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Startups For the Rest of Us

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

Tue, 01 Jul 2025 10:00:31 +0000

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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 Links from the Show:  TinySeed Institute Sponsor the Podcast or MicroConf Start Small, Stay Small The SaaS Playbook Zero to Sold by Arvid Kahl 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! Subscribe & Review: iTunes | Spotify

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