Chris Sacca is the co-founder of Lowercarbon Capital and manages a portfolio of countless startups in energy, industrial materials, and carbon removal. If it's unf**king the planet, he's probably working on it. Previously, Chris founded Lowercase Capital, one of history's most successful funds ever, primarily known for its very early investments in companies like Twitter, Uber, Instagram, Twilio, Docker, Optimizely, Blue Bottle Coffee, and Stripe. But you might just know him as the guy who wore those ridiculous cowboy shirts for a few seasons of Shark Tank. To purchase Chris's ranch, schedule a viewing at FivePondsRanch.com. P.S. This episode features a special, one-of-a-kind introduction that Chris recorded of yours truly. :) Sponsors: MUD\WTR energy-boosting coffee alternative—without the jitters: https://MUDWTR.com/Tim (between 15% and 43% off) Helix Sleep premium mattresses: https://HelixSleep.com/Tim (Between 20% and 27% off all mattress orders and two free pillows) AG1 all-in-one nutritional supplement: https://DrinkAG1.com/Tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) Timestamps: [00:00] Coming up [06:47] Chris introduces me. [11:07] Some Sacca background. [18:32] Raising pre-teen gamblers and tailgating troublemakers. [19:54] Conscious changes and rethoughts since our first interview. [26:12] The personal and professional influence of Rich and Sarah Barton. [30:18] Property management and the Zen of Kevin Rose. [35:12] Zillow Gone Wild. [36:58] Simplifications. [45:03] Remaining optimistic despite being in the business of saying no. [51:33] Living in the finite without +1 obligations. [56:54] “Wait, what’s hustle culture?” [59:48] The (lack of) trouble with kids today. [01:09:53] Raising kids to solve problems and eschew smartphones. [01:14:15] Rawdogging? You keep using that word. I do not think it means what you think it means. [01:16:05] An Andy Goldsworthy aside. [01:16:30] Taking advice from R. Buckminster Fuller GPT. [01:19:13] Assigned reading. [01:20:10] Humans vs. AI. [01:26:20] What happens to people stuck between AI job displacement and a broken social contract? [01:42:38] Counting on the human craving to convene and connect. [01:56:30] What kind of business would a younger Chris start today? [02:00:44] The prescience of The Medium is the Massage. [02:01:39] What does Lowercarbon Capital do? [02:08:44] Projects Chris is most excited about. [02:18:59] Youthful mischief and flim-flammery. [02:24:51] The premise for Chris’ upcoming No Permanent Record. [02:35:25] Cultivating the ability to face (and maybe win over) a tough crowd. [02:39:19] Chris expresses some concerns about this episode. [02:40:24] Recommended reading. [02:45:07] A worthwhile purchase of $100 or less. [02:48:03] Deez Crocs. [02:50:48] Sabotaging potential dates with authenticity. [02:59:11] Parting thoughts. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss  Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss  LinkedIn: linkedin.com/in/timferriss 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 https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Aaron Stupple (@astupple) is the author of The Sovereign Child: How a Forgotten Philosophy Can Liberate Kids and Their Parents. Naval Ravikant (@naval) is the co-founder of AngelList. He has invested in more than 100 companies, including many mega-successes, such as Twitter, Uber, Notion, Opendoor, Postmates, and Wish. Stick around after the end of our three-person conversation to listen to an exclusive bonus segment that Naval and Aaron recorded with extra practical tips, as well as incremental, day-to-day experiments you can test and apply. It’s super tactical, so you won’t want to miss it. It begins at 02:17:01. Sponsors: Sundays for Dogs ultra-high-quality dog food: https://sundaysfordogs.com/tim (save 50% on your first order) Seed's DS-01® Daily Synbiotic broad spectrum 24-strain probiotic + prebiotic: https://Seed.com/Tim (Use code 25TIM for 25% off your first month's supply) ShipStation shipping software: https://www.shipstation.com/tim (60-day free trial!) Timestamps: [00:00] Coming up in this episode [08:40] Who is Aaron, and what makes him qualified to dispense parenting advice? [13:44] Taking Children Seriously (TCS) and The Sovereign Child philosophies. [17:49] The David Deutsch influence on these tenets. [22:57] Supporting evidence and long-term case studies. [27:17] Ways Naval and Aaron have incorporated these philosophies into their own parenting. [31:13] How rules work while parenting for freedom-maximizing. [37:42] Why building knowledge beats coercion. [43:41] Non-negotiables. [46:35] Is this method of parenting only accessible to the educated elite? [50:05] Handling sibling conflict. [54:41] How do freedom-maximized kids adapt to an adulthood of endless societal rules? [58:55] When kids present counter-accountability. [01:00:41] One tool does not fix all. [01:03:52] Putting mistakes to good use. [01:08:00] Homeschooling, unschooling, and socialization challenges. [01:15:56] Building resilience. [01:20:23] Coping with food and drink cravings. [01:25:54] Avoiding the terminology of confirmation bias. [01:31:37] Sports. [01:35:09] Organically cultivating interests. [01:38:11] The pros and cons of traditional schooling. [01:47:24] Parental disagreements and avoiding hypocrisy. [01:57:18] Four categories of harm that come from rules. [02:00:38] The benefits of optional constraints. [02:05:32] Body Electric. [02:07:03] Things you should know before visiting the emergency room. [02:13:18] A hierarchy of knowledge and lessons learned from this conversation. [02:17:19] Tactics for addressing sibling (and spousal) conflict. [02:19:47] Tactics to foster learning. [02:22:54] The best baby (and adult) sitter. [02:26:07] Parenting into the teen years. [02:27:54] Tactics for forming good sleep habits. [02:31:20] Tactics for encouraging good eating habits. [02:37:34] Tactics for freedom-maximizing. [02:42:56] Tactics for minimizing screen and social media obsession. [02:55:29] Too cool for rules. [03:00:14] All information is subject to challenge. [03:03:10] Happiness and creativity cannot be forced. * For show notes and past guests on The Tim Ferriss Show, please visit tim.blog/podcast. For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss  Instagram: instagram.com/timferriss YouTube: youtube.com/timferriss Facebook: facebook.com/timferriss  LinkedIn: linkedin.com/in/timferriss 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 https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.