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

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

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

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

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

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 wins
• The shift to engineers controlling content — and what that means for creators
• How short-form video impacts long-form content
• Why the line between tech and media has essentially disappeared
• And how AI is creating for him a new renaissance — he’s gone from ideas to live products himself in a matter of days

Oh, 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

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

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

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

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

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

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

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

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

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