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

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

1 hour 30 minutes Posted Feb 12, 2026 at 12:45 pm.

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.Timestamps

Visiting Taiwan

Aggregation and AI

TikTok/Bytedance

Aggregation and AI redux

Agentic commerce

Is SaaS canceled?

Stratechery

How Ben uses AI

The TSMC break

Rapid fire

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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.Timestamps(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

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