Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again

Startups For the Rest of Us

Jul 01, 2025•40 min

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Episode description

Are you repeating any of these mistakes in your business?

In this episode, Rob Walling walks through his ‘founder regret list’, detailing 12 key mistakes from his 20-year entrepreneurial journey. In this very personal episode, he tells some stories he’s never shared publicly before.

Topics we cover:

(4:17) – Thinking venture capital was the only path
(6:12) – Launching without validating the idea
(9:26) – Choosing ideas that couldn’t be bootstrapped
(12:48) – Relying too much on books
(16:36) – Trying to do everything solo
(21:10) – The arrival fallacy
(23:19) – Delaying email list growth
(25:51) – Taking random advice too seriously
(28:43) – Overestimating skills after early wins
(30:29) – Letting anxiety steal the joy from success
(32:34) – Not letting wins build confidence
(33:50) – Holding onto a scarcity mindset

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