Ben Thompson from Stratechery on AI ads, the end of SaaS, and the future of media

Ben Thompson, the internet’s premier tech analyst, joins John for a wide-ranging conversation on the mechanics of the internet economy. They discuss the origins of Stratechery and the "1,000 true fans" model, why Taiwan is the most convenient place to live (and the best Uber Eats market), and why the public markets are wrong to think SaaS is "canceled." Ben also explains why the US failure to control the TikTok algorithm is a disaster, why he’s a "crypto defender" in an age of infinite AI content, and gives John some very direct feedback on Stripe’s ACH implementation. Full transcript on Substack: https://cheekypint.substack.com/p/ben... Subscribe to Cheeky Pint Spotify: https://open.spotify.com/show/2IHbGJJ... Apple Podcasts: https://podcasts.apple.com/us/podcast... Substack: https://cheekypint.substack.com/ Key moments 00:00:20 Visiting Taiwan 00:04:59 Aggregation and AI 00:23:53 TikTok/Bytedance 00:29:58 Aggregation and AI redux 00:35:31 Agentic commerce 00:45:08 Is SaaS canceled? 00:52:21 Stratechery 01:03:36 How Ben uses AI 01:06:06 The TSMC break 01:13:53 Rapid fire 01:20:53 Feedback on Stripe