Two Hundred Years Too Late: What I learned about AI from Jimmy Buffett

It’s just past noon on a Tuesday and I’m back at my desk after lunch, trying to shake off the particular kind of low-grade dread that comes with running a small business in early 2026.

The morning has been a greatest hits collection of founder anxiety. Client negotiations that feel more like chess matches than collaborations. Revenue forecasts that I’m increasingly convinced are just elaborate fiction. And at the heart of it is the AI revolution we’re all experiencing.

The sense is that the future is a place you’re supposed to navigate confidently… while having absolutely no idea what’s coming. And it’s not just us: all our clients are navigating the same waters, unsure of what the next day holds for the businesses.

I needed a few minutes of something that wasn’t a spreadsheet.

My wife got me a couple of Jimmy Buffett albums on vinyl for Valentine’s Day (I’m slowly collecting all of his that have been pressed). There’s something grounding about it, building a physical library of music one record at a time. I put one on. The needle found the groove.

And then “A Pirate Looks at Forty” came on.

Now look. I grew up in Miami in the 80s where you did not mess with the holy trinity of Jimmy Buffett, Gloria Estefan, and Jon Secada. So, I’ve heard “A Pirate Looks at Forty” hundreds of times.

But it hasn’t hit like this before.

If you don’t know the song, Buffett isn’t singing about a pirate. He’s singing about himself: a man who feels like he was built for a world that stopped existing two hundred years before he was born. The cannons don’t thunder. There’s nothing to plunder. And then the line that stopped me cold:

My occupational hazard being my occupation’s just not around.

I sit with that for a minute. Because that’s the feeling, isn’t it? Not quite fear. Not quite grief. Something in between. Mourning something that hasn’t fully died yet. I’m going to call it “pre-nostalgia” because that seems to put a finger on what I’ve been feeling all morning.

Some of The Smartest People I Know Are Worried Too

Earlier this morning, I’d read two pieces that are still rattling around in my head.

Ann Handley, one of the clearest thinkers in marketing, published a characteristically grounded response to the wave of AI apocalypse content flooding LinkedIn. Her argument, stripped to its core: when speed becomes cheap, judgment carries a premium. Don’t panic. Don’t grab whatever feels safe. Dig your well. Own something that compounds.

Mark Schaefer, another marketing titan, took a harder look at the same disruption and arrived somewhere more sobering. He drew a direct line to 1982, when the British Musicians’ Union tried to ban synthesizers after Barry Manilow replaced his orchestra with electronics. Futile then, futile now. His conclusion: resistance isn’t the answer. Becoming a true artist is. Battle mediocrity, not AI.

Both pieces are smart. Both are worth your time. And both are essentially survival guides for individuals trying to find their footing in a world being reorganized beneath them. It’s what left me with the “pre-nostalgia”, realizing that everything is changing, at an alarming pace, and none of us (if we’re really honest) know just how deeply or broadly it is going to change life as we know it.

It’s something every person, business, and brand is going to have to wrestle with. And sometimes, it can feel exhausting.

Meanwhile, Gen Z Is Buying iPods on eBay

Not a typo. iPods.

Gen Z — the most digitally native generation in human history — is buying discontinued Apple devices on eBay in significant numbers. Search interest for iPod Classic and iPod Nano spiked throughout 2025. eBay saw a 25% increase in iPod Classic searches in the first ten months of the year. And here’s the detail that stopped me: 32% of the people driving this revival are Gen Z. Not nostalgic millennials raiding junk drawers. Young people who barely remember these devices making a deliberate choice to use them.

Why? Because an iPod does one thing: it plays music.

No notifications. No algorithm deciding what you hear next. No infinite scroll waiting one swipe away.

One young woman told Axios she bought hers because she wanted to “cleanse herself of being on her phone.” Another said her generation is experiencing so much uncertainty that they’re reaching back toward things that once felt simple and hopeful.

Researchers are calling it “friction-maxxing”—intentionally adding inconvenience back into daily life because the frictionless, optimized version of everything has started to feel like something important is missing.

Read that again. People are paying a premium for less optimization. For more friction. For experiences that feel more human precisely because they’re less efficient.

That’s not a quirk; that’s a market signal. And it might be the most important thing I’ve read about the future of experience brands in months.

What This Actually Means for Experience Brands

Here’s what the AI workforce debate keeps missing: The disruption isn’t a threat to brands built on human experience. In fact, it’s the most powerful argument for them that has ever existed.

When intelligence becomes cheap, when content becomes abundant, when every customer interaction can be automated and every marketing message can be generated in seconds… the things that cannot be automated become the premium product. Genuine human moments. Intentional friction. Experiences that make guests feel something no algorithm can manufacture or replicate.

Handley is right that judgment carries a premium. Schaefer is right that artistry survives what competence cannot. But there’s a layer beneath both arguments that matters enormously to anyone in the business of guest experience: your guests are already the iPod kids. They’re just older, and they have more money to spend. They are actively, consciously, sometimes desperately looking for experiences that feel real in a world that is becoming increasingly synthetic.

The question for your brand isn’t whether AI changes everything. It does, full stop.

The question is whether you understand that the world it’s creating needs what you offer more, not less.

The Cannons Still Thunder

Buffett’s tragedy isn’t that he failed. It’s that the world he longed for was genuinely gone. He couldn’t design his way into a pirate era that had already sailed. All he could do was feel the loss of a life that was never available to him.

You’re not in that position. The world your brand was built for isn’t disappearing. In fact, it’s becoming more valuable by the day. Experience-driven brands exist to make people feel something real. And in a marketplace increasingly flooded with synthetic content, automated interactions, and AI-generated everything, that’s not a liability. That’s the whole game.

Buffett sang that the cannons don’t thunder anymore. And he was mostly right.

But there’s a cannon at the Castillo de San Marcos in St. Augustine that fires every single day. People travel from all over and climb to the top of the fort to hear it. They stand there, they feel the concussion in their chest, and they know — in a way no screen can replicate — that something real just happened.

That cannon is as “real” as any cannon that ever defended a harbor. And yet, in another sense, it’s just theater. The difference between the two isn’t authenticity. It’s intention. Someone decided that moment was worth creating. Worth protecting. Worth delivering every single day.

That’s what experience brands do. And that’s what AI cannot do for you.

Whatever your cannon is, whatever is real and true and authentic to you that people love—find it. And fire it every single day.