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 »
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
Buying A Mansion In Paradise Might Be Backwards Read More »
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
Why Venture Capital Funds Must Get Bigger To Compete Read More »
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
Everybody Got The SpaceX Lockup Expiration Wrong, And I’m Not Selling Read More »
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
The Stay At Home Man (Boyfriend Or Husband) Is A Great Trend Read More »
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
Why You Need Less Money Than You Think To Be Happy: A $40,000 Experiment Read More »
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
Crushing Childcare Costs Are Why Cities Are Running Out Of Kids Read More »
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 doesn’t happen 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
A Backwards Tax Identification System For Determining Your Freedom Read More »
