Moontower #42


It’s date night. You’ve been wanting to try the new spot. It’s crowded. The reward for a wait would be a cozy table pressed against your neighboring diners. Hmm. Nothing is more grating on the ears than the courtship ritual of hipsters on a date whose evening insurance policy is just a right-swipe away. Makes for feckless banter.

But you’re both feeling good. Showered. About as groomed as you’ll be on a weekend. The kids are watching iPad at home, grandma’s on sentry duty. The radio dealt Billie Jean on the way over. So you play it cool. Take the seats at the bar. Your cocktails arrive in front of you. Pause to cheers and snap an “ussie”. In the time it takes to upload it to the ‘Gram, Google settles your question — Elvis sold more records than MJ.

Phones down, back to one another. You’re discussing “who is the real king of pop”. Units-sold is just one aspect and you aren’t the types to waste time arguing facts so you deferred to the internet. More back and forth. You’re sparring with pads on. Exchanging taps. “Good point”. “True”. It’s a dance of its own. If only the hipsters could hear you. I imagine they’d cringe like a psychiatrist hearing the words “life coach”. Nevertheless, the playful dispute stays smooth until Kris responds, “Actually…”

End scene right there.

Here’s a happiness hack for you:

Read the damn room.

This date night debate is for zero stakes. It’s not about truth. It’s not the setting for a Juilliard-level surgery of pop music psychohistory. There’s nothing to gain from appealing to expertise. To invite the feeling of resignation that says every matter is already solved. How many fights could have been avoided if this moment were re-imagined? Why should the verbal monopolize the focus? There are so many other stimuli serving the moment. It’s a tyranny of intellect that the words are mistaken for the real communication that was going down.

If you can read between the lines, you’d know that I blew up a date-night by being a jerk. I was dense. Now I’ve been married too long to have done this obstinately. I hope I don’t have an insecure need to be “right”. I’m quite aware there’s a broad plane across which reasonable people can disagree. This was second level stuff.

This was about subtlety in the way I made her feel during a benign disagreement (it wasn’t about Elvis). If you are actively trying to be agreeable but come off condescending you might be mansplaining. Even if you are correct, assuming it’s a matter that has a correct, what’s the point? Reason is a slave to the passions as David Hume put it. Action springs from feeling not logic. To be effective, whatever that means in context, remember that how you say is often more important than what you say.

It’s no secret that body language and tone are tells. Non-verbal communication is an “honest” biological signal because it’s hard to fake. This week I have some fun links to help you think about how we communicate.

70% of how you look, 20% of how you sound, only 10% is what you say

  • Check out Eddie Izzard from one of my favorite all-time comedy specials Dress to Kill (Link; start at 2:20)

The Scariest Accent

  • Another from a favorite comedy skit. Trevor Noah breaks down the scariest accent. He makes a clever insight on how we perceive a foreign language vs a foreign accent. (Link)

How Not To Sound Like An Evil Robot

  • I can be so guilty of this. A short and funny guide to word choice by Slatestar. (Link)

Ecological Rationality 

  • Ecological rationality is defined as knowing which heuristic works in which environment.  Professor Kahneman is rightly lauded for being the father of behavioral psychology. It’s a field that points out all the failure modes and blind spots in our shortcut thinking. You’d think the field was settled given how large Kahneman looms. But the work of Gerd Gigerenzer says otherwise, redeeming our so-called biases in real-world settings. His disagreements with Kahneman are often quite technical and therefore less polarizing than some would like to portray. I most like how it exposes a false paradigm where rationality is pitted against mental heuristics.

Many smart, successful people fail in rationality tests inside a lab because rationality is defined rather narrowly. It’s logical rationality – about not violating some law of logic or probability. But, outside the lab, in the real-world, we cannot do well with just with logical rationality, we need ecological rationality – the kind of thinking that helps us get what we want in an environment that’s uncertain and dynamic. (Link)


  • The single biggest problem in communication is the illusion that it has taken place. — George Bernard Shaw
  • Never offend people with style when you can offend them with substance. — Sam Brown

Podcast Episodes

  • One of my top 10 podcast episodes ever is Patrick O’Shaughnessy interviewing Eric Maddox, the US interrogator in Iraq whose work led us to Saddam. Must listen. (Link)

This week we explore a rare and underappreciated skill through the lens of an incredible story. My guest is Eric Maddox, whose name you probably don’t know but won’t soon forget. Just trust me that you need to listen to this entire episode, and listen carefully—because that is what the episode is ultimately all about: how to listen to others, with care and empathy, in the age of distraction.

  • How To Improve Your Speaking Voice. World-renowned voice coach Roger Love goes on Art of Manliness (Link)

Roger explains why having a clear, confident, pleasant speaking voice is important for success in your career and your life, the biggest ways people sabotage their voice, including voice fry, uptalk, and being nasally, and how these issues can be addressed and eliminated. Roger also shares how to speak in a more masculine way, and why you’re probably not speaking loudly enough. 


  • Why singing and speaking are basically the same
  • Why the voice you have is not necessarily the voice you were born with
  • The reason so many people dislike hearing their own voice
  • The most common vocal bad habits
  • The rise of uptalk (valley talk), and how it’s different from going up in melody
  • What role does anatomy play in our speaking voice?
  • Why men try to artificially lower their voice, and the physical risks of doing so
  • Brass tacks tips for improving your voice
  • What is voice fry? Why are people doing it?
  • How to avoid sounding angry
  • Why people almost always speak quieter than they should
  • Why you mumble and how to fix it
  • Why your voice is more important than your words

The Money Angle

The State of Family Offices in 2019

Cowboy Investing summarized interesting takeaways from UBS’s annual report family office behavior. (Link)

Some interesting highlights include:

  • Differences between how different generations of wealth invest
  • The breakdown of asset classes that FO’s target
  • When I dove into the source report I thought the compensation data for FO executives looked interesting, but when I reached out to Cowboy he said “I take the performance numbers in here with a grain of salt. Big reason why I didn’t write much about it.”
  • My response to the most provocative part of the report (Link)

Saudi America

Bethany McClean, author of Smartest Guys in the Room, wrote a short and sweet book about the shale boom. I wrote some takeaways as well as a few of my own thoughts. (Link)

Climb Higher

The Short List To Get You Started

My cousin Jordan who is in his early 20s was visiting from Australia and wanted to know where he can start to learn about investing. I had some opinions but asked around as well. Check it out. (Link)

Different Approach To A Problem

The showdown of Jeopardy! GOATS has been on TV this week. James Holzhauer on how he can be beaten:

“Someone suggested they could make the questions really easy and any advantage I had is negated and I’d purely have to win on the buzzer.”

For this discussion about forward and backward thinking, check out the Waiter’s Pad post. (Link)

How Was This Written In 1961?!

The short story Harrison Bergeron by Vonnegut. (Link)

It’s a satirical, over-the-top reminder that if everything is good then nothing is.

Last Call

  • I finally got around to posting my notes on Jordan Ellenburg’s How Not To Be Wrong. I came across it from Bill Gate’s recommendation. The author’s writing draws from so much art, literature, and history that you will learn so much more than numeracy. A word of caution. There are sections that I found quite difficult compared to most pop math books. Geometry and infinity are humbling. (Link)
  • This article Why World War I films, like ‘1917,’ have a different feel than those about WWII is harrowing. When you are done with that you’ll definitely want to check out this vid that Avi sent me about the fallen of WWII. WWII was just so big and this video uses animations and data to convey it in a memorable way. When I was born we were only 30 years removed from WWII. That’s the distance between now and 1990. I wonder how its relative recency to our collective parents’ lives affected how they saw the world.
  • Jill asked me if I had any podcast recs to teach money concepts to an 11-yr old. While you can find many articles with suggestions on how to teach your kids about money, it was harder to uncover good sources for the kids to consume themselves. I compiled some and encourage you to share your own. (Link)
  • Tony Nitti (Twitter) is one of the best follows to understand tax policy. But this thread is not about taxes. It’s his personal story that highlights the tension all parents face: the requirement to prepare our children for the real world versus extending their innocence.
  • My guitar lesson this week meandered into some R&B structures. I’ve only listened to R&B casually, not actively to think about what’s going on musically. Patrick was teaching me about guys like Quincy Jones and D’Angelo. Watching a music expert break things down is such an easy way to raise appreciation for the art. He played this song by Mac Ayers which is now buried in my head and homework.

From my actual life 

It was nice to be back to knowing what day of the week it is and getting back on the fasting regimen (18/6 M-F for those who care). I thought I’d just post a list of things that I’m interested in for 2020 without comment. Reach out if any make you wanna chat.

I don’t expect to get to all or even most of this stuff. It’s not in any priority order.

  • Organizing a business fair for kids (example)
  • No-Code tools to create apps (use cases: personal trip apps, household finance, lessons. Start with Glide API)
  • Learn more about taxes
  • Backtesting and exploring Adam Robinson’s investing framework (Link)
  • Get investment portfolio in order with a more disciplined “permanent portfolio” approach (influences: Movement Capital, Demonetized, Breaking the Market, Rick Ferri)
  • Involvement with charities that teach business and STEM to underprivileged ( and HiddenGeniusProject)
  • Tons of writing backlog that I need to get online
  • A few online guides I want to write around finance and productivity topics
  • Read more books and fewer articles; continue the more balanced mix of fiction to non-fiction
  • Porting lots of my notes from Notion to Roam Research
  • Game-based teaching program for kids. Start that locally.
  • Lose 10-15 pounds, exercise more consistently
  • Remodel the backyard
  • Get acquainted with Github
  • Take an online stats course
  • Take a writing course
  • Go to a boardgame convention
  • Take a sake seminar
  • Get a few dishes/recipes under my belt. Not just cereal and eggs.
  • More consistency on guitar practice. Finally buy a new electric guitar.

…and of course

  • Continue weekly Moontowers

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