Humor and Fears: A Lighthearted Exploration

In this chapter, the speakers blend humor with deep introspection, sharing personal anecdotes that illuminate their experiences with fear and body image. They discuss the cultural subtleties of humor, particularly focusing on 'Oyaji Gyaku,' while tackling serious issues like mental health and insecurities linked to personal history. Through their engaging dialogue, they reflect on how humor can serve as a coping mechanism when confronting life's challenges.

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Brought to you by Eight Sleep’s Pod Pro Cover sleeping solution for dynamic cooling and heating, Wealthfront automated investing, and Tonal smart home gym. More on all three below.

Matt Mullenweg (@photomatt) is a co-founder of the open-source publishing platform WordPress, which now powers more than one-third of all sites on the web. He is the founder and CEO of Automattic, the company behind WordPress.com, WooCommerce, Tumblr, WPVIP, Day One, and Pocket Casts. Additionally, Matt runs Audrey Capital, an investment and research company. He has been recognized for his leadership by Forbes, Bloomberg Businessweek, Inc., TechCrunch, Fortune, Fast Company, Wired, Vanity Fair, and the University Philosophical Society.

Matt is originally from Houston, Texas, where he attended the High School for the Performing and Visual Arts and studied jazz saxophone. In his spare time, Matt is an avid photographer. He currently splits his time between Houston and Jackson Hole.

For my first interview with Matt, way back in 2015, go to tim.blog/matt.

Please enjoy!

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In Antarctica, even your neatest scotch is served on the rocks — and you have to take it with you when you’re finished. [06:12]

How we’re dealing with perpetual daylight and zero access to the internet. [08:26]

For anyone who hasn’t caught his past appearances and mentions on this show, who is Matt Mullenweg, and what keeps him busy when he’s not camping on Antarctican sea ice? [11:12]

What our morning immersed in the “patient” landscape of Antarctica has been like so far. [13:56]

Why a total solar eclipse needs to be experienced firsthand to understand why it’s such a big deal. [17:15]

Antarctican skin care and rollicking penguin imitations. [20:52]

What’s happened in Matt’s world since the last time we talked on this podcast? How does he keep each day interesting? [24:30]

What Matt has found most helpful for enduring the grieving process since his father passed away. [26:36]

You probably have a smartphone. Here’s why you should use it to record some of the time you spend with loved ones when you have the chance, and what you might talk to them about. [32:25]

Podcast tech spec updates since our last conversation that make recording possible at any temperature on Earth. [34:39]

As Matt says, “You can’t spell ‘Tim’ without ‘TMI.’” That’s why I’m going to talk about the time I sampled my own urine. [40:04]

We each answer the question posed by a card from the Holstee Reflection Deck: “What is one fear you would like to conquer?” [42:13]

Strange comfort I derived from a recent existential revelation, and where I found it. [50:48]

Next card: “If a crystal ball could tell you the truth about your life, the world, or anything else, what would you want to know?” [1:00:29]

Another card: “If you knew that in one year you would die suddenly, what would you change about the way you’re living now? Why?” [1:08:35]

At the time of this conversation, what would I put on my billboard? [1:19:20]

New card: “What are two things still on your bucket list?” [1:19:38]

We need more billionaires exploring the oceans and the non-Western worlds of ritual and myth with the same exuberance as the ones currently exploring space. [1:26:39]

Would I clone my dog Molly? Matt shares his own experience with getting to know a cloned animal after its genetically identical predecessor passed away. [1:38:49]

More bucket list items. [1:43:12]

Why Matt doesn’t curse, and what he does when he gets really angry. [1:43:42]

The next card: “Do intentions matter more or less than actions?” [1:47:29]

The last card: “What are you grateful for right now?” [1:52:07]

Parting thoughts. [1:55:07]

For show notes and past guests, please visit tim.blog/podcast.

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