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

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 very podcast feed.

It feels like they were built for this moment.

Doug explains why “the ship has not sailed” on monetizing your content with OpenAI, Anthropic, Google, and others — and how even small publishers can land real licensing deals.

We go deep on Reddit — where Doug coached CEO Steve Huffman — and how Reddit is making real money licensing content to AI while still growing traffic

He breaks down how RSL differs from ProRata and TollBit, what the first real AI licensing deals will look like, and gives his hot takes on all the AI Frontier Models— including which frustrates him most.

We also talk about competing with Google. When Doug was CEO of Ask.com, he and his boss Barry Diller turned Google from a threat into a profit-driving partner.

He teaches at UC Berkeley, is a longtime CEO, and has spent decades navigating the space between content and search engines.

And we close with how AI touches his mom, his dad, and his daughters– you get to see the human behind the CEO.

Please enjoy my conversation with Doug Leeds.

Thx, Rob

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 name ChatGPT came together in a last-minute scramble the night before launch.

And then I bring in special guest Andrew Miller — who, along with Larry Fischer, brokered the sale of Chat.com (a potential replacement name for ChatGPT) — you’ll get the real-world story of how HubSpot’s cofounder Dharmesh Shah outmaneuvered Sam Altman & OpenAI in a late-night, multimillion-dollar showdown — and how Dharmesh parlayed that into possibly the largest domain name transaction in history.

Anthony also shares:

• How ChatGPT has a translation problem no naming guru can fix.
• What Google should do with its dual-brand problem (Google and Gemini).
• Some strong words Anthony has for Elon’s rebranding of Twitter to X.
• When AI will make his own job obsolete.

And, of course, whether Anthony recommends OpenAI change its name to just Chat, or GPT, or something totally new.

Thx,
Rob

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 — and curation is about to matter more than ever. He also argues that boring things like email, logins, links, and tags are the real power tools in an AI world.

We talk about why OpenAI and other LLMs are likely headed toward ads — and why CJ still sees a future where AI could stay ad-free.

We also get practical. If CJ were starting today, he explains why he’d be okay with his work getting scraped, how he’d get discovered, and the business model he’d build.

Other Key Takeaways:

• Why small creators may move faster than big companies in the AI shift
• Why this moment feels like the early internet — and why curation wins
• Why email still drives the highest ROI in media and B2B
• Why many big companies are using AI to cut costs, not grow revenue
• Why ads are likely coming to AI tools — and one way they might not
• How CJ would launch a content business today
• Why human trust still closes deals, not AI
• Why humanized content beats automated personalization
• Why you don’t need 1,000 true fans — you may only need one
• Why trusted editors matter more as AI floods the web

If you run a media company, build products, or create content, this episode will help you see what’s changing — and what still works.

Thanks, Rob

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.

Ty and I talk about what the AI shift really means for media companies.

Not theory. Real examples.

We focus on content, distribution and money.

Key Takeaways:
• How Ty rebuilt FanFeedr—a startup that took four and a half years to build—using one AI prompt in just five minutes (using ChatGPT, Gemini, and Perplexity)
• Why Yahoo Sports shows up everywhere in AI tools—and why The Athletic from The NY Times does not
• What media companies gain and lose by blocking AI bots like ChatGPT and Google/Gemini
• Why AI agents and scheduled tasks change how products get built
• How tools like Granola, ChatPRD, and Lovable compress months of work into minutes
• What Ty learned running AI workshops with OpenAI, Perplexity, Delphi, and Listen Labs
• Why affiliate revenue may replace ads as Google traffic falls
• Ty’s simple 3-part framework for AI product development

Family too — We also talk about how Ty thinks about AI and his kids, and why human skills still matter in an AI world.

If you run a media business, build products, or create content, this episode will help you understand what’s actually changing—and what to do next.

Thanks, Rob

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
• Clint’s hot takes on OpenAI, Anthropic, Google, xAI, and Meta
• ~$20M AI licensing run rate (my estimate) — the first 9 deals with AI companies, and why that number could soon double or triple
• The content that the major LLMs pay the most for
• What a typical AI video licensing deal looks like (length, exclusivity, etc)
• How many hours of content AI companies test before scaling
• Why video, audio, ebooks, and even software code are in play
• His work with the legendary John Hendricks, founder of Discovery (and CuriosityStream)

Family too — We also talk about the impact of AI on his family. Clint shares how he thinks about using AI to capture and preserve his mom’s memories.

If you run a media business, work in AI, invest, or create content, this episode shows how these deals work in the real world.

Thanks, Rob