Signing up takes one click. Leaving takes five screens, a notice clause and, in Ed’s case, an overseas collection agency.
Ed Bennett and Chris Boyer take on the subscription trap, starting with Ed’s forgotten $150 software renewal and the AI-written dunning emails that followed. The FTC’s click-to-cancel rule died in court days before it took effect. What changed is the cost. When a machine writes personalized collection threats for free, chasing one dollar on a hundred-dollar debt starts to make sense. It’s enough to turn Ed, the show’s resident AI enthusiast, into a self-described Luddite.
Tech rec: You Can See Everything, the three-hour Elizabeth Holmes documentary from Nathan Fielder and Lance Oppenheim.
In the AI Stump, Chris asks a chatbot to design a cancellation flow nobody can finish. It says no until he calls it an example.
Easy in. Hard out. Dunned by a robot. Surprise, it’s not a toaster.
References & Further Reading
Subscriptions and Deceptive Design
- Dark pattern (Wikipedia): https://en.wikipedia.org/wiki/Dark_pattern
- Deceptive Patterns, Harry Brignull: https://www.deceptive.design/
- Eighth Circuit Vacates FTC’s Click-to-Cancel Rule (Fenwick): https://www.fenwick.com/insights/publications/eighth-circuit-vacates-ftcs-click-to-cancel-rule
- Germany: The Obligation to Provide Consumers With an Online Cancellation Button (Bird & Bird): https://www.twobirds.com/en/insights/2025/germany/germany-the-obligation-to-provide-consumers-with-an-online-cancellation-button–update-on-recent-rul
You Can See Everything
- You Can See Everything review (Variety): https://variety.com/2026/film/reviews/nathan-fielder-surprise-film-telluride-elizabeth-holmes-1236853513/
- Billy Evans’ “Theranos 2.0” startup has patents, investors and a missing CTO (Fortune): https://fortune.com/2026/10/25/elizabeth-holmes-partner-billy-evans-haemanthus-blood-testing-startup-theranos/
The “Flying” Roadster
- Tesla unveils what it says is a flying car (CNN): https://www.cnn.com/2026/10/15/business/tesla-unveils-what-it-says-is-a-flying-car
Find Us
- Chris Boyer on LinkedIn: https://www.linkedin.com/in/chrisboyer/
- Ed Bennett on LinkedIn: https://www.linkedin.com/in/edbennett/
- Chris Boyer website: http://www.christopherboyer.com
- Chris Boyer on Bluesky: https://bsky.app/profile/chrisboyer.bsky.social
- Ed Bennett on Bluesky: https://bsky.app/profile/edbennett.bsky.social

