Media and the Machine

Rob Kelly

AI is the biggest technology shift of our lifetime. This show is about how to profit from it together. Each week I talk with the founders and CEOs closest to AI and Content, the ones figuring this out in real time. I’m also building an AI content business myself and share the lessons I learn along the way. WHAT WE COVER THE TITANS: How companies like OpenAI, Anthropic, Meta, and xAI are moving, and why their decisions matter. THE INCUMBENTS: How content giants like Disney, News Corp, Universal Music Group, and Reddit are responding to AI, and what it means for creators and publishers. THE PLAYBOOK: Real lessons on AI business models, content strategy, IP licensing, distribution, and getting paid. ABOUT YOUR HOST: Rob Kelly has interviewed Steve Jobs and Bill Gates, helped pioneer early web content licensing, and built multiple companies with more than $100 million in total sales. His work has appeared on CNBC, CNN, TIME, and Entrepreneur. Beyond business, every episode explores what AI means for jobs, creativity, families, and the next generation. If you want clear thinking based on real experience in AI and media, Media and the Machine is your guide Thanks! -Rob

Episodes

  1. 4D AGO

    The AI Content Strategist Big Tech Calls First

    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

    1h 34m
  2. FEB 6

    Ex-Meta & Snap VP: How to Monetize Content Without LLMs Stealing Chickens from the Coop

    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

    46 min
4.9
out of 5
7 Ratings

About

AI is the biggest technology shift of our lifetime. This show is about how to profit from it together. Each week I talk with the founders and CEOs closest to AI and Content, the ones figuring this out in real time. I’m also building an AI content business myself and share the lessons I learn along the way. WHAT WE COVER THE TITANS: How companies like OpenAI, Anthropic, Meta, and xAI are moving, and why their decisions matter. THE INCUMBENTS: How content giants like Disney, News Corp, Universal Music Group, and Reddit are responding to AI, and what it means for creators and publishers. THE PLAYBOOK: Real lessons on AI business models, content strategy, IP licensing, distribution, and getting paid. ABOUT YOUR HOST: Rob Kelly has interviewed Steve Jobs and Bill Gates, helped pioneer early web content licensing, and built multiple companies with more than $100 million in total sales. His work has appeared on CNBC, CNN, TIME, and Entrepreneur. Beyond business, every episode explores what AI means for jobs, creativity, families, and the next generation. If you want clear thinking based on real experience in AI and media, Media and the Machine is your guide Thanks! -Rob