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

About this episode

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. Want to get your question answered? Submit your question for an upcoming episode. 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 • (26:33) – Optimizing for learning speed Links from the show: • MicroConf Europe┃Reykjavik, Iceland · Sept 21–23, 2026 • TinySeed Accelerator | Join our email list - Applications open in September 2026 • Idea to Traction