Marrying Pocket Sixes

In college while playing poker you’d eventually watch one of the most famous films for any degenerate-wannabe: Rounders. Whether you picked up cards at a home game, fraternity, or social event, everyone romanticized Matt Damon’s run for the World Series. It was the movie that shed light on Texas Hold’Em before it even became popular in Moneymaker’s 2003 breakout year. Bonus, it was filled with amazing quotes and a laughable Russian accent for John Malkovich.

Even though I own the Collector’s Edition, I don’t touch it anymore. It’s so far from the truth it’s almost lethal to mire in its mystical vapors. After this trip and re-living what can only be described as the “euphoric hell” that grinders go through, I now understand how lucky I used to run in the $2-$5 NL games.

Here are three things that I learned that can be quickly applied to startup/every day mentality.

1. Preparing to Win Not Just on Special Occasions

Before the tournament I was meticulous in my planning. I made sure I ate non-greasy, light breakfast food and that I’d chew 20 times (which is insane, but the recommended number per mouthful) per bite, which I never do. I prepared snacks for each break, coordinated when I’d do bathroom breaks, all down to the wire.

Then I realized, “Why don’t I do this every day?” Why can’t I prepare the crap out of each day wanting to win the daily baby seal cereal prize? I had chosen to not kick ass every day, which is falling short of my potential.

Play like you’re gonna win every day with a plan.

2. Variance Builds Character

There’s a saying in poker that amateurs think it’s all skill, intermediate players think it’s all luck, and the pros know it’s both. Even if you’re making the right decisions, sometimes the deck is just a cooler. The statistical “luck” that comes with short-term poker is known as variance. In context, it is usually used to explain despite you putting the money in ahead, he just two-outtered you on the river. You can constantly adapt to the table’s aggression, the type of tournament, or type of cash game but nothing will prepare you for a bad down-swing.

And by bad, I mean you can be running for months or years bad. All the best pros have known that fateful experience of “busting” out of Vegas and having to recoup a bankroll. The solution? You just have to survive it.

This trip reminded me that you need to have the balls and chubby skin to make through scrappy times. Boot-strapped startups are akin to such variances where you don’t know when your next cash flow is coming from. But you believe in yourself and the cause, so press on.

The world doesn’t reward scared money.

3. Paying Your Dues to Be a Killer

One of my poker pro buddies that I happened to meet up during this trip gave me a great explanation of why Phil Ivey is the best poker player in the world now.

“It’s all about balls,” he said as he pulled a drag on the cigarette (his smoking was proportional to the amount of poker he was playing). “Phil Ivey plays the best when he’s broke. He has a terrible gambling habit, but that’s actually what makes him a f-cking killer.” Basically, he wasn’t saving anything for the trip back home. Money was just a language of expressing how much he’d dominate you. He could care LESS about anything, and just focus on the game.

And so the pecking order develops. The penny games come up to dump money to us $1/$2 lifers, and we dump money upwards when we think we can play at those $2/$5, $5/$10 games, and the chain goes all the way to the top of the circus: Phil freaking Ivey. The one with the biggest balls of all.

With that, it brings us to a savory lesson: don’t be afraid to go all-in and fail. It kind of ties with number 2 about not being scared money, but this is its end game. There are NO short cuts anywhere, even in poker. Long-term success is still a very tangible metric within this community, and the boom-bust of gambling is the measuring ruler of our poker civilization. People who win stay, and the rest make Las Vegas a “weekend getaway” for the rest of their lives.

Learn as much as you can as you move up in your game with the due diligence that is needed, and someday you’ll be smoking a cigarette talking about the f-cking killers you swam with.