Media and the Machine

Rob Kelly
  • 4.9 (8)
  • TECHNOLOGY

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, Google, 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, creativity, IP licensing, distribution, and getting paid. Family & Our Future -- Every episode ends with me asking my guest what AI means for our jobs, our families, and the next generation. 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. Thanks! -Rob

  1. Sailing Champ Builds “the AdSense for AI”

    5D AGO

    Sailing Champ Builds “the AdSense for AI”

    My guest today is Nic Baird, co-founder and CEO of Koah Labs. Koah is building what Tom Tunguz of Theory Ventures calls the AdSense for AI. Nic breaks down: • AI token economics in plain English: why serving an AI user can cost 100 times more than serving a web user.That’s why he thinks most AI apps cannot reach global scale on subscriptions alone. • Ads are coming to AI. The question is whether they’ll be useful—or terrible? Nic says the best AI ads won’t look like pop-ups, banners, or pre-rolls. They’ll be part of the answer. • Where people will first see these ads: ChatGPT, Copilot, Google AI Overviews, Gemini, and the agents and apps outside the frontier models. • Whether Claude can really stay ad-free forever? • We get into privacy too. How do you use AI in ads without reading people’s most personal chats and creeping them out. And Koah's fundraising story is wild. Tom Tunguz reached out before Koah even had a product And after passing on 150 adtech companies he made his Series A decision in 24 hours. Nic is also an 8-time national sailing champion and his dad won the America’s Cup and is in the sailing hall of fame. We talk about Nic's scariest sailing moments and how he got to meet Larry Ellison on the world’s biggest private superyacht. Special thanks to Tom at Theory Ventures for putting Koah on my radar. Please enjoy my conversation with Nic Baird. Thx!Rob

    34 min
  2. AI Models Got the Hype—But Apps Decide Who Wins Next

    APR 27

    AI Models Got the Hype—But Apps Decide Who Wins Next

    My guest today is Andy Beach, he hails from Microsoft where he was the CTO of AI for their Media and Entertainment business. He now consults AI startups and is a VC investor at Hallstone, a firm investing in media and tech. Most people think AI'll be won by the biggest models—OpenAI, Anthropic, Google Gemini. Andy says that’s wrong. The real winners will be the apps built on top. We talk about what that looks like. Think YouTube and TikTok—they didn’t invent video, they changed how we consume it. Andy believes AI apps will do the same thing. Not just recommending what to watch, but building your whole day across Netflix, YouTube, and more. Andy points to companies like Midjourney, Runway, and ElevenLabs. They started as models—but had to become full apps to win. We also get into the “Mac vs PC” style battle between OpenAI and Anthropic. And why Apple using Gemini is smarter than building its own LLM. We cover sports including Andy's work on AI with the NBA and Motocross.You'll be amazed at the fan experience AI is gonna allow us. We also go deep on where the money is going. AI training and licensing could get even bigger Andy also shares lessons from inside Microsoft. Why they never tried to become a media company like Google.  Finally, we talk about who wins first. It’s not big studios. It’s independent creators. Small teams using AI to make better content, faster. Special thanks to Peter Csathy for putting Andy on my radar. Peter did a great interview of Andy back in early 2025 Now Please enjoy my conversation with Andy Beach. Thx!-Rob

    43 min
  3. Top Podcaster: AI Kills Info Podcasts—Not Personalities

    APR 19

    Top Podcaster: AI Kills Info Podcasts—Not Personalities

    My guest today is Chris Hutchins, host of the All the Hacks podcast — heard by over a million listeners, with more than 10 million downloads — ChatGPT describes Chris as “Tim Ferriss meets Mr. Beast with a spreadsheet.” He’s also founded and sold two companies — one to Google and the other to Wealthfront. In our conversation, Chris explains why AI could replace a huge number of podcasts — and which ones actually survive and why. He shares what he’s learning from a current test in which for the past 2 weeks he’s recorded everything he says (and I mean everything including conversations with his wife) . He shares how that experiment is changing how he thinks about the new way content will be created and consumed. He lays out a future where you don’t use apps at all — just one AI interface. He also breaks down a test where he used AI to read his podcast ads — and even his wife couldn't tell which was her husband and which was AI He explains why he stopped using OpenClaw, even though it blew him away… and how his use of LLMs has completely flipped in the past year.  Special thanks to Jay Clouse for connecting Chris and me through his amazing Creator Science Lab, including an event in Boise where Chris and I first sat down together.  Speaking of that, this episode has a bonus second part. The first part you’re about to hear is purely on AI. But then at the end, I’ve included a separate, mostly uncut conversation we recorded last year where I asked Chris tactical questions I had myself on how to build a great podcast –I hadn’t yet launched mine.  That bonus includes how he thinks about audio vs. video, when to start selling ads, how he picks which topics to work on, and how he prepared for his appearance on the Tim Ferriss show Please enjoy my conversation, parts 1 and 2, with Chris Hutchins. Thx, Rob Kelly

    1h 11m
  4. AI Stole 7M Books…Why This Publishing Insider Is Still Bullish

    APR 12

    AI Stole 7M Books…Why This Publishing Insider Is Still Bullish

    My guest today is Thad McIlroy, author of The AI Revolution in Book Publishing – and the most  strategic thinker I know on where AI and books collide.  He’s an insider who knows the big publishers but he also tracks more than 1,800 startups in the space (including 350 in AI). In this conversation Thad breaks down the“original sin” of AI in publishing—and why it’s driving so much fear and anger across the industry. We talk about why publishers are, in his words, “constipated by copyright,” and how that same mindset crippled them during past tech waves—from Amazon… to Kindle… to the Google Books project. He shares a wild story of an author who made over $100K by quickly creating 200 books using AI. He also lays out his simple “15% framework” for publishers and calls out one common approach from publishers as “pathetic.” He explains John Grisham’s AI pushback (he’s banning it) is a bad move for the Big 5 publishers.  And for those of you building startups in this space, he lays out what he calls the “Manifest Destiny” of publishing—and how AI could finally make that a reality  Make sure you stick around for the final question—Thad's story about his dad came out of nowhere (and got me weepy).  Special thanks to Zach Stewart at the Canessa Art Gallery on Montgomery Street in SF (right at the heart of AI) for connecting Thad and me.  Please enjoy my conversation with Thad McIlroy. Thx!Rob

    1h 7m
  5. The Data Center Expert’s “Ride or Die” Plan for When AI Turns

    APR 5

    The Data Center Expert’s “Ride or Die” Plan for When AI Turns

    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

    54 min
  6. Ex-Meta Dealmaker Behind $1B in Content: What Actually Wins

    MAR 29

    Ex-Meta Dealmaker Behind $1B in Content: What Actually Wins

    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 winsThe shift to engineers controlling content — and what that means for creatorsHow short-form video impacts long-form contentWhy the line between tech and media has essentially disappearedAnd how AI is creating for him a new renaissance — he’s gone from ideas to live products himself in a matter of daysOh, 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

    40 min
  7. Dow Jones Ex-Head of Innovation: Woo or Sue AI?

    MAR 20

    Dow Jones Ex-Head of Innovation: Woo or Sue AI?

    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

    45 min
  8. SPIN’s CEO: AI Can’t Break the Next Nirvana

    MAR 13

    SPIN’s CEO: AI Can’t Break the Next Nirvana

    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

    58 min
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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, Google, 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, creativity, IP licensing, distribution, and getting paid. Family & Our Future -- Every episode ends with me asking my guest what AI means for our jobs, our families, and the next generation. 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. Thanks! -Rob

Information

  • Creator
    Rob Kelly
  • Years Active
    2K
  • Episodes
    15
  • Rating
    Explicit
  • Copyright
    © Media and the Machine
  • Show Website
    Media and the Machine

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