Seeing the Disruption Isn't the Same as Surviving It

I was thinking about my time at Tribune in the 90s, and one memory keeps coming back to me. We used to claim chicagotribune.com had the first 1TB database on the Internet.

I have no idea if anyone can still prove that claim. This was 30 years ago, and a lot of the Internet from that period has disappeared. But I worked there at the time, and that was absolutely the claim internally.

More importantly, it wasn’t an absurd claim. Tribune had put the Chicago Tribune archives online. We were dealing with decades of newspaper content at a time when a terabyte was an obscene amount of storage. And that wasn’t some weird one-off experiment inside the company. Tribune was remarkably good at seeing where the Internet was going.

Cubs.com was the envy of Major League Baseball. Tribune was investing in Internet companies while much of corporate America was still trying to figure out what a website was. Some of those investments became some of the biggest stories of the dot-com era. Tribune understood that the Internet was going to be important. We invested in it, we built for it, and in some areas we were ahead of almost everyone else.

That’s what makes what happened next so interesting. The Internet didn’t sneak up on Tribune. We saw it coming. And it still destroyed the economics of the core newspaper business.

The AI version of the same question

I’ve been thinking about that as I watch the current wave of AI investment. There’s a tendency to look at companies like Google, Salesforce, Adobe, ServiceNow, and others and assume their level of investment in AI means they’re positioned for the transition. Maybe. But Tribune was positioned for the Internet transition too.

The harder question isn’t whether an incumbent recognizes the technology. The harder question is whether the business that made the incumbent successful survives when the technology works.

Salesforce wants agents to do more work. That gets complicated if fewer humans doing the work means fewer seats. Adobe wants generative AI to dramatically increase how much content people can create. That gets complicated if creating that content requires fewer professional users spending hours inside professional tools.

Google may be the best example. Google is one of the companies most responsible for the technology behind this generation of AI. There’s no credible argument that Google missed the trend. But if conversational and agentic interfaces change the way people discover information, Google still has to deal with what that means for a business built around the economics of search.

So what?

None of this means these companies lose. That’s not the point.

The lesson I took from Tribune is that seeing the disruption isn’t the same thing as surviving it. You can see it early, invest in it, build some of the best technology around it, and still discover that the thing you were right about changed the economics underneath you.