Episode 818 | What Does It Take to Be Successful? with Russ Walling
Tue Feb 03 2026
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.
Episode Sponsor:
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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!
Subscribe & Review: iTunes | Spotify
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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 today. Episode Sponsor: Hiring engineers shouldn’t feel like sorting through AI-polished resumes. G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills. No time wasters. No guesswork. Just solid developers who can deliver. G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes. Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob 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! Subscribe & Review: iTunes | Spotify