104: Creating Success on Your Terms A Conversation With Derek Sivers

On this episode of Making Elephants Fly, Terry sits down with Derek Sivers. Derek Sivers is an entrepreneur, author, and TED speaker known for his unconventional wisdom, minimalist philosophy, and remarkably succinct writing style. Best known as the founder of CD Baby , Sivers started the company in 1998 simply to sell his own CDs online. What began as a side project for fellow independent musicians grew into the largest seller of independent music on the internet, generating more than $100 million in sales before he sold the company in 2008 for $22 million and donated the proceeds to charitable music education. A former musician, programmer, and circus clown, Sivers is the author of several bestselling books, including Anything You Want , Hell Yeah or No , How to Live , and Your Music and People . His work explores entrepreneurship, decision-making, creativity, leadership, and the dynamics that turn ideas into movements. Join Derek Sivers and Terry Weaver as they talk about unconventional paths to creativity, redefining success on your own terms, and building a life and business based on what truly matters to you. The big idea from this episode: You can choose your own path, say "hell yes or no" to opportunities, and design your life and work around your values, not what the algorithm or the marketplace expects. Find out more at and join Terry at the Thing at and use the code PODCAST for a discount.

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104: Creating Success on Your Terms A Conversation With Derek Sivers is an episode from Making Elephants Fly | Conversations with High Octane Leaders, Dreamers, & Creatives by Terry Weaver.

This episode is 01:34:55 long.

This episode was published on Feb 22, 2026.

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