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 drove over, let myself in, and found three smoke alarms stacked on the garage floor with the top one screaming away. […]
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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 […]
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Happy Labor Day weekend everyone. Perhaps some of you are in the market for a new car this weekend. 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 […]
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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 […]
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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 after Labor Day, with a listing as soon as late September […]
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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 […]
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The Beeping Was Coming From Inside The House: When A Landlord Can Enter Without Notice
4:31 AMI 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 […]
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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 childcare, plus three posts and a newsletter. My wife and I were both sick, but she had it worse, so stepping up wasn't optional. What follows is mostly me talking myself […]
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Housing affordability is at a crisis low. You've read that headline a hundred times. Incomes have to rise or home prices have to crash to return to the housing affordability levels pre-COVID. It's true if you measure a home in dollars earned. It is not true at all if you measure a home in stock […]
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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 […]
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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 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 goal […]
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This summer I toured a couple of 6,000 to 7,000 square foot mansion in the Kahala neighborhood of Honolulu, all in preparation for a potential move in two or three years. We plan to move back for either 6th or 7th grade for our son and 3rd or 4th grade for our daughter, so we […]
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On August 5, chief AI scientist Jeff Dean announced he was leaving Google after 27 years. Google proceeded to lose ~$180 billion in market cap, making this the largest impact I've ever seen by one employee departing. He's co-founding Discovery Loop, a public benefit corporation aimed at using AI to automate the scientific research process […]
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On August 6, the first tranche of locked-up SpaceX shares was released. Roughly 911.5 million shares became eligible to trade in a single session. SPCX went up 6%. Then it went up again the next day, closing out a two-day gain of about 11% on the exact event everybody had circled on their calendar as […]
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According to an Indeed Hiring Lab analysis, women now hold more payroll jobs than men in America. It's only the third time this has ever happened. The first two times, during the Great Recession and just before COVID, the gap snapped back once construction and manufacturing started hiring again. This time looks different. Between February […]
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Back on June 30, I published Summer YOLO Fund: Permission To Spend, giving myself explicit written permission to blow through $40,000 in Honolulu this summer. The $40,000 was originally earmarked for investments in private startups after attending YC demo day. However, I wasn't able to invest in companies I wanted, whether due to valuations or the […]
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I write before my kids wake up and after they go to sleep. That's the arrangement. It means I'm free during summer, winter, and spring breaks, along with weekends, which is the whole point of building a lifestyle business in the first place. I gave up a handsome paycheck for the ability to always be the one […]
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Ever since two park rangers approached me at an empty public court while I was teaching my own children tennis, I've been thinking about how to make sure it never happens again. Not just to me. To anybody. The problem that afternoon wasn't that the rangers were doing their jobs. The problem was information. They […]
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Sotelo Avenue in Forest Hill is the most prestigious street to own a home in San Francisco. I know. Someone on Broadway just spit out their $28 espresso. Stay with me. For 25 years I've watched San Franciscans argue about neighborhoods when neighborhoods are the wrong unit of measurement. As a resident and multiple property […]
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