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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• (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

• MicroConf Europe┃Reykjavik, Iceland · Sept 21–23, 2026
• TinySeed Accelerator | Join our email list - Applications open in September 2026
• Idea to Traction: Stop Building SaaS Nobody Wants (book wait list)
• The SaaS Playbook
• Rob Walling Newsletter
• Zen Founder Guide to Founder Retreats by Dr. Sherry Walling
• Episode 681 | Why Launching a Second Product is Usually a Bad Idea
• SignWell (Ruben Gamez)

If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you!

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