In 1998, Matt Damon paid $10,000 to enter the World Series of Poker after playing a poker genius in Rounders. He looked down at two kings. Then the man across the table revealed what Hollywood could not prepare him for. Damon was facing Doyle Brunson, a two-time world champion who had spent decades playing for real money. Pocket kings were exactly the kind of hand an inexperienced player would be relieved to see. Only pocket aces start ahead of them. Brunson had the aces. Damon was eliminated. The interesting part is not that an actor lost to a professional. It is that Damon could lose while holding a hand he was right to consider strong. The cards did not become bad because someone else happened to have better ones. That is an expensive distinction outside poker, too. A good outcome can reward a reckless decision. A bad outcome can punish a sensible one. Judge everything by what happened afterward, and you can teach yourself the wrong lesson from both. Winning tells you who collected the money. It does not, by itself, tell you who made the better decision. Follow for the stories behind money, risk and the mistakes that look like good judgment.