I vividly remember sophomore year of college. It was 10:30pm and I was leaving my girlfriend’s apartment by car. Instead of coming to a complete stop at the stop sign, I slowly rolled on through and took a right. There was nobody on the streets, so I took a chance. That chance cost me $60. […]
How To Overcome Financial Despair For Good Read More »
Here’s something I’ve noticed: the loudest voices arguing against life insurance after financial independence almost always come from people who aren’t financially independent yet and don’t have kids. They’re still grinding toward FIRE, optimizing every dollar, cutting costs to close the gap. Makes sense for them. But once you actually get there, the calculus changes.
Why Every Rich Person I Know Still Has Life Insurance Read More »
Do you know who will most likely survive a zombie apocalypse? Green Berets and Navy SEALs who had to suffer to earn their place. If you have run six miles a day for years, jogging thirty minutes to evade the horde because there are no Ubers is nothing. If you have carried 125-pound sandbags up
Suffer Now, Thrive Later: Relish Working Brutal Hours Early in Life Read More »
At a poker game recently, I heard one of the saddest things I’ve encountered in a while: “$10 million is not enough to retire early.” Mind you, we were all sitting in San Francisco, an expensive city, but also one of the cheapest international cities in the world. So I get it, context matters. But
Of Course $10 Million Is Enough To Retire Early, Don’t Be Crazy Read More »
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 main reason I can’t convince anyone in real life to FIRE is the desire for more. The moment you hit a $1 million net worth, you start dreaming of $5 million. Get to $5 million and suddenly $10 million sounds reasonable. Hit $10 million and, well, why not shoot for $25 million and higher?
The Multi-Million Dollar Home That Ate Your FIRE Number 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 »
One of the issues we frugal people despise is going through buyer’s remorse. We don’t want to feel stupid or ripped off, so we tend to buy fewer things and experiences. Minimalism and early retirement go hand in hand. We’re always looking for a deal, partly to minimize disappointment. And if we can get something
Time Fixes Most Financial Mistakes Because You Grow Richer 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 »
