How To Change Your Point of View (POV) with Derek Sivers - Episode 2/3

2025-08-29

This is episode 2 of 3 featuring Derek Sivers. Watch it on YouTube! Derek has accomplished numerous impressive feats. He founded CD Baby. In 2008, he sold CD Baby for $22 million and donated the proceeds to a charitable trust dedicated to music education. After selling the company, he transitioned into writing and speaking. Derek's books are short, dense, and profound. In honor of his style, I've broken up my interview with him into three fascinating segments. It would be great if you could buy Derek's new...

This is episode 2 of 3 featuring Derek Sivers.

Watch it on YouTube!

Derek has accomplished numerous impressive feats. He founded CD Baby. In 2008, he sold CD Baby for $22 million and donated the proceeds to a charitable trust dedicated to music education. After selling the company, he transitioned into writing and speaking.

Derek's books are short, dense, and profound. In honor of his style, I've broken up my interview with him into three fascinating segments.

It would be great if you could buy Derek's new book, Useful Not True, from Amazon, as I receive a small commission. However, if you want a much better deal, do what I did: buy multiple copies of his book from Derek Sivers's website. It's significantly cheaper than Amazon, especially when purchasing multiple copies, as each additional hardcover copy costs only about $4 more.

How Derek Sivers and I met

Derek Sivers stumbled onto The Hidden Europe, fell in love with it, and reached out to me 10 years ago, telling me how much he loved my book.

I had no idea who he was, but soon found out.

A-list celebrities, such as Tim Ferriss, have interviewed Derek on multiple occasions.

Still, I'm not one to fall for celebrities, unless she's Megan Fox.

What makes me most thrilled about interviewing Derek is his philosophy: he's a stoic.

This guy sold his company (CD Baby) for $22 million and gave the money away to charity. He loves to experiment, travel, and think out of the box.

It pains me that he and I missed each other when I visited his city in Wellington, New Zealand. I was there for a day, and it happened to be the day that he devotes entirely and exclusively to his son. I wish he were a less responsible father.

About Derek Sivers

Derek Sivers is focused on creation, learning, and living a minimalist, highly intentional life.

Background: Born in 1969 in Berkeley, he moved frequently during his childhood, including to U.S. cities and England. His early focus on music began at the age of 14, when he was trained at Berklee College of Music. He transitioned into entrepreneurship.
Career: Started multiple companies, including CD Baby and HostBaby, sold them in 2008, and since then has focused on writing, traveling, and intrinsic creativity rather than money or fame.
Life Philosophy: Influenced by Stoicism, skeptical and open to changing perspectives, values self-strengthening for the future, and embraces the paradox that opposite views can both be true.
Work Style: Loves to work alone intensely for long hours (12+ hours daily), prefers solo creative pursuits, and values deep focus and minimalist distraction. Uses minimal tech tools, avoids apps and cloud dependence, and prefers phone conversations to in-person socializing.
Personal: American by origin, a world citizen, and expat living in various countries for extended periods. Has a 12-year-old son with whom he spends significant undivided time weekly. Identifies as an introverted extrovert with a strong social time limit, values voice communication, and dislikes noise and crowds.
Values & Traits: Minimalist in possessions and technology, single-task oriented, future-focused, deliberate, avoids addictions, hates wasting time, and values silence and quality over quantity in relationships and experiences.
Creative Interests: Loves and creates music with a focus on innovation, song craft, and high-quality recordings. Prefers analytical listening and creative originality rather than mainstream trends.

Overall, Derek leads a carefully optimized life that prioritizes creativity, learning, and meaningful personal connections, with a strong emphasis on independence, long-term thinking, and simplicity.

Connect with Derek

Derek Sivers d@sive.rs https://sive.rs/
Get my audiobooks, ebooks, and hardcovers at sivers.com/e?t=n0fw4KGN40U4D71f
sive.rs/u = USEFUL NOT TRUE: reframing because belief → emotion → action
sive.rs/h = HOW TO LIVE: 27 conflicting answers and one weird conclusion
sive.rs/n = HELL YEAH OR NO: what's worth doing?
sive.rs/m = YOUR MUSIC & PEOPLE: humanistic marketing for creatives
sive.rs/a = ANYTHING YOU WANT: make your business a utopia

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