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

This episode is brought to you by Helix Sleep! Helix was selected as the best overall mattress of 2022 by GQ magazine, Wired, and Apartment Therapy. 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 25–30{c87e2df4b343d0515d304e127afe4653a549475791ab451641a18e09bd64e760} off all mattress orders plus two free pillows 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. I do my best with nutrient-dense meals, of course, but AG1 further covers my bases with vitamins, minerals, and whole-food-sourced micronutrients that support gut health and the immune system. 

Right now, you’ll get a 1-year supply of Vitamin D free with your first subscription purchase—a vital nutrient for a strong immune system and strong bones. Visit DrinkAG1.com/Tim to claim this special offer today and receive your 1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase! That’s up to a one-year supply of Vitamin D as added value when you try their delicious and comprehensive daily, foundational nutrition supplement that supports whole-body health.

This episode is brought to you by Wealthfront! Wealthfront is an app that helps you manage and invest your money. Right now, you can earn 5.00{c87e2df4b343d0515d304e127afe4653a549475791ab451641a18e09bd64e760} APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account through its network of partner banks. That’s more than ten times more interest than a savings account at a bank, according to FDIC.gov. It takes just a few minutes to sign up, and then you’ll immediately start earning 5.00{c87e2df4b343d0515d304e127afe4653a549475791ab451641a18e09bd64e760} APY interest on your short term cash until you’re ready to invest.

And when you open an account today, you can get an extra fifty-dollar bonus with a deposit of five hundred dollars or more. Terms apply. Visit Wealthfront.com/Tim to get started.

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

• Excellent Advice for Living: Wisdom I Wish I’d Known Earlier by Kevin Kelly | Amazon
• Cool Tools: A Catalog of Possibilities by Kevin Kelly | Amazon
• The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future by Kevin Kelly | Amazon
• What Technology Wants by Kevin Kelly | Amazon
• Vanishing Asia: Three Volume Set: West, Central, and East by Kevin Kelly | Amazon
• The Latest in Technology, Science, Culture, and Business | Wired
• The Whole of the ‘Whole Earth Catalog’ Is Now Online | Wired
• What is Voluntary Simplicity? | The Simplicity Collective
• What Is Stoicism? A Definition and Nine Stoic Exercises to Get You Started | Daily Stoic
• Stoicism Resources and Recommendations | Tim Ferriss
• 1,000 True Fans by Kevin Kelly | The Technium
• A Cherished Destination for Conversation and Discussion | The WELL
• Cat’s Cradle: A Novel by Kurt Vonnegut | Amazon
• Teach English Abroad: Top 54 Countries | TEFL.Org
• The Circle of Innovation: You Can’t Shrink Your Way to Greatness by Tom Peters | Amazon
• In Search of Excellence: Lessons from America’s Best-Run Companies by Tom Peters and Robert H. Waterman, Jr. | Amazon
• Wealth Is Overrated | Wired
• Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel by Rolf Potts | Amazon
• Walden and On the Dity of Civil Disobedience by Henry David Thoreau | Amazon
• Wall Street | Prime Video
• Shoulda Been Dead | This American Life
• Futurama Death Clock | Kevin Kelly
• The Tail End | Wait But Why
• The Silver Cord by Kevin Kelly and Steve Masseroni | Amazon
• The Hidden Knowledge of Animals — Mark Plotkin on Nature’s Medicine Cabinet | The Tim Ferriss Show #537
• Dr. Andrew Weil — The 4-7-8 Breath Method, Cannabis, The Uses of Coca Leaf, Rehabilitating Demonized Plants, Kava for Anxiety, Lessons from Wade Davis, The Psychedelic Renaissance, How to Emerge from Depression, Tales from 50+ Visits to Japan, Matcha Benefits, and More | The Tim Ferriss Show #615
• The Psychedelic Explorer’s Guide: Safe, Therapeutic, and Sacred Journeys by James Fadiman | Amazon
• The Honest Drug Book: A Chemical & Botanical Journey Through The Legal High Years by Dominic Milton Trott | Amazon
• A Child’s Garden of Grass: The Official Handbook for Marijuana Users by Jack S. Margolis and Richard Clorfene | Amazon
• Jack S. Margolis’ Complete Book of Recreational Drugs by Jack S. Margolis | Amazon
• Cassandra Complex | Wikipedia
• What Is Moore’s Law and Is It Still True? | Investopedia
• Malthusianism | Wikipedia
• World Population Growth Is Expected to Nearly Stop By 2100 | Pew Research Center
• By 2060 the Total Population of Humans on Earth Will Be Less than It Is Today. | Long Bets
• Amish Hackers | Kevin Kelly
• I Stopped Using Screens on Sundays. This Is How It Changed My Life | Fast Company
• A Member of the Roche Group | Genentech
• Research: The Transformative Power of Sabbaticals | HBR
• Fostering Long-Term Thinking | The Long Now Foundation
• The Clock of the Long Now | The Long Now Foundation
• Building an Archive of All Documented Human Languages | The Rosetta Project
• The Arena for Accountable Predictions | Long Bets
• Genetic Rescue to Enhance Biodiversity | Revive & Restore
• Foundation Series Books 1-7 by Isaac Asimov | Amazon
• The Adventures of Johnny Bunko by Daniel H. Pink | Amazon
• So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love by Cal Newport | Amazon
• Cal Newport: “Follow Your Passion” Is Bad Advice | 99U
• Shantaram: A Novel by Gregory David Roberts | Amazon
• Joshua Waitzkin | The Tim Ferriss Show #2
• Searching for Bobby Fischer: The Father of a Prodigy Observes the World of Chess by Fred Waitzkin | Amazon
• Kevin Kelly’s Favorite Documentaries | True Films
• Man on Wire | Prime Video
• The King of Kong: A Fistful of Quarters | Prime Video
• A State of Mind | Amazon
• Valproate | Wikipedia
• Top 10 Benefits of Learning Drums for Adults and Children | Chinook School of Music
• The New York Times
• MythBusters | Discovery GO
• Efficiency and First Order of Retrievability in Shops | Adam Savage’s Tested
• Shipping Boxes, Shipping Supplies, Packaging Materials, Packing Supplies | ULINE
• The World’s Work Marketplace | Upwork (Formerly Elance)

PEOPLE MENTIONED

Related

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.