The River is my name for this community of like-minded people that I kept encountering over and over again in competitive domains. Las Vegas, Wall Street, Silicon Valley. They are very risk-taking. They can be contrarian. They can be difficult and very high-variance, I would call it. Meaning, it can lead to both tremendous success and a huge amount of failure. Because most of the time you think of somebody, “Oh, they’re quantitative and analytical.” You might think, “Oh, they’re, like, an actuary or an accountant.” Right? “They’re very calculating and cautious.” Right? And some people have that, but when you instead cross that with using that to compete, you get this more dynamic, Riverian personality.

So, I talked to around 200 people for On the Edge, people who are domain experts, people who are practitioners, who take risk themselves in different fields. I identified 13 common habits I’m going to distil down to just a few of my favourites.

My name is Nate Silver. I’m various things: a statistician, a poker player, and an author, most recently of ‘On the Edge: The Art of Risking Everything’.

So, a lot of people in the River are contrarian. They kind of have to be by design. In Silicon Valley, you’re making an investment in a category or a company that has not succeeded yet, and that maybe is dismissed by the rest of the marketplace, at least in public markets. What I say is that you want to be a conscientious contrarian, which means it’s okay to deviate from the consensus, but most of the time, the wisdom of crowds is pretty smart. So, like, the markets are hard to beat because it’s the consensus of lots of smart people on Wall Street and lots of smart modellers. And so, when do you have robust evidence for a particular direction? That’s kind of like part art and part science. You’re not relying on any one model, any one faction politically, any one philosophy, because people are error-prone, right? And one thing you learn if you’re betting sports, for example, is that you want multiple pieces of evidence to line up the same way. If you have two models, your average is better than one model. That’s what makes things robust is when you have multiple indicators, where they all flash in the same direction.

Another habit of good risk-takers is that they’re good estimators and good at working with incomplete information. The world moves pretty fast these days, and having a pretty good estimate quickly is often better than having a perfect estimate more slowly, right? If you’re dealing with things like markets, any competitive system, a small business that you’re running, you want to be first to market, or early to market at least. And that means that you can’t wait for all the data to show up. You have to know where the most reliable data points are early on and take real risk based on your estimation skills.

You ultimately do have to quantify your decisions to be able to make calculations. It kind of comes second nature if you’re a poker player. If you face a big bet and the bet’s for 200 bucks, right, and there’s 200 bucks already in the pot, that means you have to win the pot one-third of the time, 33 percent of the time. If you think you’re going win 34 percent of the time, you’re supposed to call. 32 percent, you’re supposed to fold. How do you tell between 34 and 32? Well, you have a lot of freaking practice because poker players play thousands and thousands of hands, but, like, it’s a very necessary skill to be explicit about this kind of thing, even if it’s back-of-the-envelope to get there, right? The output nonetheless has to be a number, and you have to make a decision based on that number.

One of my favourite aphorisms is take a raise-or-fold attitude toward life. So, look, you have 3 choices in poker. You can raise, call, or fold. People who have never played poker before — all they ever do is call. They call, call, call. They’re very passive, not taking control of the hand. If you ask a computer, it will say, most of the time you want to either be raising or folding, right? You want to take an aggressive action or quit.

I think this is a great metaphor for lots of things in real life, too. Annie Duke, a former poker player who now studies decision-making and writes as an author for a living, wrote a book called Quit, which is lots of evidence about how people are actually happier a lot of times when they quit.They quit an unhappy relationship, or a job that’s not working out, or they move cities, right? That allows you to preserve your capital, your decision-making power, your optionality. Giving yourself what may turn out to be fruitful or good decisions later on when you have more information to work with.

The world is a pretty intrinsically challenging and uncertain place, and that’s kind of why the people, the countries, the companies that will survive are people that are comfortable in uncertain environments. People are often uncomfortable with that kind of uncertainty.And so, people are seeking out safety given how complex and how confusing, admittedly, the kind of environment can be, when I think that might be a mistake, actually. If you are privileged enough to fail and then get back on your feet several times, then that’s a reason to take more risk.
(End)

• Like-minded (adjective): people who share the same opinions, ideas, or interests.
• To encounter someone (verb): to meet someone unexpectedly.
• Over and over (again) (idiom): many times.
• A domain (noun): an area of activity or knowledge.
• Contrarian (adjective): liking to express opinions that most people disagree with.
• High-variance (adjective): a lot of variation in results, unpredictable.
• Tremendous (adjective): very great in amount.
• Quantitative (adjective): relating to numbers or amounts.
• Analytical (adjective): involving the careful study and examination of facts and information.
• An actuary (noun): a person whose job is to calculate risk for insurance companies.
• To cross something with something (phrasal verb): to mix or combine two different things.
• Riverian (adjective): relating to people who form the ‘River’, the community of risk takers.
• To distil something (verb): to get or show only the most important part of something.
• A statistician (noun): someone who studies or is an expert in statistics.
• By design (phrase): intentionally, as a result of a plan.
• To dismiss something (verb): to decide something is not important or worth considering.
• Public markets (phrase): the stock market, places where shares are bought and sold.
• Conscientious (adjective): putting effort into doing something carefully and thoughtfully.
• To deviate (verb): to do something that is different from the normal way of behaving.
• A consensus (noun): a generally accepted opinion, decision, or way of doing something.
• Wisdom (noun): the ability to use your knowledge and experience to make good decisions.
• A modeller (noun): someone who makes predictions based on models (statistics).
• Robust (adjective): strong and unlikely to break or fail.
• A faction (noun): a small group within a larger organisation, often with different opinions.
• -prone (suffix): likely to experience a particular problem more often than normal.
• To line up something (phrasal verb): to arrange something in a certain way or direction.
• An indicator (noun): something that shows what a situation is like.
• An estimator (noun): someone who can guess or calculate the size, value, etc. of something.
• To show up (phrasal verb): to appear or be seen.
• A data point (noun): a unit of information from a large amount of data.
• Early on (phrase): at or during an early point or stage of something.
• To quantify something (verb): to measure or judge the size or amount of something.
• To come/ be second nature (idiom): to know something very well so that it is easy to do.
• A pot (noun): an amount of money, used for a particular purpose.
• To call (verb): a term used in poker, meaning to match the previous bet to stay in the game.
• To fold (verb): a term used in poker, meaning to give up and stop playing in that round.
• Explicit (adjective): clear and exact.
• Back-of-the-envelope (adjective, US): done quickly, not exact.
• Nonetheless (adverb): despite what has just been said.
• An aphorism (noun): a short clever saying that is intended to express a general truth.
• A metaphor (noun): a phrase that describes an object by referring to something similar.
• Fruitful (adjective): producing good results.
• Intrinsically (adverb): in a way that is a basic and important part of something.
• To seek out something (phrasal verb): to look for something, especially for a long time.
• Admittedly (adverb): used when you are accepting that something is true.
• Privileged (adjective): having a special advantage, such as money or a high position.
• To get/be back on your feet (idiom): to be successful again after having problems.

In this text, there are several examples of pseudo cleft sentences using noun phrases (‘pseudo’ meaning they have a different structure to typical it + be cleft sentences). Cleft sentences are complex sentences used to emphasise a particular part of a sentence, or the whole sentence.

Cleft sentences beginning with ‘it’

In normal cleft sentences, we emphasise different elements of a sentence by ‘fronting’ them, moving them to the front: it + be (is/ was) + emphasis

For example: ‘She asked me to help with the homework.’

• ‘It was her who asked me to help with the homework.’ (emphasis = her)
• ‘It was the homework that she asked me to help with.’ (emphasis = the homework)

• ‘It was me who she asked to help with the homework. (emphasis = me)

‘Pseudo’ cleft sentences beginning with ‘what’

We can use a ‘what’ clause + ‘be’ + emphasis to focus attention on a specific verb, noun, or a whole sentence. The emphasis is on the part outside of the ‘what’ clause.

For example: ‘We arrived late and missed the flight. I hate airport food.’

• ‘What we did was arrive late and miss the flight.’ (emphasis on the verb and verb phrase = arrive late…)
• ‘What happened was we arrived late and missed the flight.’ (emphasis on the whole sentence/ clause = … we arrived late and missed the flight)

• ‘What I hate most is airport food.’ (emphasis on the noun = airport food)

We can also replace ‘what’ with ‘where/why/who/how’, or different noun phrases, such as: ‘the person’, ‘the reason’, ‘the thing’, ‘one thing/ factor/ reason’, ‘all’  etc. to emphasise a noun or verb when using a cleft sentence:

• ‘Where she went was a mystery to all of us.’ (emphasis on the noun phrase)
• ‘The person I’m most obsessed with is David Beckham.’ (emphasis on the noun)

• ‘All he does is complain about how busy he is.’ (emphasis on the verb and verb phrase)

These structures are helpful in writing to compensate for the lack of vocal stress or intonation.

When speaking, stress the key information with your voice (e.g., “One thing I NEED is a COFFEE.”).

Examples in the text:

• What I say is that you want to be a conscientious contrarian: what clause + be + emphasis: the ‘what’ cleft structure focuses on the idea that you need to be thoughtful in giving different opinions.
• And one thing you learn … is that you want multiple pieces of evidence to line up the same way: noun phrase + be + emphasis: the ‘what’ cleft structure using one thing … + is + emphasis is used here to emphasise the need for different sources of information.
• Another habit of good risk-takers is that they’re good estimators and good at working with incomplete information: noun phrase + be + emphasis: the ‘what’ cleft structure using another habit … + is + emphasis is used here to emphasise the need for accurate predictions.
• One of my favourite aphorisms is take a raise-or-fold attitude toward life: noun phrase + be + emphasis: the ‘what’ cleft structure using one of my favourite … + is + emphasis is used here to emphasise the need to take risks.
• … all they ever do is call: noun phrase + be + emphasis: the ‘what’ cleft structure using all … + is + emphasis is used here to emphasise how most people don’t take risks.

https://www.bbc.co.uk/learningenglish/course/towards-advanced/unit-14/session-1

https://www.englishpodcastscollected.com/wp-content/uploads/2025/10/Big-Think-Why-risk-takers-win.pdf

https://www.englishpodcastscollected.com/wp-content/uploads/2025/10/Big-Think-Why-risk-takers-win.docx