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

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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.” Learn more about your ad choices. Visit podcastchoices.com/adchoices

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! Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 from the cable TV business as he could before it dwindled away. And even now, Pitaro says he hopes the new service brings in customers who don’t have cable — as opposed to getting ones who do still pay for cable to trade down. That illustrates the issue facing all of the big TV players these days: They know the future is a digital one, where they’ll have to work much harder to win and keep customers. So they’re hanging on to the old TV model as long as they can. At the same time they’re trying to build a profitable streaming future. That tension is the main thrust of this conversation I had with Pitaro this week in Disney’s new Manhattan headquarters. We also had time to get into his recent deal with the NFL, his ongoing commitment to sports betting — and whether ESPN is still committed to diversity in 2025. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 copewith 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? Learn more about your ad choices. Visit podcastchoices.com/adchoices

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? Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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?” Learn more about your ad choices. Visit podcastchoices.com/adchoices