It’s hard to remember now. But just a few years ago, sports betting was illegal in almost all of United States. And sports leagues and the media companies that worked with them wanted nothing to do with anything that even referenced gambling.

Things are very, very different now! And it happened so quickly that very few people have stopped to ask what any of this means for America, and what it will mean down the road.

Those questions — and the reasons why so few of us are posing them — turn out to be a great topic for Michael Lewis. You can hear him grappling with them in the excellent new season of his “Against the Rules” podcast series. And I was delighted to discuss all of it with him on my show. It also gave me an opportunity to discuss “The Fifth Risk” - his 2018 book about Donald Trump’s first attempt to take over federal government, which is extra-timely right now. And I couldn’t let him go without a brief chat about crypto and Sam Bankman-Fried.

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I haven’t checked in with Jessica Lessin in some time — and I have to say I picked a pretty good time to catch up with her. Because Silicon Valley is undergoing something meaningful right now, and she’s in a great position to tell us more about it: Lessin is a veteran technology reporter who founded The Information in 2013, and it has been a go-to for anyone who wants serious reporting about tech in the Bay Area and around the world, ever since.

Discussed in this episode: What’s really animating tech’s embrace of Donald Trump? What’s going to happen to TikTok? And what does the arrival of DeepSeek mean for the AI boom?

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TikTok banned itself for less than a day. Now it’s back in the U.S. - despite a law that says it shouldn’t be operating. We’re not going to weigh in on all of the… weirdness around the last few days on this episode, in part because we don’t know how it’s going to play out.

But in the meantime I wanted to talk to someone who knows how TikTok actually works — from a content creator’s perspective, at least. Adam Faze runs Gymnasium, a small production studio that specializes in TikTok videos, and so far it’s gone well: In 18 months, he’s launched two successful shows, signed up Amazon to sponsor one of them, and is ramping up to make more. He walked me through the way companies like his actually make money on TikTok, how the platform differs from TikTok clones like Instagram Reels, and how he thinks this could grow in the future. Assuming TikTok sticks around the U.S., that is.

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Why didn’t Meta’s stock move when Mark Zuckerberg announced his pro-MAGA pivot? Why do big media companies want to dump their cable TV networks — but hang on to their broadcast TV networks? What’s going to happen in Google’s antitrust case?These are all good questions, right? I think so, too. So I posed them, along with many more, to MoffettNathanson’s Michael Nathanson, one of the sharpest Wall Street analysts covering tech and media. We cover a lot of ground in a short time, and I think you’ll enjoy this one.

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I’m a lucky man. Whenever I’m baffled by the internet, and social media, I turn to my co-worker Katie Notopoulos, who is there to explain it to me. That’s because Katie’s job at Business Insider is to explain how the internet works — how the people who run big internet platforms want it to work, and what the people who actually use those platforms do on it, for better and for worse. So that’s what we’re talking about today, to help ease us into the new year.

Discussed here: Why Katie still loves the internet and technology, even with all of its many warts; how she came to be a professional chronicler of the internet; how her views on all of this are changing as her kids grow older; and poop. Lots of poop talk here. You’re gonna love it.

Note: We recorded this chat on January 6 — a day before Mark Zuckerberg announced he was going to reshape his entire company to accommodate the upcoming Trump administration. So that’s why it’s not in this conversation. Rest assured - we’ll be talking about this a lot in future episodes. Happy 2025!

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I don’t love a lot of year-end #content . But I do love talking to Bloomberg’s Lucas Shaw every year, to help put the year in media in perspective, and to think about what might be coming in 2025. And that’s exactly what we did here. Enjoy it now, or over your break. We’ll see you again in January.

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Newsletters are not a new idea. Yet every few years the media business rediscovers them, anyway — either as a way to quickly launch a startup with bigger ambitions, or as a standalone business. Tim Huelskamp took the second route in 2017, when he co-founded 1440 — a newsletter that promises to quickly bring you the most important news of the day. Again — not a new idea. But Huelskamp seems to have figured out how to build something pretty big: He says 1440 has 4 million readers, and is turning a profit on something like $20 million in annual revenue. How’d he do it? What’s he going to do next? And how will he compete with AI companies that can do all of this faster, and cheaper? I’m glad you asked: I’ve got the same questions, so I asked him myself.

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You probably shouldn't know Renee DiResta's name: She's a researcher who studies online bad behavior, not a celebrity. But the work DiReata did studying the "stop the steal" movement after 2020 has made her famous in some corners of the internet, and not in a good way: She's been harassed, pelted with subpoenas and sued twice.

Now things could get really unpleasant for her.

Donald Trump's victory means that a lot of people who have target dDiResta in the past are newly ascendant. But she tells me she's more worried about a chilling effect that could hamper anyone who's trying to learn about, and fix social media's ills. Also discussed here: what not to do when you go on Joe Rogan.

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Lots of people start media companies using money from rich people. Jason Koebler and his colleagues did it themselves, using a grand total of $4,000. That was back in the summer of 2023. Now 404 Media, the tech news + investigations site they started after leaving Vice Media, is a success story. Koebler tells us how they started, how it’s going, and what he’d like to do next.

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Tucker Carlson, Megyn Kelly and Bari Weiss all used to work for big mainstream media companies. Now they’re on the internet, building their own companies, with the help of Chris Balfe.

Balfe’s Red Seat Ventures helps online creators set up shop, produce programming, and — crucially — helps them monetize through ad sales and/or subscriptions. Balfe got his start working with Glenn Beck when the former Fox News star left and started his own online business. I always assumed we’d see other high-profile talent follow Beck’s footsteps, but it took much longer than I thought. Now it’s a reality, and the talent Balfe works with may very well have helped re-elect Donald Trump.

You can’t escape politics when you talk to someone who works with Tucker Carlson, and we spend a little bit of time on that in our chat. But this is really a discussion about how online media — primarily podcasts and YouTube — works today, and where it’s going next.

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One take you may have heard after the election: Democrats need their own Joe Rogan.

Taylor Lorenz disagrees. And Lorenz is worth listening to. For years, she has been a really sharp observer of social media and online spaces, and she built a high-profile career explaining the internet for audiences at places like the Atlantic, the New York Times and the Washington Post.

Now Lorenz is on her own, which is where she says she always wanted to end up. We talked about how and why she left the Post this year. And how she’s thinking about building her career without the advantages – and disadvantages — that come from working for a big organization.

But first we talk about the podcast election (which was also the YouTube election) and where she thinks the Harris campaign went wrong. And why she thinks liberals don’t need their own Rogan — and why they can’t get one, anyway.

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