Best Isaac Reilly Podcasts (2025)

1
What Happens To Media When The Web Goes Away, with Tony Haile 39:09

Play Pause

5d ago39:09

39:09

We built the modern media business for the web — for people who visited websites, read articles, and saw ads. What happens when no one does that anymore? That’s been one of the big themes of conversations we’ve been having on Channels with this year — with people who run big and small media properties, and with people who are trying to build media …

1
Kevin Reilly got to the top of the TV heap. Now he's in AI. 40:10

12d ago40:10

40:10

If you watched something on TV that you liked in the past few decades, there’s a good chance Kevin Reilly was involved: at various times he’s held top jobs at FX, Fox, NBC, Turner and HBO Max. But that run ended in 2020, and now Reilly is running Kartel, an AI company that… well, I’m still not entirely sure what it does. (To be fair, as Reilly note…

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What the Disney–YouTube Battle Tells Us About the End of Cable 52:39

19d ago52:39

52:39

It’s not unusual for a big TV network and a big TV distributor to fight about money. But the Disney-YouTube fight is unusual -- at the bare minimum, because it has stretched out for so long. CNBC’s Alex Sherman lives and breathes this stuff, so I asked him to walk me through it, and make some prognostications about when it might get settled (spoile…

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The Bulwark's Sarah Longwell on Why Republicans Won the Attention War 45:25

26d ago45:25

45:25

In some ways, the Bulwark feels like other small publishers in 2025: it’s found growth and profit by pushing itself out on any platform it can find. But that wasn’t the plan when the company started in 2018. Back then, it was a non-profit cofounded by Republicans who couldn’t stand their party’s embrace of Donald Trump, and wanted a place to organi…

1
The Man Who Fixed The New York Times Wants to Fix CNN 52:17

1M ago52:17

52:17

Would you pay $7 a month to stream CNN? Because CNN CEO Mark Thompson would like you to do that. I know, I know, I’m skeptical, too. But Thompson has been here before: At his last job, as CEO of the New York Times, he helped shepherd that company’s subscription business, which had a gazillion naysayers at the start. And now the Times’ business mode…

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The End of Mass Media—and What Comes Next 56:54

1M ago56:54

56:54

We spend a lot of time on this show talking to people who run media companies. We also spend a lot of time talking to media reporters. So here’s our one-man Venn diagram: Brian Morrissey runs The Rebooting, where he podcasts, writes and hosts events, all geared at making people in the media business smarter about the media business. If you want to …

1
The PR Guy Who Says the AI Boom Is a Bust 54:36

2M ago54:36

54:36

The AI story is changing fast. A few months ago, it was all promise and inevitability. Now even AI boosters are asking if the numbers make sense. Ed Zitron got there early. He runs a PR firm for a living, which means he’s supposed to help people sell their stories. But he’s become best known for tearing tech’s biggest stories apart. And he’s been p…

1
Why the Guardian Doesn't Need a Billionaire to Thrive 39:00

2M ago39:00

39:00

In lots of ways Guardian Media Group is facing the same problems as every other news publisher: A tricky ad environment, platform problems, looming AI threats. One big difference: The Guardian also has a $1.5 billion trust backing the non-profit, which seems way, way better than being owned by a run-of-the-mill billionaire who might want to meddle …

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Almost Everyone is Taking Money from OpenAI. Why is Ziff Davis suing them? 34:22

2M ago34:22

34:22

In the future, digital publishers could get run over by AI. In the present, they are deeply concerned about Google, and the prospect that the search giant is going to choke off their last reliable traffic stream. That may explain why lots of publishers are making deals with OpenAI now -- and doing a lot of grousing about Google. Ziff Davis CEO Vive…

1
The Future of Late Night TV, Jimmy Kimmel, and The First Amendment 26:53

2M ago26:53

26:53

When’s the last time you stayed up to watch a late night TV monologue? Months? Years? Decades? I’m not sure, either. But I stayed up Tuesday night to watch Jimmy Kimmel’s return. James Poniewozik, who covers TV for the New York Times, just caught up with it the next day on YouTube. Which underscores one of the odder parts of the Trump v. Kimmel fig…

1
I tried Zuckerberg's $800 Ray-Bans. Are they the future? With Alex Heath 45:00

2M ago45:00

45:00

A year ago I got try a pair of $10,000 computer goggles from Meta. The tech was super-impressive, but you couldn’t buy them them. You still can’t. Now Mark Zuckerberg is trying a similar idea. But this time around the the tech is scaled-down, lighter and way cheaper: the new version costs $800, and you’ll be able to buy them in a couple days. Why w…

1
How TBPN Made a Tech News Splash 39:10

2M ago39:10

39:10

John Coogan knows what you’re thinking: the world does not need another tech podcast. And the world does not need another podcast featuring two dudes talking. Yet Coogan and Jordi Hays have started another tech podcast, featuring the two of them talking and… it’s a hit. In the span of a year, TBPN has become the place where tech execs go to chop up…

1
This Means Woe: Owen Painter, Catharine Zeta-Jones, and Jenna Ortega! 26:46

3M ago26:46

26:46

So. Many. SPOILERS! If you haven’t watched all of Season 2 of Wednesday, go do that now and come back. We’ll wait. (No we won’t) Owen Painter, Catherine Zeta-Jones, Jenna Ortega - need we say more?! First up, Owen Painter – zombie/evil genius Isaac Night – visits Caitlin Reilly and recalls punching himself in the face while walking the streets of I…

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Woe Me The Money: Evie Templeton, Colleen Atwood, Steve Buscemi 29:24

3M ago29:24

29:24

MORE SPOILERS! Are we doing this still? This podcast is rotten with spoilers for episodes 1–7 of Wednesday Season 2. Our new fave Evie Templeton, aka Agnes DeMille, talks with Cailtin Reilly about what it was like dancing with Emma Myers, and how her deep knowledge of film history helped her to play Wednesday’s stalker… Next, an icon of cinema cost…

1
Patch’s AI Experiment: Thousands of Newsletters, Zero Humans 39:07

3M ago39:07

39:07

Everyone agrees that the decline/disapperance of local news is a big problem. No one agrees about the best way to solve it. So let’s check in on a new AI push from Patch, the people who have been trying to do local news, online, at scale, for more than two decades. Last spring, Patch CEO Warren St. John announced that he was running local newslette…

1
Woe Thyself: Emma Myers, Gwendoline Christie, Al Gough & Miles Millar 34:37

3M ago34:37

34:37

TREAD CAREFULLY! This podcast is squirming with spoilers for episodes 1 – 6 of Wednesday Season 2. We’re howling with delight! Because Emma Myers joins Caitlin Reilly to talk about all the ways that Enid is coming into her own this season. And we hear from Weems herself, Gwendoline Christie! She goes deep into the process of becoming Wednesday's gh…

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Hide and Woe Seek: Georgie Farmer, Joy Sunday, Tom Turnbull & Angela Robinson 36:10

3M ago36:10

36:10

WARNING! This podcast contains spoilers for episodes 1 – 5 of Wednesday Season 2. Your favorite gorgon, Georgie Farmer, joins Caitlin Reilly to talk all things Ajax: his relationship with Enid, his friendship with Bianca, and his true feelings for Bruno. And then Joy Sunday talks about how the adults in Bianca’s life are really NOT making it easy f…

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Oliver Darcy Thinks the Media Doesn’t Get It. So He Built Status 53:40

3M ago53:40

53:40

One thing about the internet is that it lets you build really, really fast. A little more than a year ago, Oliver Darcy was an unemployed former CNN media reporter. Today he’s the proprietor of Status, his must-read media newsletter. In our conversation, we spend a little bit of time talking through the mechanics of his two-man operation, and how h…

1
If These Woes Could Talk: Fred Armisen & Joanna Lumley 25:28

3M ago25:28

25:28

SPOILER WARNING! Yes, this podcast has lots of spoilers for Wednesday Season 2, episodes 1– 4. But you already knew that. In this episode, Caitlin Reilly sits down with legendary actors – and Addams family favorites – Fred Armisen and Joanna Lumley! Fred talks us through Uncle Fester’s extensive passport collection and reveals that Wednesday is the…

1
Why Henry Blodget is Building Another Media Company 57:56

3M ago57:56

57:56

Henry Blodget can’t help himself. The Business Insider founder is starting another media business, knowing full well how difficult the industry can be. You can watch him build it in real time: Regenerator on Substack, and Solutions on TikTok, YouTube and everywhere you hear your favorite podcasts. Henry — who hired me to work at Business Insider in…

1
Call of the Woe: Isaac Ordonez, Mark Sutherland & Tristan Versluis 28:58

3M ago28:58

28:58

ALERT! This podcast contains spoilers for Wednesday Season 2, episodes 1–4. In this episode, Caitlin Reilly asks Isaac Ordonez to reveal which member of the cast became his on-set mentor, and how he practiced Pugsley’s new power… Costume genius Mark Sutherland talks us through Wednesday’s iconic looks, Bianca’s denim jackets and Morticia’s unique c…

1
ESPN boss Jimmy Pitaro on streaming, the NFL and sports betting 48:14

3M ago48:14

48:14

The media industry has been waiting for ESPN to cut the cord for a decade. Now it’s finally happening: This week the sports TV giant will let you start streaming — without a cable TV subscription — for $30 a month. Why now? ESPN boss Jimmy Pitaro is quite frank about it: Along with his boss — Disney CEO Bob Iger — he wanted to make as much money fr…

1
The Devil You Woe: Hunter Doohan, Victor Dorobantu, Paco Cabezas 36:00

4M ago36:00

36:00

DANGER! This podcast contains spoilers for Wednesday Season 2, episodes 1-4. In Episode 2 of the Woecast, Hunter Doohan talks to Caitlin Reilly about Tyler’s transformation from meek barista to hideous Hyde! And why Wednesday still holds so much power over him. Victor Dorobantu, the man behind everyone’s favorite disembodied appendage, will reveal …

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A Busy - and Expensive - Summer for AI, with NYT's Mike Isaac 51:42

4M ago51:42

51:42

What makes a particular engineer worth $250 million to Mark Zuckerberg? What does Trump 2.0 mean — and not mean — to people building large language models? I didn’t know the answers to these questions either. So I got the New York Times’ Mike Isaac, who covers this stuff for a living, to walk me through some of the biggest questions in AI right now…

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Here We Woe Again: Jenna Ortega, Creators Al Gough & Miles Millar 31:46

4M ago31:46

31:46

BE WARNED! This podcast will contain spoilers for Wednesday Season 2, episodes 1-4. Jenna Ortega peels back the layers on the new tension between Wednesday and Enid. And that terrifying vision! Plus… Series showrunners Al Gough and Miles Millar reveal why they made Morticia Addams such a central character in this season, and what it means for Wedne…

1
Why the Algorithm is Making Comedy Boom, Again 58:53

4M ago58:53

58:53

The last time I talked to Jesse David Fox about the comedy boom it was… March 5, 2020. Since then, some things have changed. But in other ways it’s just the same: comedy - or at least, some kinds of comedy - seems almost custom-built for our current technological and cultural moment, and it’s easier than ever to get this stuff on your devices whene…

1
What is TV’s endgame? 47:28

4M ago47:28

47:28

A decade ago, Disney CEO Bob Iger freaked out the media industry by acknowledging something many of us saw coming — his previously unassailable TV business was starting to erode. But even with a 10-year warning, today’s moguls seem unable to cope with 2025’s reality: The pay TV business is permanently eroding, and there’s nothing in its place that’…

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Introducing: The Wednesday Season 2 Official Woecast 2:11

4M ago2:11

2:11

The Wednesday Season 2 Official Woecast is here and it’s as twisted, stylish, and unmissable as the show itself. Hosted by Caitlin Reilly, the Woecast is your backstage pass to Nevermore Academy and beyond, with exclusive interviews, behind-the-scenes secrets, and episode-by-episode breakdowns. Each episode, we'll dive deep into the making of Wedne…

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Why Trump is defunding NPR and PBS - and suing Rupert Murdoch 35:59

4M ago35:59

35:59

Reporting on the place you work is not fun. But it is an occupational hazard for media reporters — particularly for NPR’s David Folkenflik. That’s because National Public Radio — along with Public Broadcasting Service, its TV counterpart — is quite frequently the target of attacks from critics on the right, who would like the federal government to …

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Inside the Rise and Fall of Condé Nast with Michael Grynbaum 47:38

5M ago47:38

47:38

Here's one way New York Times reporter Michael Grynbaum described Condé Nast to me in this week’s chat: “A real exporter of American cultural influence in the late 20th century.” And here’s another one: "A kind of enchanted land” but also a “lost world." And here’s one way I’d describe it: it’s hard to imagine in 2025, but just a few decades ago, m…

1
Inside the NYT - and Everywhere Else - with Semafor's Max Tani 48:09

5M ago48:09

48:09

You’re probably a normal person, so you didn’t spend your holiday weekend talking to people at the New York Times about a local politics story that some people didn’t like. But that’s Max Tani’s job: He’s Semafor’s media reporter, which means he’s supposed to burrow into the paper of record — as well as other important media institutions — and tell…

1
Black Mirror's Charlie Brooker on the problem with tech - and people 43:47

5M ago43:47

43:47

"Black Mirror" creator Charlie Brooker knows that everyone thinks his show is about tech-fueled dystopias. But he says it's really about humans, not their tools. I loved this chat back when we recorded it in 2023, when Brooker was promoting the sixth season of his Netflix show. Now there's a new season - and Brooker's vision of the world is as rele…

1
How to become a Substack Star with Emily Sundberg 47:07

5M ago47:07

47:07

What's the best way to describe what Emily Sundberg does? Substacker? Influencer? Journalist? Brand-builder? Let's go with "yes". And she does a much better job of describing herself in our conversation, where we talk about how she went from being a laid-off marketer at Meta to a one-woman business with a devoted following and a revenue line that’s…

1
Why did Apple ice out the most famous Apple blogger? 1:04:48

6M ago1:04:48

1:04:48

If you want smart, nuanced insight into Apple’s products and would-be products, you turn to John Gruber, who’s been blogging about this stuff for more than two decades at his Daring Fireball site. So in March, when Gruber announced that Something is Rotten in the State of Cupertino — focusing on Apple’s botched plans to imbue its ailing Siri servic…

1
On the hunt for media optimism, with Semafor’s Ben Smith and The Rebooting’s Brian Morrissey 28:22

6M ago28:22

28:22

Here’s one where we try to do two things at once: Have a convo about green shoots in media with two smart guys who know media really well — Semafor’s Ben Smith and The Rebooting’s Brian Morrissey. Try to find new audiences for our respective podcasts, by cutting up that conversation into 3 parts, and distributing those parts to our respective feeds…

1
Scott Frank on Netflix, the future of Hollywood, and Dept. Q 43:42

6M ago43:42

43:42

Scott Frank used to write great movies, like “Out of Sight.” Now he’s a Netflix guy, and a super successful one: he made “Godless,” a horses-and-everything Western for the streamer, then had a pandemic-era phenomenon with “The Queen’s Gambit.” Now he’s back with “Dept. Q”, his take on the British mystery genre. You can find that one on Netflix’s to…

1
Bluesky Wasn’t Supposed to be a Twitter Rival. Now It Is. 37:01

6M ago37:01

37:01

I admit it: I most definitely rolled my eyes in 2019, when Twitter announced vague plans to build an "open and decentralized standard for social media". At the time I didn't really understand what then-Twitter CEO Jack Dorsey was trying to do — or why the head of a social media company with plenty of problems was messing around with plans to create…

1
How to Reinvent a Magazine, with Wired’s Katie Drummond 47:58

6M ago47:58

47:58

Today we’re talking about how you take a media property that’s been around for a long time, and find a way to bring in new eyeballs — and new revenue. That property is Wired — the place that told you about the internet before the internet even existed — and the person who’s reviving it is Katie Drummond, who has been running the property for a coup…

1
Meta's Adam Mosseri explains how Instagram really works - and how he wants to build Threads 58:46

6M ago58:46

58:46

Adam Mosseri's official title is head of Instagram, Meta's massive photo and video app. He also runs Threads, the Twitter clone the company launched two years ago. Unofficially, he's become one of Meta's chief explainers, frequently jumping on social media to defend and proselytize on behalf of his employer. So when I got a chance to interview Moss…

1
How Apple trapped itself in China 1:07:32

7M ago1:07:32

1:07:32

The iPhone you’re reading this on was made in China. For a long time, that fact was a huge part of Apple’s success story: Working hand-in-hand, Apple and China built a sophisticated supply chain that let Apple manufacture very complicated technology at an enormous scale. Now that relationship seems like Apple’s achilles heel, says Patrick McGee. Mc…

1
Ian Rogers tells me I need a crypto wallet 1:04:41

7M ago1:04:41

1:04:41

I wanted to talk to Ian Rogers about his fascinating career. He wanted to talk to me about Ledger, the crypto wallet company he’s working at now. So we did both things. Background: Rogers was an important figure in the digital music business, back when the music business was being fundamentally reshaped by digital. He helped the Beastie Boys get on…

1
How to fight Apple and (maybe) win, with Epic Games CEO Tim Sweeney 33:43

7M ago33:43

33:43

Today's podcast is an in-depth discussion of Apple's App Store rules and how they... wait! Don't leave! I could try to tell you why Apple's App Store rules are important to both Apple and the digital economy (sadly, I just realized I've been covering them for nearly 15 years, so they better be important). But a better messenger for that task is Tim…

1
Tariffs, Trump, TikTok: What’s going to happen to ads in 2025? 54:50

7M ago54:50

54:50

There are all kinds of ways to measure the health of an economy. The one I rely on is ad spending. One reason for that is simple: I work in ad-supported businesses, so I want to know about things are going to affect me personally. A less self-interested reason: The health of the ad business is tied directly to the way companies feel about their ove…

1
Roblox CEO David Baszucki knows what your kids are doing. 44:08

7M ago44:08

44:08

Every day some 85 million people - most of them kids - show up to play, chat and spend money on Roblox. That’s a massive audience just about any tech or media company would like to have. But David Baszucki wants more: He thinks his platform can eventually command 10% of the worldwide gaming market. I spent time talking to Baszucki about those ambit…

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How to make money in Washington, with Punchbowl’s Jake Sherman 40:19

8M ago40:19

40:19

Some people don’t want to pay for media. But lots of people are paying Jake Sherman and his team at Punchbowl News: The 4-year-old startup is thriving by providing super-insidery news and data about what’s happening in Congress. I chatted with Sherman because I wanted to get an update on his business (he says he’s not going to sell it anytime soon,…

1
NYT publisher AG Sulzberger on Trump, OpenAi and the economy 1:05:07

8M ago1:05:07

1:05:07

The New York Times faces the same challenges every other news organization faces in 2025. But it’s also in way better shape to take those challenges on: Thanks to a business model built on 11 million subscribers, it’s not nearly so worried about things like the fluctuations of the ad business, or changes in Google’s algorithm. That comparative stre…

1
Trump vs The Media, Round 2, with Sara Fischer 46:29

8M ago46:29

46:29

The Trump 2.0 era is less than three months old. But it’s already creating havoc for journalists and the companies they work for. In Washington, Trump and his team are demoting traditional media - or kicking them out of the White House entirely. In corporate boardrooms, he is forcing media owners to settle lawsuits they would normally fight, and to…

1
How long can sports keep TV alive? 43:58

8M ago43:58

43:58

Call it symbiosis. Call it co-dependency. However you want to characterize it, there’s zero debate that Big TV and Big Sports are deeply intertwined. So if the TV business is shrinking, what happens to sports? That’s the main question I had for John Ourand, the longtime sports business reporter who’s now at Puck. But I had lots of related ones, lik…

1
Inside PJ Vogt’s low budget, super successful podcast 1:05:40

9M ago1:05:40

1:05:40

Anyone who makes things thinks they could do it better if they had more. More money, time, headcount, infrastructure. Some of us find there can be upsides to doing it with less, too. That's not exactly PJ Vogt's story but I think it's directionally accurate: Vogt cohosted a huge hit podcast - Reply All - and when he decided to try again - with Sear…

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Twitch CEO Dan Clancy wants to hang on to the live-streaming crown 1:00:49

9M ago1:00:49

1:00:49

Back when I first started covering the internet, the idea of broadcasting yourself for hours on end seemed like a pipe dream for weirdos. Now it's how some people make a living. Twitch more or less created live-streaming in the U.S., which is why Amazon bought it for about $1 billion back in 2014. But now there are plenty of places to watch, and cr…