I’ve been playing poker for over 25 years, and I still love the game. Every time I sit down at a table, it feels like a time warp. Three hours can pass in the blink of an eye. The cards, the psychology, the rhythm of betting, and the social interaction all combine into something that’s
A Net Worth and Income Guide to Playing the Right Poker Stakes Read More »
The problem with writing about FIRE since 2009 is that I’ve become completely sold on the lifestyle. I know how good freedom feels, so I have a natural tendency to want everyone to achieve it too. I’m also aware I can come across as annoying when I talk about FIRE, so I try to throttle
Failing to Convince Anyone in Real Life to FIRE Despite Big Gains Read More »
As I approach 50 in mid-2027, I’ve been thinking a lot more about responsibility, legacy, and mortality. What I’ve realized is that responsible adulting is hard. One misstep and you or your loved ones could be screwed for life. Ultimately, life is a series of financial quests for survival before we die. If we don’t
Life Is Simply One Financial Quest After Another Read More »
I love startups and entrepreneurship. My obsession started when I was reselling Nerds candy in Taipei, purchased from the U.S. commissary store. To recognize and exploit a pricing arbitrage as a nine-year-old felt like winning the lottery every time a new batch arrived. In 1998, a year before graduating from William & Mary, I was
The Startup Grind Will Make You An AI Maximalist Read More »
Here is a question worth sitting with: which is actually harder to achieve, a top 1% income or a top 1% net worth? Most people assume income. The number sounds impossibly high, the competition sounds brutal, and the lifestyle of someone earning that kind of money seems reserved for a different species entirely. But after
Top 1% Income vs. Top 1% Net Worth: Which Is Harder to Achieve? Read More »
The decade-long advice to “learn to code” is losing its edge. With tools like Claude Code handling the heavy lifting, a basic three-month online course may be all anyone needs to build what they can imagine. The more important skill is investing. If you learn to invest, you can build lasting wealth and bypass the gatekeepers
Learning To Sell Is Just As Important As Learning To Invest Read More »
The S&P 500 is up roughly 100% over the past three and a half years. At its historical average annual return of about 10%, you’d expect it to be up closer to 40% over that same stretch. That’s an “excess gain” of 60%. I view this excess like free money you find on the street
Use Your Excess Stock Market Gains to Actually Change Your Life Read More »
One of the key ways to FIRE is to save and invest aggressively. You’ve forecasted your misery, therefore, you know that by the time your misery becomes a reality, you’ll have invested enough money to retire early and break free from the grind. Obviously, if you don’t forecast when you’ll be miserable, you’re probably not
How To Convince Yourself To Invest Aggressively For A Better Tomorrow Read More »
Every year or two, the market hands you a gift wrapped in anxiety. You watch your portfolio bleed, you refresh your brokerage app more than you should, and you feel helpless. But when you have children, that helplessness can flip into something more actionable. This past year, with the stock market getting crunched by geopolitical
Investing More Than The Gift Tax Exclusion Limit Shouldn’t Be A Problem Read More »
After publishing my piece on the shocking cost of eldercare, a question kept nagging at me that I couldn’t shake: when money is finite and the people you love are not, how do you decide who to help or save first? A $230,000-a-year group home in Hawaii for one person. Four parents to potentially care
A Financial Dilemma: Save Your Parents, Your Children, or Yourself Read More »
