Westcliff University Podcast Breaking Rules, Building Empires, and Living Freely with Derek Sivers
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Mar 27, 2025 
Derek Sivers, a musician turned entrepreneur and philosopher, revolutionized the music industry by creating CD Baby, the largest independent music distributor, and donating its proceeds to music education. In this conversation, he explores breaking societal rules to redefine success and happiness. Sivers emphasizes his 'Hell Yeah or No' decision-making philosophy for clarity in choices, discusses authenticity in business relationships, and advocates for creativity through curiosity, while inspiring listeners to build a meaningful legacy.
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Success Is Personal Fulfillment
- Success and happiness depend on individual values and desires, not universal formulas.
- Derek Sivers thrives in solitude and creativity, showing freedom in personal fulfillment.
Truth as Universal Observation
- Absolute truth is extremely rare; most of what we know are perspectives subject to change.
- Embracing skepticism and openness fosters better understanding and empathy among differing views.
Prioritize with "Hell Yeah or No"
- Say "Hell Yeah" only to opportunities that excite you intensely to avoid overcommitting.
- Use this approach selectively when overwhelmed, not as a lifelong rule for every decision.
