Historically, I’ve viewed stocks as funny money. It’s not real until it’s converted into something you can use. Given the lack of utility for stocks, I’ve long preferred owning real estate. Being able to touch, see, and enjoy your investment without experiencing daily volatility is a huge win. And the feel good wealth effect of
Venture Capital Paper Gains Aren’t Real But Still Feel Great Anyway Read More »
The other day I made $10 winning a set of tennis at a public park. It was a funny situation because I didn’t set out to make money playing tennis. It just happened. I was hitting with my long-time buddy, Richard, next to a young man and a couple of regulars. We asked them if
Sandbagging As A Way Of Life To Build Greater Wealth Read More »
A neighbor across the street from my rental texted me at 3:35pm on a Saturday to say something had been beeping inside my property all day and my tenants appeared to be gone. I e-mailed the tenants, drove over, heard the sound, let myself in, and found three smoke alarms stacked on the garage floor
The Reason Insurers Won’t Insure A Vacant Home Read More »
On Tuesday, September 8, 2026, an Anthropic researcher named Jacob Coxon resigned after six weeks over safety concerns and wrote about why. He said the leading labs are “racing straight to self-improving superintelligence” and gambling with everybody’s lives. The people building AI, he wrote, earnestly believe it could kill us all by the end of
The Going Rate For Selling Your Soul In The Age Of AI Read More »
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 »
