15 Best Derek Sivers Podcasts in 2025
Explore the Best Podcasts Featuring Derek Sivers
Here are 15 Best Podcasts Featuring Derek Sivers worth listening to in 2025.
Follow All1. Exploring the Meaning of Work
Follow Play Jan 16, 2025 1:02:23
Website Apple Spotify
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. The conversation touches on creativity, the fear of leaving behind successful ventures, and the excitement of exploring education and productivity. Using the metaphor of breaking out of the atmosphere, they reflect on growth and the opportunities beyond established success. (00:00) Introduction to Derek Sivers (03:07) The Concept of 'Enough' in Entrepreneurship (06:00) The Role of Money in Happiness (08:54) Defining True Financial Freedom (12:01) Future Aspirations and Purpose (15:04) Exploring Problem Areas and Education (17:58) Derek's Journey After Selling CD Baby (21:02) Finding New Goals and Passions (24:13) The Importance of Actionable Goals (26:51) Exploring New Ventures and Projects (32:33) Exploring Through Exploiting (34:53) The Comfort of Coasting on YouTube (40:51) The Fear of Change and the Unknown (46:16) The Price of Freedom: Leaving Money on the Table (50:43) Breaking Out of the Atmosphere: New Possibilities (57:08) Embracing the Unknown: Preparing for Change ? About the Podcast - Not Overthinking Not Overthinking is a podcast about happiness, creativity, and the human condition. We talk about things to help us think, do, and be better. Things like social interaction, lifestyle design, mental models...things that are hard to examine, but important to explore. And hopefully, things that make for a fun and interesting chat every week. MORE Podcast Title Not Overthinking
Podcast Description The weekly podcast about happiness, creativity, and the human condition. It's us, Ali and Taimur Abdaal, occasionally joined by guests, talking about things to help us think, do, and be better. Things like social interaction, lifestyle design, mental models... Things that are hard to examine, but important to explore. And hopefully, things that make for a fun and interesting chat every week. We'd love for you to join us.MORE Hosts Ali Abdaal, Taimur Abdaal
Guest Derek Sivers
Producer/Network Ali & Taimur Abdaal
Email ****@aliabdaal.com
Apple Rating 4.8/5 Avg Length 62 min Format Long form Get Email Contact 
2. #386 Derek Sivers on Courage, Bold Questions, & the Dangers of Chasing..
Follow Play May 30, 2025 1:34:22
Website Apple Spotify
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. (He currently lives in a 4x8 meter house in New Zealand and is building it out slowly, room by room, just to see what he needs.) Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company for $22 million and gave all the money to charity. Sivers' books (Useful, Not True, How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. He loves hearing from strangers and will reply to every email, so if you enjoyed this podcast, shoot him an email and let him know. If you dig this podcast, will you please leave a short review on Apple Podcasts? It takes less than 60 seconds and makes a difference when I drop to my knees and beg hard-to-get guests on the show. I read them all. You can watch this podcast on my YouTube channel and join my newsletter on Substack. It’s glorious. Get full access to Kyle Thiermann at thiermann.substack.com/subscribeMORE Podcast Title The Kyle Thiermann Show
Podcast Description Conversations with intellectual athletes and athletic intellectuals. If you're new here, try starting with #96 Albee Layer, #139 Matt Taibbi, #157 Peter Attia, #206 Chris Ryan, #216 Rick Hanson, #233 Steve Rinella, or #340 Mark Healey. Kyle Thiermann is a journalist, copywriter, and sponsored surfer for Patagonia. His work spans from editorial (Men's Health, Surfer, Outside) to creative (Patagonia, Yeti, MUD\WTR). He has written billboards above LAX, viral commercials seen by over a hundred million people, and steered better-for-you brands to cultural relevance with breakthrough advertising ideas. Kyle is represented by DiFiore Literary Agency and is in the process of publishing his first book. thiermann.substack.comMORE Host Kyle Thiermann
Guest Derek Sivers
Producer/Network Kyle Thiermann
Email ****@surfingforchange.com
Apple Rating 4.9/5 Avg Length 79 min Format Long form Get Email Contact
3. How to Find the Mindsets that Work For You (ft. Derek Sivers)
Follow Play Apr 02, 2025 1:27:35
Website Apple Spotify YouTube
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. That spins off into everything from remixing creative influences (metal + Dixieland jazz, anyone?) to why most podcasts—including mine—have gotten painfully predictable. We talk artistic reinvention, Bob Dylan, Bowie, Miles Davis, why most “thought leaders” are just regurgitating each other’s ideas, and why I'm ending the podcast as you know it—and what’s next! We also dive into the deeper stuff: the emotional power of belief, authenticity vs. performative vulnerability, therapy culture, and why sometimes the most liberating thing you can do is reject what everyone else thinks is necessary—relationships, kids, all of it. This was one of the most honest, meandering, and creatively energizing conversations I’ve had in a while. If you’re into big questions, unconventional ideas, and the occasional musical metaphor, this one’s for you. Derek’s new book- Useful, Not True: https://www.amazon.com/Useful-Not-True-Derek-Sivers-ebook/dp/B0D86K4XF5 Sign up for my newsletter, Your Next Breakthrough. It will help make you a less awful person: https://markmanson.net/breakthrough Follow me: https://instagram.com/markmanson/ https://twitter.com/IAmMarkManson https://facebook.com/Markmansonnet/ https://linkedin.com/in/markmanson/ https://www.tiktok.com/@iammarkmanson MORE Podcast Title SOLVED with Mark Manson
Podcast Description Mark Manson is a three-time #1 New York Times bestselling author and 20-year personal development industry veteran. Solved is the most comprehensive, evidence-based, overly-researched podcast on the planet to help you get an issue in your life, err... solved.MORE Host Mark Manson
Guest Derek Sivers
Producer/Network Mark Manson
Email ****@markmanson.net
Apple Rating 4.9/5 Avg Length 150 min Format Extended Get Email Contact
4. Derek Sivers: Lessons from Making (and Giving Away) a Fortune
Follow Play Jul 07, 2025 54:11
Website Apple Spotify
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.” During our show, we discuss how to overcome self-limiting beliefs, why we over-value our instincts (and what to do instead), and a new (and more useful) approach to setting goals. Derek also shares the one thing that all of his heroes have in common, and his thoughts on what the best thing is that you can pursue in your life. You can learn more about Derek by visiting his website sive.rs. We invite you to share your feedback about this show with us on social media. We’re @crazygoodturns on all of the platforms. Don’t forget to subscribe or follow us on the podcast service of your choice. If you already subscribe, we’d really appreciate a 5-star review: https://podcasts.apple.com/us/podcast/crazy-good-turns/id1137217687 We appreciate you listening and sharing our episodes. Thank you! MORE Podcast Title Crazy Good Turns
Podcast Description We tell inspiring stories about people who do amazing things for others.
Host Frank Blake
Guest Derek Sivers
Producer/Network Joyful Noise Productions
Email ****@crazygoodturns.org
Apple Rating 4.9/5Facebook 6.7KTwitter 1.5K Avg Length 44 min Format Long form Get Email Contact
5. Derek Sivers on Giving Away His $22 Million Dollar Fortune and Burning the Ships
Follow Play Oct 04, 2024 1:10:39
Website Apple Spotify
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. His annual ritual for reversing prejudices. And so much more. Chapters 00:00 - Intro 00:19 - Useful Not True 03:35 - How Derek Comes Up With Book Topics 07:35 - Spending the Past 15 Years Exploring 12:06 - Optimizing for Personal Growth 14:52 - Burning Ships 20:27 - Negative Impacts of Wealth 22:14 - The Burden of Philanthropy 26:17 - A Day in Derek’s Life 28:53 - Is Derek Introverted? 30:12 - Derek’s Hard No’s 35:35 - Derek’s Nomadic Blood 38:01 - Derek’s Fame 42:38 - Derek’s Thoughts on AI 57:12 - Overcoming Prejudices 59:25 - Doing What Scares You 1:01:54 - Learning to Appreciate China 1:06:48 - Closing ? Find Derek on: Website: https://sive.rs/ His Now Page: https://sive.rs/now His Latest Book: https://sive.rs/u ? Find Andrew on: Twitter/X: @awilkinson LinkedIn: @awilkinson Website: https://www.neverenough.com/ Sign up for Andrew's newsletter MORE Podcast Title Never Enough
Podcast Description I talk to interesting people for a living. You get their cheat codes. Join me as I go deep on what they do, how they do it, and the messy realities of success.
Host Andrew Wilkinson
Guest Derek Sivers
Producer/Network Andrew Wilkinson
Email ****@tiny.com
Apple Rating 4.8/5 Avg Length 71 min Format Long form Get Email Contact
6. #24 - Derek Sivers (author of philosophy and entrepreneurship) — The pursuit..
Follow Play Oct 30, 2024 1:42:48
Website Apple Spotify
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.rs/ MORE Podcast Title Big Mistake
Podcast Description Welcome to Big Mistake the podcast that unpacks the failures and mistakes of top professionals. So to make us (and hopefully you) feel better about the mistakes we make in our careers and lives, we’ll be talking with high performers to understand the behind-the-scenes (and less glamourous moments) of the business world. See you in there! Miriam & AnnaMORE Guest Derek Sivers
Producer/Network Big Mistake
Avg Length 75 min Format Long form Get Email Contact
7. Reframing the Good Life One Experiment at a Time with Derek Sivers
Follow Play Aug 27, 2025 1:14:18
Website Apple Spotify
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. He’s a slow thinker, an explorer, a xenophile, and loves a different point of view. In New Zealand, he lives in a house that he designed himself, based off the notion that houses should grow from how people actually live, not from a master plan — so he waits to add walls until he figures out what he needs. That’s just one of his more radical ways of thinking. We were pleased and he was pleased that we asked him questions that he had never been asked before about how to live, about spirituality, parenting, and architecture. This conversation is full of surprises, and we hope you enjoy it. Links: Useful Not True How to Live For more from Derek, check out his website or follow him on Instagram and Twitter We love hearing from our listeners! Leave us a voice message, write to the show email, or send us a DM on any of our socials. If our conversations support you in your own reframing practice, please consider a donation on our Patreon, where you can also hear bonus episodes, or tipping us on Ko-fi. Subscribe to the Reframeables Newsletter. Follow us on TikTok, Twitter, Instagram, and YouTube too. MORE Podcast Title Reframeables
Podcast Description Do you feel alone in your own head when it comes to navigating life’s big and small problems? Do you find self-care language a little too self-focused but know you still need to do the work? Join us on Reframeables and eavesdrop your way into some new perspectives — we promise you'll feel less alone as you listen. We are Nat and Bec, two very different sisters who come together each week to reframe some of life's big and small stuff. Nat's a PhD whose favourite phrase is “let’s reframe that!” Bec's an artist who tends more toward “why me?” Through candid, vulnerable yet entertaining conversations with each other, as well as guests, we find a way to meet in the middle each week and offer you, our listeners, new perspectives along the way. From a painful divorce that still needs processing, to grief that sticks around, to the simple day-to-day problems of managing a grumpy teenager, to a dynamic interview with Giller winner Ian Williams or radio personality and co-star of the Jann Arden podcast Caitlin Green sharing her vulnerable story of loss: Join our intimate conversations with authors, actors, activists, and voices from the crowd — those who inspire us to think differently about the world so we can reframe living in it. MORE Guest Derek Sivers
Producer/Network Rebecca & Natalie Davey
Apple Rating 4.2/5 Avg Length 50 min Format Long form Get Email Contact
8. Derek Sivers — Embracing Simplicity, Owning Your Weirdness, and Designing..
Follow Play Jun 24, 2025 1:30:48
Website Apple Spotify
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. Since then, he’s become a bestselling author of books like Anything You Want, Hell Yeah or No, and Useful Not True, each filled with punchy, poetic wisdom earned from experience. In this episode, we explore how to treat your life like a design problem, why marketing is part of the art, and how vulnerability and weirdness aren’t liabilities—they’re the keys to resonance. Whether you’re building a company, making games, or just trying to figure out how to live a more meaningful life, this conversation will challenge your assumptions and invite you to take that first small but deliberate step. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit justingarydesign.substack.com/subscribeMORE Podcast Title Think Like A Game Designer
Podcast Description In Think Like a Game Designer, award-winning designer and Stone Blade Entertainment CEO Justin Gary speaks with world-class game designers and creative experts from various industries. Each episode deconstructs the creative process, offering insights into the art of game design and the broader cultural, technological, and business influences shaping a myriad of creative mediums. Join us for actionable advice and unique perspectives that will enrich your understanding of what it means to be creative in and out of the gaming world. justingarydesign.substack.comMORE Host Justin Gary
Guest Derek Sivers
Producer/Network Justin Gary
Email ****@gmail.com
Apple Rating 4.9/5Facebook 54 Avg Length 72 min Format Long form Get Email Contact
9. Derek Sivers | Life as a Musician Before CD Baby, Getting Unstuck Creatively..
Follow Play Jan 27, 2025
Website Apple Spotify YouTube
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 Podcast Title Moby Pixel Show
Podcast Description Welcome to the Moby Pixel Show! Join me for insightful conversations with amazing creators from the music and app development world.
Guest Derek Sivers
Producer/Network Moby Pixel
Apple Rating 5.0/5 Get Email Contact
10. Episode 142: Derek Sivers: How To Keep Growing
Follow Play Feb 14, 2025 1:46:54
Website Apple Spotify
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) Obvious to you, amazing to someone else (05:19) How Derek thinks about money (13:03) Deep happy vs. shallow happy (21:00) Following an innate drive and desire (24:07) 18 months of feeling adrift (30:04) To find direction: read a lot and wait for energy (31:18) The power of heroes and anti-heroes (36:05) Egotists and hedonists (40:00) Changing your mind and keeping your identity small (44:37) Think of yourself as a student, not a preacher (47:42) Personal growth over wealth growth (53:00) Prioritizing openness (56:59) What lifestyles or beliefs is Derek against? (01:04:50) The downside of optimism in Derek's personal life (01:14:24) Dating, marriage, and the role of women in Derek's life (01:23:55) How to save a life with $2,000 (01:27:50) Derek's thoughts on philanthropy (01:33:54) "Useful Not True" (01:38:39) A prequel to "How To Live" (01:41:13) "Useful Not True": the truth of many answers and perspectives MORE Podcast Title Keep Talking
Podcast Description "Keep Talking" exists to have conversations that might help to make a better society and a better culture. I believe that each guest has important information and stories to make public. And it's something that I want to share.MORE Guest Derek Sivers
Producer/Network Dan Riley
Apple Rating 4.8/5 Avg Length 69 min Format Long form Get Email Contact
11. Derek Sivers: Turning Thoughts into Action
Follow Play Mar 06, 2023 1:18:28
Website Apple Spotify
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. In this episode, Derek shares his wisdom on values, reflection, conventionality, and success, inspiring listeners to chase their dreams, no matter how big or small. The conversation also delves into some of the most popular books that have influenced Derek's life and work, including Almost Perfect by Erika Lemay and Awaken The Giant Within by Tony Robbins. [00:00:32] Welcoming Derek Sivers [00:01:15] The Art of Turning Ideas into Action [00:02:50] The Importance of Clarity and Self-Reflection [00:04:30] Why Derek Joined Meg Walker’s Podcast [00:06:10] Derek’s “Click Moment” at Summer Camp [00:08:45] Discussing Success and Ambition [00:11:20] Embracing a Nomadic Lifestyle [00:14:00] Aligning Actions with Core Values [00:16:35] Derek’s Immediate Career Plans [00:19:10] Congruence Between Actions and Desires [00:21:55] Impact of Books on Derek’s Life [00:24:40] Unconventional Decision-Making [00:27:30] Conventional vs. Unconventional Behaviour Across Cultures [00:30:15] Family Bonds and Musical Nostalgia [00:33:00] Expressing Natural Urges and Parenting [00:35:45] Positive Change and Personal Autonomy [00:38:20] The Benefits of a Positive Mindset [00:40:55] The Changing Landscape of Community [00:43:30] Conclusion and Call to Action for Audience Feedback Guest: Derek Sivers https://sive.rs/ Host: Meg Walker Instagram: @themegmethod YouTube: @themegmethod Coaching Podcast: THE MEG METHOD Website: www.themegmethod.com Sound: Brooklyn Fraser and Alicia Navarro MORE Podcast Title My Kind of People
Podcast Description My Kind of People is a podcast celebrating leaders and community members from across the world who all share a passion for positive change. Each week we will explore the power of community, leadership, passion and positivity and the beauty that can be created when these values come together.MORE Guest Derek Sivers
Producer/Network Meg Walker
Apple Rating 4.9/5 Avg Length 64 min Format Long form Get Email Contact
12. 39. The Man Who Gave Away $22 MILLION Dollars: CD Baby Founder Derek Sivers..
Follow Play Oct 22, 2025 1:08:02
Website Apple Spotify
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. In this deep-dive conversation, Derek shares his counter-intuitive rules for life, business, and creativity. We explore his famous philosophy of "If it's not a 'Hell Yeah!' it's a 'No'," the power of radical simplification, and why sometimes, the best decision is to walk away from a potential billion-dollar opportunity to protect your time and peace of mind. Interview Guest: Derek Sivers https://sive.rs/ https://www.youtube.com/user/dereksivers https://x.com/sivers For Derek's books: https://sivers.com/ Location: Tyler: Motiversity Office Derek Sivers: Home Studio Follow Tyler https://www.youtube.com/channel/UC3tWHKc-RcOeVlGyZQxtppQ https://www.instagram.com/TylerWaye/ https://www.linkedin.com/in/tylerwaye/ http://tylerwaye.com/ Hosted on Acast. See acast.com/privacy for more information. MORE Podcast Title The Icons Motivational Podcast
Podcast Description The best life, mindset and success advice from the world's most iconic people. The Icons — from NBA and NFL Hall of Fame players, to iconic CEOs and chart-topping artists — share the lessons and stories that helped them go from normal every day people to superstars. Join host Tyler Waye — renowned work expert and Motiversity’s Executive in Residence — in discovering how The Icons defied all odds, succeeded in the face of adversity. Tyler and guests talk mindset, work ethic, failure, career advice, routines, motivation, life stories, leadership and how each icon got through the hard times in their journey to the top. Upcoming guests on The Icons include an NBA Hall of Fame player, NFL Hall of Fame player, and a singer-songwriter and actress, best known for massive global chart-topping hit. If you’re ready to start your journey to becoming an icon or just need some motivation or inspiration from someone that you look up to, tune in to The Icons podcast by Motiversity. Follow The Icons on YouTube for the full videos: https://www.youtube.com/channel/UCnTBBvGdqe4TZHQJi-3HH9Q and Motiversity for shorter, cinematic edits: https://www.youtube.com/motiversity Hosted on Acast. See acast.com/privacy for more information.MORE Guest Derek Sivers
Producer/Network Motiversity
Apple Rating 4.0/5 Avg Length 56 min Format Long form Get Email Contact