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

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 1 July 2025

⏱️ 40 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	A book can help you learn more, can give you the knowledge to be more successful,
0:05.6	but you still have to put in the work, develop your skills, and push things forward on your own.
0:11.4	And you're going to have to make a lot of hard decisions with incomplete information
0:15.2	and ship, ship, be right most of the time and get things out the door in order to be successful.
0:20.8	At a certain point, you do have to stop reading business books and start... ship, be right most of the time, and get things out the door in order to be successful.
0:25.3	At a certain point, you do have to stop reading business books and start shipping. Welcome. Welcome back to another episode of Startup to the Rest of Us.
0:44.3	I'm your host Rob Walling, and in this very personal episode, I walk through my founder
0:50.1	regret list, 12 mistakes that I will never make again.
0:55.0	I say this is a personal episode because there are several stories that I'm going to share
1:01.0	as I walk through this list that I don't believe I've ever shared in public before.
1:06.5	And it wasn't out of any desire to shield these or somehow keep them hidden.
1:12.6	Just several of them hadn't given the deep thought required to really dig in to the mistakes that I made over the years,
1:22.4	over the last 20 plus years of my journey as a founder.
1:26.6	I've been asked over the years, what are the biggest mistakes that I've made?
1:32.2	As a founder, as an investor, as an entrepreneur, probably as a human.
1:35.5	That's a different list, I'll admit.
1:37.6	And I always struggled to come up with a list that I felt was meaningful and genuinely things that I regretted,
1:46.8	things that I wished I had done differently along the way.
1:49.1	Sometimes I come up with one or two or three,
1:50.9	but I sat down for an extended period of time and really thought this through,
1:55.6	and I came up with 12 mistakes that I'll be running through in this episode.
2:04.8	Before I dive into those, if you haven't checked out the SAS Institute,
	...

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