15 Best Derek Sivers Podcast Appearance and Guest Interviews

1. Derek Sivers on The Kyle Thiermann Show

Play Feb 16, 2026 1:35:47
Apple Spotify Episodes
Episode Title #408 Whatever Scares You, Go Do It - Derek Sivers (Repost)
About Episode In case you missed the last episode, my big news is that I relocated to Brooklyn for the next few months. My fingers are numb as I write this, but I do love it. Also, I’m capping off my book tour on February 19th at Patagonia SoHo. If you’re in town, I would love to meet you in person. You can RSVP here. Okay, what else? Right, the latest podcast. You see, I’m an informational grazer, nibbling on bits of media here and there but rarely sitting with a concept long enough to fully digest it...MORE Host Kyle Thiermann
Producer/Network Kyle Thiermann
Email ****@surfingforchange.com
Apple Rating 4.9/5 Avg Length 81 min Format Long form Get Email Contact Get access to full database of 2.7M podcastsCreate podcast lists, export in spreadsheet or CSV file with email contacts and start your podcast outreach in minutes.Sign Up for Free with Email Continue with Google

2. Derek Sivers on Social Work Mums

Play Feb 09, 2026 15:25
Apple Episodes
Episode Title #007 - The Power of Saying 'No'
About Episode In this episode, entrepreneur and philosopher Derek Sivers joins the show to discuss why most ‘opportunities’ are actually distractions in disguise. Sivers breaks down his framework for protecting your time by distinguishing between what is truly important versus what is merely urgent. He explores the internal psychology of saying ‘no’ with conviction, the importance of knowing who you are creating for, and why being committed to a problem is more valuable than being committed to a specific so..MORE Avg Length 17 min Format Short form Get Email Contact

3. Derek Sivers on Abundant Thinking

Play Dec 30, 2025 1:07:17
Apple Spotify Episodes
Episode Title #130 - Throwback: A Masterclass on Reframing, Beliefs, and Perspectives -..
About Episode You see the world your way, but I see it differently. Todays episode is an absolute gem... How do our beliefs, perspectives and thoughts shape who we are, the results we get, and people around us. Most of our thoughts are useful but not true. Today we speak to Derek Sivers, Derek is a deep thinker. He has authored many books one of which being Useful Not True which is the topic of our discussion today. Buy my book: Click Here Thank you from the bottom of my heart. MORE Producer/Network Elan Gelfand
Apple Rating 5.0/5 Avg Length 41 min Format Long form Get Email Contact

4. Derek Sivers on The Icons Motivational Podcast

Play Oct 22, 2025 1:08:02
Apple Spotify Episodes
Episode Title 39. The Man Who Gave Away $22 MILLION Dollars: CD Baby Founder Derek Sivers..
About Episode In this truly unique and insightful episode of The Icons, host Tyler Waye sits down with Derek Sivers, the legendary founder of CD Baby and a modern philosopher on simplicity, focus, and "hell yes" decisions. Derek Sivers built CD Baby from a small side project into the largest seller of independent music online, eventually selling it for $22 million and giving the proceeds to a charitable trust for musicians. But his story isn't about the money; it's about the mindset...MORE Host Tyler Waye
Producer/Network Motiversity
Email ****@informseries.com
Apple Rating 4.0/5 Avg Length 58 min Format Long form Get Email Contact

5. Derek Sivers on Reframeables

Play Aug 27, 2025 1:14:18
Apple Spotify Episodes
Episode Title Reframing the Good Life One Experiment at a Time with Derek Sivers
About Episode Bec first heard Derek Sivers on the Tim Ferriss podcast, and was immediately interested in this countercultural person who sold a multimillion dollar company and then moved to New Zealand to do something completely different. He’s interested in learning and iterating, and he did say he would answer every email — so we decided to test him. He answered right away. Derek has been a musician, a circus performer, an entrepreneur, and a speaker...MORE Producer/Network Rebecca & Natalie Davey
Apple Rating 4.2/5 Avg Length 51 min Format Long form Get Email Contact

6. Derek Sivers on Crazy Good Turns

Play Jul 07, 2025 54:11
Website Apple Spotify Episodes
Episode Title Derek Sivers: Lessons from Making (and Giving Away) a Fortune
About Episode Derek Sivers is one of the most interesting thinkers of our time. He’s been a professional touring musician, a circus performer, and a successful entrepreneur who sold his company for millions – and then gave away his proceeds from the sale. Since selling the company, Derek has become a speaker, writer and author of five books including his latest release, “Useful Not True...MORE Host Frank Blake
Producer/Network Joyful Noise Productions
Email ****@crazygoodturns.org
Apple Rating 4.9/5Facebook 6.8KTwitter 1.5KInstagram 11.2K Avg Length 44 min Format Long form Get Email Contact

7. Derek Sivers on Think Like A Game Designer

Play Jun 24, 2025 1:30:48
Website Apple Spotify YouTube Episodes
Episode Title Derek Sivers — Embracing Simplicity, Owning Your Weirdness, and Designing..
About Episode About Derek Sivers Derek Sivers has worn many hats, musician, entrepreneur, author, and philosopher, but his work maintains a single throughline: a relentless pursuit of living deliberately. He first found success by founding CD Baby, an indie music platform that revolutionized digital distribution before he sold it for over $20 million and donated most of the proceeds...MORE Host Justin Gary
Producer/Network Justin Gary
Email ****@gmail.com
Apple Rating 4.9/5Facebook 54Instagram 1K Avg Length 74 min Format Long form Get Email Contact

8. Derek Sivers on The Kyle Thiermann Show

Play May 30, 2025 1:34:22
Apple Spotify Episodes
Episode Title #386 Derek Sivers on Courage, Bold Questions, & the Dangers of Chasing..
About Episode When I started this podcast more than 7 years ago, I listed Derek Sivers as my dream guest (sorry Kelly Slater). Sivers’ gift, I believe, is the willingness to question the premise of all things, delightfully, humorously, and give anyone in his orbit the choice to follow a more original path. An author of philosophy and entrepreneurship, he’s known for his surprising quotable insights, pithy succinct writing style, and commitment to minimalism...MORE Host Kyle Thiermann
Producer/Network Kyle Thiermann
Email ****@surfingforchange.com
Apple Rating 4.9/5 Avg Length 81 min Format Long form Get Email Contact

9. Derek Sivers on SOLVED with Mark Manson

Play Apr 02, 2025 1:27:35
Website Apple Spotify YouTube Episodes
Episode Title How to Find the Mindsets that Work For You (ft. Derek Sivers)
About Episode I’ve got a special episode for you today. I sat down in person with my longtime friend and first-ever podcast guest, Derek Sivers. We haven’t recorded live before, and honestly, it shows—in the best way. It’s raw, weird, and filled with the kind of conversations we usually when we’re just hanging out together. We dig into Derek’s new book, Useful, Not True, and the big idea behind it: that our beliefs don’t need to be true to be helpful...MORE Host Mark Manson
Producer/Network Mark Manson
Email ****@markmanson.net
Apple Rating 4.9/5 Avg Length 131 min Format Extended Get Email Contact

10. Derek Sivers on Keep Talking

Play Feb 14, 2025 1:46:54
Apple Spotify Episodes
Episode Title Episode 142: Derek Sivers: How To Keep Growing
About Episode Derek Sivers is a TED speaker, an essayist, a businessman, a musician, one of my favorite thinkers on the planet, and the author of many books including his most recent, Useful Not True: Whatever Works For You. ------------ Book Dan to do an interview or a meeting ------------ Keep Talking Substack Spotify Apple Podcasts Social media and all episodes ------------ Support via Venmo Support on Substack Support on Patreon ------------ (00:00) Intro (01:00) Your actions reveal your values (03:25) ..MORE Producer/Network Dan Riley
Apple Rating 4.8/5 Avg Length 69 min Format Long form Get Email Contact

11. Derek Sivers on Moby Pixel Show

Play Jan 27, 2025
Apple Spotify YouTube Episodes
Episode Title Derek Sivers | Life as a Musician Before CD Baby, Getting Unstuck Creatively..
About Episode Derek Sivers (@sivers) has been a musician, producer, circus performer, entrepreneur, TED speaker, and book publisher. While Derek is probably best known for starting CD Baby, his books, blogs, and interviews are where he is most celebrated today. In our conversation, we talk about his life as a musician before CD Baby, how he handles negative feedback, and how to get unstuck creatively. I learned a lot from our talk, and I hope you get something out of it too!MORE Producer/Network Moby Pixel
Apple Rating 5.0/5 Get Email Contact

12. Derek Sivers on Not Overthinking

Play Jan 16, 2025 1:02:23
Website Apple Spotify Episodes
Episode Title Exploring the Meaning of Work
About Episode In this episode of Not Overthinking, Ali and Taimur sit down with Derek Sivers to explore the journey of entrepreneurship, the concept of 'enough', and the role of money in happiness. Together, they discuss true financial freedom, future aspirations, and finding purpose in work. Derek reflects on his experience after selling CD Baby, navigating feelings of loss, setting new goals, and embracing change...MORE Hosts Ali Abdaal, Taimur Abdaal
Producer/Network Ali & Taimur Abdaal
Email ****@aliabdaal.com
Apple Rating 4.8/5 Avg Length 62 min Format Long form Get Email Contact

13. Derek Sivers on Big Mistake

Play Oct 30, 2024 1:42:48
Apple Spotify Episodes
Episode Title #24 - Derek Sivers (author of philosophy and entrepreneurship) — The pursuit..
About Episode Derek Sivers has been a musician, circus performer, entrepreneur, and speaker. Today, he is a slow thinker, explorer, author and xenophile. In this episode we chat about: Minimalism in business and life: why happiness comes from needing less, not having more How to get world-class mentorship without any mentors The difference between a mistake and an accident The truth about busyness Clarifying the "hell yeah or no" philosophy Self-reliance and trusting your gut Derek Sivers: https://sive...MORE Producer/Network Big Mistake
Avg Length 75 min Format Long form Get Email Contact

14. Derek Sivers on Never Enough

Play Oct 04, 2024 1:10:39
Apple Spotify Episodes
Episode Title Derek Sivers on Giving Away His $22 Million Dollar Fortune and Burning the Ships
About Episode About the episode In this episode, Andrew sits down with Derek Sivers, a writer, programmer, and entrepreneur turned explorer, who challenges everything you thought you knew about success and fulfillment. From giving away millions to embracing the unexpected, Derek's approach may be the antidote to our never-enough culture. Join us as we explore: Why he gave away his $22 million dollar fortune.  Why he's an explorer not a leader. How he has "burned the ships" over and over again...MORE Host Andrew Wilkinson
Producer/Network Andrew Wilkinson
Email ****@tiny.com
Apple Rating 4.8/5 Avg Length 71 min Format Long form Get Email Contact

15. Derek Sivers on My Kind of People

Play Mar 06, 2023 1:18:28
Apple Spotify Episodes
Episode Title Derek Sivers: Turning Thoughts into Action
About Episode Welcome to this exciting episode of My Kind of People podcast, where we feature none other than Derek Sivers, an acclaimed writer, author, and visionary entrepreneur. As the mastermind behind the wildly successful online platform CD Baby, Derek has helped countless independent artists reach new heights and turn their ideas into action...MORE Producer/Network Meg Walker
Apple Rating 4.9/5 Avg Length 64 min Format Long form Get Email Contact