The Proper Way to Be a Degenerate Gambler

I enjoy gambling way more than the average person. It is the obsessive side of my personality where I love to get engrossed deeply in something. My personal gamble of choice has always been roulette.

I was hooked the first time I played. I was freshly 18 and was in international waters for the first time on a cruise ship to the Bahamas.

As me and my friend walked past the casino, something we’ve seen on tv but never in real life, we decided we should try our hand at a game. The first thing we saw was a Roulette table and the dealer was nice enough to teach us the game.

I didn’t know much about the Roulette except the famous Wesley Snipes line, “Always bet on black.”

So that’s what I did. I turned $5 into $10 in an instant.

From there, I continued to bet small and used my math skills to come up with a gambling strategy that has served me well since that day. I’m sharing the principles with you here:

1. In any game of CHANCE, always decide what you’re going to bet on BEFORE you sit down. Following your gut in the moment is a fools errand.
2. In any game of SKILL, always decide your strategy AND your counters to how your opponent(s) may respond BEFORE you sit down to play. We’ll focus more on games of chance in this post and I may talk about games of skill in the future.
3. Bet small on a big bet (something that is risky [low odds] can return big) and moderate on your hedges (these should be solid payouts with low risks taken — like a 50/50 coin flip). Hedges are the bets you make just in case your big bet doesn’t play out. It provides downside protection and lowers the overall risk you take.
4. Hedge your bets in ways that if you win, your hedge will increase your winnings but if you lose on your big bet, the your hedges might still cover it. For example, if your Roulette number is Black 22, don’t hedge your bet by placing additional wagers on RED or the “1st 12.” Instead, bet around your number. This would mean placing a $1 bet on BLACK 22, a $5 bet on the “2nd 2”, and a $5 bet on EVEN. In this situation, you are strategically placing your bets in ways that when you win (e.g. BLACK 22 hits exactly), you’ve doubled down on it and win even more from the other hedges you made (You’ve turned an $11 wager into $62). But let’s say BLACK 22 doesn’t hit. You still have a chance to win if it lands in the “2nd 2” or if the number is EVEN since you are betting 61% of the board (the odds are still in the casinos favor but you’re giving yourself a solid chance at least). There are still two scenarios left for you, you can hit BLACK only and get $10 back on a $11 (you lose $1) or you can miss completely and lose the full $11. Either way, by betting in this way, you keep yourself in the game for longer since you’ll lose less but win more when you do win.

That’s the idea on my  high level gambling system that has served me well over the years. It’s not the most optimized system, but it’s directionally right. Using variations of this, I’ve won much more than I’ve ever lost at the casino (or in investing in general).

You have to take bigger chances to actually come out ahead, but protect your downside  with hedges that increase your overall earnings when you hit big.

My last note is to always pay yourself (and the dealer — be a decent human) when you win and know the maximum amount that you’re willing to lose before sit down. When you reach that max, your day is done.

Go into games of chance with the pre-decisions made BEFORE you sit down and you’ll be able to live with the results no matter the outcome.