Episode 818 | What Does It Take to Be Successful? with Russ Walling

2026-02-03

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Is perfectionism quietly sabotaging your career or startup dreams? In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers. They discuss how growing up with a shared emphasis on hard work, sports, and achievement created both strengths and struggles and how lessons learned in construction, poker, and entrepreneurship still apply to building great companies...

Is perfectionism quietly sabotaging your career or startup dreams?

In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers.

They discuss how growing up with a shared emphasis on hard work, sports, and achievement created both strengths and struggles and how lessons learned in construction, poker, and entrepreneurship still apply to building great companies today.

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Topics we cover:

(04:10) – How early lessons in hard work and sports shaped mindset
(07:46) – Learning to be comfortable being uncomfortable
(12:03) – The dark side of perfectionism
(16:51) – Overcoming fear of failure and learning to take risks
(19:04) – What poker taught Russ about risk and decision-making
(21:52) – The Armageddon Beer story
(28:53) – Why both brothers chose entrepreneurship
(31:08) – Redefining leadership: collaboration over fear
(35:24) – The three traits that drive lasting success
(43:45) – Why hard work is still the ultimate differentiator

Links from the Show:

Discretion Capital M&A Advisory for SaaS Founders doing $2-25M
The SaaS Playbook by Rob Walling
Rob Walling (@robwalling) | X

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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