Digital Ads in 2026: The Challenges of Transitioning Your Team to Digital

“You can’t teach an old dog new tricks.”

You hear that warning a lot when you plan for the future. I know I heard that plenty when I was a publisher helping ad sales teams transition from a print-focus to digital.

As far as business expressions go, there are few that I disagree with more than that one. Its dismissing message bears no reality on what I experienced in helping salespeople and advertising teams make the leap to digital ad sales.

So let’s dispel this oft-repeated phrase, once and for all.

What We Can Learn From Evolving ChatGPT Fan-Out Queries

I think OpenAI is using fan-out queries, and the site: operator in particular, as one method of reducing spammy outputs in their answers derived from internet content. I believe it’s their effort to improve the quality of retrieved sources while taking early steps to combat spam and low-quality information in their results. It reminds me of what Google has tested with E-E-A-T, but ChatGPT style. 

 

Claude Vs. Pangram: The Watermark Wars Are On! 

There has been a growing tug of war between publishers and authors over AI. Until recently, I thought we were slowly beginning to figure out some reasonable ground rules. If you ask an AI to write your book and put your name on it, that’s one thing. If you write the book and use AI to check spelling, grammar, citations, chronology, repeated paragraphs or whether you’ve gotten somebody’s name wrong, that should be something very different. The line between those two things can get blurry, but at least we’re beginning to acknowledge that there is a line. Anthropic may have just made the whole thing worse — maybe on purpose? 

 

We Tracked a Shipment of Rare Books. It Ended at an Amazon AI Training Facility

Amazon is buying massive quantities of books, scanning them for AI training data, and destroying them in the process. A 404 Media investigation was able to reveal Amazon’s book buying operation, which hasn’t been previously reported, by placing a tracking device in a rare book we suspected would be acquired by an AI company for training data, and following it around the country to its final destination.