EPISODE 72

No guest and no notes on Jason's side, so Kevin runs the board for once. The two dig into the question underneath every pricing decision: what unit of value are you actually selling? Jason retraces underpricing his agency in the early days and the shift from billing hours to building productized services with near-zero marginal cost, while Kevin walks through losing a deal to a competitor selling raw phone minutes, where the buyer admitted the product was worse and bought it anyway. From there they get into using AI to reconcile invoices against vendor spend down to the penny, a sweep that turned up 23 fraudulent charges and an education in BIN enumeration. They cover the strange state of the market, where a public company doing $275M gets taken private at 2x forward revenue while venture-backed startups raise at 100x. And they close on the AI back office: Kevin's 76 scheduled agents, the 13 supervisor agents he built to watch them, and the eight days of automations that reported success, success, success while quietly writing results to a directory that didn't exist.

CHAPTERS

00:32 – No guest, no notes: a solo episode

00:51 – What unit of value are you actually selling?

02:24 – "I did what most people do and I underpriced"

04:26 – Losing a deal to phone minutes

08:50 – Letting AI reconcile your invoices and vendor spend

12:41 – 23 fraud charges and BIN enumeration

15:02 – Weave goes private: 2x revenue vs. 100x rounds

17:09 – The private and public markets dance

19:21 – 76 agents, 13 supervisors, and "successfully failing"

21:57 – Most people are bad managers

25:34 – DHH's Linux distro and talking to your OS

26:50 – Founder Mode top five

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