Episode 22: CD Baby Founder and Author, Derek Sivers, Shares his Phenomenal Life Journey with Matthew Mayer

An episode of the Going Solo with Matthew Mayer podcast, hosted by Matthew Mayer: Stories with Amazing People, titled "Episode 22: CD Baby Founder and Author, Derek Sivers, Shares his Phenomenal Life Journey with Matthew Mayer" was published on July 23, 2025.

July 23, 2025 · Going Solo with Matthew Mayer

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Summary

CD Baby Founder, Derek Sivers, shares his amazing life journey with Matthew Mayer. From Growing up in Hinsdale, Illinois, to graduating from The Berklee College of Music, and then on to joining a Circus as a ring leader and performer, Derek would eventually go on to Build one of the most transformational music distribution platforms that would change the music scene as we know it today. After dedicating a decade building his company and helping thousands of musicians around the world reach listeners because of a distribution system he led the way on, Derek would also go through immense tough times. In the year 2007, Derek Sivers had one of the most tumultuous years of his life. This included going through a Divorce in which his life savings was drained, 90% of the company he founded was no longer his, all of his own employees, led by his good friend and VP, led a mutiny against him, and the woman he was madly in love with, married another man. After selling his company (in which he set up millions to go to charity), Derek continued on his life’s curiosity of ventures including authoring hundreds of articles and several books including Anything You Want, Your Music and People, Hell Yeah or No, How to Live, and his latest Useful Not True. Derek Sivers continues to share writings, insights, and philosophies that invite people of all walks of life to listen and share. From Derek’s Website at https://sive.rs/ Derek Says the following: I’m ambitiously focused on creating – More than anything, I want to make lots of stuff. I want to make articles, books, websites, music, companies, systems, apps, and especially new ideas. This shapes most of my life decisions. Saying no to almost everything, so I can have lots of time for making. At the age of 14, I decided I wanted to be a successful musician. Knowing it’s something that millions want, but only one-in-a-million achieve, I knew I’d have to be fiercely focused, persistent, savvy, and work like an Olympic athlete in training. In other words, not casual. I was single-focused obsessed with being a successful musician from age 14 to 29 — crucial years when many of my friends were feeling lost. It had me waking up early to practice, staying up late to write, saying no to all distractions, and reading whatever I could to improve. Then, at age 29, I accidentally started a company, so I was narrow-focused on creating that for 10 years, through the age of 39. I also want to learn lots of stuff, especially different approaches to thinking and living. That’s why I read so much non-fiction, and want to keep moving around the world. I connect with those who stretch, strive, and grow. I can’t relate to those who chill, hang out, watch TV, party, etc. I’ve optimized my life for creating and learning. I’ve cut out most things from my life that most normal people do — (like hanging out or media consumption) — in pursuit of my bigger goal. My life philosophy I’ve always had an uncommon approach to life, mostly shaped by my ambition. But when I read a book on Stoicism I realized I wasn’t so unique. My own self-created philosophy lined up almost exactly with this ancient philosophy. Especially the point about strengthening yourself for a more difficult future. But I’m also very skeptical, and was surprised to find that’s also a philosophy. Meaning: for almost anything on this page, the opposite may also be true. I don’t trust what I tell myself. It’s not a lie — it’s my truth at the time. But an opposite point of view can replace it when I shift my perspective.