90. Bryan Cressey: Author of Be A Winner

22 Sept 2022 · 50 min
BookThinkers: Life-Changing Books

22 Sept 2022 · 50 min

0:00

In this episode of the Book Thinkers Life‑Changing Books podcast, private‑equity veteran and author Bryan Cressey discusses the ideas behind his book Be a Winner: Life’s Handbook for Joy and Success. He explains that the book was originally written for his three daughters and later expanded to help young professionals transitioning from school to work, offering them a practical, trial‑and‑error framework for navigating the real world. Cressey emphasizes that mistakes are essential learning tools, that the world changes dramatically after graduation, and that the people who make the most mistakes—and learn from them—become winners. He shares his views on mentorship, recommending aspirational, selective mentors and the need to cull draining relationships. He outlines the traits he values in entrepreneurs: speed, active listening, taking action, and a proven track record. Listening is described as an empathetic, heart‑centered practice. Success is defined as mission‑driven and multidimensional, requiring intentional time allocation across professional, family, and service domains. Purpose is portrayed as evolving over a lifetime, with multiple purposes co‑existing. Cressey connects purpose to his philanthropic work with the Above and Beyond addiction‑recovery centers, arguing that helping others generates lasting joy, a concept he links to Stoic philosophy. He discusses the importance of company culture—values, empathy, teamwork, and a broader mission to help the world—as a foundation for lasting enterprises. He recounts a personal struggle with humility versus arrogance in investing, describing how adopting a humble, consultative approach restored his success. Personal health habits (vegan diet, regular exercise) and a curiosity‑driven mindset are presented as sources of energy. Finally, he offers suggestions for the podcast format (concise key‑lesson summaries) and points listeners to his social media and YouTube videos for further learning.

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