I used to play online poker for a living. If I was asked about it during a job interview today, I would say that those five years were instrumental in developing my abilities in financial management, game theory, risk assessment and patience. If I was asked about that time by a friend, I would say that it took away any perspective I might have had about working hard and following instructions, but it was worth it because I got to enjoy an early retirement, even though I Benjamin Button’d myself into having to have an actual job now.

The only gambling you can do as an adult that doesn’t make people think you’re a degenerate is with stocks. When I was young I would buy shares in real companies with fake money, and then when the newspaper would arrive each morning I would grab only the business section to check on my progress, leaving the comics and infantile jumbles to the others. I still dabble in the market, but it’s never held the same weight as when I was a kid. Mostly now I do it to keep my foot in the door, so I can surprise people with knowledge about things they really don’t expect me to know, based on my appearance and affinity for not giving a shit. I’ll say things like, “Uber was able to delay their IPO after a $3.5 billion injection from Saudi Arabia, and General Motors helped out Lyft in January before they went public. I’m keeping my eye on Huang Lu, this rickshaw driver in Chinatown, but he should be able to stay private for a while as long as the SEC doesn’t figure out how many angel investors he has.” They’ll look impressed, but I’ll overhear them later telling someone else they only wanted me to stop talking so they could get another drink.

Now I mostly invest in companies I’m actually rooting against, like Monsanto, so I can hedge my life. I mean, of course I want the company to fail and everything, based solely on a completely biased documentary I saw – okay, that somebody told me about – a few years ago, but I have so little power to make that happen, that in order to not go completely crazy about my inability to enact change, I at least make some money every time they make the world a little shittier and boost their own already fat bank accounts. In an economic structure where access to money is so essential in determining your friends, hobbies, happiness and survival, bet hedging helps you manage the extremes and stay relatively stable amid constant tumult. Like if I was one of those legitimately fanatical sports fans, I’d certainly bet against my team every time they played. The impact of their loss would be mitigated by my financial gain, keeping my stress level down and my health intact.

Gambling is a big part of the culture back home in Newfoundland. For some reason we just can’t get enough of the waps. That’s what we call slot machines, and the name is derived from that beautiful sound you make when you hit the buttons and the cherries light up in a row. There’s also this church fundraising event they do every now and then called Chase the Ace. It doesn’t really matter how you play, but it’s centred around people not understanding odds and seemingly not caring if the church ends up with a gold altar and a new pony for the sisters. Even with the obsession that comes from chasing that ace every week, the most popular gamble around is Regatta Roulette. Tucked right between George Street Fest and the Folk Fest weekends, on the first Wednesday in August, St. John’s has this annual rowing festival down in Quidi Vidi where everyone gets drunk and nobody watches rowing, because why would you. That mid-week day is a civic holiday for the whole city, that is, unless the weather’s garbage, which it often is. In this case, the event is moved to the Thursday, and everyone’s supposed to go to work on Wednesday. Even in the middle of summer, the forecast can’t really be trusted, but still the first Tuesday of August ends up being one of the biggest days to go drinking. Everyone’s counting on the Regatta going ahead and getting the day off, but even if it doesn’t, the gamble is always worth it.

December 7 – Dan Bilzerian gets a gamboling gambler
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