I wanted to talk to Ian Rogers about his fascinating career. He wanted to talk to me about Ledger, the crypto wallet company he’s working at now.

So we did both things.

Background: Rogers was an important figure in the digital music business, back when the music business was being fundamentally reshaped by digital. He helped the Beastie Boys get on the internet, long before every band did that. Then he helped bring digital music to millions of people in the MP3 era - first at AOL, then Yahoo — and then in the streaming era — first at Beats, and then Apple Music. Then he did digital stuff at LVMH, the luxury goods conglomerate. Now he’s chief experience officer at Ledger, a French company that has sold 7 million physical storage devices for crypto.

I remain confused and skeptical about crypto, but I’m always open to hearing from folks who are passionate about it — to see if they can convince me that I’m missing something. And the most persuasive argument I hear is usually from folks like Rogers — people who were around when the internet was novel and exciting in the 90s, and think they’re seeing the same kind of tectonic shift this time around. It’s a pitch that’s part FOMO — you wouldn’t want to be one of the people who thought the internet was a fad in 1995, right? — and part blue-sky optimism: What if it was 1995 and you could get in on the ground floor of the internet? Take a listen and let me know what you think.

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Today's podcast is an in-depth discussion of Apple's App Store rules and how they... wait! Don't leave!

I could try to tell you why Apple's App Store rules are important to both Apple and the digital economy (sadly, I just realized I've been covering them for nearly 15 years, so they better be important). But a better messenger for that task is Tim Sweeney, the CEO of Epic Games - the company behind Fortnite.

Sweeney has spent 5 years fighting Apple in court - and by his estimation has sacrificed $1 billion in revenue - over the way Apple runs its App Store. For most of that time it seemed like a futile effort.

But last week a federal judge handed Epic what could be a huge victory, and could potentially cost Apple a meaningful amount of revenue. Apple is going to appeal that ruling, but for now, Sweeney sees this a win for his own company, and many other developers who've chafed at the fees they have to pay Apple every time a consumer wants to give them money.

And if you think none of that matters to you, a normal person, Sweeney is happy to explain why (he thinks) you're wrong.

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There are all kinds of ways to measure the health of an economy. The one I rely on is ad spending.

One reason for that is simple: I work in ad-supported businesses, so I want to know about things are going to affect me personally. A less self-interested reason: The health of the ad business is tied directly to the way companies feel about their overall health. So if things turn south, you’ll often see it in falling ad spend.

And as the industry gets increasingly digital, that means it’s that much more responsive to changes in the economy: When the pandemic hit 5 years ago, ad spend all but disappeared for a couple months — and then roared back once companies realized how much spending had shifted online.

So that’s the background for my chat with Smartly CEO Laura Desmond, who I often rely on for a state-of-the-state when it comes to the ad industry. Desmond is a longtime ad biz veteran, and at her current gig she works directly with digital clients, helping them figure out where to place their money and the best way to optimize their campaigns. So she’s got excellent insight into the most sensitive spenders in the market.

Desmond’s takeaway: Long-term changes like a possible TikTok ban just don’t show up on most advertisers’ radars. But potential tariff impacts, which could hit by late May, could be a big hit — if they materialize.

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Every day some 85 million people - most of them kids - show up to play, chat and spend money on Roblox. That’s a massive audience just about any tech or media company would like to have. But David Baszucki wants more: He thinks his platform can eventually command 10% of the worldwide gaming market.

I spent time talking to Baszucki about those ambitions and what has to happen to make it a reality. But I also wanted to spend time getting him to explain what exactly Roblox is, and why its low-fi, user generated games resonate with his audience. It’s an unlikely special sauce that has made the company, which spent years flying under the radar, worth some $40 billion today.

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Some people don’t want to pay for media. But lots of people are paying Jake Sherman and his team at Punchbowl News: The 4-year-old startup is thriving by providing super-insidery news and data about what’s happening in Congress. I chatted with Sherman because I wanted to get an update on his business (he says he’s not going to sell it anytime soon, despite lots of speculation to the contrary).

I also had a basic, outside the Beltway question: In a world where Congress spends a lot of time not passing bills, what exactly does Punchbowl cover? He was happy to spell it all out for me.

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The New York Times faces the same challenges every other news organization faces in 2025.

But it’s also in way better shape to take those challenges on: Thanks to a business model built on 11 million subscribers, it’s not nearly so worried about things like the fluctuations of the ad business, or changes in Google’s algorithm.

That comparative strength also gives NYT publisher AG Sulzberger the ability to do things his peers can’t or won’t do: Like suing OpenAI for copyright infringement, instead of taking a cash settlement. Or calling out the likelihood of a press crackdown if Donald Trump was re-elected - a call he made in September that looks very prescient today.

We talk through both of those issues in this conversation, and a bunch more - like the role of the NYT opinion section, how willing the Times is to experiment, and how the paper thinks about the economic turmoil we now find ourselves in.

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The Trump 2.0 era is less than three months old. But it’s already creating havoc for journalists and the companies they work for.

In Washington, Trump and his team are demoting traditional media - or kicking them out of the White House entirely. In corporate boardrooms, he is forcing media owners to settle lawsuits they would normally fight, and to submit to investigations from newly aggressive regulators.

Again: We’re just at the beginning of this new era. What’s coming down the pike? I asked Sara Fischer, the excellent and Washington-wired media correspondent, to walk me through it

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Call it symbiosis. Call it co-dependency. However you want to characterize it, there’s zero debate that Big TV and Big Sports are deeply intertwined. So if the TV business is shrinking, what happens to sports?

That’s the main question I had for John Ourand, the longtime sports business reporter who’s now at Puck. But I had lots of related ones, like: Now that (some) college students are getting paid to play sports, how does that affect the TV product itself? What’s happening to the local sports networks that bring you baseball, basketball and hockey? And is the sports betting media boom drying up?

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Anyone who makes things thinks they could do it better if they had more. More money, time, headcount, infrastructure.

Some of us find there can be upsides to doing it with less, too.

That's not exactly PJ Vogt's story but I think it's directionally accurate: Vogt cohosted a huge hit podcast - Reply All - and when he decided to try again - with Search Engine - he had a lot less to work with. That shaped his thinking about the company he wanted to run and the product it puts out each week. It seems like it's working, and Vogt walks us through the details and his decisions.

Also joining me: Zach Mack, who has helped other people (like me) make podcasts for years, made one that only he could make. Go listen to his "Alternate Realities" series on NPR's Embedded - but first listen to how he made it.

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Back when I first started covering the internet, the idea of broadcasting yourself for hours on end seemed like a pipe dream for weirdos. Now it's how some people make a living.

Twitch more or less created live-streaming in the U.S., which is why Amazon bought it for about $1 billion back in 2014. But now there are plenty of places to watch, and create, live streams. How does Twitch fend off competitors? How does it convince its most popular streamers to keep streaming? And how will Amazon eventually make real money from the operation, which is was still in the red a few years ago?

Those are all questions I asked Twitch CEO Dan Clancy, at a live taping at South by Southwest. Clancy also got to hear firsthand from Twitch's users and partners in a Q&A session at the end of our chat. Thanks to everyone who came out, and thanks to the folks at the Vox Media podcast network for putting it all together.

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