Why Most Marketing Fails in an AI World

9 min readOct 30, 2024

Last week, a CEO showed me his company’s latest marketing campaign. The design was flawless. The copy was crisp. The targeting was precise. By every conventional measure, it was perfect.

It also felt completely empty.

This emptiness isn’t unique. HubSpot’s Brian Halligan has observed that fundamental shifts in how people shop and buy have broken the traditional marketing playbook. The old rules — focusing purely on optimization, following best practices, copying what worked before — don’t create meaningful differentiation anymore.

Look at what’s happening in the market:

Generic “thought leadership” content floods every channel (including, if I’m honest, some of my early attempts that still make me cringe)
Template-driven marketing creates a sea of sameness
Best practices have become common practices
Tactical excellence yields diminishing returns
Audience trust continues to erode

We’re caught in what I call the Optimization Trap: Getting better and better at things that matter less and less. And believe me, I’ve optimized my way right into that trap more times than I can count.

Consider HubSpot’s own evolution. They didn’t just create better marketing software. They created an entirely new category called “inbound marketing.” While competitors were optimizing outbound tactics, HubSpot challenged the fundamental assumptions about how marketing should work. They didn’t just sell a tool; they sold a transformation in how businesses could attract and engage customers.

The Three Fatal Flaws of Modern Marketing

The Commodity Cycle
Most marketing focuses on what you do rather than why it matters. Take a look at any industry — marketing agencies, consultants, software companies — and you’ll see the same claims repeated across every website. “We help businesses grow.” “We drive results.” “We deliver solutions.” When everyone says the same thing, even saying it better doesn’t help you stand out.
The Pattern Problem
Watch how quickly effective marketing approaches become diluted. Remember when “swipe up” Instagram Stories felt novel? Or when behind-the-scenes content seemed fresh? The moment something works, it gets copied, templated, and optimized until it loses all impact. I see this in my own industry. Frameworks that worked brilliantly for early adopters become increasingly ineffective as they get repeated and repurposed.
The Trust Gap
When everything is optimized for conversion, nothing feels authentic. Audiences develop pattern recognition and tune out anything that triggers their “marketing speech” detector. Think about your own behavior. When was the last time you clicked on a “limited time offer” or responded to a “schedule a call” button? We’ve become blind to these optimized approaches.

Breaking Free: The Human Advantage

The solution isn’t to compete in the optimization race. The solution is to play an entirely different game. Here’s how the landscape is shifting:

Old World:

Focus on tactics and techniques
Optimize for short-term metrics
Scale through automation
Build based on best practices
Differentiate through features

New World:

Focus on insight and impact
Optimize for long-term trust
Scale through human connection
Build based on core beliefs
Differentiate through perspective

Take HubSpot again. While their competitors were optimizing email templates and lead scoring algorithms, HubSpot was teaching businesses to think differently about their entire approach to marketing. They didn’t just sell software — they sold transformation.

This shift isn’t just theoretical. I’ve watched businesses transform their market position by making one fundamental change. They stopped trying to be better and started being different.

Consider Basecamp’s approach. While every other project management software company talks about features and functionality, Basecamp talks about calm. They don’t compete on having the most integrations or the fanciest automation. Instead, they take clear stands against the chaos of modern work culture. They’ve built their entire brand around a philosophy, not just a feature set.

The Five Principles of Human-Centric Marketing

Truth Over Technique
Share real insights from real experience. I’ve learned this lesson repeatedly: my most impactful content isn’t when I’m following best practices — it’s when I’m sharing hard-won insights from actual experience. Even my failures have become valuable assets because they’re authentically mine.
Clarity Over Cleverness
Don’t try to sound smart. Try to make sense. The best marketing doesn’t impress people — it helps them understand something they’ve always felt but never had words for. Look at how Basecamp’s Jason Fried writes about work. He doesn’t use jargon or buzzwords. He simply articulates what everyone’s thinking but no one’s saying.
Conviction Over Conversion
Stand for something bigger than your business. Watch how Patagonia operates. They don’t just sell outdoor gear — they fight for environmental conservation. Their marketing isn’t focused on optimizing conversion rates. It’s focused on living their values. And paradoxically, this commitment to something bigger than sales often drives more sales.
Context Over Content
Don’t just share information — share understanding. This shift is crucial in an AI world. Any tool can generate content, but only humans can create context. Only you can help people make sense of their challenges in a way that’s meaningful to them.
Connection Over Perfection
Build real relationships with real people. I’ve seen this in my own business. My perfectly optimized emails get decent results. But my honest, personal messages — even with typos — often generate the deepest connections and best opportunities.

The Implementation Challenge

Here’s where most businesses stumble. They understand these principles intellectually but struggle to implement them. They know they need to be different but fear stepping away from proven approaches.

I get it. I spent years in that same trap. Every time I tried something different, I’d get nervous and revert to “best practices.” But here’s what I’ve learned. The risk isn’t in being different. The risk is in remaining the same in a world where sameness is a death sentence.

Moving From Theory to Practice

I watch businesses struggle with this transition every day. They nod along with these principles, maybe even pin them to their office walls, but then immediately revert to safe, templated approaches when it’s time to execute.

Let me show you why this happens — and more importantly, how to break free.

The Marketing Courage Gap

Most businesses face three pivotal moments where their commitment to differentiation gets tested:

When competitors copy their successful tactics
The instinct? Double down on optimization. Make the successful approach even more efficient. The opportunity? Take it as a signal to innovate again. When everyone copies your approach, it’s time to create a new one.
When metrics temporarily dip
The instinct? Retreat to “proven” approaches that feel safe. The opportunity? Trust that meaningful differentiation builds lasting advantage, not just short-term spikes.
When major investments are on the line
The instinct? Play it safe to protect the investment. The opportunity? Realize that in today’s market, safe is risky.

I’ve faced each of these moments. Early in my business, I had a content format that worked brilliantly. Then, I watched competitor after competitor adopt the same approach. My metrics started sliding. Instead of innovating, I tried to optimize harder. Better headlines. Better timing. Better distribution.

Nothing worked. Because the problem wasn’t the execution — it was that the approach itself had become commoditized.

The breakthrough came when I stopped trying to win the optimization game and started playing a different game entirely.

Creating Your Different Future

Here’s what this looks like in practice.

Start with the Customer Clarity Exercise
Examine your Sacred Cows
Map your Conviction Points

Start with the Customer Clarity Exercise:

What does your market say they want?
What do they actually want?
What do they not even know they want yet?

This gap — between expressed needs and deeper aspirations — is where breakthrough positioning lives.

Look at how Peloton approached this. The market said they wanted convenient exercise equipment. But Peloton saw something deeper: people wanted to feel part of an elite fitness community from home. They didn’t just build a better exercise bike. They created a new category of connected fitness experiences.

Next, examine your Sacred Cows:

Which “best practices” do you follow without questioning?
What would happen if you deliberately violated them?
Where are you optimizing something that should be reimagined?

Buffer did this brilliantly with their approach to company culture. While other startups were optimizing standard workplace practices, Buffer questioned everything — publishing everyone’s salaries, making remote work truly remote, building radical transparency into their operations. They turned their internal practices into a powerful marketing advantage.

Finally, map your Conviction Points:

What do you believe that others don’t?
Which industry assumptions make you angry?
What truth are you willing to defend, even if it costs you business?

Strong convictions, clearly articulated, create magnetic marketing. They attract the right people and repel the wrong ones, which is exactly what effective marketing should do.

The Path Forward

The market is splitting into two distinct groups:

Those who compete on optimization
Those who compete on differentiation

The middle ground is disappearing. You can’t be sort of different, kind of unique, or almost authentic. The businesses that thrive will be those who commit fully to meaningful differentiation.

This isn’t just about marketing. It’s about having the courage to be who you actually are in a market that pressures you to be like everyone else.

Your Next Move

Start small, but start now. Take one piece of your marketing — a single email, webpage, or presentation.

Instead of asking, “How can I optimize this?” ask, “How can I make this meaningfully different?”

Don’t just improve the execution. Question the assumptions. Challenge the format. Reimagine the possibility.

Because in a world where AI can optimize anything, the only sustainable advantage is being irreplaceably human.

And that’s something no algorithm can optimize.

The Choice Ahead

Every business faces a critical decision in today’s market. You can continue optimizing what everyone else is doing, fighting for increasingly smaller advantages in increasingly crowded spaces. Or you can do something different.

I’m not talking about being different for difference’s sake. I’m talking about having the courage to:

Share the insights only you have
Take the stands only you can take
Create the transformation only you can deliver

This isn’t just about standing out. It’s about survival.

Because here’s what’s coming.

AI will continue getting better at optimization. It will get better at writing headlines, crafting emails, and generating content. It will get exponentially better at doing everything everyone else is doing.

But it can’t be you. It can’t have your insights, your experiences, and your perspective on what needs to change in your industry.

That’s your advantage, not in competing with AI, but in doing what AI can never do: being meaningfully, authentically, and strategically different.

The market won’t wait for you to figure this out. Your competitors won’t wait for you to find your voice. Every day you spend trying to optimize sameness is a day you fall further behind.

The best time to start was years ago. The second best time is now.

Take one piece of your marketing — just one — and make it unquestionably yours. Don’t ask how to make it better.

Ask how to make it different.
Ask how to make it true.
Ask how to make it matter.

Because, in the end, the businesses that thrive won’t be the ones with the best optimization. They’ll be the ones who had the courage to be different when everyone else was trying to be better.

That’s not just a marketing strategy. That’s your future.

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