The Complex Elegance and Constant Contradictions of Derek Sivers

Dr. Chris E. Stout
6 min readDec 1, 2022

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. Derek launched another business, Wood Egg, publishing guides on how to do business in Asia. He’s lived all over the US as well as London, Oxford, Singapore, and currently New Zealand, with his son.

Derek is a sought-after speaker and an 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.

I first saw Derek speak at World Domination Summit, in Portland back in 2015, and I’ve been a fan ever since.

In our conversation, we start with what he may be best known for — his creativity. In…