Cheeky Pint
Des Traynor on reinventing Intercom twice and the “four horsemen” of good AI companies
24 Sep 2025
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-intercomTimestamps: (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) Cofounder dynamics(01:11:04) Predictors of company success(01:15:56) How AI-native is Intercom?
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