My guest today is JC Cangilla.

JC was Head of Entertainment Deals at Meta, where he led a 20-person team spending $1 billion+ per year acquiring content to power experiences across Facebook, Instagram, and Oculus

He worked with everyone from major studios to influencers to bring content like The Walking Dead, Red Table Talk, and the Simone Biles documentary onto Meta’s platforms.

Before Meta, he co-founded a digital entertainment studio that he sold to Discovery/WarnerMedia.

In our conversation, he shares:

• The top 2 things Big Tech algorithms use to decide what content wins
• The shift to engineers controlling content — and what that means for creators
• How short-form video impacts long-form content
• Why the line between tech and media has essentially disappeared
• And how AI is creating for him a new renaissance — he’s gone from ideas to live products himself in a matter of days

Oh, and a quick note — I ask JC about Moltbook, the Reddit-like social network for AI agents… Well, shortly after our interview, his former employer Meta acquired Moltbook – its 2 co-founders are now part of Meta’s Superintelligence Labs. Things sure are moving fast.

A Special thanks to creator and entrepreneur Michael Sklar for connecting me with JC.

Please enjoy my conversation with JC Cangilla.

Thx!
Rob Kelly

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