Retirement

I get investments wrong all the time. Losing money is part of the process to financial independence. But after I FIRE’d in 2012, the math changed. With no paycheck to bail me out, I could no longer afford big mistakes. This post will help you think about life after FIRE, and share why it’s critical […]

When you were a kid, did you ever dream of growing up to be someone’s exit liquidity? Probably not. But every time you buy shares in a company IPO, that’s exactly what you become. Whether being an early investor’s exit liquidity is good or bad is hard to say in the short run. In the

I recently received a great comment on my post, Why All Rich People I Know Still Have Life Insurance. It was the last line that stood out. Here’s what Marc had to say. I had life insurance ($1M) through my employer back when I worked full time, but since I cut back to ~10 hours per

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. 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. Every single person I

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

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

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 I care about to achieve it too. I’m also aware I can come across as annoying when I talk about FIRE, so I

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

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

If you’re one of the 8,000 Meta employees getting laid off in May, the difference between a good and great outcome could be worth $50,000 or more. The main reason for the layoffs the company mentioned is to offset their massive AI CAPEX. I’ve spent 14 years helping people negotiate severance packages, including engineering my

For those who work in AI, let me share a cautionary tale based on history. You may be getting incredibly rich right now, but there’s little point in being rich if your safety is constantly at risk. Back in 2008, I was working in finance at Credit Suisse Group in San Francisco. There were constant

I must live in a bubble. Because in my circle, I don’t know anybody who has a car worth more than 1/10th of their annual gross income. I came up with the 1/10th rule for car buying over 15 years ago to help people achieve financial freedom sooner. Thousands have followed this standard rule since,