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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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 the news of the day - first in a daily livestream, and later in clips that circulate around the internet.

And Coogan and Hays are carving out a niche for themselves: Insidery, in-the-know, but also not that serious about the whole thing. They don’t have a huge audience, but they have an influential one, and the beginnings of a very intriguing business.

I talked to Coogan about how TBPN got off the ground, how it works today, where he and Hays go from here — and whether their success has built a playbook for others to follow.

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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 newsletters for thousands of communities across the U.S., without employing a single human to make them. This week, I asked him how it’s going.

No one is going to mistake these “Patch AM” emails for a fully-staffed local news outlet — and in fact Patch relies on other local outlets to help populate their newsletters. But they also seem like a well-meaning effort to provide residents with something, as opposed to nothing. Or, in St. John’s words: He’s providing them with a Kind bar, not a 5-course meal.

Does that make you nervous about the future of news? Or optimistic? Somewhere in between? Take a listen and let me know what you think.

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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 he thinks about the future. But I wanted to focus our chat and something that’s a little harder to sum up: How Darcy’s reporting and writing fits into the larger media landscape in the Trump 2.0 era, and why he goes out of his way to spell out exactly what’s happening. “We say the things that everyone else is thinking and no one is else saying,” he says. I think that’s part of it. Another is that Darcy is uniquely well-suited to covering right-wing media — which used to be on the fringes and is now squarely mainstream - because he used to be a right-wing media creator himself. So he’s particularly clued in to the way a lot of this stuff works, and impatient that others can’t or won’t see it.

Oh, and Darcy has one bit of advice for people running big media operations wondering how they can get influential creators to work with them: “Don't let them leave.”

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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 2007, back when it was called Silicon Alley Insider — sat down for a chat about what’s changed in media and the internet over the years, and what hasn’t. We also took time to talk about the AI boom, whether it’s a bubble, and why bubbles can be useful. It’s a blast from the past and a look at the future, all in one chat. Enjoy!

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