My guest today is Jennifer Elliott, a veteran engineer in data centers, whose customers include some of the largest players in the world like Google, Meta, AWS, and Netflix

She is highly technical, lives in Silicon Valley, and has invested in multiple AI startups

But, what makes Jennifer so fascinating is the duality.

At the same time she’s bullish on AI, she’s also actively preparing ​​for a future where AI becomes — in her words — an ‘apex predator’ that could take humans out

She’s already building a list of her ‘Ride or Die’ people and designing an off-grid ‘Hidey Hole’ bunker community.

We get into exactly what concerns her about AI — including the surprisingly simple way she thinks it could attack, the personality traits of her Ride or Die people, and the two locations she’s already scouting out.

One of them happens to be a place where Peter Thiel spends time.

She also shares her take on the one way a startup could beat Nvidia — the most valuable company in the world.

This conversation feels both extreme and oddly familiar — because I think we all have a Jennifer in our lives… someone thinking a few steps ahead about worst-case scenarios.

Special thanks to the artist Sean Orlando for connecting me with Jennifer— go Glenview Elementary!

Now please enjoy my conversation with Jennifer Elliott.

Thx,

Rob

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