Episode 781 | A Founder's Regret List: 12 Mistakes I’ll Never Make Again
Update: 2025-07-01
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
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!
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