Once both our children began school full-time in 2024, my wife and I had more breathing room. At least six hours a day of free time. No more wrangling toddlers in the chaos of the early years. I used the time to finish Millionaire Milestones, which became a USA Today bestseller in 2025. Now I’m
Financial Despair Is When You End Up Paying Money To Work Read More »
In 2012, two months before my 35th birthday, I engineered my layoff from a 13-year career in investment banking. At the time, it felt like the riskiest thing I had ever done. Was I really going to blow up my career right as my earning power was about to compound? It did not seem wise.
Why It’s Easier To FIRE At 35 Than At 50 Read More »
Ever wonder why Honolulu, Hawaii has the highest median life expectancy of any city in America? Sunshine, moderate temperatures, walkability, and an unhurried pace do wonders for your mental and physical health. As a relatively low-stress guy who doesn’t have to commute to a day job to sit in meetings all day, every time I
Live Where The Weather Is Great, Invest Where It Isn’t 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 »
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 »
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 »
There are layers to freedom, and most of us only ever peel back two. The first layer is breaking free from your parents. Some people manage it the summer after high school. Others are still depending on dad to pay their new credit card charges at 37. The second layer is breaking free from work.
You’ll Never Be Free From The Government: Introducing The Leash Ratio Read More »
Recently, I shared a sample budget of a family of four earning $408,000 a year on Twitter, the amount third-party data deems necessary to feel comfortable in San Francisco. To be clear, this wasn’t my budget and it wasn’t a recommendation. It was an illustration of how fast a six-figure household income disappears once taxes, shelter,
Why Americans Are Richer, Happier, And Healthier Than You Think Read More »
I toured a $9 million house in Honolulu to better understand the luxury housing market. I love real estate, and visiting nice homes for sale is one of my favorite hobbies. My parents are 81 and 78 and live in Honolulu. Like many people their age, they have a few health issues, and I’d like
How The Rich Justify Buying $9+ Million Homes They Barely Use Read More »
