Generosity and Better Questions Matter

Welcome back to another in-between-isode, with one of my favorite formats: the good old-fashioned Q&A.

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TIMESTAMPS:

• [00:00:00] Start.
• [00:02:12] Why I tend to choose the dull edge over the bleeding edge of tech.
• [00:04:27] Leopold Aschenbrenner: The closest thing to an AI Nostradamus.
• [00:05:32] What humans still do better than AI.
• [00:07:55] The bull and bear case for Alphabet.
• [00:11:30] Three things for which you should never use AI.
• [00:16:05] Can AI be as creative as humans?
• [00:17:01] Rising above the AI content flood.
• [00:19:19] Chris Hutchins on optimizing workflow with OpenClaw and Claude Code.
• [00:22:02] AI under the hood at Team Ferriss
• [00:26:37] Making career jumps in the age of AI displacement.
• [00:30:20] Cultivating a respectful community of 1,000 True Fans
• [00:34:49] Dog training as community management.
• [00:36:03] My favorite color
• [00:36:21] Coyote’s steady state and the future of Cockpunch/Varlata.
• [00:38:03] Essential reading from my own bookshelf.
• [00:40:48] Most breathtaking places I’ve visited.
• [00:41:44] Optimizing time and networking effectively at conferences.
• [00:47:34] Choosing what not to do when your company’s growing quickly.
• [00:49:12] Psychedelic practitioner red flags (and why you should watch Kumaré).
• [00:52:35] The career I’m pursuing in an alternative universe.
• [00:53:29] Dog training the right way with Molly the rescue mutt and Susan Garrett.
• [00:55:28] Thoughts on Enneagram for matchmaking.
• [00:57:02] Quantum computing: Fascinating, terrifying, and probably not 30 years away anymore.
• [00:58:18] Maintaining friendships across ideological lines.
• [00:59:49] The compounding upsides to selective ignorance.
• [01:02:04] In-common humor: The glue that binds the most resilient relationships.
• [01:02:36] The inspiration behind my blog post about 20+ years of “optimizing.”
• [01:04:28] Simple ways to make the world shine brighter.
• [01:05:16] The No Book.
• [01:05:37] The 18th question: “What is the most generous interpretation of this?”
• [01:07:42] The best way I’ve found to experience a new city with limited time.
• [01:08:18] How “Ozymandias” informs the priority I place on wealth accumulation.
• [01:09:59] Relationships over riches.
• [01:11:16] What I consider the top three values for kids: Optimism, resourcefulness, physical activity.
• [01:13:04] Weirdness in the wilderness and succumbing to a shipwreck scam.
• [01:14:21] Ask your best friends when they’ve seen you at your best — and what superpower you’re blind to.
• [01:17:33] Is courage internal or external? Can it be learned?
• [01:19:27] Parting thoughts.

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