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

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 business. 

Every episode ends with me asking my guest about the impact of AI on our families and future. 

Please follow the show to get new episodes when they launch.

Thx! -Rob