I played poker professionally before writing about politics or building election models. What really attracts me about gambling is the mindset that drives this behavior—a way of thinking that unites a group I call “The River.”
The River is a vast ecosystem of like-minded people, including everyone from low-stakes poker pros to crypto kings and VC billionaires. It is a way of thinking – analytical, abstract, competitive, contrarian – and a way of life. Most “Riversiders” were not rich and powerful, but those who were rich and powerful were often riversiders.
I call the following “13 Habits of Highly Effective Risk-Takers.” River's quantitative risk-takers and physical risk-takers — astronauts, deep-sea explorers, NFL players — all have these characteristics in common. Based on my research, I hold the view that there is something inherent in people who seek out risk and successfully overcome it. How much do you share with them?
Successful risk takers stay calm under pressure
Staying calm when others lose is a rare quality—and essential for a winning gambler. It doesn't matter how well you perform in everyday situations – you'll never reach the top of your profession if you choke when the pressure is on.
They have courage
In poker and sports betting, the vast majority of players lose money. Reaching the top requires careful balance. Overconfidence can be deadly in gambling, but playing poker with the best is not for the faint of heart.
They have strategic empathy
They put themselves in their opponents' shoes – but don't mistake this for emotional empathy. In psychology studies, there is a negative correlation between systems thinking – what Riverians are skilled at – and empathic behavior. Strategic empathy comes up a lot in poker—which is both a mathematical game and a human game.
They are process-oriented, not results-oriented
They play the long game. “Don't aim for results” is a mantra that has been ingrained in the minds of many poker players. Yes, in the long run, it's the results that matter, but one good thing about River is that our compensation ultimately depends on objective measures.
They took pictures
They are clearly aware of the risks they are taking and they are comfortable with failure. In an episode of the American version of Officethe incredibly stupid owner, Michael Scott, incorrectly copied hockey player Wayne Gretzky's quote: “You miss 100% of the shots you don't take.” There is something to be said about this.
They have a bullish or bearish attitude
They abhor mediocrity and they know when to give up. The cardinal sin of poker is that most players hold them too often. There are three basic actions in poker: calling, folding, raising the bet. People press the call button too much. They call because they want to gamble, but although players call when they should fold, they also call when they should raise.
They are prepared
They make good intuitive decisions because they are well-trained – not because they “protect it.” What bothers private equity investor and adventurer Victor Vescovo about Top gun: Maverick is Tom Cruise's assertion that you should improvise your way out of a difficult situation: “The best military operations are very boring ones, where everything goes exactly according to plan. No one was ever in any danger,” he said. “You want to minimize risk. While Top guns looks great on film, that's not how you try to take that target down.”
They have high attention to detail
They understand that attention is a scarce resource. In poker, one of the unusual features of the game is that most of the time, you have nothing to do, precisely you have to wait a lot. You need to carefully regulate your mental abilities, conserve your energy but still be ready for action.
They can adapt
They are good generalists, taking advantage of new opportunities and responding to new threats. I call this personality type Fox. Think of the words of Greek poet Archilochus: “The fox knows many things, but the hedgehog knows one great thing.” Foxes look for opportunities, wary of complacency and being too attached. This is a routine with some exceptions. Startup founders, in particular, need to be laser-focused on one big thing and willing to do it for a decade or more.
They are good estimators
They are Bayesians, comfortable quantifying their intuition and working with incomplete information. Does the difference between 90% and 93% really matter?
They try to stand out, not blend in
Independence of mind and purpose are hallmarks of high achievers.
They are intentionally contradictory
They have theories about why and when conventional wisdom is wrong. There is a difference between independence and opposition. If I choose vanilla and you choose chocolate because you prefer chocolate, then you are independent. If you choose chocolate because I choose vanilla, then you're doing the opposite. Riverians could be accused of being contrarians when they were truly independent. If I do the conventional thing 99% of the time and you do it 85% of the time, you'll seem rebellious by comparison—but really you're still going with the flow.
They are not motivated by money
They are not ascetics, but poker players are different for two reasons. First, they compete so fiercely that money is mainly used as a way to score points; and second, gambling with such high stakes requires a certain sensitivity to them.
Adapted from On the sidelines: The art of risking everything, by Nate Silver.