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#386 Derek Sivers on Courage, Bold Questions, & the Dangers of Chasing Status

May 30, 2025

Guest

Derek Sivers

Derek Sivers, an author and former musician known for his quirky insights, dives into the essence of courage and the value of asking bold questions. He reflects on his noble decision to donate $22 million from his business sale to charity, emphasizing the release from chasing status. Their conversation explores the importance of genuine communication in relationships, the transformative power of confronting fears, and the joy derived from unexpected passions like ping pong, all while navigating the fluid nature of self-identity.

01:34:22

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INSIGHT

Surfing Defines Time Horizons

Growing up surfing shaped Kyle's sense of time around two-week wave forecasts only.
This surf-centric worldview made long-term planning difficult but prioritized being present at great waves.

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ANECDOTE

Bold Question on Deathbed

Derek asked his dying grandfather the bold question, "What's it like to know you're about to die?"
His grandfather joyfully shared acceptance and excitement about death, leaving a lasting impression.

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ADVICE

Ask, Don’t Lecture Kids

Stay in questioning mode with your kids to encourage deeper conversation.
Use prompts like "What?", "Give an example", and "Why do you think that?" to keep dialogue open.

Get the Snipd Podcast app to discover more snips from this episode

Introduction and Call to Support an Ad-Free Podcast

02:32 • 3min

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Surfing Waves and Ping Pong Tales

05:13 • 20min

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Navigating Life's Conversations

25:22 • 28min

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The Logic Behind Generosity: Rethinking Wealth After a Major Sale

53:31 • 4min

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Philanthropy and Loyalty in Personal Growth

57:48 • 9min

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Embracing Fear for Growth

01:07:07 • 7min

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Navigating Self-Identity and Growth

01:14:32 • 18min

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The Joy and Brain Benefits of Ping Pong

01:32:24 • 2min

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Brain Rules for Aging

John Medina

#28501

Cows, Pigs, Wars and Witches

Marvin Harris

Marvin Harris answers perplexing questions about human behavior by showing that cultural practices, no matter how bizarre they may seem, stem from identifiable and intelligible sources. He explains how societies create rituals to avoid harming their natural ecosystems, such as the Middle Eastern ban on pig products due to ecological concerns. The book also delves into the origins of warfare as a means of population control and discusses the role of religious movements and witch hunts in historical contexts.

#224

• Mentioned in 58 episodes

Guns, germs, and steel

The Fates of Human Societies

Fabián Chueca

Jared DIAMOND

(MEI )DAI MENG DE (Diamond J. ) XIE YAN GUANG YI

In this book, Jared Diamond explains why Eurasian and North African civilizations have survived and conquered others. He argues that differences in societal development arise primarily from geographical causes. The book details how agricultural societies developed immunities to deadly diseases, advanced in technology, and formed centralized political structures, ultimately leading to the conquest of other societies. Diamond also discusses the impact of germs, domesticated animals, and environmental factors on human history.

#6456

• Mentioned in 4 episodes

Brain rules

John Medina

In 'Brain Rules,' Dr. John Medina shares his expertise on brain science, detailing 12 principles that scientists know for sure about how our brains work. The book covers topics such as the importance of exercise for cognition, the critical role of sleep in learning, the myth of multitasking, and how stress affects learning. Medina uses fascinating stories and humor to make brain science accessible and practical for teachers, parents, and business leaders. The book emphasizes how our brains are wired differently, how we are designed to never stop learning and exploring, and how to optimize our brain's performance in various aspects of life.

#686

• Mentioned in 28 episodes

Anything you want

Derek Sivers

In 'Anything You Want,' Derek Sivers shares 40 powerful lessons learned from his experience of accidentally starting and growing CD Baby into a successful business. The book emphasizes the importance of creating a business that is a 'utopia' or perfect world, where the focus is on making dreams come true for both the entrepreneur and the customers. Sivers stresses that business is not just about money but about helping people and making them happy. He also highlights the advantages of starting with no money, the irrelevance of traditional business plans, and the importance of prioritizing customer needs over personal gain. The book includes memorable stories of his mistakes and successes, including his interactions with Steve Jobs and the impact of his decisions on his business.

#741

• Mentioned in 26 episodes

Hell Yeah or No

What's Worth Doing

Derek Sivers

This book by Derek Sivers is a collection of short, concise chapters offering practical wisdom on decision-making, prioritization, and living a fulfilling life. The central philosophy is that one should only commit to things that elicit a 'hell yeah' response, and say 'no' to everything else. This approach helps in avoiding burnout and ensuring time and energy are dedicated to the most important and exciting activities. The book covers themes such as what’s worth doing, fixing faulty thinking, and making things happen, providing numerous mental models and life lessons to apply in daily life.

#3082

• Mentioned in 8 episodes

Your Music and People

Derek Sivers

In 'Your Music and People,' Derek Sivers shares a philosophy on getting your work to the world by emphasizing creativity, consideration, resourcefulness, and connection. Although the book uses music as an example, its principles are applicable to any creative field. Sivers discusses how marketing is an extension of your art, the importance of being considerate and helpful, and how persistence and specificity are key. The book is praised for its practical advice and inspiring perspective on building a successful creative career.

#584

• Mentioned in 30 episodes

How to Live

27 conflicting answers and one weird conclusion

Derek Sivers

In 'How to Live', Derek Sivers presents a collection of 27 independent chapters, each offering a different philosophy on how to live. These chapters often contradict each other, arguing for various approaches such as being completely independent, committing to one career or person, being fully present, or delaying gratification. The book is designed for reflection as much as instruction, providing actionable directives without quoting philosophers or naming specific ideologies. It invites readers to consider multiple perspectives and find their own way, emphasizing that there is no one right way to live life.

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.

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