Stop Treating Content Like a Subscription You Keep Forgetting to Cancel

You know that agency you hired. The one with the slick deck, the smiling account rep, and the promise that they'd "handle your content." Six months in, you've got a grid that looks vaguely on-brand, a handful of posts celebrating International Coffee Day, and a monthly report full of impressions that somehow never translate into anything that resembles revenue. You're paying $5,000–$10,000 a month for logo-on-template work, and somewhere in the back of your head, you know it's not working — but you also don't have time to deal with it, so the invoice keeps getting approved.

If that hit a little close to home, good. Keep reading.

Because the real problem isn't the agency. The real problem is the way you're thinking about content itself.

Most founders running a $5–$10 million business treat content like a necessary evil — something you bolt onto the side of the business, like a gym membership you renew every January and use twice. A marketing tax you pay to feel like you're keeping up. The result is that you're constantly stressed about it, constantly behind, constantly spending money on it that you can't quite justify, and never quite sure if any of it is actually doing anything.

Here's what I want to propose instead: content isn't a marketing line item. It's infrastructure. It belongs in the same conversation as your people, your systems, your equipment, and your real estate. It's not the logo decal on the side of your van. It's the engine.

And once you start treating it that way, the whole math changes.

The Trust Economy Is Coming For Your Competition (Let It)

Gary V was right: attention is the currency of this era. But attention was just the ante. The real game has always been trust — and trust is about to become the scarcest resource on the internet.

We are living through an AI content explosion. Every business, every "thought leader," every guy who just read a book about thought leadership is now mass-producing content at scale. It's everywhere. It all kind of sounds the same. And increasingly, your customers — who are not idiots — can feel the difference between something that was genuinely crafted and something that was generated, lightly proofread, and scheduled.

The pendulum always swings back. And when it does, the brands that built something real — real voice, real perspective, real expertise — will have an almost unfair advantage over everyone who spent the last five years playing the quantity game.

This isn't a distant prediction. It's already happening in your own buying behavior. Think about the last time a piece of content actually made you trust a business enough to pick up the phone or book a call. It wasn't the third post in a row about their company values. It was something that felt like it was written by a human who'd actually lived through the problem you're having right now.

That's what you're building toward. And you're behind — which is fine, because most of your competitors are even further behind, burning budget on Scottish Kilt Day posts and wondering why nothing is working.

The Timeless Triangle Nobody Talks About in the Content Strategy Deck

Here's what the digital-first crowd conveniently forgets: the reason people buy from people hasn't changed since before anyone had a website.

Think about the shoemaker on Main Street. You went to him for three reasons. He was genuinely good at his craft — you'd seen the work, you trusted the product. He was present in your world — nearby, accessible, part of the fabric of your daily life. And he was connected to your community — his daughter went to school with your daughter, you saw him at the same church, you were neighbors in the truest sense. Those three things — craft, proximity, and relationship — created a bond of trust that no competitor could easily break.

Nothing about that dynamic has actually changed. What's changed is the geography.

Your Main Street is now a scroll. Your community is now a niche audience scattered across LinkedIn, a subreddit, and an industry Slack group. Proximity doesn't mean being down the block — it means showing up consistently in the places where your people already are, so often and so usefully that you become part of their world. And craft? Craft still matters. Maybe more than ever, in a world drowning in content that was clearly generated in forty seconds and scheduled by a bot.

Your content strategy, done right, is how you build all three sides of that triangle in a digital world. It's how you demonstrate craft, create proximity, and earn the kind of relationship that makes you the obvious first call when the problem gets serious enough to spend money on.

Donald Miller put it cleanly in StoryBrand: the customer is the hero. You are the guide — Yoda, Morpheus, the grizzled mentor who's been where they're trying to go and can show them the path. The moment your content stops being about how great you are and starts being about how well you understand their journey, everything clicks.

The shoemaker didn't take out ads about how many shoes he'd made. His craft was visible. His presence was felt. His community did the marketing for him. That's the model. You just have to rebuild it for the scroll.

Your Customers Aren't Searching for You. They're Searching for Their Problem.

Here's the insight that most businesses miss entirely: your customer doesn't know they need you yet. They know they have a problem. They're Googling the problem. They're describing the problem to an AI. They're venting about the problem in some industry subreddit at 11pm while their spouse watches something they're not interested in.

The words they use in those moments are not the words in your pitch deck. They're messier, more frustrated, more specific. And those words — the raw, unfiltered language of the problem — are what should be living on your website, in your headlines, and throughout everything you publish.

So how do you find those words? You talk to your actual customers. You read your reviews and your competitors' reviews. You go where your customers go — the forums, the Facebook groups, the Reddit threads — and you collect the unfiltered, unpolished language of people who have the problem you solve. Then you mirror it back.

When someone lands on your website and feels like you've read their mind, that's not magic. That's research turned into craft. And it's the foundation of content that actually converts.

The Brutal Math of "Just Do More Content"

Let's put some real numbers on the spray-and-pray approach, because this is where a lot of founders get stuck.

Option A: Build an in-house content team that can produce quality, consistent output across multiple channels. You're looking at $20,000–$30,000 a month, minimum. For a $5–$10M business, that's a significant percentage of your revenue going to a function that most of your team still considers a "nice to have."

Option B: Hire one of those smaller agencies — the ones that are actually affordable and show up in your inbox three times a week. You're spending $5,000–$10,000 a month. What you're getting is Canva templates with your logo on them, a content calendar full of industry "holidays," and a monthly call where someone very enthusiastic explains why your engagement is up 12% this month (on posts that nobody who could actually buy from you ever saw).

Neither of these options is stupid. They make sense in a world where content is a marketing cost center — something you're spending on to maintain visibility. But that's the wrong frame.

I spent years working on television campaigns for major brands. We would spend six months and millions of dollars developing a single 30-second commercial that would run for a few weeks and then disappear forever — licensing restrictions on the locations, the talent, the music meant it couldn't even live in an archive. Create, spend, vanish. That cycle made little sense even when broadcast reach was everything.

It makes zero sense now. Not for the Fortune 500, and definitely not for you.

When content is disposable by design, you're on a treadmill that goes nowhere. You're not building anything. You're just spending to stay in place, burning your team out, and quietly dreading the next content planning meeting.

The 95/5 Rule: Most of Your Content Should Age Like Wine, Not Milk

Not all content is created equal. Some content is inherently timely — a reaction to a news story, a take on something trending in your industry, a moment-specific post that makes sense right now. That content has its place.

But it should represent about 5% of what you produce. The other 95% should be built to last — content that answers the enduring questions your customer will still have three years from now, that captures your genuine point of view on problems that don't go away with the news cycle, that earns a bookmark instead of a scroll-past.

You've seen the alternative in your own feed. The automated tools pushing out a cheerful graphic for every obscure holiday — Flag Day, International Bagel Appreciation Week, that one where you're supposed to celebrate your coworkers with an emoji. Nobody is calling their accountant because they posted a graphic about World Emoji Day. That's not a content strategy. That's anxiety dressed up as activity.

The businesses winning the content game right now are the ones treating their best content like catalog assets — pieces that get repurposed, rerun, extended, and built upon, rather than retired the moment they fall off the front page of the feed.

Content That Compounds: The Stranger Things Model

Here's the investment framing that actually changes behavior.

Some investments are like government bonds. They're safe, they return a modest 3%, and in 30 years you'll have a small, respectable pile of money. Some content is like that — it performs fine, gets some traction, does its job. Good enough.

Other investments are like holding Apple stock from 2001. Modest inputs, dramatic compounding, and thirty years later you're in a different category entirely. That's the content that hits — that resonates so deeply with your audience that it gets shared, referenced, rediscovered, and built upon for years after you originally posted it.

There's a reason Netflix asks, "Are you still watching?" Stories compound. You don't binge because of one episode. You binge because of arcs. Depth. Familiarity. Investment. A show like Stranger Things didn't just tell a story — it grew with its audience. The original cast literally aged on screen. New viewers discover Season 1 years later and feel like they've entered something alive, not something archived. The content didn't expire. It deepened.

That's compounding content. And it's not reserved for prestige TV.

In business, compounding content looks like this: a consistent point of view developed over years. Frameworks refined publicly. Ideas tested, challenged, and strengthened through real conversations. A body of work that signals depth — not trend-chasing, not algorithm-gaming, but the kind of accumulated credibility that takes time to build and is almost impossible to fake.

Authority is often just tenure plus consistency. You may be wrong sometimes. You may have hot takes that age poorly — you look back two years later and either cringe or feel like Nostradamus. That's fine. What compounds is the pattern of showing up. A framework you develop today becomes the backbone of your sales conversations for years. A podcast episode recorded this month gets discovered by a perfect-fit client in 2028 when they search for exactly the problem you solved in it. The publications that have been writing about the same industry for twenty years aren't always the most brilliant. They're the most present. Tenure is a form of trust that can't be faked or bought — only earned over time.

Your Content Is Ignoring Half Your Business

Most content strategies only aim outward. You make content to attract customers, build brand awareness, generate leads. That's the whole conversation.

But here's what nobody talks about: the same human beings who are scrolling their phones, conditioned to process information in 60-second bursts, trained by a decade of TikTok and YouTube to have the attention span of a golden retriever at a tennis ball factory — those are also your employees. That's your sales team. That's your ops manager. That's the new hire who needs to get up to speed.

And yet most businesses still communicate internally like it's 2004. Long email chains. Meeting agendas nobody reads until 30 seconds before the meeting. Standard operating procedures buried in a Google Drive folder that hasn't been opened since the Obama administration.

What if you applied the same communication intentionality inside the business that you're (trying to) apply outside it? Short, clear, purposeful. Designed to actually land. Documented in a format people will actually consume.

This is content not as a marketing function but as an operating system. And it leads directly to the thing most founders say they want and almost nobody actually builds: a business that can run without them in it every single hour of every single day.

The Part Where Your Content Becomes an Asset You Can Actually Sell

Now we get to the layer that almost nobody is talking about, and it might be the most valuable piece of this entire conversation.

Every framework you develop. Every training you build. Every process you document. Every piece of institutional knowledge that currently lives only inside your head or the heads of your two most senior employees — that's intellectual property. And right now, for most businesses, it's invisible. It exists, but it's not organized, it's not accessible, and it's definitely not compounding.

Here's what happens when you start treating that knowledge base like an asset: it becomes the infrastructure for a business that scales without you. New locations can be stood up faster because the playbook is documented. New hires get up to speed in days instead of months because the training exists in a format they can actually use. Clients onboard more smoothly because the process is captured and repeatable.

And — this is the part that's worth sitting with — when it comes time to sell, to step back, to bring in a partner, or to finally take a vacation that doesn't involve checking Slack every four hours: the business has a brain that lives outside of you. That's not just operationally valuable. That's what the multiple on your sale price is made of. Businesses that run on documented systems and institutional knowledge get better valuations than businesses that run on the founder's memory and availability. Full stop.

There's also the AI dimension, which is no longer a future consideration. The difference between an AI assistant that makes your business smarter and an AI assistant that just confidently says wrong things is what you feed it. Garbage in, garbage out. An AI trained on a rich archive of your actual thinking, your real customer language, your processes, and your principles will produce outputs that sound like you and solve real problems. An AI with no knowledge base is just hallucinating in your brand colors.

Build the knowledge base. It's your competitive moat, your succession plan, and your AI training data all in one.

Information Is Everywhere. Transformation Is the Point.

Remember when the internet was supposed to solve everything? The thesis was that poverty, conflict, and ignorance were essentially information problems. Give people access to knowledge and watch the world improve.

We now have all of human knowledge in our pockets, and the world's problems are largely still intact. It turns out information without context, relevance, and a path to action is just noise with better distribution.

The same is true for your content. A great content library that nobody acts on is an expensive archive. The measure of content that matters isn't how many people saw it. It's how many people did something different because of it. Did they call? Did they buy? Did they refer someone? Did they change how they think about a problem in a way that made your solution the obvious answer?

That's the standard. Not impressions. Not engagement rate. Not the number of posts this month. Transformation.

So What Does This Actually Look Like?

You start by deciding that content is infrastructure, not overhead. That decision changes the budget conversation, the time conversation, and the priority conversation.

You get ruthlessly specific about who you're talking to — not "business owners" or "professionals," but the exact person with the exact problem you solve best. You learn their language by actually talking to them and reading what they write when they think nobody important is watching.

You build your content around pillars that reflect the real, enduring problems your customer faces. You produce less than you think you should, but you make it count. You build a repurposing system so your best work gets extended, not retired: a post becomes an article, an article becomes a video, a video becomes a module, a module eventually becomes a product.

You document internally as you go. Every meeting, every process, every client conversation is raw material for a knowledge base that makes your business less dependent on any single person — including you.

And you play the long game. Because the businesses that show up consistently, stake out genuine positions, and build a real body of work over time will have an almost insurmountable advantage over the ones still publishing Scottish Kilt Day graphics and hoping the algorithm changes in their favor.

The Window Is Still Lit on Main Street. Make Sure Yours Is.

The shoemaker analogy holds up because the fundamentals haven't changed. People still buy from people they know, trust, and feel connected to. What's changed is the geography — your Main Street is a scroll, your community is a niche, and proximity now means showing up in the right places with something worth paying attention to.

The businesses that win the next decade won't be the ones who posted the most. They'll be the ones who built the deepest trust — with customers, with their teams, and with the systems that let them actually step away from the business without everything quietly falling apart.

Your content is either building that or it's burning your budget trying to. The only question is which one you're going to decide it should be.