If I could go back to the year 2000… what would I do differently and what does that mean for AI in 2026?

In 2000, I was wrapping up a computer science degree at College of Computing at Georgia Tech doing a Java developer internship. I was an early adopter of the internet. I used Google when people didn’t trust it. I got on Gmail early.

I could see it would change the world. But I didn’t know organizations well enough to see how they would need to transform.

I thought about tools.I thought about cool technology.I didn’t think deeply enough about how entire organizations would need to transform.

That’s the mistake I see many businesses making with AI today.

So what would I do differently? And what can we learn now?

1. Don’t chase the tool. Rethink the strategy.

In the early 2000s, everyone urgently needed a website.

I remember a trucking company CEO asking me to build a site with a giant, clickable photo of a truck. It sounded impressive. But there was no clear connection to revenue, operations, or competitive advantage. It was fear of missing out.

Today with AI, I hear:“We need Copilot.”“We need ChatGPT.”“We need an AI chatbot.”

But when I ask a room full of executives why AI I get divergent answers. Sometimes it feels like FOMO more than a plan to change their business.

The better question is:What pain points are we eliminating?What decision cycles are we compressing?What cost structures are we changing?

AI is not a feature. It is a strategic shift.

2. Don’t let caution drown out imagination.

Back then people said:“You can’t trust Google like the library card catalog.”“What if you mistype CNN and end up somewhere with fake news?”

The concerns were real. But they dominated the conversation.

With AI today, we hear:“What about hallucinations?”“What about security?”“What if employees misuse it?”

Those are important issues. But if caution crowds out imagination, we miss the opportunity.

The internet was imperfect in 2000. AI is imperfect in 2026.

That doesn’t mean it isn’t transformative.

3. Assume the business model will change.

An insurance friend once told me people would never buy insurance over the internet. It was too relationship-driven.

Netflix was mailing DVDs. That seemed like a perfectly fine business.

Many companies optimized what they already had instead of asking how the economics of their industry might fundamentally shift.

With AI, I see organizations focused on incremental productivity gains. It is a great start, but they should be rethinking pricing, service models, staffing models, and even what their “product” is.

AI will not just make work faster. It will change what work is.

4. Don’t laugh at early failures. Study them.

When Webvan (online grocery delivery) failed in 2001, people said, “See? People will never buy groceries online.”

We interpreted early failure as permanent impossibility instead of an early signal.

Today, someone tries using an AI earpiece in court to fight a red light ticket and it becomes a viral joke. Or an AI video has an obvious flaw. We laugh.

But I would wager that in the future, AI legal advisors will be normal. Maybe not in the clumsy form we see today. But the signal is there.

Early experiments often look awkward.They are still pointing toward the future.

5. Help people rethink how they work.

A former power company CIO once told me she didn’t understand why someone on her team would want someone to email her meeting notes with action items. She fundamentally didn't believe in email.

Today we cannot imagine operating without that. AI is not just about drafting emails faster.

It changes how knowledge is captured.How junior employees learn.How leaders make decisions.How organizations scale expertise.

If I could go back to 2000, I would spend less time building websites and more time helping leaders rethink their operating models.

I saw the internet coming. I just didn’t think big enough about transformation.

That is the lesson I’m trying to apply to AI now.

The internet did not just digitize business. It reorganized it.

AI will do the same.

The question for leaders today is simple:

Are we adding a clickable truck to our homepage?Or are we redesigning the highway?

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