How Publishers Can Win When AI Replaces the Click
Media and the Machine
September 30, 2026
This week’s episode is a little different -- because I’m the guest! I was honored to appear on The Media Copilot podcast, hosted by Pete Pachal. Pete has spent more than two decades in tech and media, including senior roles at CoinDesk and Mashable.
Speakers Rob Kelly, Pete Pachal
TopicsTechnologyBusiness
Rob Kelly (0:03)
Welcome to Media and the Machine. I'm Rob Kelly. This show is about AI and how to profit from it. I believe this is the biggest technology shift of our lifetime. I'm a three-time founder and CEO of content-driven businesses, and each week, I talk with the people on the inside of AI and content. The ones building this new world and learning what works firsthand. I'm an optimist about AI, but I'm also a realist, so every show ends with me asking our guests, what AI means for our jobs, our families, and our future.
This week's episode is a little different because I'm the guest. I was honored to appear on the Media Copilot podcast hosted by Pete Pachal. Pete has spent more than two decades in tech and media, including senior roles at CoinDesk and Mashable. Today, he teaches folks in PR, journalism, and media how to keep up with AI.
Pete and I covered a lot of ground. We get into the spreadsheet I keep, which tracks 99 AI licensing deals, what I've learned from them. I share when and why I think OpenAI will settle its lawsuit with The New York Times before its IPO, and how OpenAI can help grow the Times business. We dig into Yelp's content licensing deal with OpenAI, a business model I call Licensing Content to Commerce, where Yelp can turn an AI answer to Revenue.
Pete gets my take on why I believe we are far from running out of content to train AI on, and we get into my own use of AI, including how I increased my writing productivity 8.7x without being a spammer. Now, please enjoy my conversation with Pete Pachal, for this time, he's the one asking all the questions.
Pete Pachal (1:49)
Give me a little more background on your relationship with both journalism and the business side of media.
Rob Kelly (1:57)
Yeah, well, I grew up on Wall Street. My dad taught me to love business. He, I was one of those nerdy little guys who at 13, my dad dressed up in a Brooks Brothers suit and dragged me into the office as a kid, maybe 12, 13 years old. And he just taught me to love it like a game, kind of like folks like sports or read the Wall Street Journal, like I read the sports columns and I love sports. And dad told me I should write for the school newspaper. So I did. He rarely gave me advice, by the way, so I took it. And that was a lot of fun. And then I started writing about tech, much like you, and I wrote for a company called CMP Media, one of the favorite companies I've ever run across in Manhasset, New York, Long Island.
They had great customers. So folks like Steve Jobs and Bill Gates would agree to sit down with me for interviews. And nothing to do with me, just I had a few hundred thousand people are going to write them a check.
And you still remember the thrill of a byline, right? Seeing your own name.
Pete Pachal (2:57)
First time I see your name in print, when it was print.
Rob Kelly (3:01)
Nothing like it. Yeah. Nothing like it. And then I decided to, I found that was like spectating and I wanted to get in the game more. So I started running the content licensing business for CMP Media and they had 16 magazines, a million articles and my job, as the only one who did it, was to sell that feed to LexisNexis, Bloomberg, Dow Jones News Retrieval and it was a great business, highly profitable. I'm sure we'll get into that later.
And that got sort of my, whetted my appetite for the business side of things. I then founded or CEOed three different startups. And my last startup in early 2018, OnGig, I got lucky in that I had a smart co-founder, Kevin, and we started using Google's AI back in 2018 This is, you know, four plus years before ChatGPT. We're using machine learning, natural language, incredible stuff at the time, by the way. Still is, in fact. And Google had us in twice to present to them. I'm so humbled by that. But we were one of their only customers too. So it's funny to have a big company like that. And OnGig was using their AI and paying them. So they had us in twice to talk to a 50, 100 person team.
Then I created this newsletter, Daily Doc, just for fun. And I started using ChatGBT, because it launched around the same time. It ADEX my productivity, so I was sold on AI.
And along came the New York Times suing OpenAI. I thought that was interesting. Few months later, the Wall Street Journal owner, News Corp, made a $250 million deal with OpenAI. And I thought, you know, you love content like me and media. I thought that was just the most unusual thing.
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