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Latest Posts
The Downside Of Living In A Nice Neighborhood Nobody Warns You About
Part of the American dream is to climb the property ladder and live in the nicest neighborhood possible. We spend more than half our lives at home, so we want a neighborhood that offers as much peace, quiet, safety, and convenience as our budget allows. As an old man with young kids, long gone are…
FIRE Makes Taking On New Debt A Non-Starter
I recently shared that I'm 49 and out of cash because a venture capital fund called capital much faster than I expected. I assumed a conservative 30% of my commitment would be called in year one. Instead, 46% was called in just six months. On a $1 million commitment, that's $460,000 out the door…
Broke Again At 49, And This Time There Is No House To Blame
After stretching for the nicest house I could barely afford in 2023, I ended up living paycheck to paycheck for six months. It was stressful enough that I picked up a part-time consulting gig to shore up liquidity. Thankfully, stocks and real estate kept rebounding after a rough 2022, and the broke…
Why It’s Easier To FIRE At 35 Than At 50
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. […] The post…
Financial Despair Is When You End Up Paying Money To Work
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 […]…
Will the AI Bubble Destroy our Retirement?
Wow, how about that stock market? It’s a phrase we keep having to dust off and use again, as the years go by and the market keeps surprising us. When it crashes, some of us worry because we see our retirement stash shrinking. But even when it rises to record levels and then to super-duper-crazy
Live Where The Weather Is Great, Invest Where It Isn’t
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…
Venture Capital Paper Gains Aren’t Real But Still Feel Great Anyway
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…
Sandbagging As A Way Of Life To Build Greater Wealth
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 […] The post…
The Reason Insurers Won’t Insure A Vacant Home
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 Going Rate For Selling Your Soul In The Age Of AI
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,…
How Mezzi Uncovered Over $300,000 In Hidden Stock Exposure
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…