Marketing in an AI Era

Note: this is an early draft of a lesson I'm writing. It's still pretty raw! If you have feedback, leave it below, or join the membership and post your comments in the private Discord.

"Suddenly, the whole universe has shifted." – Mikkel Malmberg, macOS app developer

The world of software development has fundamentally changed. AI and tools like Claude Code are empowering more people than ever to write and ship code.

In the next few years, we'll see more product launches than ever before.

But while building is getting easier, marketing is going to get harder. All those new apps and features being launched will mean customers will be inundated with announcements, ads, and pitches. Folks already feel overwhelmed with the number of messages they get every day; it's only going to get worse.

In the age of AI, marketing is the new superpower.

As my friend Tyler King says, “Building apps was never the hardest part; distribution was.” In a world of AI-generated apps, reaching and connecting with customers is what gives you leverage.

AI is bad at marketing

In my experience, LLMS (like Claude and ChatGPT) give terrible marketing advice.

Why? Marketing is standing out; it's about rising above the noise so people take notice of you and investigate further.

Because of how they are trained and how we use them, LLMs have a strong "gravitational pull" toward the most common, safe, and probable patterns.

This means the tactics and approaches that ChatGPT (and other tools) suggest will be basic, washed-out, and average. Average is what kills companies.

With so much noise, potential customers won't notice an average product being marketed in an average way.

Case study: asking ChatGPT for marketing advice

I recently saw a clip of a founder asking a business influencer for advice on promoting his trading card vending machine business.

The influencer's answer was to pull out his phone and speak to ChatGPT: "Hey ChatGPT, give me five really powerful ideas that would make me the most money (as fast as possible) for my vending machine business."

ChatGPT replied with these ideas:

  • "Interactive AR experiences. Integrate augmented reality features into your vending machines."
  • "AI-powered personalization. Use AI to analyze purchasing patterns and offer personalized recommendations or discounts via the vending machine interface."
  • "Mobile app integration. Develop a companion mobile app that lets users track their purchases, earn rewards, and be notified about new stock or limited-time offers."

The influencer was trying to make a point: "See? Marketing is easy now that we have ChatGPT."

But these ideas are generic and don't fit this founder or his product category.

This owner owns simple "gumball style" slot machines; it's not practical to add augmented reality, AI personalization, or a mobile app here. Also, these ideas sound like expensive, time-consuming, risky bets.

What gives any business an advantage in a market is how well they understand the market. Every market has characteristics that determine how you should approach it.

What makes the difference? The founder, how well they understand the market, and what built-in advantages they have.

Founder mode

Patrick Collison, the founder of Stripe, describes the characteristics of founders who win in a given market:

"You need to have excellent judgment in your problem area."

Where does "excellent judgment in a problem area" come from? Good judgment is the result of your experience, wisdom, and insight. It's the intuition you've developed by building things and observing how real customers behave.

It's understanding the unspoken frustrations that customers won't articulate in a survey but will reveal in a casual conversation. It's having a gut feeling for which features matter and which are distractions. It's knowing where your typical customer hangs out, what they're paying attention to.

This kind of embedded knowledge is the real competitive advantage — and it comes from accumulated experience.

My friend Nathan Barry didn't just wake up one day and decide to build Kit, an email newsletter tool for creators. He was a creator. He spent years writing and launching apps, books, and courses. All of that experience soaked into his understanding of what creators actually need. When it came time to build and market Kit, he had intuitions that were grounded in years of lived experience.

I experienced something similar with Transistor. Jon and I didn't just decide to enter the podcast hosting market; we'd been in and around podcasting for years. I'd been hosting podcasts, attending conferences, and hanging out with other podcasters in online forums. When we launched, I already knew which communities to show up in, which people to reach out to, and what messaging would resonate — because I was the customer.

People often ask me: "I'm in the XYZ industry. What are the best ways to reach customers?" And my response is always: you should already know. If you're unfamiliar with the conferences, YouTube channels, Slack groups, podcasts, meetups, and newsletters that people in your category engage with, that's a bad sign. You need to be the expert on your target customer.

This is what Collison is really getting at. "Excellent judgment in your problem area" isn't just about product decisions. It's about knowing, instinctively, where to find your people and what will get their attention.

A successful business idea and a successful marketing strategy emerge from the experiences, connections, skills, insights, and resources you've accumulated. Most good opportunities are not obvious, especially to outsiders. You're looking for evidence of unmet demand in a category you understand deeply.

If you feel like you're "bad at marketing," your first step should be to immerse yourself in your market. Start a podcast and interview people in your space. Attend meetups and conferences. Get curious about how your customers actually make decisions. The founders who win will be the ones who've been soaking in their category long enough that the right moves feel obvious.

This lesson isn't finished! I'll continue writing it in the coming days. What do you think so far? If you have feedback, leave it below, or join the membership and post your comments in the private Discord.

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