Wallet Hacks

Your craziest side hustle? Mine was that time in college I gambled online…

My wife and I met while we were in college together in Pittsburgh. When we started dating, a few of my friends mentioned to her that I would “gamble online a lot but that it was OK, because I was good at it.”

And I was good at it… but I wasn't good at gambling, I was good at taking advantage of promotions.

(and I can thank my college friends Jason W. and Matt B. for introducing me to it in the first place!)

I was an online casino promotion hunter.

Back then, as is the case even today, you could get a deposit bonus every time you joined a casino. Deposit a dollar amount and you would get a percentage (100-500%) as a bonus. You could cash out once you wagered both your deposit and the bonus a certain number of times.

In the beginning, the multiple was 4 times. Deposit $100, get $100, put $800 into play (4 x $200) and you could withdraw your cash.

That multiple would creep up over time. 8x, then 12x, then 16x. It was at 16x when I stopped.

To hit the wagering multiple, I would play Blackjack (optimal strategy, courtesy of the awesomely-named Wizard of Odds) until I hit the limit, then cashed out. I never felt the pull to keep playing because there were a ton of casinos. We used to keep spreadsheets, that's how many casinos there were.

(Looking back, I kind of wish I had known Colin of Blackjack Apprentice, he could've taught me a few things!)

Nowadays, this is much much harder and with far lower yields. I just peeked at some random casino (Lucky Red Casino) and they offer a 400% up to $4000 bonus but you had to wager it THIRTY times. Oh and only wagers on slots, keno and scratch cards counted. That's bananas, those are terrible games (both odds-wise and entertainment-wise!).

How much did I make? I don't recall how much I made over the course of about a year but it was in thousands. Some casinos I walked away with a few hundred, some I walked away with nothing, and a few rare cases I cashed out with over a thousand dollars.

I've lost and won $1,000+ blackjack hands. That taught me how casino chips, especially internet casino chips, don't feel like money anymore. A thousand dollars to anyone is a lot of money. And I was an idiot who wagered it twice!

Incidentally, both were equally horrifying.

You know how poker players, who have spent countless hours playing, have seen every hand lose? It's like that in anything, including blackjack. Having a 20 and getting beat by a dealer getting 21. The sense of dread and inevitability you get when you have a 14 and the dealer is showing a face card. Oh and when the dealer flips over a 2 and a 3 and slowly walks his way to a 20 to beat your 19.

Why did I stop? I was running out of casinos where cashing out was easy (biggest reason) and the multiple was getting too high. It was taking too long to finish off a casino and honestly it was getting boring. The payout and payout frequency was getting lower because of the wagering multiple, which is the point, and the novelty of gambling online had worn off.

Did I learn anything? A few things actually.

First, there's always an opportunity to take advantage of a promotion, especially in a market where a lot of the other participants aren't taking advantage of it. Most of the people who signed up to those promotions wanted to gamble. Those people were subsidizing me and my friends going out and promotion hunting. We had more time than money so we could hop from place to place and “work” for our cash.

Next, I recognized how my body responds to stress. It's funny because sometimes I don't consciously recognize it's a stressful situation but my body does and I can recognize that, which is useful.

Lastly, I learned I don't really enjoy gambling that much. I play poker with friends but I'd never go to a card room full of strangers. I'll sit down at a table with friends, but I rarely do it by myself. I think it's because the odds are never in your favor. So unless I'm being entertained otherwise, I would rather buy my own beer and do something else.

That said, promotion hunting was a fun time because I had a positive expected value whenever I signed up to a casino. 🙂 Of all my college side hustles, that one was probably the most interesting and “craziest.”

What's your craziest side hustle?