One of the reasons I accepted Portfolio Penguin’s book deal in 2019 was to demonstrate to my kids the importance of work. Not working sets a bad example if you are a FIRE parent. If I spent two and a half years ideating, writing, editing, and marketing a book they could eventually find in a bookstore,
Children Doomed To Follow In Their Parents’ Professional Footsteps Read More »
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 the days
The Downside Of Living In A Nice Neighborhood Nobody Warns You About Read More »
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 instead
FIRE Makes Taking On New Debt A Non-Starter Read More »
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 feeling faded. I promised myself
Broke Again At 49, And This Time There Is No House To Blame 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 »
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 »
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 »
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 »
