Looking back on your entrepreneurship journey, which decisions made the biggest impact?

In this solo episode, Rob Walling breaks down the 10 decisions that shaped his success, like choosing action over perfection, learning fast from failure, and building a financial cushion to take smarter risks. It’s an honest look at what worked and the choices that made the biggest difference.

Topics we cover:

(2:53) – Stop reading, start shipping
(4:48) – Learn from mistakes and change course
(6:47) – Build a financial cushion
(8:38) – Write publicly about your journey
(13:04) – Make bigger, but manageable bets
(15:21) – Embrace the unsexy, grindy work
(18:05) – Identify blind spots to grow faster
(19:39) – Set clear goals and stick to them
(21:26) – Know when to persist, pivot, or quit
(24:40) – Don’t make decisions in emotional moments

Links from the Show:

MicroConf Connect
Start Small, Stay Small
Comic Lab Podcast
TinySeed Institute

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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Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions

Startups For the Rest of Us

Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions