The Complex Elegance and Constant Contradictions of Derek Sivers

Tim Ferriss says that Derek Sivers is one of his “all-time favorite humans… a philosopher-king, programmer, master teacher, and merry prankster.”

Derek is an international man of mystery, or maybe contradiction. He’s known and loved by millions, done three super-popular TED talks, but he prefers to be alone, certainly when he’s working and creating, or “playing” as he’d more likely call it.

Derek graduated from the Berklee College of Music in Boston and has worked as a professional musician and plays a number of instruments. He started a record label, booking agency, and recording studio, and he is the accidental founder of CD Baby which became the largest seller of independent music on the web, with over $100M in sales for over 150,000 musician clients. He sold CD Baby in 2008 for $22 million, giving the proceeds to a charitable trust for music education, as well as a more recent donation of a quarter-million dollars in book-sales to charity.

He’s been featured in the documentary “Your Own Way Out,” on the highs and lows of digital nomads. He’s lived all over the US as well as London, Oxford, Singapore, and currently New Zealand.

Derek is a sought-after speaker and author of four very popular books, “Anything You Want 40 lessons for a new kind of entrepreneur,” “Your Music and People.” “Hell Yeah or No,” and most recently, “How to Live: 27 conflicting answers and one weird conclusion,” which we will focus most of our conversation on in this episode.

Oh, and one more thing, he was a clown and worked in the circus for 10 years.

Derek lives his life in full and provides the rest of us with the tools and inspiration to do likewise. This is an episode not to be missed.

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Dr. Chris Stout Clinical Psychologist

Dr. Chris Stout is a licensed clinical psychologist and international humanitarian with a diverse background in various domains. He is the Founding Director of the Center for Global Initiatives (a Top-Rated Nonprofit) and is the Executive Producer and Host of the popular “Living a Life in Full” a top-ranked podcast with an audience of over 3 million. He was a Fellow in the School of Public Health and Full Professor in the Department of Psychiatry in the College of Medicine at the University of Illinois, Chicago and prior to that he held an academic appointment at Northwestern University’s Feinberg School of Medicine. He served as a NGO Special Representative and had the honor of speaking at the United Nations; he holds the distinction of being one of only 100 world-wide leaders appointed to the World Economic Forum’s Global Leaders of Tomorrow and was an Invited Faculty at the Annual Meeting in Davos.