My guest today is Mark Riley. He was the Head of Innovation at Dow Jones and is now Founder and CEO of Mathison.ai.

If you run or build a media business, this one is about how to survive—and grow—in the AI world.

At News Corp, Mark met with more than 110 AI companies—before ChatGPT even launched—and now coaches publishing CEOs on how to grow with AI.

In this chat, we get into:

• Whether publishers should woo or sue AI companies, or take a middle ground (Mark gives examples of each)

• We get His blunt view on how much traffic AI will (and won’t) send

• He shares The most “untouchable” media business in an AI world

• And whether the AI Models themselves can do real journalism

• AI's impact on Classifieds (Mark launched the Wall Street Journal's "Mansion" section and worked at Gumtree (the UK version of Craigslist)

Mark’s also got some great inside stories from his time at Dow Jones, such as:

• Presenting to News Corp’s Founder & CEO Rupert Murdoch just two weeks into the job
• And what it’s like walking past Fox News every day on his way into the Wall Street Journal—same building, very different ideologies

Thanks to Pete Pachal of Media Copilot for putting Mark on my radar—he did a great interview with him in early 2025.

Please enjoy my conversation with Mark Riley.

Thanks, Rob

My guest today is Jimmy Hutcheson — the CEO of SPIN and a private equity investor hunting for the next great media brand.

If you like music and tech, you’re going to love this one.

Jimmy bought SPIN from Billboard about six years ago — and since then the company has grown revenue 17X

Its TikTok following rivals Rolling Stone.

Today SPIN is far more than a magazine. – It runs major events, licensing deals, brand partnerships, documentaries — and even a record label.

SPIN might be as close to an AI-proof media company as any I’ve seen recently.

Jimmy shares why he’d love to buy Pitchfork from Condé Nast…

We talk about whether SPIN would ever go IPO – no one’s ever asked him in public.

He also shares how he would launch a media company today, from scratch.

And Jimmy tells some funny anecdotes about what he found when he first entered the storage locker holding SPIN’s entire archive (going back decades) — including a photo of a famous rock star that had to be touched up because they had a zit.

We of course talk about how SPIN is approaching AI — from blocking AI scraping to exploring new licensing deals with AI companies.

Please enjoy my conversation with Jimmy Hutcheson.

Thanks! Rob

My guest today is Tommy Petrov, the Ukrainian-born Co-Founder and CEO of CopySight AI.

Tommy and his team are small, but they’ve built something big. It’s called the Similarity Score — think of it as a FICO score for copyright risk in the age of AI.

Whether you’re Disney protecting Star Wars or a creator making something new, CopySight helps measure how close AI-generated content is to existing intellectual property.

For example, when someone uses Midjourney or Gemini to generate an image that looks like Darth Vader — or visuals that feel like they came straight out of Studio Ghibli — CopySight analyzes the output and assigns a score from 1 to 100 based on how similar it is to the original work.

Tommy explains that scores under 35% are usually considered safe territory, while scores above 75% can become a legal smoking gun.

Tommy has interviewed more than 70 General Counsels about AI content risk. What makes his perspective different is that he’s not a lawyer — he’s a creator. Before founding CopySight, he worked as a Creative Director at Snap and Meta.

Today, he works with legal teams and art directors at major Hollywood studios like Sony and Paramount, as well as the Russo Brothers at AGBO.

In our conversation, Tommy weighs in on OpenAI’s upcoming AI-generated film Critters — whether its IP could get flagged and whether a film created with AI can even be copyrighted.

But this conversation isn’t just a legal debate. We also talk about perhaps the biggest content question of all: what happens to art when AI makes creation so easy that fewer people bother to create anything truly original? And if that happens, what content do these AI models train on next?

Please enjoy my conversation with Tommy Petrov.

Thx,
Rob Kelly