Before I die, I have a whole bucket list I want to get through. One item is experiencing what it’s like to be a startup employee whose company goes public. If you’re considering joining a startup, or already at one waiting for your lockup to expire, this post is for you. I spent 13 years in […]
What It’s Like Waiting Out A 6-Month IPO Lockup As A Startup Employee 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 »
With the World Cup on, I’ve been thinking about all the parents currently spending $3,500 to $7,000 a year on travel league soccer, dreaming their child might one day wear the national team jersey. Some elite club families are spending $8,000 to $15,000 a year once you add tournament travel, hotels, and private training. Watching
The Optimal Time to Stop Paying for Your Kids’ Activities Read More »
FIRE is ultimately about being set for life. You build a portfolio big enough to cover your expenses, and then your one job is to not blow it up. But here’s the tension worth talking more about. The moment you give up your paycheck, you also give up your single biggest wealth-building engine: active income.
The Dumbbell FIRE Investing Method To Safely Build Max Wealth Read More »
If you want a greater chance of building more wealth than the average person, live in one of the most expensive cities in the world. These cities are expensive for a reason. They contain the most valuable companies, the richest people, the most capital, and the best universities on the planet. Yes, the competition is
Live In The Most Expensive City You Can Afford To Build Wealth (And Have More Fun) Read More »
One of the reasons I want to live close to my parents is to help with the little things they don’t feel urgency about. Back in 2023, I visited and asked why there was a hole in the kitchen ceiling with a rag on the floor beneath it. A leak, he said, though he wasn’t
The Power Of Doing Nothing: How I Lost $120,000 By Not Waiting Read More »
In anticipation of investing in some YC Demo Day startups, I transferred $50,000 from my Fidelity brokerage account to my Citibank checking account. This was right after I’d already wired $56,100 to meet a capital call for a new traditional venture capital fund I committed to. In a previous post, I wrote about the difficulty of committing
Summer YOLO Fund: Permission To Spend More and Save Less Read More »
This past Father’s Day, June 21, 2026, I had a choice to make. I could play pickleball from 9am to 12noon at an indoor club called Flyte, a 30-minute drive north. Or I could take my kids 30 minutes south to the Bay Club Redwood Shores for swimming and tennis and pickleball lessons. For over
How To Overcome The Guilt Of Not Taking Care Of Your Own Kids Read More »
Most of us take the safe road. We go to college, get a job, and spend the next 30 years hoping our employer doesn’t one day decide we’re suddenly redundant. I know this path well because I walked it for 13 years before I finally worked up the nerve to do my own thing in
The Entrepreneur’s Journey: From Mexico To A Symantec Exit Read More »
Life is hard if you want to outperform average. To reach a USTA 5.0 level in tennis takes an endless amount of practice. To get promoted to Managing Director in banking, you first have to survive a decade of 70+ hour weeks just for a shot. And if you want to be your own boss and build
The Incredible Satisfaction of Never Giving Up: A Lesson In Grit Read More »
