This past April was the podcast’s 10-year anniversary, and the platform River helped listeners organize parties around the world in more than 180 cities! More than 4,000 people RSVP’d. I was able to join about 40 cities via Zoom for quick hellos and drinks (huge thanks to Rae and Ana for the quarterbacking), and I had a blast dropping in on the Paris meetup in person. Thanks to everyone who gathered for wine, celebration, and meeting like-minded people! After all the parties, and as a thank you for their hard work, I invited all of the hosts to a private Q&A. And that’s what you’re about to hear.

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Timestamps:

[00:00] Start

[07:08] A focus on reinvention.

[07:43] Optimization.

[08:30] Recent joy.

[09:22] A CØCKPUNCH update.

[10:19] How the day’s going so far.

[10:55] Argentina affection.

[11:51] Intriguing investments.

[12:53] Top three snacks.

[13:12] AI thoughts.

[14:15] Modern dating.

[16:32] Self-experimentation to come.

[17:42] Analyzing the past decade’s risks.

[20:06] Outthinking a career bottleneck.

[21:09] My current big project.

[22:19] Peptides.

[22:37] Be wary of high conviction.

[23:06] Preparation for high-stakes presentations.

[24:42] Kid stuff?

[24:56] Getting the most out of a Tim Ferriss meetup.

[26:13] In-person conferences planned?

[26:18] IBS relief.

[27:03] Personal heresies.

[28:26] What makes conferences worthwhile for me?

[29:00] Longevity and healthspan.

[33:21] Tips for a father-and-son Kumano Kodo walk.

[34:49] A barbell distribution approach to life.

[35:31] Who would I resurrect for a podcast interview?

[36:24] Do I consult any mentors regularly?

[36:54] Ayahuasca and antidepressants.

[38:16] Incentivizing potential mentors.

[39:13] Adventures in babysitting.

[40:04] GLP-1 for depression/anxiety.

[40:37] Cheap but choice art.

[41:05] Finding a book agent.

[41:28] Making positive, in-person connections.

[41:44] Unmentioned things I’d like to talk about.

[43:39] Is there room for the irrational?

[45:59] Blogging in the age of AI.

[46:39] Binaural beats.

[46:56] 4-Hour Dog Training?

[47:00] Best $1,000 spent lately.

[47:55] Javier Milei.

[48:07] Best thing I spent an “assload” on.

[48:34] Painting.

[48:45] 10-20 minutes on the acupuncture mat.

[49:15] Dating apps.

[50:15] Favorite sci-fi movies.

[51:21] Reflecting on the impact this show has had on others.

[52:23] Why was I in Europe for six to eight weeks?

[52:31] The mood-altering effects of Q&A.

[52:48] Where do I see myself in 30 years?

[53:08] Workout routines for older parents.

[54:13] How I walk and talk for podcasts.

[54:33] Would I consider becoming a single parent?

[55:38] A $1 million coffee mug?

[56:52] Brazil.

[56:59] A small but mighty staff.

[57:07] Attracting event attendance.

[59:08] Visualization or affirmations?

[1:00:20] Today I learned this about Hodinkee.

[1:00:26] What would this look like if it were easy?

[1:00:32] What I ask show listeners when I meet them.

[1:00:50] Eschewing endorsement remorse.

[1:01:19] Music I like.

[1:01:52] State, story, strategy.

[1:01:59] The (not-so) funny thing about interviewing comedians.

[1:02:17] Parting thoughts.

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