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

Startups For the Rest of Us

Rob Walling

Management, Entrepreneurship, Business, Marketing

4.8 • 792 Ratings

🗓️ 8 July 2025

⏱️ 28 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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! Subscribe & Review: iTunes | Spotify

Transcript

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0:00.0	I never bet the house.
0:01.4	I didn't rack up credit card debt.
0:03.3	I didn't gamble on my mortgage.
0:05.4	But as my confidence, my experience, and my savings grew,
0:09.2	I started making bigger bets with my time, with my money, and with my energy.
0:14.0	And when those bets paid off, they created leverage that helped me stair step my way into the life that I wanted.
0:29.5	It's another episode of startup to the rest of us.
0:32.6	I'm Rob Walling, and in this episode, I talk about why I succeeded my 10 best entrepreneurial decisions.
0:41.7	This episode is the counter episode, if that's a term I can coin, to last week.
0:47.8	So it's a continuation of sorts.
0:50.0	In last week's episode, I talked about my biggest regrets, my biggest mistakes.
0:56.0	And as I put that episode together, I realized, and yet I still succeeded.
1:01.1	So why is that?
1:02.8	And I started thinking, well, it's because I made these other decisions that even in spite of the
1:09.3	regrets and the mistakes, I still made it. I still achieved
1:12.5	what I wanted to achieve. And of course, I'm still achieving things today. I have new goals,
1:17.2	but realistically, most of the goals for my life growing up were to be an entrepreneur and to
1:22.5	have enough money that I could work on whatever I wanted to work on when I wanted to work on
1:26.8	it. And, you know,
1:28.5	having achieved that now 10 years ago or so, I enjoyed reflecting on both things I did well and
1:35.9	the things I did not do so well. But this episode should be more upbeat than last week's because
1:41.1	it's about success. It's about things that I did right. Before I dive
	...

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