Kirk's Hammer: How to Become a Good Bettor

Last newsletter I talked about what I think are the inherent skills of a good bettor. Things like pattern recognition, emotional control, and being naturally analytical. And while those skills are important, there are plenty of people with those skills who never find out that they are good at betting.

A lot of people go their whole lives just assuming betting is bad or a waste of time. Some of those same people might have been great at it, some I’m sure do far better things and couldn’t care less, but many don’t find out because they never tried.

Becoming good at betting is unique. In most areas of life, if you want to get good at something, you go learn about it. There’s usually a plethora of information out there on how to improve—whether it’s playing piano, cooking, coding, lifting weights, whatever. But with betting, it’s not like that.

In fact, I’d argue that the hardest +EV (positive expected value) bet you’ll ever make is your very first one. Because the hardest part of betting is getting to the point where you even understand what a good bet looks like. Most people believe the house always wins, which is mostly true, but that barrier keeps them from ever considering that you can win betting. I remember specifically having an argument in university that it doesn’t matter what you bet, the house has a vig so all bets are equally bad. That argument obviously was wrong, but I believed it to be true.

On top of that, no one with a real edge wants to hand it over. Even in other markets—take stocks for example—you’ll find smart people who are willing to talk about the strategies they use, at least to some degree. The stock market is so much larger than betting that discussing what makes you good have far less consequences. But with betting, it doesn’t work like that. If one other person learns the exact edge you have, it can destroy its value. So people keep quiet.

What fills that void? Mostly noise. The vast majority of people who speak publicly about betting are not experts, but they brand themselves as if they are. If you follow them, you’re more likely to move further away from being good than closer. If you’ve found yourself paying $1000+ to be in a betting seminar, you might have taken the wrong path.

That said, good bettors do talk about betting, they’re just usually vague. And while that vagueness frustrates some people, if you’re willing to think deeply about what’s being said, you can still extract nuggets of insight that can completely change the way you understand betting. This has happened to me on numerous occasions: I’ll be listening to a betting podcast, and something someone says suddenly clicks. It creates an aha moment, and I end up making a drastic improvement in my betting process.

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Choosing Who You Listen To

There’s an interesting thing about life in general: you can’t be an expert in everything, so you have to outsource knowledge. You pick people you trust to guide you in fields where you’re not the expert. But if you pick the wrong people, you can create a negative feedback loop.

You end up absorbing bad information, thinking you’re learning from an expert, and then you build more and more confidence in opinions that are flat-out wrong.

A huge part of my gambling journey was simply listening to as many smart people as I could. I didn’t need them to hand me their edge; I just needed to learn how they thought, what they cared about, and how they processed information.

One of the best places to start is podcasts. I’d heavily recommend going back and listening to as many Circles Off episodes as possible. People sometimes look at this in a binary way—“Oh, he’s not giving away his secrets, so it’s useless.” But I think that’s a mistake.

In reality, one tiny nugget can completely reframe how you think about betting. But you have to put in the hours to find those nuggets.

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Learning From the Wrong Paths

Let me be clear: you will go down wrong paths. I did. For example, I once paid for Action Network’s “reverse line movement tool” or whatever the hell it was. That was the dumbest money I’ve ever spent. But at the same time I didn’t know better, but I quickly realized it was crap and moved on.

The key is to not get married to bad ideas. Test them, recognize when they’re failing, and cut them loose.

And don’t limit yourself to only learning from bettors. Some of the best insights I’ve had came from people who weren’t even talking about gambling.

I didn’t only learn from bettors. Some of the biggest leaps I made came from listening to people who weren’t even talking about gambling at all. For basketball, Zach Lowe was the first real turning point. I basically started my basketball education through him. I knew he was smart, so I paid attention to what he thought mattered. The benefit of doing that was twofold: I could use his expertise as a compass, and at the same time I could challenge it. If I thought he was wrong about something, I’d test that hypothesis myself. That’s how you start forming your own independent opinions.

After that, I gravitated to Nate Duncan. I wanted to get better at evaluating players, and he’s very sharp in that area. I wasn’t just listening for his conclusions on players, I was listening to how he evaluated them. He’d say things like, “This guy is a good two-foot leaper,” or “That player never helps off his man.” Hearing that, I’d think, okay, I’m going to start looking for those things when I watch games, or I’ll test whether those traits matter in my models. It’s about taking someone else’s framework and seeing if it actually works in practice.

Adam Levitan is another great example. I’m not a football expert at all, and he mostly talks about DFS, but it’s obvious he knows what he’s doing. If you can project players accurately in DFS, you can translate that same skill set into projecting props. So I listened to what he cared about and used those stats as a baseline. He is also awesome at evaluating coach speak, a huge skill when it comes to betting props. He’s probably the best I’ve heard at filtering through all the noise and figuring out what actually matters. That’s been hugely useful not just for football, but across sports in general.

The point is: you don’t need someone to say, “Here’s how I beat the NBA.” You need to figure out how they think. Then you adapt that thinking into your own framework.

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The Importance of CLV

This brings me to one of the biggest reasons I’m a CLV (Closing Line Value) maxi. The feedback loop is fast. If you’re onto something, you’ll know pretty quickly.

To get good, you have to get in the game. That doesn’t mean you need to risk big money right away. What it does mean is you need to track your bets meticulously and see how the market reacts. Within 5–10 bets, you’ll probably start to get a feel for whether you’re onto something, and within 20–30 bets, you’ll have a really good sense of whether you’re adding value or just wasting time. You’d need hundreds if not thousands of bets to truly know you’re good without CLV.

If you’re just starting out, paper betting and tracking CLV is a fantastic way to accelerate your learning. Don’t spend eight months trying to build the perfect model before placing a single bet. That’s way too slow. Shorten the feedback loop. Test, track, iterate.

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Putting It All Together

So, how do you actually become a good bettor?

1. Accept the barrier to entry. The hardest part is understanding what makes a good bet in the first place. Don’t expect anyone to hand you their edge.
    
2. Be ruthless about who you listen to. Pick sharp people. Avoid fake experts. Understand that vagueness from a real bettor is worth more than “certainty” from a bad one.
    
3. Look outside betting. Learn how smart analysts think in their field—whether it’s basketball, football, or even business—and borrow their frameworks.
    
4. Test everything. You will go down wrong paths. That’s fine. Just don’t stay there.
    
5. Track CLV relentlessly. It’s the quickest way to know whether your process has potential.
    
6. Iterate fast. Don’t spend forever building something in theory. Put it into practice, get feedback, and adjust.

Once you learn how to win one way, it starts to snowball, edges stack and you become better and better, but you have to be humble and willing to be wrong and adaptable.


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