Derek Sivers once believed success meant scaling bigger and moving faster. Then he built CD Baby, sold it, and gave the proceeds away – not because he had to, but because he realised enough was already enough.
As a writer, entrepreneur and modern business philosopher, Derek has spent years stripping life and business down to their essentials. What remains when you remove ego, growth for growth’s sake, and societal expectation? Clarity. Freedom. The space to choose.
In this conversation, Derek joins Kevin St. Clergy to explore why redefining success starts with questioning the stories we've been told. They uncover the cost of distraction, the power of radical focus, and how letting go (not adding more) can lead to bigger breakthroughs.
In this episode, Kevin and Derek will discuss:
(03:17) Accidental entrepreneurial journey
(07:27) Odometer metaphor and purpose
(11:31) Turning blame into empowerment
(13:36) Control what you can
(17:24) Making musicians happy as success
(20:38) Card table vs glamorous booths
(26:03) Prioritise focus over distraction
(27:15) Start with why for happiness
(31:20) Stop over-quoting and say it simply
(34:26) What truly makes you happy
(38:36) Think long-term for longevity
(40:01) Broaden identity and embrace growth
Derek Sivers is an entrepreneur, writer, and former musician best known for founding CD Baby and donating its multimillion-dollar proceeds to charity. A modern business thinker, he challenges conventional wisdom and advocates for simplicity, intentional living, and purpose-driven work through his bestselling books and global talks.
Connect with Derek:
Derek’s Website: https://sive.rs/
Elain’s LinkedIn: https://www.linkedin.com/in/elainelinhering/
Resources Mentioned:
Can Negotiate Anything by Herb Cohen: https://www.amazon.com/dp/0553281097
Grit by Angela Duckworth: https://www.amazon.com/dp/1501111116/
How To Change by Angela Duckworth: https://www.amazon.com/dp/B08LQZDDDS/
New Happy by Stephanie Harrison: https://www.amazon.com/dp/139872212X
Stumbling on Happiness by Daniel Gilbert: https://www.amazon.com/dp/1400077427/
Daily Stoic by Ryan Holiday: https://www.amazon.com/dp/0735211736/
Outlive by Peter Attia: https://www.amazon.com/dp/0593236599
Anything You Want by Derek Sivers: https://www.amazon.com/dp/1991153317/
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