Kirk's Hammer: Back to the Betting Stuff

After a nice run of WNBA-themed topics, today I’m getting back to mostly betting stuff. I’m going to run through some random heuristics I often think about but have never written down, and then I’ll discuss the new banger episode of the Risk of Ruin podcast.

Quick Disclaimer

Before I get into any of my thoughts, I need to emphasize: anything I write is really, REALLY bad advice if you’re not a winning originator.

I imagine if you’re reading this, you’re probably at least somewhat familiar with winning in betting—or you’re my mom. Hi mom.

Everything I write here comes from the perspective of someone originating bets and winning. If you try applying this to negative EV bets or as a top-down bettor, it won’t help—it’ll probably hurt. That said, I’m guessing if you’re reading this, you might have some desire to become an originator. If that’s true, these are good things to think about as you take those steps.

Why You Should Try Originating

If you’re a top-down bettor or a mover with no desire to originate, I’d say you’re making a mistake. That’s dumb of me to say—more successful originators make my life harder—but I’ll say it anyway.

Being an originator is awesome. As a top-down bettor, you’re a bit of a slave to your computer. You feel guilty being away, because that’s how you make your money.

Sure, you need to stay locked in when you’re originating too, but taking time off feels less bad. The actual work is 100x more fun, and there’s a pride in winning that doesn’t come from top-down. It’s also way easier to maintain accounts, you can bet at shops that won’t kick you off, and it’s far more scalable if you’re good at it.

Alright, now to some heuristics.

Why You Should Make Really Bad Bets

By “really bad” bets, I mean ones that end up with horrible CLV or futures that, in hindsight, had no shot.

There’s a natural—and correct—desire to avoid negative EV bets when you’re a winning bettor. But the fear of a bet being bad often makes us miss EV in spots where the edge is conditional or hidden.

The classic example is injury analysis:

Let’s say Jokic is questionable, and Denver is -3. You think it’s 50/50 he plays. You make the game PK if he’s out, Denver -9 if he’s in. That’s an obvious wager, even if he ends up not playing and you’re holding a steaming pile of shit.

For a long time, I would avoid bets like this—too scared of the downside risk—even though it’s an obvious +EV spot.

Another example: small data problems. You notice a trend in NFL holding penalties and remember a quote from a league official. You think there’s a 20% chance it’s a real edge the market hasn’t caught yet. That’s worth acting on—even if there’s an 80% chance you’re clicking into a fully developed market with zero edge.

Future markets are similar. A lot of betting comes down to small data problems. If you see a player look incredible in their first preseason game, and think it might be material, I’d argue you should take a shot—even if there’s a high chance, you’re acting on air.

I think a lot of this comes down to not wanting to be wrong. Being wrong sucks—it’s embarrassing, it hurts the ego—and let’s be honest, bettors have pretty big egos.

But if you’ve been right a lot in the past on standard bets, taking chances on conditional probabilities is a great way to maximize total EV—even if it leaves you with some duds along the way.

Don’t Mistake Negativity for Realism

A buddy said to me recently: “I think the world’s fucked. I don’t see any reason for optimism.”

I rattled off a bunch of facts: life expectancy up, poverty down, technology booming. My point wasn’t that everything is great—there’s plenty to worry about—but that pessimism often gets mistaken for realism.

Flip the statement: “The world is perfect. I see no reason for negativity.” That would get dismissed immediately as idiotic. But if you say the opposite— “The world is fucked. No reason for optimism.”—it gets treated like a wise quip.

Both statements are equally dumb.

The Contrarian Trap

Most successful bettors are naturally contrarian—it’s both a cause and a correlation. Winning at betting is easier when you see things differently, and to even believe you can win, you almost have to be a contrarian.

But being contrarian doesn’t make you smart or good at betting.

There are plenty of times when the consensus is right—and plenty of times when the consensus hasn’t even gone far enough.

It reminds me of Goodhart’s Law: When a measure becomes a target, it ceases to be a good measure.

Being contrarian is useful—until you start trying to be contrarian. Then you get lost in bad takes and worse bets.

When you’re betting, don’t think in terms of the public being on your side or if you’re going against the grain. You can think of why the line is set in this manner, and that can be helpful, but the overwhelming goal should be “this bet is good”.

Risk of Ruin

If you haven’t listened to the most recent (or any) Risk of Ruin podcasts, you absolutely should. The guy never misses.

This one in particular was awesome—especially if you want to get into exchange markets.

If someone asked me the best way to make a significant amount of money betting in the next few years, my number one recommendation would be to focus on Polymarket and Kalshi, specifically none-sports markets.

Domer was an awesome guest. He’s obviously a huge winner, but nothing he does seems totally out of reach. Not to say he’s not smart—he’s clearly sharp—but he even mentions he’s not the best at analyzing live election markets and hired a team to do that for him.

I get asked some version of “Why do you win?” or “What do you know that’s unique?” And there’s really no single answer. It’s more like there are a thousand small things I know that I can quickly piece together. It’s not one thing.

That felt very similar to Domer. He talked about waking up on Israeli time to follow the election there, having Twitter lists ready for any country’s politics—all stuff that, when you hear it, makes total sense. But none of it is rocket science.

He also mentioned taking time to become one of the world’s leading experts on the Pope, then a few months later, forgetting everything.

One thing I thought he missed: you don’t need to be the top expert in the world. Most world experts on the Pope don’t bet. You just need to be one of the top experts among bettors.

Overall, it was a great listen—and a rare, honest insight from someone winning at a super high level.

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