Startups For the Rest of Us

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


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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.

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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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