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#753: Derek Sivers and Kevin Kelly

July 10, 2024

The Tim Ferriss Show


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! Sponsors: Wealthfront high-yield cash account: (Start earning 5.00% APY 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. Helix Sleep premium mattresses: (25–30% off all mattress orders and two free pillows) AG1 all-in-one nutritional supplement: (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) Timestamps: [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. * For show notes and past guests on The Tim Ferriss Show, please visit For deals from sponsors of The Tim Ferriss Show, please visit Sign up for Tim’s email newsletter (5-Bullet Friday) at For transcripts of episodes, go to Discover Tim’s books: Follow Tim: Twitter:  Instagram: YouTube: Facebook:  LinkedIn: Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, Margaret Atwood, Mark Zuckerberg, Peter Thiel, Dr. Gabor Maté, Anne Lamott, Sarah Silverman, Dr. Andrew Huberman, and many more. See Privacy Policy at and California Privacy Notice at