This summer, my new AI investment advisor, Mezzi, discovered roughly $300,000 of hidden stock exposure in Google I didn’t know I had. It sounds a little absurd, given the amount. But I’ve been investing in Google for over 15 years, and with a complicated net worth it’s hard to track everything accurately when your mind anchors […]
How Mezzi Uncovered Over $300,000 In Hidden Stock Exposure Read More »
Perhaps some of you are in the market for a new car. I’m definitely not. After almost a year of deliberating between replacing my 2015 Range Rover Sport or continuing to fix it, I’ve finally decided to keep fixing it indefinitely. The main reason is that we may relocate to Honolulu in 2028 for my
The Hidden Costs Of Buying A New Car Nobody Warns You About Read More »
I’m reading a great little book called The Practice Of Not Reacting: Zen Wisdom For A Happy Life by Ryushun Kusanagi. The publisher is Portfolio Penguin, the same publisher for my 2027 book, Your Children Will Be OK. One of the core concepts is that all of us want to be recognized for our contributions. At work, at
The Sting Of Not Being Recognized, And How You Cure It Read More »
Ever since graduating from business school in 2006, one of my favorite ways to learn is through case studies. And there’s no better case study for understanding the IPO quiet period than Anthropic’s upcoming IPO. Anthropic is expected to publicly file its IPO prospectus by the end of September, with a listing as soon as
The IPO Quiet Period Explained: What Anthropic Can And Cannot Say Read More »
In April 2026, I gave up my private sports club membership. The stock market was correcting again due to the war in Iran, oil and inflation had shot up, and I figured it was time to cut expenses and simplify. The membership was $185 a month. On top of that I paid $25 per guest
The Sad Reason People Go Private, And It’s Not Status Read More »
I have been a landlord since 2005, the year I rented out the very first property I bought in San Francisco after buying a single-family home. Since then I’ve been through all sorts of disputes. Neighbors texting me that my tenants were running across their roofs during Fleet Week. A heaping pile of trash left
The Beeping Was Coming From Inside The House Read More »
I wrote this post because I needed a kick in the pants. I was finishing my fifth straight day of seven to nine hours of nonstop childcare, plus three posts and a newsletter, and I still had four more days to go. My wife and I were both sick, but she had it worse, so I
The Golden Window To Spend Time With Your Kids Is Smaller Than You Think Read More »
Housing affordability is at a crisis low. You’ve read that headline a hundred times. Either incomes rise or home prices crash to get back to pre-COVID levels. That’s true if you measure a home in dollars earned. It’s not true at all if you measure one in shares owned. Every affordability index compares income to
Build A Taxable Stock Portfolio The Size Of Your Dream Home Read More »
After publishing The Untold Burden Of Being Your Family’s Financial Provider, I got this comment from a reader named Brian: “I can identify with this post as I am the family CFO / CIO. I think you are WAY overcomplicating this. What is wrong with merely investing in VTI / VXUS and chill? My returns have
Take More Risks To Avoid Being Financially Average Read More »
Something funny happened after I spent $3,000 fixing up my 2015 Range Rover Sport. A 2026 Range Rover Sport in the same black on black with only 905 miles became available. It was the perfect setup, because buying a brand new car is a serious waste of money. When you’re the family’s financial provider, your
The Untold Burden Of Being Your Family’s Financial Provider Read More »
