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An Interview with Ben Thompson by John Collison on the Cheeky Pint Podcast

An interview with me by John Collison on the Cheeky Pint podcast about AI, ads, and the history of Stratechery.

An Interview with Ben Thompson by John Collison on the Cheeky Pint Podcast

Thursday, February 12, 2026

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Good morning,

Today’s Stratechery Interview is with me! On January 27 I sat down with Stripe President John Collison in the Cheeky Pint pub in Stripe’s offices for an episode of the Cheeky Pint podcast. There is a YouTube video of the interview that you can watch here, or, you can read the transcript below.

In this interview we discuss life in Taiwan, ads in AI, and how Mark Zuckerberg’s obsession with being a platform has harmed Meta. Then we talk about the TikTok deal, the impact of AI agents on ads and e-commerce, and, a week before Wall Street’s meltdown, discuss whether or not software is dead. We also discuss the history of Stratechery, and why I’m skeptical about bundles in the future, as well as my concern about TSMC’s conservative approach to CapEx.

As a reminder, all Stratechery content, including interviews, is available as a podcast; click the link at the top of this email to add Stratechery to your podcast player.

On to the Interview:

An Interview with Ben Thompson by John Collison on the Cheeky Pint Podcast

This interview is lightly edited for clarity.

Topics:

Life in Taiwan

John Collison: Ben Thompson is the founder and author of Stratechery, the newsletter that everyone in tech reads to make sense of what’s happening. He’s also early to the premium newsletter model that’s become very popular in media nowadays. For many years, he ran Stratechery as a solo founder in Taiwan. Cheers.

Good to see you. Cheers.

JC: It feels like people in San Francisco have not properly discovered Taiwan as a tourist destination. Do you agree with that characterization? And what’s your recommendation?

People always ask me about Asia, and the way I always characterize Taiwan is, there’s lots of great places to visit in Asia, and I would put Japan top of the list. But I like to think I went to Japan before it was cool.

JC: Yeah. Nothing against Japan.

Well, the whole thing with Japan is going to Japan pre-smartphone was a completely different experience than going there post-smartphone. Like you think, “Oh, the subway system’s amazing, the trains…” — try navigating that with no smartphone and nothing’s in English. Japan used to be very low on English, it’s still lower than places like Taiwan.

JC: It’s surprisingly low.

Yeah. And the way to visit Japan is you just walk, don’t go to set destinations. Whereas the way I would talk about this is places to visit, but the best place to live is undoubtedly Taiwan. The one word everyone says for Taiwan sounds not that impressive, but the word is “convenient”, it is the most convenient place to live.

JC: 7-Eleven has really good food.

It’s actually downstream from the Japanese because Taiwan was a Japanese colony for the first 50 years of the 20th century, and it’s laid out a lot like — why is it great to walk around in Tokyo? Because Tokyo is all mixed use, that’s how Taipei is as well. You have these big blocks where the exterior will be commercial and the interior of these big blocks is all residential and the first floor is all like small shops or restaurants, things like that. So wherever you live, you basically have access to everything all around you.

But I think the downside as a tourist is it’s kind of an ugly city. Taiwan’s kind of notorious for just these dumpy, dilapidated buildings, then you go inside and they’re palatial on the inside. Taipei is very, very rich. It’s in the top 10, I think, as the number of billionaires in the world or something like that, all downstream from building out China. It’s a very beautiful country. From Taipei, 30 minutes to the ocean, 30 minutes to the mountains, East Coast is amazing.

JC: But if people listening to this are visiting, I feel like one thing they should do is — it’s a mistake to try and use Yelp or anything like that too much because you should maybe just try and go to a night market and follow your belly and see what looks good, there’s a lot of excellent street food, and so that’d be one thing is don’t try to over-plan.

Well, here’s the problem though, where tech has made it worse, I would argue. When you’re living there, Taiwan is arguably the greatest Uber Eats market ever because there’s just amazing options. It’s all delivered by scooter, so it’s always like 10 minutes to get dinner. I think you were going to ask me about difficulties moving to the States, not having access to that is definitely one of them. But the problem is that it’s such a huge market now that I think there are fewer and fewer restaurants, in that a lot of these places actually just straight up close their storefronts are just ghost kitchens basically and all they do is just make Uber Eats orders all day.

JC: I see. Famously, the restaurant economy and places like Taipei would have been really good, but it’s gotten worse because people are eating in more with Uber Eats and stuff like that.

I think so. As far as walking around and just like stuff on — there’s still plenty of places, it’s still great. But there’s a number of restaurants that I used to always take people to, like holes in the wall that I knew were super good beef noodles or something, and I remember a couple times like, “Oh, you can’t actually go eat there anymore, but they’re still an Uber Eats”.

JC: That’s a bummer, it’s like a separate problem. The San Francisco problem at restaurants is that nobody drinks anymore and so the restaurants lost a major revenue source.

It’s so bad you had to get a pub in your own office!

JC: Exactly, we’re trying just firsthand to fix it.

Be the change you want to see in the world.

JC: Should people visit places beyond Taipei?

Oh, for sure. Yeah, Taipei is great, it’s great to walk around. Taipei 101, which is obviously very much in the news these days with the scaling.

JC: But you can go up the elevator on the inside.

You go up there because there’s a massive ball at the top.

JC: The mass damper, yeah.

Yes, which is amazing. If you’re into engineering, that’s actually a very underrated thing. National Palace Museum is amazing, but the East Coast in particular is incredible. There is a train, but driving, you’re driving on the coast.

JC: It’s like a lost coast of Hawaii, kind of.

Exactly. There’s an incredible gorge called Taroko Gorge that was really messed up by an earthquake a couple years ago, so I don’t know if it’s even reopened yet, but I used to take people to that all the time because it’s world class.

JC: Yeah. It is impressive that they said, “We’re going to build the tallest skyscraper in the world in a very frequent earthquake region”.

Yeah, it’s a beautiful skyscraper. It worked out well for Netflix.

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