Kirk's Hammer: What makes someone good at betting?

I recently watched a Phil Galfond YouTube video called “What Makes Phil Ivey The GOAT.” The video overall was awesome, and I recommend watching it. The part I found most fascinating is that Ivey’s technical skills are barely discussed. I’m not a poker expert by any means—I know very little about the game. I’m sure Phil is still great technically; however, when other players discuss what makes him so good, that is far from the main focus. A long stretch of the video discusses how even after optimizers became prevalent in poker, Phil seemingly never used them and still dominated. He recognized that other players had started using these solvers, and his instincts allowed him to put players in uncomfortable spots and use it to his advantage. He had an almost supernatural ability to read people and situations—a gambler’s instinct that let him exploit pressure, hesitation, and uncertainty in ways most players couldn’t even see, let alone capitalize on.

As the Phil Ivey of sports betting, of course this video really resonated with me. (This is a joke, everyone—please don’t flame me.) In all seriousness, the idea of that instinct that good bettors have has always fascinated me, but it’s never been something I’ve really been able to put into words. A lot of people don’t know this, but throughout my betting journey, I’ve had a 50/50 partner since day one. We went to school together and studied the same things (business and analytics). My partner essentially does the entire back end of our operation. He does all the modeling, scraping, and builds all the interfaces we use. I do not have any of those abilities—he’s better at math than me, he’s a proficient coder (I suck at coding), he’s far better in Excel than me, and he’s awesome at building.

Although my partner is better than me at nearly everything, we both agree that I’m the better bettor. Throughout our time betting, I’ve typically been the one who comes up with the ideas for edges, model improvements, and generally has final say on what actually gets bet. This has been true since the first day we started. At the beginning, we were purely arbing, and I instinctively knew pretty quickly that it actually made sense for us to pick sides based on which books were offering the arbs. Then I was able to pick up that these lines were off for a reason—and that we could probably figure out why. I also was quite good at just manually picking off bad NBA openers, which allowed us to start formulating a basketball model that could win.

This instinct—the ability to win at betting—is something I’ve thought a lot about, and I see it in many people I talk betting with. Some people I talk to have incredible domain knowledge about specific sports; some are incredible at math and modeling, yet are just OK bettors and don’t win huge. Others have a baseline level of both, yet are massive, massive winners. The phrase I often use for this instinct is “seeing clearly”—as in, people who have this winning instinct are able to quickly see the signal through the noise, understand what’s worth focusing on, and trust their intuition.

Of course, this isn’t purely instinct—it’s something that gets far better with experience. And my explanation is quite simplistic and doesn’t really get to what that skill actually is. So, for this newsletter, I did something a little different: I asked people who I consider elite at betting what they think makes a good bettor.

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I sent the same question to everyone:

For the newsletter this week I’m doing something a bit different. The topic is going to be “what makes someone a good sports bettor,” and I’m reaching out to a bunch of bigger winners in the space. Pretty much the question is: what are the skills that make someone specifically good at sports betting? Not ignoring math or modeling, but why are some people who are amazing at those skills not able to win big, while others who aren’t particularly good are able to figure it out? Why do some oddsjammers win some money but can’t figure anything out beyond that, and some just instinctively see that there’s more to be won and build something big?

Although the question was quite broad and could be answered in a million ways, almost every bettor touched on two main themes (though each described them slightly differently): analytical intuition and risk tolerance.

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Analytical Intuition and Imagination

I’ll be honest—I was really hoping this would be the main response from the people I asked, because it’s what I was trying to touch on at the start of the newsletter. That being said, the responses did a much better job explaining this than I did.

Here’s every answer I got that I thought fell into this bucket:

Shipper

“The number one skill that is present among most big winners is the ability to think critically. The amount of nuance that is present in this extremely specialised, very odd ecosystem is crazy, and it means that hard-and-fast rules fall over very quickly.

Think about some of the known truths of the NBA: teams play worse when they are leading; the home team losing game one of a playoff series gains a meaningful bump in game two; teams play differently dependent on their physical proximity to their bench. These once upon a time were not baked into the market. Think about all of the other assumptions that may fall over if tested!

Those same distortions exist on the market side. Books hold many assumptions that may prove to be incorrect if the bettor can break them the right way.

All of these are prodded by the mind that thinks critically rather than the one that religiously follows instruction.”

Jay Croucher

“A very innate, strong sense of probability. I suck at math and can't code but when I was a kid I knew roughly the % chance my football team had of winning a match at a given point of time and that basic sense is the biggest reason I've been successful betting.”

Peanut Bettor

“Being a first principles thinker. There are so many ways to win, but almost all of them you need to create for yourself.

Having the curiosity/open mindedness to ask what’s really happening and analytical skills to break down the problem into smaller subsets that allow you to determine what factor is actually driving the result. And whether it’s originators predicting game outcomes, top-down bettors trying to project the closing line, or movers trying to decipher best ways to get the most ROI down, everyone is playing one big game of cause and effect.”

Adam Ewenstein

“Imagination. Basically, an ability to not get stuck in a rut. Keep improving methods, finding more markets you can beat. Finding more ways to get outs or people to send you bets, etc. Many people have success for a while but some aspect of the business dries up.”

Rufus

“When I was younger, I used to think anyone with good stats knowledge could do this, and I was just lucky there weren’t more math/stat PhD types in the field. After interviewing many of these types in 2013, I realized I was wrong. It’s about problem solving and thinking logically and creatively. I believe it takes a certain mindset and you need to have quant skills in my opinion to originate successfully, but that’s not sufficient. The far bigger thing is creativity, persistence, and for lack of a better term ‘hackiness.’”

Anonymous responder

“There are lots of ways to find edges. Understand where your edge is potentially coming from. Could be entirely math-based, could be ball knowledge with math to back it up, or it could be understanding where a book’s assumptions might be wrong. Either way, you need to think about where the edge comes from.”

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Reading through the responses, it was apparent how much alignment there was around this core idea—what I tried to describe earlier as “seeing clearly.” But everyone I asked put much better language to it. Whether it was Shipper talking about critical thinking, Peanut breaking things down through first principles, or Jay describing his internal sense of probability, the throughline is this: the best bettors think a certain way—they’re curious, imaginative, and deeply analytical. They ask better questions, challenge assumptions, and constantly iterate. They’re able to quickly understand if they’re on to something, or if their idea has no merit. Adam called it imagination, which I think nails it—this ability to keep evolving and finding new edges. Rufus framed it through problem solving and creativity—realizing that quant skills are just the entry fee, but it’s mindset, persistence, and what he calls “hackiness” that truly separates winners.

Creativity and imagination are discussed so rarely when people talk about betting, but they’re quietly some of the most important traits a bettor can have. The final quote sums it up best: there’s no single way to win, but the winners all understand where their edge is coming from, and they know how to press it.

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Risk Tolerance

The other most common response from the people I asked was about risk. Honestly, I wasn’t really expecting this answer, but after reading the responses, I completely agreed. I think I didn’t consider it because I actually think of myself as quite risk averse—however, using any objective standard, I obviously have a solid appetite for risk.

As an aside, it makes a lot of sense that this was one of Chris’s answers—he often talks about how people who win aren’t betting enough, and there’s only so much time you have an edge, so you should push it. He absolutely lives by that mantra. Huge bets make me uncomfortable, and you should only take this advice if you’re a confirmed winner, but Chris has taught me a lot about how I should be accepting a lot more risk. One time Chris and I had a bet together and it was one of the bigger bets I’ve ever had. I told him he could have 60% and I’d take 40%. Later on, he told me he thought I was insane for that decision—and that’s the reason he makes more money than me even though I’m the better originator. I think about that a lot.

Jay Croucher

“Optimally calibrated risk tolerance doesn’t always overlap with pricing ability. The best bettors don’t have arbitrary mental blocks that make them understake in outlier EV situations—and they don’t overstake to chase any losses either.”

Chris

“Ability to stomach losses / comfortable betting big.”

Adam Ewenstein

“Things that separate a small-mid winner from someone who can make a lot or be a professional: 1) the right balance of not being risk averse or a degenerate—most people aren’t in that sweet spot.”

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What all of these answers get at is that pricing well and thinking clearly are necessary—but not sufficient. You still have to pull the trigger, but also know when to take your hand off the gun. I know many bettors who are really good but can never dive into the deep end of big bets, and as a result haven’t won that much. On the other hand, you hear tons of stories about people who figure out how to win but are degenerates and give it all back. The best bettors have a kind of emotional calibration that matches their analytical one—they know when to push, when to hold, and they don’t let fear or ego distort either. They don’t go on tilt.
 

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