True story: every now and again I hate writing. And I’ve made my living by moving words around a printed or digital page for over 30 years now.

I believe many things about newsletters. The relevant belief here is that anyone can write a newsletter (and that every business should have one).

Now, you might be worried that you can’t string words together in a way that makes sense. That isn’t a reason not to write. It’s just a feeling.

However, everyone has knowledge to share. And you know more about your business/industry than your customers.

Here are a few ideas that will get you moving on your next (or even first) newsletter.

Don’t Write

Staring at a blank screen, cursor mocking you with its stationary, steady beating, sucks for professional writers. It can be even more intimidating when you’re unsure of what you want to say.

So don’t write it.

Say it.

Transcription is free these days. Open up a Google Doc, turn on Voice typing, set a timer (I like 20-minute bursts when “writing” by talking), and start talking.

It’s fine to ramble, go on an extended rant, say things out of order, and just in general muddle through. That’s just what writers call the “ugly first draft.” Mine are often fugly.

Let me use this post as an example. This final version is the fourth draft. The first draft ended up as two posts squished together. I gutted the genAI section (below) because the rest of it was how I think about using genAI to write and it wrecked the flow (which will now be its own post for Thursday or next week).

The second draft was a brain dump of more ideas to help you write because when I started going off on a genAI tangent, I forgot some basic things I had wanted to share. The third was a fleshing out of the post in general (and removing most of the ideas I added, it was too much) and revising the flow.

This fourth and final version was a final run through to tighten the title and subhead, trim and tidy the language, spell and grammar check (I have been using ChatGPT for that as it catches grammar issues better than any word processing software I’ve ever used), and to add the CTAs (calls to action — that’s the “hire me” stuff in here).

Four isn’t a magic number. It’s just the number of major changes I made to this one. Sometimes there are more versions; now and then I get it right in one. Oddly enough, I’ve found over the years that length has zero to do with the need for revisions.

OK, moving on from the mini-tutorial there, back to talking it out. You do need to think about what you want to say. That’s where your customers enter this conversation.

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Answer Customer Questions

Your customers ask you questions. These are gold. As you answer them, take notes. If you have a newsletter that “only” answers every customer question, you’ll almost certainly have a successful newsletter.

You don’t need to make it more complicated than this.

You’ve Run Out of Questions. Now What?

While you should never run completely out of customer questions, maybe they slow to a trickle because you’ve done such a good job of answering them online. Whatever business you run — butcher, baker, or candlestick maker — you know more about your profession than your customers.

You’ve probably forgotten more about it than most people will ever know. Think back to when you were in the early days. What would have been useful for you to know then that can help your customer now? Write about tips and tricks and suggestions and hacks (hmmmm, maybe those are all one thing). The point is to think about what might be useful to your customers and potential customers and share that (a chef provides his favorite tips for cutting veggies; an auto mechanic shares tips for how to improve gas mileage; a software vendor shares productivity advice; etc.).

Turn on your phone’s timer for 20 minutes. Finish this sentence until the timer dings: “My customers would be better off if they knew . . .”

Don’t filter. Just write (phone, computer, notebook, papyrus, whatever).

Or talk. I like to do this exercise with pen and paper because I think better that way. I’d encourage you to try it that way first, but if it doesn’t work for you, do it differently the next time.

Steal From Yourself

You almost certainly already have source material sitting in your files and inbox. Take a look through:

• Emails you’ve written customers

• Proposals

• Sales-call notes

• FAQs

• Estimates where you explained why something costs what it does

And don’t forget to look at your reviews; positive or negative, they’ll give you ideas.

If you’re realizing the ideas aren’t actually the problem, that’s useful too. Maybe what you’re missing is the structure, setup, or time to turn those ideas into a newsletter you can keep publishing.

Edit with Claude or ChatGPT

I’m not your 3rd grade English teacher, but genAI can act like one for you. Even the free version of either tool will do an effective job of placing YOUR words in order while suggesting others.

Use genAI to help put your words and thoughts into order. Do NOT use genAI to imitate yourself.

I used ChatGPT to create three editing prompts (prompt is just the fancy word for telling the AI what you want it to do).

They are long, so I’ve created a Google Doc for you. (Click here to make a copy of the free editing prompt pack.) Don’t let the length bother you. Use them as they are and copy/paste them into your genAI tool of choice. Over time, you’ll learn how to tweak and create them for yourself. These will get you started.

While I would encourage you to read the output from Prompt 1, make your own decisions about its recommendations, and then use those notes with Prompt 2, genAI can do a surprising amount of the editing work for you.

The step you CANNOT skip: read the final copy with an eagle eye to ensure the tool didn’t add something made up or drastically misinterpret something you said. It will sometimes.

GenAI is a tool. You are responsible for using the tool well — and for the final output.

If you want even more ideas, read this one:

Get Going

A newsletter doesn’t require you to be a great writer. It requires you to have something useful to say and a way to capture it. If you’ve been on the fence about creating a customer newsletter, I hope you use these tips to tip you over to the “doing” side of that fence.

“But I don’t feel like writing,” I can feel you thinking.

Well, Buttercup, we all have to do needed things we don’t feel like doing.

I do this for a living and I don’t always wanna. It can be hard to get ideas out of your head and into a newsletter. Do it anyway. You won’t regret it.

Thanks for spending part of your day with me. Comments, criticisms, and witticisms welcomed.

And if you’ve made it this far thinking, “Fine, fine, I should do a newsletter — I still don’t want to build the whole thing from scratch,” that’s what Newsletter-in-a-Box is for.

You get the strategy, structure, setup, and 12 starting topics so you’re not staring at a blank screen every time you need to publish.

Let’s have a short conversation about your newsletter, what’s getting in the way, and where/how/if I can help. No pitchslap. No hard sell. I’m ready when you are: bryant@simplyusefulmarketing.co.

We love email.

We also love to bitch about email.

Too much of it. Too many notifications. Too many people who reply all when they absolutely should not reply all (and don’t get me started on the genAI-generated replies!).

Yet email is the spine of a remarkable amount of modern life.

Work. Receipts. Travel confirmations. Password resets. Invitations. Bills. News. Offers. Plans with friends. That meme someone absolutely had to send you. Sign up for an app? Email. Buy something online? Email. Forgot your password? Email.

It’s useful. It’s ubiquitous. And despite past predictions of its death, it remains very much alive.

So maybe we should start thinking about the inbox a little differently.

Your customer’s inbox is their homepage.

I don’t mean your website doesn’t matter. Of course it does. It is your online storefront and “proof of business life” so to speak.

But there’s an important difference between the two — a website is essentially transactional; an email is a link in the relationship chain.

Someone has to decide to visit your website. They find you in search, click a link, see something on LinkedIn, remember your URL — somehow, they have to come to you.

The inbox works the other way.

Once someone gives you permission to email them, you get to go to them.

That’s a very different relationship.

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People Are Already There

I’m not just dreaming this up from my imagination and too much tea.

Ninety-three percent of respondents to ZeroBounce’s 2026 email research said they use email every day. Forty-two percent check their inbox three to five times a day. Thirty-five percent said they spend between two and five hours a day in email.

More importantly for businesses, people actually want you there.

In Optimove’s 2026 consumer research, 60% chose email as their preferred digital channel for hearing from brands, compared with 50% for social media ads, 37% for push notifications, and 34% for text.

Newsletters give you a particularly useful reason to show up.

Omeda analyzed nearly 2 billion newsletter sends during the first half of 2026 and found a median open rate of 31.6%. Open rates are imperfect — privacy protections and automated opens have made them squishier than they once were — but people are clearly still opening and engaging with newsletters.

Omeda’s second-quarter research goes a step further: newsletters were its strongest email category for engagement.

Which is why, if you want to get into your customers’ inboxes, I think a useful newsletter is one of the best ways to do it.

Your Website Still Matters

AI is changing search and is the cause of a new constellation of acronyms around getting your content discovered, cited, summarized, or turned into “the answer” by ChatGPT, Google, and the rest.

I’ll leave that particular acronym safari for another day.

The point is that you should still be creating useful content on your website. Search engines and AI systems need something to discover.

A newsletter simply furthers your reach without duplicating the work.

Publish the useful article on your website and it can be discovered by a new audience.

Send it to your email list and it gets delivered to your existing audience.

Website or inbox, in this context they’re really two different mechanisms: discovery and delivery.

Delivery has one enormous, obvious advantage: You already know somebody wants to hear from you.

That’s a Gift. Treat It Like One.

This is the part businesses seem determined to screw up.

Someone gives you permission to enter one of the most heavily used communication spaces in their life, and too many businesses’ first instinct is:

EXCELLENT. SEND THEM MORE COUPONS.

The same Optimove study that found email was consumers’ preferred marketing channel also found that 55% considered it the most overwhelming channel during high-volume shopping periods.

People like email.

They don’t necessarily like what businesses do to it.

So use the access you’ve been given.

• Send a useful newsletter.

• Welcome someone when they sign up.

• Thank them when they buy something.

• Let them know when you have something genuinely useful or interesting to offer.

• Stay in touch.

Just remember that an email address isn’t simply another field you successfully added to your CRM:

It’s permission to continue the conversation.

That permission is incredibly valuable because the Web is often transactional. Someone searches, visits, reads, buys — or doesn’t — and leaves.

Email gives you the opportunity for there to be a next time.

And another one after that.

You’ll never own this homepage. You don’t need to. You just need to keep earning your place in it.

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

If you’d like a newsletter that gives people a reason to keep letting you into their inbox, let’s have a short conversation: bryant@simplyusefulmarketing.co.

And don’t worry, I don’t pitchslap or hard sell. I’m looking for an honest conversation about what you’re trying to do, what’s getting in the way, and whether I can help.

Musical Coda

Stumbled across Tyler Childers about 2 years ago. Love his voice. One of my favorite love songs; not quite as perfect as “In Spite of Ourselves” by John Prine and Alice Dement though.

When I say the basics don’t change, the basics don’t change.

I wrote the original version of this piece in 2020. And even then, much of it was based on things I’d already been doing and talking about for years. I may have written an even earlier version a few years before 2020.

I reread it this week expecting to find a bunch of advice that had been rendered obsolete by six years of new platforms, new technology, AI, algorithm changes, and whatever marketing bright and shiny thing we’re all supposed to be chasing this week.

Nope.

Some of the mechanics have changed. I wouldn’t talk about blogging and newsletters as completely separate things anymore. Search has changed dramatically. There are new tools and new ways to distribute what you create – Hello, there, Substack!

Note: like most of the basics, this isn’t rocket science. Much like losing weight advice boils down to “eat less, do more,” these fundamental tactics can become a content marketing foundation anyone can win more business with.

1. Publish Useful Content Consistently — Make the Newsletter the Hub

In 2020, I treated blogging and newsletters as separate tactics. I’ve rolled them together here. For most small businesses today, there’s little reason to treat them as separate activities. If you’re publishing useful content online, add an email signup and send it directly to people who want to hear from you.

Whatever the hell you call it — a blog, a newsletter, an article, this thing I’m writing, a piece of content — creating and sharing useful information consistently is one of the simplest (though not easy) tactics any business can use to attract new leads and customers.

Share information and ideas that address your customers’ points of pain. Answer their questions and keep doing that.

Why publish? Because useful content gives people a reason to find you, pay attention to you, remember you, and eventually trust you.

A newsletter is the most direct trust-building tool you own. It isn’t an email. Email is how you deliver it, whether that’s via Substack, HubSpot, Kit, or whatever platform you happen to use. Those are plumbing.

Social media can introduce people to you. Search can help them find you. Your website gives them somewhere to learn more. But once someone subscribes, you can communicate with that person directly without depending on an algorithm to decide whether they see what you published.

The list is yours. More importantly, the relationship is yours.

And the newsletter itself can be the content. An article like this can be the newsletter. It can also live on your website, become several LinkedIn posts, provide ideas for videos, or be repurposed in whatever ways make sense.

Create one useful thing. Send it directly to the people who asked to hear from you. Then use the other channels to help more people discover it.

What should you write about? Marcus Sheridan built his pool business using a wonderfully simple idea that eventually became They Ask, You Answer: answer every single one of your customers’ questions honestly and openly.

Repeat.

That’s it.

The format matters far less than whether what you send is useful. A newsletter can be 100 words or 2,000. It can be one article, several short items, curated links, video, or some combination of all of them.

Once you have someone’s attention, don’t squander it. Show up regularly. Be useful. Earn the next open.

2. Personas

Who’s your ideal customer? Research and identify your ideal customer(s) and create a persona for each, complete with name, photo, and a bio.

Then focus your efforts on providing those people the information they actually need, delivered in the ways they’re most likely to consume it — email, video, social media, articles, or whatever else makes sense.

You don’t have to turn this into a six-week research project. You do need to know who you’re trying to help.

3. Useful Content; Various Formats

The customers of the company across the street may have customers who hate to read, but will watch hours of videos. Yours might love articles and newsletters and skip over video. Persona research will help you determine the method you use to deliver content — video, ebook, infographic, etc.

The content must be useful to be effective.

Create informative ebooks (which can be compilations of your existing content), infographics, videos, podcasts, case studies, how-to guides, presentations (like webinars), and more that you can use as lead magnets.

Don’t confuse “more content” with “better marketing.” One useful piece that answers a real customer question beats five pieces created simply because somebody told you that you need to post five times a week.

4. Social Media

Used well, social media is like pouring gas on a fire. Use social media to only push your product, and it’s like dumping cold, wet sand on your efforts.

The first and most important thing to keep in mind is that there’s no single “perfect” social media plan applicable for everyone. Your audience might be on Facebook and hate Instagram. Others might love Pinterest. And there will always be another app and social site.

Use social media to share useful information — yours and other people’s. I’m less interested today in rigid formulas about how many posts should be yours versus somebody else’s. Be useful. Be interesting. Participate.

Use social media to meet your customers. Social media is both one-to-one and one-to-many. When you answer a customer’s question in a social media space, you’re creating a relationship with that customer. Because of the public nature of social media, you’re also showing yourself as a helpful partner rather than a company just interested in selling to everyone else.

Develop a social media presence where your ideal customers congregate. Learn the rules for that particular channel. Then become a member of the community. Share good information. Be human. Don’t make a hard sell.

And remember what social is especially good at: distribution. It can introduce people to your thinking. Whenever possible, give those people a path toward a relationship you can continue outside the platform.

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5. Email Nurture Campaigns

Email remains the backbone of many great marketing strategies. There are dozens of ways to use email to nurture leads into becoming customers and to provide excellent customer service. A short list includes:

• Cart abandons. When someone goes to an action landing page (to register for a webinar, make a purchase, etc.) but doesn’t complete the desired action, create a short email sequence to nudge them to completion. If you’ve ever put a product in your cart and then not bought it, you’ve gotten one of these.

• New customer welcome. Create a sequence of emails over a few weeks to welcome a new customer, provide advice on how to get the most out of their purchase, invite them to join an online community (if you have one), and even upsell.

• Educational nurture. When a lead downloads an information asset (an ebook, for example) or attends an event (like a webinar), create an email sequence to share related articles, other content assets like infographics, and even third-party information that educates your lead. Gently insert offers later in the sequence to invite them for a call, a free trial, a discount offer, etc.

Help people. Follow up. Stay useful. Make an appropriate offer when the time is right.

And if you have a customer or prospect list sitting there mostly unused because you don’t have the time, system, or content to stay in touch consistently, you probably don’t need another marketing channel. You need to start using the audience you already have. If that sounds familiar, reply (bryant@simplyusefulmarketing.co) and tell me what’s getting in the way.

6. SEO — Search Engine Optimization

Search looks very different than it did in 2020. Traditional Google results now compete with AI-generated answers, social search, video, Reddit, AI assistants, and other ways people look for information.

But the useful part of the old advice survives: people still have questions, and you still want your business to be one of the places they find good answers.

SEO is a vast topic and an industry/profession of its own. But you don’t need to be an expert to take advantage of practical advice:

• Write for people first. Make the thing genuinely useful.

• Make it easy for search engines — and increasingly AI systems — to understand what the thing is about. That means using headings as well as having a sitemap for your website.

• Pay attention to the actual words and questions your customers use.

• Then stop trying to trick algorithms and go make something worth finding.

Get Going

The sooner you begin, the sooner you’ll begin to see success. Don’t overthink, but take the time to think through your objectives and create a strategy. Decide which marketing tactic you’ll begin with given time and/or budget constraints and go.

Six years after writing the original, I’d add one more thing.

Don’t let the number of things you could be doing prevent you from consistently doing a few useful things well.

You do not need every channel. You do not need every tactic. And you definitely do not need to rebuild your marketing every time somebody announces that everything has changed.

Because they haven’t.

Comments, criticisms, and witticisms welcomed.

Love to hear your thoughts!

If your problem isn’t knowing that you should be marketing but finding the time, consistency, or extra pair of hands to actually get it done, that’s the kind of problem I help solve.

Reply to me, bryant@simplyusefulmarketing.co, and tell me what keeps falling off your marketing to-do list. If there’s a sensible way I can help, I’ll tell you. If there isn’t, I’ll tell you that too.

MUSICAL CODA

Edited while listening to one of Tom Petty’s best albums.

The only digital point of connection you own with your customers is their email address.1

If you still think Facebook or LinkedIn or Instagram or insert-your-favorite-platform-here shows everything you share to everyone who follows you . . . well, no. They don’t.

The platforms decide who sees what, generally based on algorithms designed to predict what will keep each user engaged.

And the numbers can be brutal. One 2025 analysis of brand accounts found the average Instagram post reached about 3.5% of followers. Facebook was roughly 1–2%.

These are essentially advertising platforms masquerading as community platforms. We are their product, not their customer. Their customers are the advertisers trying to reach us.

Use them. I do. Just don’t confuse having followers with owning a way to reach them.

Email gives you that.

Trust

I’ve written about trust endlessly because it’s the foundation for nearly everything in your marketing.

Show up, be useful, repeat — and familiarity becomes trust. Repetition helps people remember you exist and builds trust that shifts them from prospect to customer.

Trust isn’t a hazy, granola-munching, tree hugger feel-good intention. It’s measurable, and it’s a multiplier. Customers spend more. The market forgives mistakes faster.

This is why I’m annoying about newsletters. They aren’t magic, but the impact on your business can be magical. A newsletter is a concrete strategy to own your customer relationships. It’s where you show up consistently, using plain language, about what you actually heard from your customers, until familiarity becomes trust, in a channel nobody can take away from you.

And trust has an ROI of its own.

Sales

I believe marketing needs to be useful and helpful. I also believe you do that — in addition to being a good human being — so that you can make more sales.

Marketing has to make a business money, directly or indirectly.

We just covered indirectly. Now the direct part.

Email lets you sell through:

• Links to relevant products and offers inside a useful newsletter.

• Direct promotional emails — new products, services, special offers, coupons, events.

• Nurture sequences that move someone from interested to ready to buy.

• Abandoned-cart emails for ecommerce.

• Reorder, replenishment, renewal, or expiration reminders.

• Win-back campaigns to customers who haven’t bought from you lately.

• Post-purchase cross-sells and upsells.

You’ve already done the hard part: earned access to someone who knows your business. Email gives you repeated opportunities to turn that existing relationship into revenue.

The Research That Backs This Up

You’ve probably seen some version of this statistic if you’ve done any research into email marketing ROI: email generates $36 for every $1 spent.

Is $36 precisely correct for your business? Of course not. But is it a good shorthand way to show how valuable email can be? As the Kool-Aid Man would say, “Oh, yeah!”

Litmus surveyed nearly 500 marketers for its 2025 State of Email research. Thirty-five percent reported returns between $10 and $36 for every $1 spent, another 30% reported $36 to $50, and 5% reported more than $50. Newsletters were the highest-ROI email type reported by both direct-to-consumer companies and agencies/professional services.

The UK’s Data & Marketing Association landed in almost exactly the same neighborhood. Its 2026 Marketer Email Tracker, based on responses from 250 marketers across sectors, reported £40.96 returned for every £1 spent.

Now, specifically on newsletters: HubSpot surveyed more than 400 newsletter professionals for its 2025 State of Newsletters report. Twenty-five percent said their newsletters had produced substantial profit growth over the previous year, and 45% expected newsletter profits to increase significantly over the next 12 months. The primary way those newsletters made money was by marketing products, services, or memberships inside the newsletter itself.

Content Marketing Institute gives us another newsletter-specific data point from outside the email-platform world. In its 2026 B2B Content and Marketing Trends research, 1,015 B2B marketers ranked email newsletters as the second-most effective channel for distributing thought leadership: 54%, behind only LinkedIn at 76%.

Different surveys. Different methodologies. Different numbers.

Same conclusion.

Email makes businesses money. And newsletters are one of the ways it does it.

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Collection

You have to get your customers’ emails.

This can become complicated, but it doesn’t need to be to start.

Ask at the point of sale. Whether you have a physical register, online checkout, appointment desk, or service counter, simply ask customers if they’d like to receive useful information and offers from you. Bare bones: a sign-up sheet in a notebook or clipboard will do.

Put signup opportunities on your website. Homepage. Footer. Checkout. Booking confirmation. Contact forms. Don’t make someone hunt for the privilege of hearing from you again.

Give them a reason. A discount works. So does early access, a genuinely useful guide, a loyalty program, useful tips, or information customers actually want. DMA’s 2026 research found discounts and offers were the strongest signup driver, but useful information, loyalty programs, email receipts, and brand trust all worked too.

Use the physical world. QR codes on receipts, packaging, counter cards, invoices, menus, event signage — anywhere customers already interact with your business.

You don’t need every email address.

You need to steadily collect email addresses from people who already have a reason to care about you — and then give them reasons to keep caring.

Facebook, LinkedIn, Instagram — use them. They’re useful places to find people. Just remember whose land you’re building on. The goal is to turn rented attention into a relationship you can keep. Collect the email address. Send something useful. Keep showing up. Make offers when you have something worth selling. Repeat. You don’t need a giant list. You need customers who know you, trust you, and can hear from you when you have something worth saying without letting the algorithm decide who gets to hear from you.

If you have customer emails sitting in a spreadsheet, CRM, or point-of-sale system and know you should be doing more with them, you don’t need a giant marketing plan. You need a useful reason to show up in their inbox consistently. That’s what I build with my Newsletter-in-a-Box service. Drop me a line, tell me where your sticking points are, and let’s figure out how a newsletter fits into your marketing plans: bryant@simplyusefulmarketing.co.

Marketing is simple. Not easy — but not as complicated as the people selling you solutions want you to believe.

I’ve spent 30 years in and around publishing, editing, and marketing. I’ve seen trends arrive with fanfare and then slink off into the underbrush. Beneath it all, the same handful of fundamentals keep helping smart businesses grow.

I’ve written about each of these eight fundamentals individually or within other posts. Here, I’m putting them all in one place and how they flow, connect, and support each other.

Before getting to these eight fundamentals, here’s a challenge marketers in every industry face — over-focusing on a hot new trend and leading with that rather than how what they do benefits their customer.

Every Industry Has Its Version of “The Cloud”

We often over-hype the new while ignoring the basics of what it is you actually do.

Back in the mid/late 90s, ASP (application service provider) was a topic I started covering. That morphed into software-as-a-service (SaaS) by the mid-2000s and we all know it as the cloud/apps today.

The problem isn’t this ongoing shift, which reflected real changes in the underlying technology. It was watching product marketing focus on the delivery method (which is, at root, what this is — the software sits on someone else’s servers rather than your own in-house infrastructure) rather than the benefits of the product they actually sold. I’d spend half of some product briefings listening to the cloud provisioning strategy before hearing anything about how the product helped the customer.

I thought that was stupid at the time. Since then, I’ve learned more about marketing and think it’s even dumber. Now, there are benefits to provisioning your IT stack differently and there were some vendors doing good market education around that.

But the general vibe was still “this is new and sexy so lets focus on that.”

Just about a decade ago, same thing happened with RPA (robotic process automation). It’s a genuinely useful functionality (that, honestly, I only vaguely understand), but limited. Industry vendors with products even tangentially connected to RPA slapped it all over their product marketing.

Today they’re doing the same thing with AI. New buzzword, same feature set.

Every industry has its version of “the cloud:” something shiny enough to distract you from the simple, consistent work that actually drives results. Yours does too. Maybe it’s a platform, a format, an algorithm change, whatever a guru tweeted this morning.

The cost of chasing the shiny thing isn’t only money. Every time you chase the new thing, you abandon the compounding you’d started somewhere else and go back to zero. Most new tactics aren’t new anyway — they’re either distractions or old lessons applied to new delivery methods. The fundamentals underneath haven’t changed: identify a customer problem, solve that problem, keep doing it.

The rest of this piece is those fundamentals, which are kinda boring. Not boring? Watching your business — and bank account — grow.

Nobody Cares About You

The first fundamental is the hardest one for most businesses to swallow: 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.

That’s not bad news. It’s liberating.

In the late 2000s I co-created a sponsored webinar program that’s still running today. My job was to host, recruit an expert speaker, and prep the sponsor — who got five minutes and a shot at the Q&A. I gave “the talk” to 60 or so sponsors over five years. One of my regular speakers named it that over beers at a conference, and it stuck.

The talk went like this: No one cares about you. Nobody registered to hear how wonderful your product is — your logo is already on the registration page; they know you sell something. They’re here to understand a problem they have. Lead with useful information, not speeds n’ feeds.

Most sponsors listened. About 20% didn’t.

We surveyed every attendee as each webinar closed. As best I remember the numbers, overall event approval ran about 4.5 out of 5. Sponsors who followed the talk landed slightly under that. Sponsors who ignored me and did their usual song and dance? Ratings tanked, with comments like “awful sales pitch at the start.”

Same stage. Same audience. Same amount of speaking time. The only variable was whether they made themselves the hero or the customer the hero.

Every word of your marketing does one or the other. Choose the customer. The irony is, when you stop shouting about yourself, people usually start listening.

Shut Up and Listen

If nobody cares about you, the obvious question is: what do they care about? And the answer isn’t in a brainstorm. It’s not in a competitor’s blog. It’s in your customers’ mouths, and too many businesses never bother to pay more than lip service to listening.

The most popular post for one of my copier clients wasn’t written by a me or my team. It was written by one of their repair techs, about formatting tips in Word for better copies. It wasn’t an idea I ever would have thought of. He could — because he spoke to customers daily and knew this was a real challenge for them. That one post led to a string of sales opportunities.

That’s what listening gets you (including me listening to MY client). The questions your customers actually ask — the ones your techs, your support staff, your salespeople hear every single day — are your content strategy, sitting right there, free. The experts are already in your office. The problems are already in your inbox. You don’t have to guess what to write; you have to stop guessing and start paying attention.

Listening also hands you the customer’s language. Not your industry’s word salad — the words they use to describe their own problem. Use their words back to them and something happens that no amount of clever copy can fake: they feel understood. The company that stands out is the one making the customer feel understood.

Everything downstream of this — what you write, how you say it, what you offer — is only as good as what you heard first.

Write Like a Human

Once you know what the customer’s problem actually is, the next question is how you talk about it. And here’s where smart people sabotage themselves: they reach for clever.

I’ve spent the first 20 years of my career around people who are brilliant but terrified to sound unprofessional — like if they use “use” instead of “utilize,” the business gods will smite them. So they default to jargon, buzzwords, and meaningless platitudes, and end up sounding exactly like everyone else.

Clever feels safer than clear. Clear language is specific, and specific pins you down. “We help small B2B firms get more repeat customers from their existing list” is measurable — someone can come back in six months and ask whether it happened. “Empowering digital transformation through next-generation solutions” is slippery. Nobody knows what it means, which means nobody can hold you to it. That’s the appeal. Jargon isn’t a vocabulary problem, it’s a hiding place.

Clever is writing to impress. Clear is writing to be understood.

I wasn’t immune either. For years I curated an ECM newsletter for a professional association, and I’d periodically swap the plain, “here’s what’s inside” subject line for a clever one that made me giggle. Got my teeth kicked in nearly every time. Opens down. Shares down. Click-throughs down. And like a goldfish bumping its nose on the other side of the bowl, a month or two later I’d think “THIS time it’ll be different.” Never was. I was trying to show how smart I was instead of helping my readers.

It’s not just me. Mailchimp’s analysis of 40-plus million emails found the highest open rates went to the dry, descriptive stuff — the “{Company} January Newsletter” type of subject line. Plain-language research points the same direction: rewrite copy in plain English and comprehension and retention both climb. My giggle-inducing subject lines were losing to the most boring construction available.

Clarity is credibility — if you need to look up a word before putting it in your marketing, your customer will too, and that friction kills decisions.

I do my best to write at an 8th grade level because it’s easy to digest.

Write like yourself. Focus on being useful over being great because great can cause you to freeze up while useful feels like swapping stories over beers.

Plus, this isn’t 8th grade English class. Nobody’s grading your prose or grammar. They’re asking, “did this help me?”

Consistency Compounds

So you’re solving the customer’s problem, in plain language, based on what they actually told you. Now you have to keep doing it. This is where most marketing dies.

“Making money IS sexy. It’s never boring.”

That’s Baron Gemmer, who owns an ECM consultancy, answering me at an AIIM conference 13 years ago when I complained that the industry’s marketers chased sexy over the boring stuff that works. His line has stuck with me ever since, because it reframes the whole thing: the work is boring, but the results never are.

One post doesn’t change anything. A hundred posts do. Do the things. Do them again. Repeat. If there’s a secret sauce, that’s it.

There’s psychology underneath this, not just grit. Familiarity drives preference. When the stakes are high, people don’t hunt for novelty — they choose what feels known. Familiarity lowers perceived risk and makes decisions easier, especially when no option feels perfect. Repetition builds recognition. Recognition becomes comfort. And comfort is what people reach for when it’s time to choose.

And consistency compounds in a second way: the content itself is an asset. Two blog posts I wrote for copier clients — about how to remove a black line from a copy — sat at the top of Google’s results for years. Neither was clever. Neither was optimized by some SEO sorcerer. They answered a question real customers were asking repair techs, and they generated traffic and leads for a decade. That’s what you miss when you’re always eyeing the next tactic.

Look at any platform. Big launch, heat and noise, then a steady decline to a dribble. How many Substacks have 3 or 14 or 20 posts and then... nothing? People quit before boring pays off.

You don’t need to go viral. You need to stay visible.

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Trust Is the Conversion Strategy

Here’s what all that consistency is actually building. Show up, be useful, repeat — and familiarity becomes trust. Trust becomes the reason people remember you when they’re finally ready to buy.

That always felt a little squishy to me — linking trust to revenue. So I went looking for the research. Turns out the numbers aren’t subtle.

PwC (2024): 46% of consumers purchased more from companies they trust; 28% paid a premium; roughly 40% walked away after trust broke. BCG’s Henderson Institute found the 100 most trusted companies delivered about 25% compound annual shareholder return from 2019–22 — against 10% for the global index. That’s 2.5x.

And it’s not just an enterprise phenomenon. Datamax Texas, a former client, is a copier company — an industry often trusted at roughly used-car-dealer levels. They focus on creating “Raving Fans,” measure it relentlessly, and have averaged a 93.2 on their NPS-style score since 2012. Nine out of ten customers willing to recommend a copier company, because they do the basics: communicate, fix issues, train their people. They bake trust into their business model.

Trust isn’t a fuzzy halo. It’s measurable, and it’s a multiplier. Customers spend more. The market forgives mistakes faster.

Executives consistently overestimate how much of it they have, by the way — PwC found 84–95% of executives believe customers highly trust them, while only 27–52% of customers agree. Don’t delude yourself. Trust has to be earned, day after day after day after day.

Don’t Build on Rented Land

If trust is the asset, the next question is where you keep it. And here’s one of the truths of today’s Internet: everything you build on a social platform, you build on rented land.

You don’t own your audience on LinkedIn, Facebook, Instagram, TikTok, or here on Substack. You borrow them. One algorithm “improvement,” one policy change, one throttled reach, and the attention you spent years earning evaporates. Google’s doing its version too — using everyone’s content to answer queries on the results page so nobody has to visit the site that created it. You. Are. Not. In. Control.

Use the rented land — it’s a great place to meet people and amplify what you do. But you want to own the relationship, and the only digital relationship you own is the email address someone hands you. It’s direct, one-to-one, and permission-based. You decide when to send. They decide when to read. No middleman, no panic when the platform moves the goalposts.

This is why I’m annoying about newsletters. Not because newsletters are magical. A newsletter isn’t one tactic among many. It’s what owning the relationship looks like in practice — the place you show up consistently, being useful in plain language, about what you actually heard from your customers, until familiarity becomes trust, in a channel nobody can take away from you.

As I was editing this, I realized that last line is overblown a little bit. To send emails, we all rely on one of the various email delivery platforms. If you repeatedly send spammy content, email as a channel can be taken away from you. However, you aren’t spammy, right? So not a problem for you.

Ask for the Sale

Marketing needs to help deliver revenue. While educating the customer is foremost, we all need revenue to stay in business.

So: ask for the money.

I saw a post recently that I mostly agreed with — stop buying $500 courses from people who’ve never built anything, tell the truth — right up until the line “drop the funnel.” No. Drop the bullshit smeared all over funnels — the fake scarcity, the countdown timers on offers that never expire, the 47-minute webinar that’s the online version of a 70s Tupperware dinner party. But everyone making fun of funnels has one. They just call it “ecosystem” or “customer journey.”

At some point a stranger discovers you, decides you’re worth paying attention to, and decides you’re worth paying. That mechanism is a funnel. Renaming it doesn’t change what it does.

A funnel is three stages: someone finds you, someone starts to trust you, someone buys from you. The problem with the gross ones is they skip the middle — the trust part — and substitute psychological pressure for it. Stranger to “buy my $997 thing” in 48 hours.

But if you’ve done everything above — listened, shown up, been useful, earned trust over months — a clear offer is just the next thing that happens. Not a hard sell. A clear one. “If you need help with this, here’s what working with me looks like.” A sentence or two. After you’ve spent months being useful, saying “I also do this for a living” isn’t manipulation. It’s running a business.

A funnel built on manipulation deserves scorn. A funnel built on being useful is just commerce working the way it always has.

Play the Long Game

Last fundamental, and it’s the one that decides whether any of the others get a chance to work: time.

Content marketing usually starts showing results in about 9 months from when you begin. Sometimes sooner, sometimes later, but 9 months is the sweet spot — based on research and my own experience with clients. That’s not dragging out a retainer but how trust-building actually works.

Back in 2015, as content marketing slid down Gartner’s Hype Cycle, Velocity Partners dubbed the Trough of Disillusionment the “Orange Spot of Oh Shit” — that moment when all the hype collided with the reality that this stuff was harder than it looked. Early excitement gives way to frustration before long-term results kick in — and most companies give up in that dip. Which is precisely when they should double down. 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.

Then there’s the ongoing efforts that makes 9 months look like nothing.

John Deere published the first issue of The Furrow in 1895. A farming magazine, from a tractor company. It’s still going. Five years later, Michelin started handing out a guide to good restaurants — because if people drove further to eat well, they’d wear out more tires. The Michelin Guide is now the global signal of excellence in cooking, and it’s still running too. Neither one was a campaign. Neither one was clever. Both were built on the same premise: help your customer with something they actually care about, and keep doing it.

You don’t need a century. Marcus Sheridan saved his pool company during the 2008 crash by answering customer questions on his blog — including the one every competitor refused to touch, what a pool costs. He traced $2 million in sales to that single post.

Same fundamental, three different centuries.

Patience isn’t passive. It’s the discipline to keep going when the numbers say you shouldn’t. And it’s only sane if you believe the underlying premise: that helping people is the way to earn their business. If you don’t believe that, none of this works — the moment marketing asks you to choose between being helpful and being impressive, you’ll choose you, and the whole thing collapses.

Nobody’s going to hand you permission to start. There’s no better month, no cleaner quarter, no timeline where this suddenly gets easy.

There’s just the next thing you publish, and whether it helps somebody.

Marketing is a promise you keep — over and over — until people believe you.

Do the work. Be worthy of the belief.

Nine months from now, you can still be meaning to get consistent with your marketing — or you can have nine months of useful content, an audience that knows you, and an email list you own behind you.

If you want the second version without adding another recurring job to your week, that’s what Newsletter-in-a-Box is for. I’ll help you turn what you already know into a useful newsletter and get it out the door consistently.

Learn about Newsletter-in-a-Box here or email me at bryant@simplyusefulmarketing.co.

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

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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.