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 — which means we’re also getting at some of the biggest questions in tech.

Warning: This is a pants-free episode. Probably still Safe For Work, though.

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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 whenever you want. Or whenever the algorithm thinks you want it.

Fox is a great person to talk to about this stuff: he covers comedy very, very seriously over at Vulture, and on his Good One podcast, and he has a lot of thoughts about the way tech - and perhaps politics - is shaping the stuff that makes us laugh.

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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’s likely to generate the same kind of revenue and profit.

But the people who run Big TV are trying to find answers, anyway. So I asked Lightshed analyst Rich Greenfield to talk through some of their moves. What will David and Larry Ellison do once they finally buy Paramount? What are the prospects for ESPN’s soon-to-launch streamer? What about Fox’s soon-to-launch streamer? Who’s going to buy all of these ailing cable TV networks that are coming on the market? And what kind of deals - if any - can get done in the Trump 2.0 era?

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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 stop funding it. Now it looks like they’ve gotten their way, and the two networks are going to lose a combined $500 million a year.

So what happens now? And how did we get here? And should the federal government be funding media organizations at all? We discuss.

And, since Folkenflik is also one of my go-to Rupert Murdoch experts, I asked him to stick around and opine about Donald Trump’s libel suit against Murdoch and his Wall Street Journal. Who has more to lose, and who is likely to blink first?

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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, magazines were incredibly important — and Conde Nast was the most important, most glamorous magazine publisher in the world.

We know why all of that has changed — in large part because of the technology that allows you to listen to this conversation. But Empire of the Elite, Grynbaum’s excellent new book, focuses mostly on how Conde reached its peak influence, and how it sustained it for years.

Also discussed here: Money money money. Also: Why Jeff Bezos is very unlikely to buy Vogue in the near future.

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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 you what’s going inside and why it actually matters.

So we spent a bunch of time in this chat talking about Tani’s story about a controversial-at-least-online Times story . In part because I find the whole thing fascinating (I’m not normal). And in part because it gives you a pretty good idea of what being a media reporter entails in 2025.

Also discussed here: When is something a tweet, and when is it a story? Why is this a “weird moment in media”? And why was 2024 the “fragmentation election?”

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"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 relevant as ever.

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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 up and to the right.

A very quick primer for those of you haven't heard of Sundberg and her Feed Me newsletter  - she’s building a very interesting publishing company that revolves around her reporting, insights and taste, aimed at people who make good money and spend some of it on very nice restaurants, shops and hotels in places like London, LA and New York. My assumption is that a slice of her audience doesn’t do any of that at all — but wants to read about people who do.

In olden times, Sundberg might have a column in a glossy magazine - and in fact she spent some time working at places like New York magazine on her way up. Today what's left of the glossy magazine world would love to attach itself to her. It’s a very 2025 proposition.

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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 service with state-of-the-art AI — lots of people paid attention. Including, apparently, folks at the very top of the Apple org chart.

I talked to Gruber about the fallout from that post. Which is pretty interesting! But there’s a lot more going on in this conversation. It’s partly about the friction Apple has been generating lately — not just about its AI efforts, but the way it runs its App Store, and the way it interacts with developers — and why all of that does and doesn’t matter.

And it’s also about the delightfully retro practice of running an ad-supported blog in 2025. That works very well for Gruber, but it seems like the new Grubers of the world are doing their work on YouTube or Substack. He’s got some thoughts about that, too.

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Here’s one where we try to do two things at once:

Which is to say: You can hear more of the this conversation by heading to Semafor’s Mixed Signals pod, and you can hear a different slice of the chat by heading to Brian’s Rebooting pod. It’s an experiment, based on the thesis that the people who listen to one of our shows would be very interested in listening to the other shows. Did we get it right? What can we do to make it better? Please let us know.

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