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

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

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

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 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

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