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

Startups For the Rest of Us