THE STORY
Before the Internet
I remember a time before the internet. It didn't really arrive until my late teens, maybe early twenties. And for anyone who's grown up with it — which is most people reading this — it's genuinely hard to convey what an absolute revolution it was.
I'm a hockey fan. If I wanted to know whether the Kings won the night before, I had three options: wait for the TV news and hope the sports segment hadn't already aired, catch news radio at 20 and 50 past the hour, or wait for the newspaper to land on the doorstep in the morning.
That's it. Those were the choices.
When the internet arrived, it felt like magic. Genuinely uncharted territory. Suddenly information was just there.
The Wizard
Flash forward to the early nineties. I'm managing a big rock band. We'd heard about these things called websites. Cool indie bands had them. The Beastie Boys had one through their Grand Royal label. We wanted one.
So I got introduced to Chris.
Chris had built websites for a handful of indie bands — maybe three or four. And to us, he was a wizard. He could do something almost nobody else could. This was before computer science became a broad major, before software development was everywhere. He had real, rare knowledge, and he'd built relationships in the entertainment industry on the back of it.
We brought him in. A few band members, my boss, me. Chris laid out his vision for what the site could do. Things the indie bands hadn't been able to afford — dynamic content, the ability to update things without rebuilding from scratch. We were hooked. He had us completely.
Then he told us the price.
Forty thousand dollars.
In today's money, that's probably closer to a hundred thousand. At least one band member wanted to physically remove him from the room on the spot.
We knew the bands he'd built sites for didn't collectively make $40,000 a year. We knew the band had just started making real money and that people were already lining up to separate them from it. And we knew — even then — that this number had nothing to do with cost. It had everything to do with leverage. Chris was one of the only people who could do this, and he knew it.
To his credit: that's business. He wasn't wrong about his leverage. He was just insufferable about it.
He kept saying: this is what it costs. Over and over. No flexibility. No junior option. No negotiation. This is what it costs.
We eventually found someone else who built us a perfectly good site for $6,000. And I stopped thinking about Chris entirely.
Best Buy
Until a couple years later. I'm in a Best Buy, wandering past the tech repair counter. And there's Chris. Blue shirt. Name tag.
Being the petty person I occasionally am, I walked over. Hey Chris. How's the web building business?
His eyes went to the floor. Then he got defensive. Told me we just didn't understand the technology. That we weren't hip to it. Still holding the line, even standing behind the Geek Squad counter.
He never varied. Not once. Not even then.
And it stuck with me.
THE INSIGHT
He Wasn't Wrong About the Technology
That's the thing that keeps coming back to me about Chris. He wasn't wrong about the internet. He saw it clearly, early, and correctly. He understood the value before almost anyone in the entertainment industry did.
He was wrong about the window. How long he had it. How fast things were going to move.
GeoCities launched. Suddenly anyone could build a basic website for almost nothing. The specific, rare skill that Chris had turned into a commodity almost overnight. And because he'd spent his entire window insisting on $40,000 instead of adapting his model — different price points, junior help, volume — he had nothing left when the window closed.
Chris had a real edge. He held it too tight. The world moved. He got left behind with his blue shirt at Best Buy.
The people most at risk in any major technology shift aren't the ones who ignore it. They're the ones who learn one version of it, plant their flag, and refuse to move.
Strong convictions, loosely held. That's the mantra. Have a point of view. Commit to it. But stay open to being wrong, to the market moving, to the window shifting. If Chris had come back at $20,000 — or even $25,000 — we probably would have done it. He would have made a fortune for a month's work. He didn't. And I suspect he knows that.
The Wizard becomes Name Tag Boy
THE FRAMEWORK
Where We Are With AI Right Now
Here's what I keep thinking about: we are at the exact moment with AI that Chris was at with the internet. Maybe just a few months past it.
It's still clunky in places. It's moving extremely fast. And the people who understand its value early — really understand it, not just the buzzwords — are the ones who will be in the best position when everything settles.
But the lesson from Chris isn't just about the technology. It's about how you hold what you know.
1. Learn it genuinely. Not the surface. Not the talking points. The actual capability — what it can do, what it can't, where it's heading. Chris understood the internet. His mistake wasn't ignorance.
2. Hold it loosely. What's true about AI today may be GeoCities in three years. The specific edge you have right now is not permanent. Build on it, yes. Bet everything on it staying exactly as it is? No.
3. Watch the window. The internet moved fast. AI is moving faster. The window of any particular advantage is shorter than it looks from inside it. The people who get into trouble are the ones who think they have more time than they do.
4. The risk isn't ignorance. It's rigidity. The people who will get left behind aren't the ones who haven't heard of AI. They're the ones who learned one version of it and stopped there.
THE TAKEAWAY
The question isn't: will AI take my job?
The question is: how fast can you move when the window shifts?
Chris knew the answer to the first question better than almost anyone in his world. He just never asked the second one.
Don't be Chris.
Winning at Work is about how careers actually work — not how people pretend they work. This is Part 1 of a series on AI and your career. If someone sent this to you and you'd like to subscribe, visit the link below.