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In a world where everything online disappears in 24 hours, why are books still the thing we remember? I recently sat down with Rob Walling — a serial entrepreneur who has started six companies, bootstrapped five of them, and written multiple bestselling books, including Start Small, Stay Small and The SaaS Playbook.

What struck me most in our conversation wasn’t just his track record. It was how deeply he believes in books as a creative act and a lasting force in a noisy world.

Timestamp:

00:00 – Why Rob felt familiar before we even met
01:26 – Why books still matter in a world of social media
02:57 – How Start Small, Stay Small quietly became a classic
04:06 – Being “first to the niche” and serving developers-turned-founders
05:06 – Validating a book idea with a landing page and real emails
07:29 – Is SaaS creative? How Rob channels his creativity into business and books
11:13 – Why I started my podcast to interview Gay Hendricks
17:45 – Modeling creativity and entrepreneurship for our kids
20:11 – Rob’s take on AI, startups, and the future of content
34:22 – The lasting power of books vs. content
40:07 – The books that changed Rob’s life
47:11 – What his next book will cover and why it matters

Full show notes

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