I Blew $1,000,000 in One Week

I once blew a million bucks in a week trying to impress people I didn’t even like. Meanwhile, Nomadic Matt spent just $27,000 traveling the world for 18 months—and built a life most people only dream about.

Heart of Fiscal Darkness

We only know if things are worth doing when and if people — of their own free will and with their own real money — pay for them. Otherwise, the transaction is likely to be a scam or a mistake.

To Win, Just Don’t Die

I’ve spent decades bouncing between writing, poker, investing, chess—and the quiet misery of failing at all of them. Over 2,000 rejection letters. Empty bank accounts. Eight-hour chess defeats. But through all the pain, I’ve learned something: whether you’re trading markets or taking creative risks, you have to really like yourself to keep going. Here’s why.