Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies

Cheeky Pint · Sep 24, 2025 · 1h 18m · transcript

Des Traynor, cofounder of Intercom, sits down for a Cheeky Pint with John Collison to discuss the growth of Fin (Intercom’s AI customer service agent), why selling AI products is hard, advice for product marketers, and cofounder dynamics.

Full transcript on Substack: https://cheekypint.substack.com/p/des-traynor-on-reinventing-intercom

Timestamps:

(00:00) Intro

(02:58) Reinventing Intercom

(06:31) Fin

(18:06) 1M resolutions a week

(24:22) Selling AI

(29:34) Product marketing

(37:18) Listening to users

(44:14) Usage-based billing

(45:14) Advice for startups

(52:09) AI pricing

(01:07:27)…