Episode 847 | What Second Time Founders Do Differently, Pricing AI Agents, and More Listener Questions (Rob Solo)

Would you spend a year on distribution for a product that doesn't exist yet?

In this solo episode, Rob answers listener questions about how second and third-time founders think differently, from filtering a dozen good ideas down to one, to why distribution and validation matter more the second time around. He also digs into how to sell and price AI agents, and whether a long enterprise sales cycle is worth the wait for a bootstrapper.

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Topics we cover:

(2:54) – Selecting an idea after an exit

(5:26) – Using spreadsheets and advisors to filter

(8:52) – Founder retreats for big decisions

(10:01) – How to sell an AI agent

(12:32) – Pricing agents on value replaced

(17:13) – What later-stage founders care about

(18:59) – Distribution and validation for repeat founders

(23:12) – Long enterprise sales cycles