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 notes in our chat, it’s a young company that’s still figuring it out itself.)

But I really wanted to talk to Reilly to get his POV on TV, which more or less peaked when he was working in the industry. Now, of course, it is in what appears to be permanent decline, while its remaining participants try to merge their way to safety.

Why did TV flourish in its not-that-long ago Golden Age? And why didn’t its leaders see — or act on — the threat that streaming/digital/internet tech would have on their industry?

You probably have some ideas yourself. Now you get to hear it directly from a guy who was there, at the top.

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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 (spoiler alert: he thinks some football fans who pay for YouTube TV may be unhappy for a while longer.)

Then Sherman and I move on to the other Big Media deal: the battle for the company we currently call Warner Bros. Discovery, but is likely to be owned by someone else, in some form…. eventually.

Discussed here: why, really, did Larry and David Ellison put in multiple offers to buy another media company weeks after they bought Paramount? What would they do with WBD if they got it? And are any of the theoretical other buyers for all or parts of WBD real?

Bonus question for you: did I use the word “degradation” correctly in this one?

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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 organize, debate and push back.

Over the years the site turned itself into a for-profit, and found success selling Substack subscriptions — it’s currently on pace to do more than $12 million a year from those alone, says CEO Sarah Longwell. But it has really caught fire in recent years by embracing YouTube. “The thing that made the biggest difference was when we decided to turn the cameras on,” she says.

I talked to Longwell this week about the Bulwark’s evolution, and the tension between running a mission-driven company and one that wants to make money. And since Longwell still does political consulting and focus group work, I also talked to her about the state of the art when it comes to political media — and why she thinks Republicans are so much better at it then Democrats.

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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 model is the envy of everyone in journalism.

Can he do it again? One big difference is that the Times launched its paywall all the way back in 2011, before everyone was asking consumers to pay for monthly subscriptions for everything. I also have a hunch that the Times brand registers more deeply for its audience than CNN does for its. But now we’ll get to find out.

Meantime, all of this is happening as CNN parent Warner Bros. Discovery is likely to get sold, yet again. Which means all of the work Thompson and his team are doing could get upended by a new management regime.

But that’s the future. For now, it’s very much worth listening to Thompson make the case for CNN, and TV news in general.

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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 hear from a guy who understands the big picture, but also the practical realities of operating, he’s your guy.

Brian has been preaching the gospel of small media for some time, so we start there: What is the upside of running a scaled-down media company these days — and what happens to all the businesses that spent years chasing scale?

And yes, Brian and I also talk about AI, and what it will and won’t do for (and to) media. But we also spend a lot of time talking about Google, and the enormous power it currently has — particularly when it comes to the company’s Discover feature, which drives an astonishing amount of traffic.

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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 pushing at the economics behind the AI boom, via his newsletter and podcast, for some time.

We talk about how he built a career out of skepticism, why the media keeps falling for big tech’s favorite stories, and what happens if the AI party ends early.

(And yes: I wrote the paragraphs above with an assist from ChatGPT — mostly so I can imagine Zitron fuming when he reads this.)

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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 with the paper.

But CEO Anna Bateson says the Guardian needs to be a self-sustaining publisher. So it has been steadily, and successfully, getting readers to shoulder the load, via donations, which now account for 40% of the company's revenue.

We talk about how and why the Guardian switched its business model; why it still wants ad money; how the British, lefty news shop is trying to break into America yet again, and why asking readers for donations is, and isn't, like asking them to pay for subscriptions.

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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 Vivek Shah is going the other way: he's one of only two big publishers to sue OpenAI (the other one is the New York Times) and he says his portfolio of sites would like more traffic from Google, but is confident things will work out.
Shah and Ziff Davis never got the attention some of their digital peers did a decade ago. On the flip side, they're still standing in 2025. So this is a POV worth paying attention to.

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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 fight - it revolves around a time slot and a format that has been on its way out for a long time.

So how did late night TV become a flashpoint in a crucial First Amendment fight? And how long is it going to stick around?

James is the perfect person for this discussion: Not only does he watch TV (or YouTube) for a living, he’s also become a professional Trump-watcher, because Trump is a TV character. (Trump and TV are the subject of James’ excellent 2019 book). But make no mistake: the threats he’s making — on his own and with the help of his regulators – are very real.

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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 would you want to wear a computer on your face - no matter how much it costs and how much they weigh? And why do all the big tech companies keep trying to make this happen? I have some ideas, but Alex Heath is deeply sourced on this stuff, so asked him.

Up until this week, Alex was a star tech reporter at The Verge. Now he’s off on his own, with Access (a podcast) and Sources (a Substack). He’s kicking off his foray into indie media with a long interview with Zuckerberg, so we used that as a jumping off point to talk about Zuckerberg’s political shift, his AI obsession, and his big bet on wearable tech.

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