Derek Sivers and Kevin Kelly (#753)

This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited. The episode features segments from episode “Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions” and “Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World?

Please enjoy!

Bios of guests may be found at

Listen to the episode on Apple PodcastsSpotifyOvercastPodcast AddictPocket CastsCastbox, YouTubeYouTube MusicAmazon MusicAudible, or on your favorite podcast platform.

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Transcript for the full Derek Sivers episode | Transcript for the full Kevin Kelly episode | Transcripts for all episodes

#753: Derek Sivers and Kevin Kelly

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


  • [05:47] Notes about this supercombo format.
  • [06:50] Enter Derek Sivers.
  • [07:20] From pig show busker to circus ringleader.
  • [10:42] Derek’s framework for developing confidence.
  • [13:05] “The standard pace is for chumps.”
  • [18:51] Relaxing for the same result.
  • [24:01] The origins of “HELL YEAH! or no.”
  • [26:25] “Busy” implies a life out of control.
  • [28:03] What inspired the automation of CD Baby?
  • [33:22] Derek’s billboard.
  • [34:32] Good advice at any age: “Don’t be a donkey.”
  • [40:24] Enter Kevin Kelly.
  • [41:02] Kevin’s biggest regret.
  • [43:13] Finding contentment in minimalism and “voluntary simplicity” without starving to death.
  • [50:33] Kevin’s epiphany when he embraced writing as a late bloomer.
  • [56:40] Why Kevin promised himself he would never resort to teaching English while traveling abroad.
  • [59:07] Finding purpose through resilience and the creator’s dilemma.
  • [1:06:50] Why the appeal of being a billionaire is overrated.
  • [1:11:05] Middle-aged optimization.
  • [1:15:28] Realizations following a “six months until death” challenge.
  • [1:20:08] Kevin’s Kickstarter-funded project linking angels and robots.
  • [1:22:41] Why a self-proclaimed ex-hippie waited until his 50th birthday to try LSD for the first time.
  • [1:28:43] Why a population implosion is probable in the next 100 years.
  • [1:36:05] The greatest gift you can give to your child.
  • [1:38:21] The criteria for Amish technology assimilation.
  • [1:45:03] What technology-free sabbaticals can do for you.
  • [1:48:53] Long Now Foundation’s vision of a better civilization.
  • [1:53:33] The graphic novel teaching young people how to become indispensable.
  • [1:54:52] An antidote to misguided “follow your passion” advice.
  • [1:56:44] Kevin’s favorite fiction book.
  • [1:59:15] The resource Kevin compiled for documentary lovers.
  • [2:02:47] A name Kevin considers synonymous with “success” (and why success is overrated).
  • [2:05:46] What Kevin would change about himself.
  • [2:07:59] Daily rituals.
  • [2:10:44] How Kevin accumulated enough books to fill a two-story library.
  • [2:15:19] How Adam Savage from MythBusters transformed Kevin’s method of organization.
  • [2:17:14] The project everyone should undertake at least once in life.
  • [2:19:30] Does discovery equal invention?
  • [2:20:12] Kevin’s advice to his younger self.
  • [2:23:16] Parting thoughts.


Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube

Connect with Kevin Kelly:

Website | Twitter | Instagram | YouTube


The Tim Ferriss Show is one of the most popular podcasts in the world with more than one billion downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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