American

The old line attributed to Seneca — “luck is what happens when preparation meets opportunity” — is partly right. You do need to be prepared enough to recognize a good thing when it shows up. But the showing-up part? You can’t schedule that.

Two stories of random chance (and my choices) sending my life down entirely separate paths.

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The No Way Pile. In 1994, I applied for an editorial internship at AIIM, a professional trade association. Got the job. A few years later, I became editor. While cleaning out the office, I found the intern applications. My resume was in a manila folder with “No Way” written on the outside. Now, I knew I wasn’t the first intern. John Harney had brought in a journalism student who was apparently so annoying she was dumped after 2 weeks. Never asked him why he pulled me in after that. But that one act set the course of my career for the next 20-plus years (and even now as I’m back in that industry).

The Alternator. Sophomore year at Southern Miss. I was supposed to drive to Jackson to visit a woman I’d been writing letters to all summer. My alternator died. The replacement part was supposed to come in Thursday, car fixed Friday, I’d be on my way. Part didn’t come in.

So I ended up in my buddy Jason’s dorm room that evening. Called Rebecca, told her I couldn’t make it. Literally as I hung up the phone, a woman named Candice walked in from the party next door, slid down the wall (she was a wee bit buzzed and took a wrong turn to the bathroom), and we started talking. Two weeks later, she smacked me on the head with a rolled-up program at a campus concert. I crawled over the seat and sat next to her. We were together from that night in 1990 until 2007. Two daughters. One grandson.

If the alternator part had arrived on time, I drive to Jackson. I never meet Candice. My daughters don’t exist. Everything after that moment is different.

Fate? Nah, just a logistical failure of a part not arriving on schedule.

Chance put me in Jason’s room that night. But I still had to talk to the woman who slid down the wall. John pulled my resume from the No Way pile — but I still had to show up and do the work once I got the interview.

You can’t control the random events. But you can be ready to take advantage of them when they arrive. And in marketing, you don’t have to wait for chance to put you in front of people. You can go build something that does it on purpose.

The Fates are fickle. Your marketing shouldn’t be. Stop waiting for Clotho to spin you some customers. Go build something.

PS — If you’ve been meaning to start a newsletter but keep waiting for the right moment, the right template, the right name that’s the Fates laughing at you while Atropos sharpens her shears. I help businesses build newsletters that show up consistently so you’re not relying on chance to bring customers to your door. Reply to this email or hit me at bryant@simplyusefulmarketing.co and let’s create your own fate.

Here’s something nobody selling AI wants you to think about too hard: every promise being made about enterprise AI — agents, copilots, RAG, agentic workflows, whatever the vendors are calling it this quarter — depends on a foundation that doesn’t exist in most organizations.

Not because the AI is bad. Because the information underneath it is a tottering tower of redundant, outdated, trivial, ungoverned, mislabeled, duplicated, scattered, and often unfindable content.

ROT, if you want the acronym. Redundant, outdated, trivial. The IDP (intelligent document processing; formerly ECM, formerly Document Capture, and even more formerly, microfilm and micrographics) industry has been talking about ROT for decades. It hasn’t gotten better. It’s gotten worse — there’s just more of it now, spread across more systems, with AI piled on top like a penthouse suite bolted onto a building with no plumbing.

I know this because I’ve been watching this industry not fix these problems for 30 years from a position of editor, marketer, and ghostwriter.

I started in the industry as an editorial intern at AIIM in February 1995. True story: when I was cleaning out the office a few years later after becoming editor, I found my resume in the “No Way” pile. I stumbled into this industry sideways through an open screen door — and never totally left.

One of the things that has stuck with me across all of those years is how little things have changed at the core. I recall a “paperless workflow” poster in the editor’s cube when I started that, with some slight updating, wouldn’t be out of place today. The one thing I wish had changed — and it hasn’t — is the gap between the need for what the IDP industry produces and the actual implementation of those tools by organizations.

That gap is about to matter a lot more than it used to. Because every promise being made about AI depends on the stuff this industry has been trying to get organizations to do for three decades.

I recently saw a conversation about trying to find research on converging information management teams with knowledge management teams inside large enterprises. A big multinational had asked an industry analyst (who has been in the industry since the late 80s) if any such research existed. He couldn’t find any.A practitioner who’d tried it at a large retailer said the two teams couldn’t even get past the fact that they didn’t share the same vocabulary. They worked at it for a while, got busy with their own goals, and drifted apart. I recalled suggesting something similar to AIIM leadership 16 or 17 years ago and they weren’t interested.

If the professionals whose literal job is managing information can’t converge their own teams — inside organizations that know they need to — what hope does a generic enterprise have of getting AI-ready across departments?

Note: I used both Claude and ChatGPT to compile this. Everything here is pulled directly from my thinking. The comparison of 2014 to today’s issue is all genAI, but pulled directly from the ebook (explained immediately below) or sites I directed the tools to look at. It’s my work, including most of the language. For those interested, I explain what I did at the end of this tome.

The Comparison Test: 2014 to Today

In 2014, I pulled together an ebook to market the AIIM conference that year. I stumbled across it last week and had the thought “Huh, I wonder how much of what’s in there are the exact same issues as now.” The title was “From InfoChaos to Information Opportunity.” It was a preview of the AIIM Conference – each speaker and sponsor contributed a short piece that we published online and then used in the ebook. I edited the thing and gave the designer instructions for what I wanted it to look like. I remember the conversations back then and they’re the same ones the industry is having today. The ebook (I’ve embedded it below) covered governance, fragmentation, findability, cloud sprawl, legacy workarounds, workflow exceptions, paper, metadata, change management, and the eternal struggle to get business value out of unstructured content.

I directed both Clause and ChatGPT to read it and then pointed it at what current vendors and analysts like AIIM, Gartner, McKinsey, Deep Analysis, Hyland, OpenText, IBM, Forrester, and others are talking about right now.

The overlap is not subtle.

Of the 10 big problem areas from the 2014 ebook. About 8 of them are still being discussed in almost identical terms. If you allow for the AI-era vocabulary swap — “information chaos” becomes “AI-ready data,” “ECM” becomes “content intelligence,” “information governance” becomes “AI governance” — it’s closer to 9 out of 10.

The industry has been better at changing labels than solving root problems.

Here’s the list.

1. Governance, retention, privacy, and compliance

Still the same fight. The 2014 ebook treated governance as foundational — eDiscovery risk, privacy exposure, the absence of real retention policies. Johnny Lee’s chapter was literally titled “I Don’t Need Governance” with the parenthetical “(or lower ediscovery costs or access to my content or...)” — that sarcastic tone tells you how far behind organizations were – 12 years ago.

In 2026, AIIM’s Global Summit has an entire opening keynote on AI governance and regulatory compliance — the EU AI Act, ISO 42001, cross-border data rules. Gartner predicts half of all organizations will adopt zero-trust data governance by 2028 because AI-generated content is creating a whole new class of unverified information to manage. And Gartner’s 2026 Magic Quadrant for data and analytics governance platforms has expanded significantly into unstructured data governance — something the 2025 edition barely touched.

Different acronyms. Same risk. Same organizations dragging their feet.

2. Fragmentation and silos across repositories

In 2014, the problem was file shares, SaaS silos, Dropbox, laptops, and phones. Alan Pelz-Sharpe — who is still covering this industry, now through Deep Analysis [Note: I’ve know Alan since the late 90s and currently do some marketing work for Deep. On the bullshit scale of 1 to 10; he’s a zero.] — called it a “Polar Vortex” of fragmentation that had dumped a pile of problems in its wake. The goal of one master file, stored and managed in one location, was a worthy ECM goal, he said, but it proved too impractical for most.

Today, AIIM’s own research says the average enterprise manages over ten information management platforms. Forrester says organizations store content across an average of 21 systems. Hyland’s new CEO — who came from the structured data world at Informatica — says content management was “perennially a black box.” His exact framing: large language models now allow you to give structure to unstructured data, so you can do the things we’ve been doing with structured data — without structured data. That’s a vendor pitch for solving a problem the industry identified a decade ago.

Same problem. More tabs open

3. Findability, metadata, search, and dark data

The 2014 ebook had an entire section on metadata being taken for granted. Another chapter complained about dark data straining IT budgets “for no good reason.” People couldn’t find anything, and the metadata that would have helped them didn’t exist or wasn’t maintained.

In 2026, AIIM is still centering “knowledge enrichment” and “knowledge discovery” as conference tracks. OpenText is selling tools to automate metadata tagging and surface content across repositories. The AIIM/Deep Analysis Market Momentum report found that unstructured data knowledge bases are spread across multiple applications. And according to recent industry research, only 11% of organizations have high metadata management maturity.

Twelve years of progress and we’re still swimming in information we can’t properly classify or find. That’s not a technology gap. That’s an effort gap. The technology exists. It has for a while. People just haven’t done the work.

4. Cloud, mobile, remote work, and BYOD versus control

The 2014 ebook was already panicking about information leaking through personal email, unmanaged devices, and free sharing tools. Monica Crocker’s chapter — one of the best in the ebook, a person with a sense of humor writing about a real problem — described how Land O’Lakes “grasped the cloud in a panic” because employees were storing company content on thumb drives and personal accounts. Her line about what happens when you don’t build an official solution stuck with me: people will “staple together a tar paper shack without adequate sanitary facilities and invite their friends to live there, too.”

That was 2014. Today the leak surface includes AI embedded in browsers, desktops, and operating systems. Shadow IT has become shadow AI. Gartner’s 2026 CIO survey found that 84% of enterprises expect to increase GenAI funding this year — but the governance to match that spending doesn’t exist yet. The devices changed. The control problem didn’t. And the tar paper shacks now have chatbots in them.

5. Legacy systems and poor usability driving workarounds

The ebook said it plainly: when the official system is painful, people route around it.

I wrote about this in 2022 when I did a presentation for the AIIM Florida Chapter. One of the things that sticks out to me across 30 years is that gap between the need for what this industry produces and the implementation of those tools by organizations. The technology exists. It works. People just don’t use it because it’s a pain in the ass — or it was implemented without anyone asking the people who would have to use it what they actually needed.

In 2026, Hyland is still pitching migrations from legacy ECM to its unified cloud platform. OpenText is positioning its AI Data Platform as a way to “activate” content trapped in old systems. The word “activate” is doing a lot of heavy lifting there — it means the content has been sitting around doing nothing. For years. In systems people hate.

Meanwhile, Hyland’s CEO is adamant that delivering AI and cloud value “should not start with a content migration” — which tells you that’s exactly what some organizations are being told to do. And if migrations are still the conversation in 2026, the legacy problem hasn’t gone anywhere.

6. Workflow and process automation that breaks on exceptions

In 2014, ibml’s Dan Lucarini warned about “casual capturers” passing errors directly to the most expensive workers in the loop — underwriters getting bogged down with missing paperwork because the capture step was pushed out to people who didn’t know what they were doing. BancTec said it simply: connect content and process.

In 2026, Forrester makes what it calls a critical and often-overlooked point: AI agents need clear, step-by-step instructions to perform enterprise tasks reliably, and in most organizations, that process knowledge still lives in fragmented workflows, undocumented tribal knowledge, and unofficial workarounds. Forrester’s readiness test is blunt: ask yourself if you know exactly where to find the documentation for how your organization actually does the work. If the answer is “no” — and it usually is — your AI agent is going to be about as useful as a new hire on day one with no onboarding, no training, and no one to ask.

I’ve been saying this for a while: companies are generally shit about understanding workflows, and agentic AI will depend on workflows and workflow orchestration to provide actual business value. Color me dubious of that happening any time soon.

The happy path gets automated. Real work still lives in the exceptions.

7. Paper, manual intake, re-keying, and accuracy problems

The 2014 ebook explicitly complained about re-keying and the stubborn persistence of paper. I.R.I.S.’s Frank Tiedt literally listed “time spent re-keying data” as a top business problem and noted that it was “tedious, time consuming and generates arthritis.” I appreciated the honesty.

In 2026, the AIIM Global Summit agenda includes a session on a nonprofit — Boys Hope Girls Hope — that had to digitize decades of paper records before it could even begin to use AI for classification and routing. And the AIIM/Deep Analysis research found that 58% of organizations report capture inconsistencies and 62% report incomplete data.

Are we getting closer to a paperless office? I’ve been asking that question for 30 years. Paper never really died. Neither did manual entry and the errors that come with it. The industry still talks a big game about transformation while plenty of core processes remain stubbornly manual.

Here’s an “ebook” I created for World Paperfree Day in 2012. I’ll try to download and embed, but the interwebs are being finicky. Click the image to see the whole thing. Scanners are faster. Capture/recognition tools are WAY better. Same problems exist.

8. People, process, change management, and executive sponsorship

Technology was never the whole issue. The 2014 ebook’s chapter on zero-based information governance laid out eight tenets, and the first three were executive mandate, cultural attention, and personal accountability. Deborah Juhnke wrote that without those three things, information governance initiatives fail. Early technology purchases, she said, mask the problem and often fall short of full implementation.

In 2026, McKinsey says nearly two-thirds of firms have failed to scale their AI projects. Forrester describes a “vicious cycle” where lack of employee trust leads to weak governance, which leads to perpetually deprioritized data cleanup, which leads to AI tools that underperform — which further erodes trust. Around and around it goes.

Different decade, same management failure mode. And it’s the one that matters most because you can’t buy your way out of it. You never could.

9. Getting business value out of unstructured content

In 2014, John Mancini’s keynote (John was AIIM’s president at the time) framed four questions for the industry, and the last was the simplest: how do we get any business insight out of all the information we’re gathering?

In 2026, that same question shows up wearing much fancier trousers. It’s now called “AI-ready data,” “content intelligence,” “RAG,” “knowledge enrichment,” and “agentic AI.” Gartner predicts that through 2026, organizations will abandon 60% of AI projects because their data isn’t ready. Hyland says 80% of enterprise content is usually unstructured, disorganized, and incomplete. AIIM’s own mission statement is still centered on helping organizations “manage and prepare unstructured data for AI and automation.”

The Hyland CEO framed it well: content management was perennially a black box. CIOs would ask him at Informatica what he could do for their unstructured data. Now that LLMs exist, the answer is theoretically “a lot.” But only if that content is clean, governed, and accessible. Most of it isn’t.

Same core problem. Better outfit.

10. “Social business” as a standalone theme

This is the one that feels more renamed than identical. The 2014 ebook gave it a full keynote. Pelz-Sharpe’s chapter explored what social business even meant, and whether the enterprise social networks of that era could deliver real value or were just “social for social’s sake.”

In 2026, nobody uses the phrase “social business” or talks about enterprise social networks as their own category. But the underlying concern — how people collaborate, share know-how, and connect knowledge to work — has been absorbed into broader conversations about collaboration layers, knowledge discovery, copilots, and AI-assisted work.

The problem persists. The framing doesn’t stand on its own anymore.

So You Say You Want an (AI) Revolution

Now, let me clarify something because I don’t want to come off as a Luddite screaming into the void.

AI is genuinely powerful. Not “powerful” in the way a lot of the hype around AI wants you to believe — actually, functionally powerful in specific, focused applications. GenAI and agentic AI can find connections across vast amounts of data and information that a human simply doesn’t have the time or speed to process (hello this thing thing you’re reading here). In bounded, well-scoped use cases — claims intake, invoice processing, document classification, contract review, onboarding, fraud detection — the gains are real and measurable. Deep Analysis has been saying for years that IDP was the first really profitable application of GenAI in enterprise, and that’s only become clearer since. Firms using AI-powered due diligence tools are already cutting contract review time significantly. That’s not vaporware. That’s working technology applied to a well-defined problem.

Where it works is where the content is clean, the process is documented, and the scope is narrow enough that the AI doesn’t have to guess about context. In other words: the exact conditions that most business don’t have.

And that’s the gap this whole piece is about.

AI is a useful tool. I use it every day. I’m using it right now — again this piece was almost entirely compiled using genAI, drawing on my stored thoughts and past writing. It’s a prediction engine trained on data that gives the illusion of intelligence because it does stuff really, really fast. And yes, it is extremely useful, as limited as it is.

But AI doesn’t think for you. It can’t. It’s a server in a rack . . . somewhere.

Now apply that same thinking to the enterprise AI narrative.

I keep hearing that AI is going to take over everything. That it’s going to replace knowledge workers, eliminate back-office staff, and automate the enterprise. And the executive class is sprinting to make that narrative real — or at least to use it as cover for headcount cuts they wanted to make anyway.

Here’s a question worth asking: is anyone pushing the “AI will devastate entire career paths” narrative who doesn’t have a financial stake in that being true? Altman, Amodei, Nadella — they’re running companies with billions in infrastructure bets that only pay off if adoption is fast, broad, and deep. That doesn’t make them wrong about the long arc. It makes them unreliable narrators about the timeline.

And the timeline is where reality gets interesting.

Deloitte’s 2026 State of AI report found that only 25% of organizations have moved even 40% of their AI pilots into production. Talent readiness sits at 20%. Governance at 30%. Data management at 40% — and these numbers actually decreased compared to last year. Companies are less prepared than they were 12 months ago, even as they set more ambitious goals. PwC’s 2026 Global CEO Survey found 56% of CEOs report getting “nothing” from their AI adoption efforts. And MIT says 95% of generative AI pilots fail to move beyond the experimental phase.

Meanwhile, 60% of hiring managers admit they emphasize AI’s role in reducing hiring because it sounds better than citing financial constraints. When New York gave companies a legal form to formally attribute layoffs to automation, zero out of 160 companies — including Amazon and Goldman Sachs — checked the box. Companies are publicly blaming AI for cuts they won’t legally attribute to AI.

The hype is doing the damage the technology hasn’t earned yet.

But AI can’t do any of that on a foundation this shaky.

Here’s why I’m dubious, and it ties directly to the 10 problems above:

AI agents depend on documented workflows. Most organizations don’t have them (problem #6). Forrester says process knowledge lives in tribal knowledge and unofficial workarounds. You can’t agent your way through a process that isn’t written down. I read recently about an AI agent on a website negotiating a cut-rate deal with a customer — 8,000 pounds (was in the UK) of service for 2,000. It could have even been two agents negotiating with each other. That’s what happens when you deploy agents without understanding the workflows they’re supposed to follow.

AI models depend on clean, governed, findable data. Most organizations don’t have that either (problems #1, #2, #3, #9). Gartner says 63% of organizations either don’t have — or aren’t sure if they have — the right data management practices for AI. Only 11% have high metadata management maturity. The average enterprise manages content across 10+ platforms with manual processes bridging the gaps. That’s not a foundation for an AI revolution. That’s a foundation for a very expensive AI disappointment.

AI readiness depends on people and change management. The hardest problem of all, and the one technology can’t solve (problem #8). McKinsey says nearly two-thirds of firms have failed to scale their AI projects. Forrester’s “vicious cycle” — distrust leads to weak governance leads to bad data leads to bad AI leads to more distrust — is the same people-and-process failure mode this industry has been watching for decades.

AI still needs the basics the IDP industry sells. You simply can’t digitally transform an organization — with or without AI — without capture and process automation tools. That was true when I was writing about it in 2022 (or 1995). It’s true now. Every agentic workflow, every RAG deployment, every copilot rollout depends on documents being captured, classified, indexed, stored, governed, and retrievable. If you can’t find the right document, your AI can’t either.

Deep Analysis put it best in a recent piece: “We are not here to stop the AI train; we are here to lay the tracks so it doesn’t derail spectacularly at the first curve.” They describe the AI opportunity for information management professionals as requiring “intelligent guerrilla warfare” — not grand head-on assaults but strategic, essential infiltration. Making governance, structure, and the ethics of information impossible to ignore. Because without that foundation, as they put it, “this entire glittering AI edifice is built on a ghost — the ghost of messy, uncontrolled, and profoundly dangerous data.”

That’s not my hyperbole. That’s an analyst firm that has been covering this market for decades. And, again, I know these guys and do work with them. They are some of the smartest folks I’ve ever met whose work and advice has been informing the IDP industry for decades. In short, they’ve shaped it.

Behind every customer-facing automation, there’s some poor monkey in the background pushing all the right buttons to provide that good customer experience (I’ve been that monkey on the back-end of HubSpot automations). The “promise” of AI agents talking to each other is supposedly going to remove this pain from us. Given that companies are generally shit about understanding workflows and agentic AI will depend on workflow orchestration to provide actual business value — color me dubious of that happening any time soon.

So AI will absolutely automate parts of the enterprise. It already is in bounded, well-scoped use cases — claims intake, invoice processing, document classification, onboarding. The kind of tightly defined, document-heavy work this industry has been chipping away at for decades. Celonis — the sexy process mining company — touts invoice processing and accounts payable as part of their platform. Same low-hanging fruit capture vendors have been picking for 40 years (40 is not a typo, this stuff has been around for a long time). Some things never change.

But the broad, sweeping, “AI is coming for everyone’s job next Tuesday” narrative? That requires clean data, strong governance, documented processes, good metadata, findable content, and systems people actually use. Most organizations don’t have any of those things. They didn’t have them in 2014. They don’t have them now.

The Lazy Marketer Problem Isn’t New Either

One more thing, because I see this playing out in my own world of marketing, especially content marketing.

The lazy marketer (and the cheapskate C-suite) who skimps on marketing — who views it as a checkbox, not a differentiator — has always looked for cheap shortcuts. Content mills outsourcing to Fiverr for $12 blog posts. Keyword stuffing. Stenography “reporting” that just restates a vendor press release. None of this is new. AI just allows that process to move faster with worse results if there’s no human intelligence, filtering, and taste applied.

Having been on the receiving end of marketing slop from IT vendors for most of my career starting in the mid-90s, I can un-merrily report that people often write worse than AI. Because if genAI is giving us average, that means it’s trained on even worse content than what it spits out.

The same dynamic playing out at the enterprise level — executives hoping AI will compensate for missing effort — is playing out in marketing too. The exec who says “why are we paying a content person when AI can write blogs” is making the same mistake as the law firm that stops hiring junior associates. They’re cutting based on the demo, not the results.

But that’s a piece for another day.

The Word Salad Hasn’t Helped

The word salad changes every few years. ECM became content services became intelligent information management became IDP became “AI-ready content.” I once jotted down all of the phrases used for process and capture technology — intelligent capture, intelligent document capture, intelligent automation, hyperautomation, digital transformation, capture 2.0, process automation, intelligent process automation, intelligent document automation, digital process automation — and I found vendors using multiple combinations in the same paragraph on the same Web page. If there’s any whiff of AI, the product is “intelligent.”

Here’s one I copied from a vendor website a few years ago:

“Hyperautomation with Intelligent Document Processing, Business Process Management, Robotic Process Automation, Automated Governance, and Integration.”

I’m not making that up. That is from an actual vendor website. They intentionally pushed “publish” on that garbage.

What does that even mean? I have no idea. And I’ve been reading about and/or covering this stuff for 30 years.

For the vendors out there: what’s that confusion doing to your customers?

The constantly changing terminology doesn’t just cause confusion. I suspect it has actively hurt industry adoption over the years. Every time the industry renames itself, organizations have to re-learn what they’re buying. That friction adds up. And now AI is layered on top of that confusion, promising to solve problems that require the very tools organizations couldn’t figure out how to buy under the previous three names.

The Honest Version

When a CEO announces that AI will transform the company by Q3, what I hear is: “I don’t have the patience to fix the foundation, so I’m going to pretend the foundation doesn’t matter.”

It matters.

Given how slowly companies have addressed these problems over the past 12 years — the past 30, if I’m being honest — expecting AI to sweep through the enterprise like wildfire is not a plan. It’s a fantasy. AI will move quickly in narrow, well-defined lanes where the content is clean, the processes are documented, and the governance is in place. (Or it’ll move quickly and the press will have a field day covering those clusterfucks.) It will move slowly everywhere else.

And “everywhere else” is most of the enterprise.

This is actually good news for IDP vendors if they frame it right. Every organization that wants to use AI needs what this industry sells first. The capture, the classification, the indexing, the governance, the workflow automation — all of it. AI doesn’t replace the need for information management. It makes the need for information management urgent in a way that two decades of conference keynotes never could.

The opportunity isn’t “AI will do it all for you.” The opportunity is “you literally can’t do AI without doing this first.”

Like everyone, I’m probably wrong. Just not in the way it looks like I’ll be wrong.

I don’t think AI is going away or slowing down in capability. I think the organizations trying to use it are going to keep tripping over the same problems they’ve been tripping over since 2014 — and since 1994, if I’m being honest. The technology will keep getting better. The foundations will keep lagging behind. And the gap between the keynote and the cubicle will keep being wider than anyone with a financial stake in AI wants to admit.

2014’s information chaos is 2026’s AI-readiness problem. Same mess. Better branding.

I’m heading to the AIIM Global Summit in Baltimore at the end of April since that’s where I live (well, at least the lobby, not paying to go). If you’re an IDP or information management vendor and your marketing sounds like the word salad I just described — or worse, sounds like every other vendor in the space — I can help with that. Social ghostwriting, newsletter ghostwriting, content strategy grounded in 30 years in this industry. Reply to this email or reach me at bryant@simplyusefulmarketing.co.

For more on the specific challenges facing AI and automation adoption in this space, I’d recommend reading Deep Analysis — particularly their pieces on the lengthy hikes awaiting AI in 2026, the demand for hyper-specificity, and how information management professionals can avoid losing the opportunity AI presents. They’re one of the few analyst firms that don’t buy into the bullshit. While you can accuse me of bias, I’d say the same if I weren’t working with them. I don’t pander to anyone.

How I Compiled This.

I did not “write” this, yet this is all me just the same. So I’m in a Slack group of folks I knew from my time at AIIM — analysts, users, consultants (some of the smartest folks in the IDP industry you can find). There’s an underlying “why the hell don’t more companies pay attention to this shit” vibe in some of the conversions. (Talk to a vendor in the industry, you’ll get the same vibe.)

I was literally looking for something else and noticed that 2014 sneak peek. So I though, “Hmmm, genAI is good for brute force comparison, let me run this against what’s out there today.” So I did. I had ChatGPT read it and compile the main themes. Then directed it to look at those themes relative to what’s out today across a few vendors, AIIM, analyst, and consultant sites. I was like, “Well, shit, that’s pretty good.” So I ported it over to Claude, and ran it through again. After a few tweaks, you’ve read the result.

It is me. Other than the 10 point comparison, which is almost entirely AI, the rest is pulled directly from my thinking and words — which is a combo of prompts (thinking and framing), a webinar presentation and article based on that I wrote, the preview document (which was conceived, assigned, and edited by me; except for the vendor stuff, John had done that), and various other snippets and background AI research I’ve done in both GPT and Claude.

As for the 10 point comparison — that’s exactly where the power of AI lies. It would have taken me a full day, maybe longer, to go point by point with this. That ability to pull together massive volume is spectacular. It’s dangerous because we need to doublecheck for sanity, but . . . wow.

So while I didn’t “write” this in the traditional sense, it’s me. My words. My thinking. My edits on anything GPT/Claude popped out that I didn’t like. I’m pretty sure I won’t “write” many things like this, but it can be useful in some situations.

For anyone interested, this is the AIIM 14 ebook that inspired this thing.

Aiim14

5.43MB ∙ PDF file

Download

Download

Musical Interlude

Amy Winehouse from Jools Holland (a fantastic UK music show). Sigh. Wish she HAD taken rehab seriously. What a fucking loss.

Joss Stone. I love the Dusty Springfield original. My favorite Dusty is after this, but Joss does a good job on this cover. She’s pretty great. Been a few years since I’ve listened to her.

But, OMFG, Dusty . . . She of course rules on the above song, but this . . . yeah, baby. Do yourself a favor, hit a road trip and push play on Dusty in Memphis or a day when you’re doing some cooking.

Have loved this Trampled By Turtles Song since I first heard it on the The Way Way Back (a movie that I thought was a comedy because I saw Steve Carrell; it is funny, but not a comedy). Anyway, this song rules (the soundtrack is good top to bottom too).

Come into the world alone

And you go out of the world alone
But in between, there’s you and me
Oh-oh

Man, if that ain’t life and the desire to connect, I don’t know what is.

Just as I was scheduling, Etta popped up. I’m not one of those “oh, music was so much better when . . . “ but, damn, you ain’t getting better than this.

This is the first in an occasional series I’m calling Marketing and the Movies. The concept is simple — I watch (or rewatch) a movie I love or have always wanted to see, and any time an action, plot twist, or character decision reminds me of a marketing lesson, I write it down.

First up: the 1963 classic, Jason and the Argonauts, with the superb Ray Harryhausen’s animation. Questionable acting, glorious stop-motion animation, and a surprising number of useful things to say about running a business.

If you enjoy a Greek myth and like a sword and sorcery movie, this one’s for you. I know, I know; not everyone’s cup of tea but the article will still be worth your while.

Let’s go.

Make People Feel Special and They’ll Do Hard Things for/with You

To select the crew of the Argo, Jason holds what is basically an Olympic competition — archery, discus, the works. This is a journey to the end of the earth. Nobody knows if they’re coming back alive. And yet people are competing for the right to go.

Because they feel special. They feel chosen.

If you make someone feel like they’re part of something worth doing, they’ll go out of their way to help you. That applies to customers, collaborators, and anyone you want on your ship.

Brains Over Brawn

After the competition, Hylas arrives late and misses his spot on the Argo. He challenges Hercules for a place. Hercules selects discus throwing and points out to sea at a large rock. “No man has ever hit that rock with a disc.” Hercules, because he’s Hercules, hurls a disc a quarter mile and clangs it off the rock.

Hylas — slim, not muscular — takes his disc and skips it across the water like a frisbee. It bounces right off the rock.

Brains over brute strength.

Sometimes when you’re staring at a problem, stop bashing your head against the wall. Take a step back. Look at it from a different angle. Check if the wall ends two or three feet to your left and just walk around it. If you can’t go around, go over, under, or through. There’s usually a unique solution — you just have to stop relying on pure force long enough to find it.

Believe in Your Abilities

Jason was transported by Hermes to Mount Olympus where Zeus gave him his quest and also five chances to call on Hera for help. Zeus also offered to hand-pick his crew and give him a ship. Jason refused — he knew he had a plan and could handle it himself.

Don’t use help you don’t need. If you can do it, do it — especially if there are strings attached to the offer.

But Also: Get Help When You Need It

Hera is the figurehead (though at the back of the ship – look, I didn’t film it), for the ship. In tight, impossible spots, Jason talks to Hera through it. No one on earth is a god, obviously, but there’s no shame in learning from someone who knows more than you do. And if you can pay with money rather than time, you’re one step closer to where you want to be.

Get help when you need it. You probably need it more often than you think.

The Gods Are Fickle

The gods in this movie are basically watching TV and meddling. Zeus and Hera are married and constantly competing, and, really, the entire pantheon is essentially an inbred trailer park soap opera — only worse, because they have actual power over people’s lives.

But they do have power. And they use it.

In our lives, there are powerful forces that shape the world we’re in — market shifts, algorithm changes, economic headwinds — that you can’t control and sometimes can’t even see. It’s trite, but still true. You can’t always fight the current. Sometimes you just have to go with it, and just hope you can stay roughly on course — or simply don’t drown.

Don’t Take More Than Is Given

Hera directs the Argonauts to a safe island to repair the ship. Simple instructions: fix the boat, drink some water, don’t take anything, be on your way.

Hercules finds a treasure room underneath a giant bronze statue — Talos — and helps himself to whatever catches his eye.

Talos, naturally, tries to kill all of them.

Don’t take more than is given. Just be decent and don’t be greedy.

Everyone Has a Weakness

Talos is a hundred-foot-tall bronze golem with a big sword. Impervious to everything the Argonauts throw at him. But like a lot of mythology, the monster has a weak spot — he’s full of some kind of boiling liquid, and there’s a plug in his heel. Jason sneaks behind him, loosens the cap, the oil flows out, and Talos goes down.

Everyone has a weakness. You, me, your competitor. Know your own and guard against them. And, not to change the light-hearted nature of this post, understanding your competitors’ weaknesses is also a damn good thing.

On a more positive spin, you also need to understand your customers’ pain because your job is to provide a product or service that soothes it or makes it go away.

Sometimes You Have to Stop, Pause, and Reset

Talos picks up the Argo and drops it into the sea. The ship gets torn a new asshole. So because Hercules was a greedy idiot (if you read mythology he’s not nearly as charming as the guy in the Disney movie), they have to take even more time to repair the ship.

Sometimes you get stuck. You make a wrong choice. You anger the wrong giant iron golem. It happens. Take a step back, recalibrate, move on.

Ignore the Heads. Go for the Heart.

You know the Hydra myth. Cut off one head, two more grow back. Jason finally kills it by ignoring the heads and stabbing the thing in the body.

Same thing in marketing.

We all live under the illusion that we make decisions rationally. We very, very rarely do. We make an emotional decision and then retroactively apply logic and data to justify what we’ve already decided.

I’m not saying lie or make outlandish claims. But your writing should appeal to emotions — appeal to how your product will make someone feel, paint a picture of how their life will be different. Once you’ve got them by the heart, the head will usually follow.

If your newsletter reads like it was written for heads instead of hearts — all features, all logic, no feeling — that’s the kind of thing Newsletter-in-a-Box is built to fix. I help you find the stories and angles that actually make people care. If you’re curious what that would look like for your business, reply or email me at bryant@simplyusefulmarketing.co.

Be Helpful and Make Connections

Later in the movie, Jason rescues a woman from a shipwreck near the Clashing Rocks. Turns out she’s the high priestess of Colchis — and she ends up saving his life at the end. And, of course, she falls in love with Jason.

You never know when the person you helped out of a jam turns out to be the one who opens a door for you later.

The friends you make online — on Substack or LinkedIn or wherever — probably aren’t high priestesses. (If you are, please friend me.) My high school English teacher used to say, “Friends are like shoes; you’ve got them, use them,” which still makes me laugh. There’s truth in it, though. True friends will support you. And even if a friendship never “comes in handy,” it’s never a bad thing to have a friend.

Be Direct

Near the end of the movie, the king has cornered Jason and his men by a temple. His command to the hydra/dragon teeth skeletons is simple: “Kill them. Kill them all.”

Sometimes the most direct course is the best one. (It didn’t work out for the king, but that’s beside the point.)

Tell people what you want them to do. When you’re clear and direct, you’ve got a better chance of them actually doing it. Don’t hide the fact that you’re a business with something for sale — even if you’re a business of one. Especially if you’re a business of one.

Fate Is Not a Strategy

Fate makes a great story device. It’s a terrible way to run your business.

Nothing is fated. Results come from whatever actions you take today and tomorrow. Be consistent. Keep going. Twenty years from now, when you’re kicking back on the beach in Maui, you can say it was fated — but it wasn’t. It was work.

Even Gods Get Bored

There are recurring shots of the Greek gods lounging around a pool, watching Jason and the Argonauts like it’s Netflix.

No lesson here. Just struck me as funny that even gods need something to watch. I suppose eternity gets dull.

There are no new ideas in marketing. But sometimes a 62-year-old movie about Greek myths reminds you why the old ones hold up.

Skip the disc across the water. Go for the heart, not the heads. Show up, do the work, and don’t steal from giant bronze statues.

Next month: Conan the Barbarian. Mostly just the one god; CROM!; and more swords.

Also, if you’ve got a movie suggestion; I would LOVE to hear it. I’ve got tentatively: Krull, Beastmaster, Sword and the Sorcerer, The Hobbit (the Rankin-Bass cartoon from the 70s), Excalibur, and Dragon Slayer on the list.

PS — If you’ve been meaning to start a newsletter (or restart the one that’s been collecting dust since September), I can get you from blank page to first send without it becoming your new part-time job. Reply with what kind of business you run and I’ll tell you what the lightest version looks like. bryant@simplyusefulmarketing.co

A newsletter is the most direct trust-building tool you own.

It should and can be the critical connection point with your customer.

Not a flashy one. Not a viral one. A steady, reliable one — the kind that builds trust the same way showing up on time and doing good work builds trust. Over time, people start to expect you. They start to rely on you. And when they’re ready to buy, you’re the name that comes up.

That’s what a newsletter does when it’s working. It helps. It educates. It can amuse. It earns attention instead of begging for or demanding it. And unlike social media, where a platform decides who sees what you post (yes, even here), a newsletter lands in someone’s inbox because they asked for it.

That’s a one-to-one relationship. And it’s the only one in digital marketing that you actually own.

That subscriber list is yours. And every issue you send is a chance to grow it — someone forwards it to a colleague, a reader shares it on LinkedIn. Each one of those moments adds a person to an audience you own, not one you’re renting from an algorithm.

Everything else I’m about to explain — what a newsletter is, what it isn’t, how it works — flows from that. The trust-building part is the point.

It’s a Container Word

Think of the word “book.”

The thing every book has in common is two covers with some dead trees and ink sandwiched between them. Beyond that, it could be an illustrated manuscript from the 1300s, a tabletop art book, a huge historical tome, or a 25-cent Bantam paperback from the 50s.

A newsletter works the same way.

It can be a hundred words delivered daily — Seth Godin’s been doing that for roughly 20 years now — or it can be a monthly deep-dive that runs novella-length. It can be one article, five short bits, curated links with commentary, an image followed by an essay about the image, or a combination of all of those things. It can be delivered by email, by paper, or — if you’re old enough — by fax.

The format is the least important thing about a newsletter. What matters is whether it’s useful to the person receiving it.

Subscribe now

Don’t Confuse the Delivery Truck for the Package

One quick distinction, because it trips people up.

Email is a delivery mechanism. It’s how most newsletters reach people. But email is not the newsletter — the same way UPS is not the thing inside the box.

And when someone says “I have a Substack” what they mean is they have a newsletter on a platform. The platform is just plumbing. If the same content lived on a WordPress site with a subscribe button, it’d work (mostly) the same way.

This matters because if you ever decide to move platforms — and you might — your content and your subscriber list are what you take with you. The platform is replaceable. The relationship with your readers is not.

A Newsletter Is Not a Sales Email

Confusing these things can cause real damage to your marketing efforts.

If someone says they have a “newsletter” and all they do is pitch you — webinar invitations, product announcements, case studies that are thinly veiled press releases — that’s not a newsletter.

That’s a pitch with a subscribe button (if you ever hear “email marketing” that’s what they’re talking about).

The mechanism is the same. The design can be identical. But the intent is completely different.

A pitch-with-a-subscribe-button delivers no value on its own. It exists entirely to make a sale. It says “buy me.”

A newsletter says “trust me — and when you’re ready, buy from me.”

A newsletter answers customer questions. It’s helpful. It’s useful. It treats the reader’s attention like the gift it is. And over time, that builds the kind of trust that makes selling easier.

Intent is the distinction between a newsletter and email marketing.

But You Do Want to Stay in Business, Right?

Being useful and making sales are not opposites.

The difference isn’t whether you sell in your newsletter. It’s whether you’ve earned the right to ask. If you’ve spent issue after issue helping people — answering their questions, giving them something they can actually use — then asking for the sale isn’t pushy. It’s natural; a next step rather than an interruption.

So within your newsletter, believe in your product. Include a CTA (call to action) — that’s marketing-speak for “ask the reader to do something,” whether it’s reply to the email, book a call, or buy the thing you sell. You should always include one. You do want to stay in business, right?

And on the back end, if you’ve got a decent email tool — HubSpot, Kit, whatever — you can see who’s opening, what they’re clicking on, and use that information to make smarter, better-timed sales outreach. The newsletter builds trust on the front end and gives you data on the back end. It’s doing double duty.

If the part you dread isn’t the writing but the figuring out — what to send, how often, where to put the ask without feeling gross about it — that’s what Newsletter-in-a-Box is built for. Reply to this email or hit me at bryant@simplyusefulmarketing.co.

A Quick Side Note: Newsletters as Products

Some newsletters are the product — people pay directly for subscriptions, or the newsletter generates ad revenue. There are plenty of those in my inbox.

That’s not what I’m talking about here.

I’m talking about the newsletter as a marketing tool — a vehicle that builds trust, connects you with your customers, and creates the conditions for sales. Similar fundamentals, different playbook.

But that’s an entirely different post.

The Fax Machine Days

The first newsletter I ever wrote (well, compiled, it was essentially condensed press releases from mail — until the late 90s/early 2000s and the email takeover, I got 3 to 4 plastic mail bins full of press releases each week) — was delivered via fax. This was 1996. Every Friday night, I spent two to two-and-a-half hours after five o’clock feeding four to five thousand names through in chunks of six or seven hundred, praying they went through.

We actually charged extra for email delivery when that became an option — because it cost us more to send emails than faxes. If that seems inconceivable today, it was the reality at the time.

Point is: newsletters aren’t new, though the tools to manage and send them are MUCH easier to use these days.

Be You

Your newsletter should sound like you. If you can take your name and logo off of it and no one can tell it’s you because you ran it through legal and marketing and three execs with conflicting styles; start over.

Make it sound like a human being who knows their business and gives a damn about their customers.

This matters more than the design, more than the platform, more than the frequency. If the personality is right, people will forgive almost everything else.

And if you’re thinking “but I’m hiring someone to write it for me, so how is it still me?” — that’s exactly the job. A good ghostwriter doesn’t replace your voice. They get it out of your head and onto the page in a way that sounds like you on your best day.

A newsletter isn’t a platform, a particular format, or an email.

It’s how you show up, stay useful, and build the kind of trust that turns readers into customers — one issue at a time.

PS — If “I’ll start a newsletter when things settle down” has been on your to-do list for more than six months, things aren’t going to settle down. I can get you from blank page to first send without it becoming your second job. bryant@simplyusefulmarketing.co

Musical Fun

A couple-three songs in the background as I pulled this together.

Between this and John Batiste at the end, I’m really missing home in SW Louisiana and needing a trip to New Orleans.

I always think this is Van Morrison

“OOOHH! OOOHH! OOOHH!” If you know, you know.

You can never go wrong listening to Bill Withers, or being lucky enough to start your day with someone who you look at, teeth unbrushed, still groggy from sleep and think “the world’s alright with me.”

I’m late to the John Batiste party, but better late than never.

No one wakes up thinking about your company.

We wake up staring at our own navels; worrying about our own problems, looking for answers to our own questions, trying to get through the day with fewer hassles and better results.

That’s not bad news for your marketing.

It’s liberating.

I co-created a sponsored webinar program in the late 2000s that is still running in essentially the same format. My role was to host, recruit an expert to present, and work with the sponsor (they got 5 minutes and a chance to chime in during the Q&A) and speaker to make sure the session flowed and the audience got value.

I must’ve given “the talk” to 60 or so sponsors over the five years I ran it. One of my regular speakers started calling it that over beers at a conference and the name stuck.

It went like this:

No one cares about you.

No one is registering to hear you talk about how wonderful your product is. They are there to understand the topic at hand and how to address a problem they have. They already know you have a product or service that can help because your logo is right there on the registration page. You need to show that you understand the business problem – the pain they have.

Lead with useful information, not speeds n’ feeds.

You can use the time as you choose because you paid for it, but if you lead with features, folks WILL tune out. I have the survey stats to prove it.

The drop-off in ratings for the folks who ignored me were brutal. We sent a survey link to everyone as we closed each webinar. Overall event approval was about a 4.5; the same for expert speakers, while slightly lower for the sponsors who listened to me.

For those that didn’t, approval dropped into the 2ish range along with comments like “awful sales pitch at the start.” I wasn’t a marketer in those days but I remain semi-curious about any difference in sponsor email outreach (they got one shot at access to the registration list) results for the majority of sponsors who listened versus the 20% or so who chose to ignore me and did their usual song and dance.

I do this for companies — build newsletters that focus on being useful instead of being loud. bduhon@simplyusefulmarketing.co

Nobody cares about your company at the start. They care about whether you understand their problem. Whether you can explain it clearly. Whether you can help.

What are their problems?

What’s keeping them up at night?

What do they despise about the current options on the market?

When you’re wrapped up in proving how smart you are or how impressive your product is, you miss the opportunity to hold a conversation. To listen. To learn. To adapt.

And there’s another benefit.

Competing on price and features makes you sound like a commodity.

Features can be copied. Prices can be matched. Buzzwords get slapped onto every damn thing in sight.

You can see that as vendors in the IDP space (intelligent document processing; where I’ve spent most of my career) slapping “AI” onto their feature set whether it belongs there or not. The result is a blur of sameness. Similar promises. Similar vague claims. Similar bloated language. Customers are left trying to figure out who actually does what — and your sales team gets to clean up the mess.

You’d think these companies would learn; they did the same thing with RPA (robotic process automation) seven years ago.

The company that stands out isn’t always the one shouting the loudest.

It’s the one making the customer feel understood.

The one explaining the problem clearly.

The one focusing on outcomes instead of jargon.

The one proving, over time, that it gives a shit.

That last part matters.

Because when you stop shouting about yourself and start showing up with useful information, something important happens.

People begin to trust you.

Not all at once. Not because of one brilliant webinar or killer LinkedIn post or clever campaign.

Over time.

Familiarity becomes trust.

Trust becomes the reason people remember you when they’re finally ready to buy.

So, yes, nobody cares about you.

Good.

That means you can stop trying to be the hero of your marketing.

Because the hero is the customer; you’re just there to help them complete their journey.

P.S. I help companies stop shouting about themselves and start saying things their customers actually care about. If your marketing is stuck in “speeds-n’-feeds” mode, let’s talk: bduhon@simplyusefulmarketing.co.

I saw a post the other day I mostly agreed with — stop buying $500 courses from people who’ve never built anything, stop wrapping empty platitudes in authority, tell the truth.

Preach.

Then came the line that made my left eyelid twitch: “Drop the funnel.”

No.

Drop the bullshit that’s been smeared all over funnels — the fake scarcity, the bait-and-switch webinars, fake countdown timers on offers that never actually expire. Drop that.

But don’t drop the funnel itself.

Because everyone making fun of funnels has one. They just call it something else — “ecosystem,” “customer journey,” “my process.” At some point, a stranger discovers you, decides you’re worth paying attention to, and eventually decides you’re worth paying. That mechanism is a funnel. Renaming it doesn’t change what it does.

The concept isn’t broken. What’s broken are the folks who use manipulation tactics to pull people into their funnels and products.

A funnel built on manipulation deserves scorn. A funnel built on being useful — showing up, earning trust, asking for the sale when you’ve earned the right — is just good business.

So don’t throw it out. Fix it.

And since “fix it” is vague advice that helps no one, let me show you what a simple, honest funnel looks like — and how to build one without spending a dime on some guru’s course.

What a Funnel Actually Is

A funnel is three stages:

Someone finds you.

Someone starts to trust you.

Someone buys from you.

That’s it. That’s the whole thing.

The reality involves more touchpoints — lead scoring, nurture campaigns, SEO, digital ads — but the skeleton is always these three stages. Tactics are legion. The process is always similar.

This image from Rand Fishkin is the foundation for how I think of funnels (because it was one of the first things I read on the topic and it stuck).

I also imagine customers as butterflies. They are blown by the wind. They fly in zig zags. They alight on this flower, then another and another.

But, somehow, they can migrate all the way from Canada to Mexico.

Every business on earth has this whether they use the word “funnel” or not.

My funnel is very simple. Someone reads one of my LinkedIn posts or Substack Notes. They’re curious enough to click through to my newsletter. They read a few issues. Somewhere in there, they realize I know what I’m talking about and that I’m not trying to sell them something every five seconds. Eventually, they reply to one of my emails or book a call. Some of them become clients.

That’s a funnel. No countdown timer. No “only 3 spots left.” No 47-minute webinar that’s actually a hostage situation. Just useful content, consistency, and a clear offer when the time is right.

Why Most Funnels Feel Gross

The problem isn’t that funnels exist. The problem is that too many of them skip the middle.

The middle is the trust part. It’s the stage where someone goes from “who is this person/company?” to “I think this person/company might be able to help me.” That takes time. It takes showing up more than once. It takes giving people something useful without immediately asking for their credit card.

Hustlebro funnels jump from “stranger” to “buy my $997 thing” in 48 hours. They manufacture urgency because they haven’t earned attention. They use psychological pressure as a substitute for trust.

That’s more like one of those antlion traps — nobody is eating except the larvae at the bottom of the funnel.

An honest funnel gives the trust stage room to breathe. Weeks. Months. However long it takes for the person on the other end to decide — on their own terms — that you’re worth their money.

You can nudge. You should ask.

But there’s a world of difference between a clear offer and a manufactured crisis.

If you’re reading this and thinking “I know I need a system but I keep not building one” — that’s the exact problem Newsletter-in-a-Box solves. I’ll help you set up a simple, honest funnel that runs on useful content instead of pressure tactics. Reply or email me at bryant@simplyusefulmarketing.co and tell me where you’re stuck.

A Simple Funnel You Can Build This Week

Here’s what a basic, honest funnel looks like for a small business. No special software. No course required. No Goo-Roo required.

Top: They Find You

Pick one platform where your customers already spend time. LinkedIn. A local Facebook group. Substack Notes. Instagram. Wherever.

Post something useful 3 to 5 times a week. Not pitches. Not “exciting announcements.” Answer questions your customers actually ask you. Share something you learned. Offer a quick tip someone can use today.

This is how strangers become aware you exist. It’s not complicated. It’s also not optional — if you’re invisible, nobody’s buying anything.

Cost: free.

Middle: They Start to Trust You

Drive people from social to a newsletter. This is the one relationship you actually own. Social platforms can throttle your reach, change the algorithm, or disappear tomorrow. Your email list is yours.

Pick a platform: Substack, Mailchimp’s free tier, Kit (formerly ConvertKit) — they all do the same basic thing at the free level. Collect emails. Send emails.

Then send something useful on a regular schedule. Weekly is great. Twice a month is fine. The cadence matters less than the consistency. Show up when you say you will. Don’t waste their time. Don’t make every email a sales pitch.

This is where trust compounds. Every issue that helps someone is a small deposit. Over time, those deposits add up until you’re the person they think of when they need what you sell.

Cost: free.

Bottom: They Buy

Include a clear offer in every newsletter. Not a hard sell — a clear one. There’s a difference.

“If you need help with this, here’s what working with me looks like.”

“I wrote a short guide that goes deeper on this — it’s $7 on Gumroad.”

“Reply to this email and tell me what you’re dealing with.”

That’s it. A sentence or two. After you’ve delivered value, you’ve earned the right to say “hey, I also do this for a living.”

For digital products, Gumroad lets you sell PDFs and downloads with zero upfront cost — they take a small cut when something sells. For services, your email address is the most sophisticated sales tool you need at this stage.

If you want something a step up from an email address as your call to action, create a simple landing page. One page. One offer. One action. Substack does this natively for newsletter signups. For anything else — a free guide, a consultation booking, a product — Carrd ($19/year) or even a single page on your existing website works fine. The landing page doesn’t need to be beautiful. It needs to be clear: here’s what you get, here’s what to do next.

Cost: free until someone pays you, which is the whole point.

Follow Up Like a Human

When someone replies to your newsletter, respond. When someone comments on your LinkedIn post with a real question, answer it. When someone DMs you, have an actual conversation.

This is where services get sold — 14-email automation sequences DO have their place, but are often overkill. Sales boils down to one human being paying attention to another human being and providing a product or service they want/need. All of these online tech tools are delivery and infrastructure. Trust is built person to person.

I realize this sounds stupidly simple. That’s because it is. The execution is where it gets hard — showing up consistently, writing when you don’t feel like it, resisting the urge to pitch before you’ve earned it. But the structure? A child could draw it on a napkin.

Cost: free forever.

The Whole Toolbox, Zero Dollars

In case you skimmed the above and want the quick-reference version:

Newsletter platform — Substack, Mailchimp free tier, or Kit free tier. Pick one. Don’t agonize.

Digital product sales — Gumroad. Free to start, they take a percentage per sale.

Landing pages — Substack (built in for newsletter signups), Carrd ($19/year), or a single page on your existing site.

Content creation — Google Docs. Or whatever you already use to type words.

Images — Canva free tier. Or your phone.

Video — your phone, turned sideways. (I learned the sideways part the hard way at a conference in 2014. We live and hopefully learn. Note: upright recording works fine for TikTok, Instagram, and YouTube Shorts.)

Tracking — a spreadsheet. Name, date, what happened, what’s next. You don’t need a CRM until you have enough clients to justify one.

Total startup cost: $0.

Total ongoing cost: your time and your willingness to show up.

The Funnel Isn’t the Enemy

Dishonesty is the enemy. Impatience is the enemy. Treating people like conversion metrics instead of humans with problems — that’s the enemy.

The funnel is just the shape that commerce takes when it works. Someone finds you. Someone trusts you. Someone pays you. That’s been true since before the Internet existed and it’ll be true long after whatever platform we’re arguing about today is gone.

Build something simple. Make it useful. Stop apologizing for having a way to turn attention into revenue.

That’s running a business, not manipulation.

The people telling you to “drop the funnel” will keep selling to you through theirs. The difference between them and you is that you’ll be honest about it.

PS: If you read all of that and thought “I should really get my newsletter going” but you know you won’t do it alone — that’s exactly who I built Newsletter-in-a-Box for. One conversation and I can tell you what the lightest version looks like for your business. bryant@simplyusefulmarketing.co