Winning the Wrong Way: Lessons from a Drunken Gambler
“Any time you make a bet with the best of it, where the odds are in your favor, you have earned something on that bet, whether you actually win or lose…”
— David Sklansky, The Theory of Poker
Most investors don’t lose money because they lack intelligence. They lose because they mistake outcomes for skill.
A few winning trades, a hot stock tip, or a lucky streak can seduce even the most rational person into thinking they’ve cracked the code. But if you’re serious about trading—especially options—you can’t afford to play that game. You need a strategy where the odds are tilted in your favor, not just this week, but over years of repeated decisions.
That’s what professional traders focus on: not the latest market move or guru prediction, but process. Boring, methodical, repeatable process. It’s the only thing that compounds in the real world.
I learned this not from a textbook or a trading desk—but from a $1 craps table in downtown Las Vegas long ago.
Let me explain.
Back in my early 20s, when I was living in beautiful Flagstaff, Arizona, I’d occasionally drive to Las Vegas — not to chase a big win, but to make what I still consider one of the smartest bets in the casino: the free odds bet in craps.
For those unfamiliar, in the game of craps, placing odds bets behind your pass line wager allows you to bet at true odds — meaning the house has no edge on that portion of the bet. It’s one of the only wagers in a casino where the expected value is exactly zero for the house. So why would the casino even offer it? Simple: most players either don’t know it exists or choose not to take full advantage. They prefer bets with flashy payouts and awful probabilities — the kinds that keep the lights on in Vegas..
Just like in trading, I defined my risk from the outset — fresh out of the halls of the University of Oregon with humble means, $100 was my hard limit. I wasn’t chasing a jackpot; I was there to make calculated bets and enjoy the process. And just like I do with options trades, I wanted to stretch every dollar. So I’d head to downtown Vegas, where I could find low minimums and high odds multiples. The best odds. The most efficient use of capital.
It didn’t take long to find a $1 table offering 100x odds. And not long after, I found myself next to a man who had clearly been enjoying both his payday and the free drinks. Loud and visibly intoxicated, he boasted about his recent winnings.
I smiled and wished him well. But as I watched him play, it became clear he was making one bad bet after another — long-shot propositions with terrible probability. You know, Yo 11, and the sort. Still, he was winning. And loudly.
To put things into perspective: In craps, “Yo 11” refers to a one-roll proposition bet that the next roll will total 11 (a 6 and a 5). It’s called “Yo” to avoid confusion with “seven,” especially in a noisy casino.
Here’s what you should know:
- Payout: Typically 15 to 1
- Probability: 2 out of 36 combinations → roughly 5.56% chance of hitting
- House Edge: Around 11.11%
Bottom line:
It’s a flashy, low-probability bet with a high house edge — exactly the kind of wager the casino loves and experienced players avoid. It’s the gambling equivalent of buying weekly out-of-the-money lottery options — fun if you’re lucky, but not a strategy you build around.
Meanwhile, I was quietly sticking to high-probability, low-edge bets — the kind no one cheers for. The kind that win in the long run, but often lose in the short term. My balance dwindled. His grew. And with each improbable win, a crowd formed around him. They admired the outcome, never questioning the process.
Eventually, he started pressing his bets. Bigger and bolder. I’ve seen this story play out too many times — not just at the craps table, but in options trading. Traders hit a lucky streak, get overconfident, and size up dramatically. It’s almost always how things unravel.
Sure enough, he gave it all back. His winnings, his paycheck — gone. Probability always has the final word.
And me? I kept grinding. Despite being down to just over $30, I stuck with my system. Probability started to work in my favor again, and I ended the session slightly above break-even.
The lesson here is both simple and foundational: Your long-term success isn’t determined by any single trade, day, or even month of performance. It’s shaped by the quality of your decision-making process — how you evaluate risk, define your edge, size your positions, and stick to your rules.
Anyone can get lucky once. A few good outcomes don’t prove you’re a good trader — just as a few losses don’t mean your strategy is broken. What matters is whether your decisions are repeatable, rooted in logic, and statistically sound.
When you judge your trades solely by their outcomes, you fall into the trap of resulting — a cognitive bias where you mistake luck for skill, or randomness for insight. That kind of thinking leads to chasing heat, abandoning sound strategies after short-term pain, and ultimately blowing up.
But when your decisions are based on a well-reasoned process — one designed to tilt the odds in your favor — you can weather the randomness, because you’re playing a long-term game. Over time, good process compounds. Randomness cancels out. And probability pays you back.
In both gambling and investing, randomness is always at play. If outcomes were all that mattered, we’d evaluate every decision based on whether it worked — ignoring how and why it was made. That’s a dangerous trap. It’s how investors get fooled by luck, abandon good strategies, or chase performance.
A sound process doesn’t guarantee success on every bet. What it does is stack the odds in your favor. Over time, that’s what separates consistent traders from the noise chasers.
This is exactly why I’m drawn to options—they allow me to take the other side of the trade and act like the house. In most cases, I’m selling options where the buyer only has about a 15% to 30% chance of success. That means I’m starting each trade with the odds stacked 70% to 85% in my favor.
Try finding odds like that with a stock, ETF, or mutual fund.
Of course, having the odds on your side isn’t enough. Without proper risk management, even high-probability trades can unravel quickly. That’s why I size my positions conservatively, define my risk before entering a trade, and make sure no single trade can damage the portfolio. The edge comes from consistency—not just in strategy, but in protecting capital so you can keep playing the game.
Most self-directed investors don’t operate this way. They buy what’s been going up. They follow headlines, trends, and gut feelings. Rarely do they think in terms of statistical advantage or process. They’re the drunken gambler — loud when things are working, unaware of the risks they’re compounding.
Markets reward discipline, not noise. Probability is the compass. Strategy is the map. The rest is just variance.
So, what’s the takeaway?
If you want to trade like the loud guy at the craps table—chasing long shots, riding luck, and ignoring the math—Wall Street will gladly accommodate. It’s built for that kind of behavior. Brokers love it. Market makers live off it. But if you want to trade like the casino—quiet, disciplined, and focused on edges that compound—you need a process. And you need to stick to it when it’s least comfortable.
That’s what The Option Premium is all about.
Each week, I break down what the market is implying, not just what the headlines are shouting. I walk through high-probability setups, volatility conditions, expected moves, and portfolio-aligned trades that put you in the position of the house—where odds work for you, not against you.
If that sounds like the kind of strategy you want to follow, I’d love to have you join the growing community of options traders reading The Option Premium. It’s free, it’s focused, and it’s built for investors who care more about process than prediction.
Because in the end, the gamblers blow up. The disciplined survive. And the ones who truly understand probability? They thrive.
Thanks for your time. I hope you found this helpful.
Andy Crowder
