Derek Sivers’ 20 Paradoxical Truths for a Good Life

The most popular guest ever to appear on Tim Ferriss’ podcast will change how you think — and live.

Tim Denning
Ascent Publication
Published in
10 min readJul 20, 2020

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Image Credit: sivers.org

Derek Sivers is perhaps the most bizarre human being on Earth.

He shot into the spotlight when he appeared on the most downloaded podcast episode of The Tim Ferriss Show to date and shared the idea of “Hell Yes or No.” It was a simple tool to make every decision in your life.

Derek shared during the interview with Tim how his career started in the circus. He then went on to start a business called CD Baby that helped artists sell their music on the internet.

That tiny little business he started by accident went on to become the largest seller of independent music on the web with more than $100M in sales. Derek says, “ I didn’t even want the money from the sale.”

So in a rather bizarre move that would define his career and make millions of people listen to this single podcast episode that featured him as a guest, he gave away the vast majority of the money to a charitable trust that supports music education (the thing that made him successful).

I became fascinated with Derek. He offered simple advice and short paradoxical truths directly from his own life. Derek…

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Tim Denning
Ascent Publication

Aussie Blogger with 1B+ views that made me 7-figures — Get my free email course: https://timdenning.com/1k-mb