Media and the Machine

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...

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...

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...

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...

My guest today is Doug Leeds, co-founder of RSL. 

He’s tackling the question every media CEO and content owner is asking right now: how do you get paid by AI companies — including even if you’re small?

He’s already working with Reddit, People Inc., USA Today and others — a collective representing nearly half the content AI models train on. That gives RSL real leverage across the table from the AI giants.

RSL stands for Really Simple Licensing. Doug’s co-founder, Eckart Walther co-created RSS over 25 years ago — the standard that powers this ver...

My guest is Anthony Shore.

Anthony is a linguist who's been naming brands for 36 years -- and using AI for just as long. He’s helped bring more than 270 names to market, and he’s directed, created, or developed names like Accenture, Tonal, Fitbit Sense, Yum Brands, JetBlue, Verizon, and Qualcomm Snapdragon.

I get Anthony's take on:

• Which AI answer engine has the best name (ChatGPT, Gemini, Claude, Perplexity, and Meta AI).
• The wild, laugh-out-loud emails between Elon Musk, Greg Brockman, and Ilya Sutskever as they debated what to call OpenAI.
• How the na...

My guest is CJ Chilvers.

CJ has written three books — Principles for Newsletters, A Lesser Photographer, and The Van Halen Encyclopedia. By day, he’s Senior Content Strategist at StudioNorth. 

His job is simple: get the most ROI for every word.

Since ChatGPT launched, CJ has been ghostwriting about AI for major tech companies. He’s had a front-row seat to how B2B marketing is really using this technology.

CJ believes small creators have a two-to-three-year head start on big corporations. He says it’s 1995 all over again — a...

My guest is Ty Ahmad-Taylor.

Ty is a founder and two-time CEO who has spent his career at the center of media and tech. He started at The New York Times, built and sold his startup FanFeedr to Samsung, and later became a product VP at Meta and Snap. 

Today, he’s on the boards of GoPro and SFMOMA—and working hands-on with AI.

One of the wildest parts of this conversation: Ty rebuilt a startup that once took four and a half years to build… in just five minutes with AI.

My guest is Clint Stinchcomb, CEO of CuriosityStream (NASDAQ: CURI).

Two years ago, CuriosityStream was known as “the Netflix of Documentaries.” Today, it is on track to earn more money from AI content licensing than from subscriptions.

Clint and I talk about how AI licensing really works for content-driven/media companies. 

We use CuriosityStream as a real example, not a theory. 

We focus on deals, content, and money.

Key Takeaways:
• How Clint built 2M+ hours of content (video and beyond) to license to AI Giants
• Cli...

I’m Rob Kelly, and this is Media and the Machine, a show about the biggest technology shift of our lifetime and how to profit from it (together).  

Each week I talk with founders and CEOs closest to AI and Content, the people figuring this out in real time. I’m also building an AI content business myself and sharing what I learn along the way.

I'm a 3-time founder and CEO and earlier in my career interviewed such tech leaders as Steve Jobs and Bill Gates.

This isn't just about busin...