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.

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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.

*

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Ep. 29 Jason Grechanik: Live From Peru