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 tim.blog/combo.

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube, YouTube Music, Amazon Music, Audible, or on your favorite podcast platform.

This episode is brought to you by Wealthfront high-yield cash account, Helix Sleep premium mattresses, and AG1 all-in-one nutritional supplement.

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

Listen onApple Podcasts

Listen onSpotify

Listen onOvercast

#753: Derek Sivers and Kevin Kelly

This episode is brought to you by Helix Sleep! Helix was selected as the best overall mattress of 2025 by Forbes and Wired magazines and best in category by Good Housekeeping, GQ, and many others. With Helix, there’s a specific mattress to meet each and every body’s unique comfort needs. Just take their quiz—only two minutes to complete—that matches your body type and sleep preferences to the perfect mattress for you. They have a 10-year warranty, and you get to try it out for a hundred nights, risk-free. They’ll even pick it up from you if you don’t love it. And now, Helix is offering 20% off all mattress orders at HelixSleep.com/Tim.

This episode is brought to you by AG1! I get asked all the time, “If you could use only one supplement, what would it be?” My answer is usually AG1, my all-in-one nutritional insurance. I recommended it in The 4-Hour Body in 2010 and did not get paid to do so. And right now, when you first subscribe to AG1, you’ll get an AG1 Welcome Kit, a bottle of Vitamin D3+K2, a Morning Person hat, AND you’ll get to try each new flavor of AG1 and their new sleep supplement, AGZ. That’s $126 in free gifts for new subscribers! Visit DrinkAG1.com/Tim to claim this special offer today

This episode is brought to you by Wealthfront! Wealthfront is a financial services platform that offers services to help you save and invest your money. Right now, you can earn a 3.50% base APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s nearly nine times more interest than an average savings account at a bank, according to FDIC.gov as of 09/26/2025 (Wealthfront’s 3.50% APY vs. 0.40% average savings rate). Right now, for a limited time, Wealthfront is offering new clients an additional 0.65% boost over the base rate for three months, meaning you can get 4.15% APY, limited to $150,000 in deposits. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started.

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC, member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.50% Base APY on cash deposits is as of November 7, 2025, is representative, subject to change, and requires no minimum. If you are eligible for the overall boosted rate of 4.15% offered in connection with this promo, your boosted rate is also subject to change if the base rate decreases during the three-month promotional period. Tim Ferriss, who is not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. See full disclosures here.

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

SHOW NOTES

[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.

SELECTED LINKS FROM THE EPISODE

Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube

Connect with Kevin Kelly:

Website | Twitter | Instagram | YouTube

SHOW NOTES

SELECTED LINKS FROM THE EPISODE

PEOPLE MENTIONED

Coyote

A card game by Tim Ferriss and Exploding Kittens

Keep exploring.

SHOW NOTES

SELECTED LINKS FROM THE EPISODE

PEOPLE MENTIONED

Share this:

Coyote

A card game by Tim Ferriss and Exploding Kittens

Keep exploring.